- Mn(OAc) 3Induced C-4 Arylations of Quinazoline 3-Oxides with Arylboronic Acids
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The use of manganese triacetate as an oxidant component in the C-4 arylations of 2-aryl-quinazoline 3-oxides with arylboronic acids is reported. The new protocol was applied to prepare new 2,4-diarylated quinazoline 3-oxides in good to high yields. The me
- Samandram, Rashinikumar,Koruk?u, Meliha ?etin,Co?kun, Necdet
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p. 210 - 216
(2021/09/13)
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- N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols
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New Pincer type Pd(II) complex [Pd(NNO)(PPh3)] (1) prompted synthesis of quinazolinones via dehydrogenative coupling of readily accessible alcohols, and o-aminobenzamide is described. A diverse range of quinazolinones has been synthesized efficiently with good to excellent yields employing low catalyst loading (0.5 mol%) under the aerobic condition without any additives/oxidants. A plausible mechanism for the construction of quinazolinones has been proposed via cyclic aminal intermediate. Large-scale synthesis attests to the productiveness of the current strategy.
- Anandaraj, Pennamuthiriyan,Kamatchi, Thangavel Sathiya,Ramesh, Rengan
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- A bagasse-supported magnetic manganese dioxide nanoparticle: applications in the selective aerobic oxidation of alcohols and one-pot tandem oxidative synthesis of quinazolinones
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Magnetic manganese dioxide nanoparticles (MnO2-Fe3O4) were coated on sugarcane bagasse as a sugar industrial waste and bio-support (MnO2-Fe3O4@bagasse) via an in situ reduction strategy, in which potassium permanganate was used as the precursor of MnO2 and sugarcane bagasse as a bio-support and reducing agent of KMnO4. The synthesized bio-based catalyst was characterized by X-ray diffraction, thermogravimetric analysis, inductively coupled plasma optical emission spectroscopy, scanning electron microscopy, energy dispersive spectroscopy, Brunauer–Emmett–Teller surface area analysis, and vibrating sample magnetometer analysis. The catalyst was successfully utilized in the selective aerobic oxidation of primary and secondary benzylic alcohols to their corresponding carbonyl compounds and one-pot tandem oxidative synthesis of 2-(substituted)quinazoline-4(3H)-ones from the o-aminobenzamide and aromatic alcohols in the absence of oxidizing reagent or initiator. Graphical abstract: [Figure not available: see fulltext.]
- Farhid, Hassan,Hajishaabanha, Fatemeh,Rashidi Vahid, Adina,Shaabani, Ahmad,Shaabani, Shabnam
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- Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamide with benzonitriles in PEG
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A simple and efficient Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamides with benzonitrile in PEG under metal and ligand‐free condition. All substituted benzonitriles were also well participated with the formation of the corresponding products in moderate to good yields.
- Botsa, Sathish Mohan,Karasala, Bharat Kumar,Matcha, Sowbhagya Lakshmi,Vidavalur, Siddaiah
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- Method for synthesizing 2 -phenylquinazolone compound by taking styrene compound as raw material
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The invention discloses a method for synthesizing a 2-phenyl quinazolinone compound. The method comprises the steps of adopting a styrene compound and 2-aminobenzamide as reaction raw materials; underthe combined action of a palladium catalyst, a ligand and oxygen, reacting to obtain the 2-phenyl quinazolinone compound, wherein the reaction temperature is 80 DEG C to 110 DEG C, a reaction formulais as shown in the below figure, and R is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, nitro or methoxyl. The method provided by the invention has the beneficial effects that the raw material styrene compound is cheap and easy to get, so that the method is more economical; a preparation method is simple and convenient to operate, and the obtained product is easy to post-process, so that the method is suitable for large-scale industrial production; no high temperature and high pressure is needed, and a reaction condition is mild; the method is short in reaction time, high efficient to react, high in yield, and higher in reaction efficiency after reaction amplification.
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Paragraph 0087-0096
(2021/03/03)
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- Electrochemical synthesis of quinazolinone: via I2-catalyzed tandem oxidation in aqueous solution
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The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C-H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then effectively cyclizing amides to various quinazolinones.
- Hou, Huiqing,Ma, Xinhua,Lin, Yingying,Lin, Jin,Sun, Weiming,Wang, Lei,Xu, Xiuzhi,Ke, Fang
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p. 17721 - 17726
(2021/05/29)
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- Electro-oxidative cyclization: Access to quinazolinones: Via K2S2O8without transition metal catalyst and base
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A K2S2O8-promoted oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones was successfully achieved under undivided electrolytic conditions without a transition metal and base. The key feature of this protocol is the utilization of K2S2O8 as an inexpensive and easy-to-handle radical surrogate that can effectively promote the reaction via a simple procedure, leading to the formation of nitrogen heterocycles via direct oxidative cyclization at room temperature in a one-pot procedure under constant current. Owing to the use of continuous-flow electrochemical setups, this green, mild and practical electrosynthesis features high efficiency and excellent functional group tolerance and is easy to scale up.
- Hou, Huiqing,Hu, Yongzhi,Ke, Fang,Sun, Weiming,Wu, Xianghua,Yu, Ling,Zhou, Sunying
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p. 31650 - 31655
(2021/11/30)
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- Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach
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Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.
- Das, Siuli,Mondal, Rakesh,Chakraborty, Gargi,Guin, Amit Kumar,Das, Abhishek,Paul, Nanda D.
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p. 7498 - 7512
(2021/06/30)
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- Synthesis, in vitro cytotoxic, anti-Mycobacterium tuberculosis and molecular docking studies of 4-pyridylamino- and 4-(ethynylpyridine)quinazolines
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A series of 4-(pyridylamino)- and 4-(ethynylpyridine)quinazolines were successfully prepared via Sonogashira cross-coupling and dechloroamination reactions on the C(4)-Cl position of the requisite 2-(p-phenyl)-4-chloroquinazolines. The prepared compounds were characterized by means of 1H- and 13C-NMR, FT-IR and mass spectrometry techniques. The structure of 2-(4-chlorophenyl)-4-(2-(pyridin-4-yl) ethynyl) quinazoline from the 4-(ethynylpyridine) series was confirmed by single crystal X-ray analysis which indicates monoclinic crystal system and P21/c space group. Compounds from the 4-chloro-, 4-(pyridylamino)- and 4-(ethynylpyridine)-quinazoline series were evaluated for anti-Mycobacterium tuberculosis (Mtb) properties in vitro employing rifampicin as a reference drug. The results from the Alamar Blue assay (Mtb H37Rv strain) revealed promising MIC90 ranging from 125 μM. The cytotoxicity of the synthesised compounds was tested against the Raw 264.7 microphage cell line at a maximum concentration of 50 μM. The possible mode of interaction against the Mtb was theoretically explained through molecular 3ZXR protein and the more prominent hydrogen bond is observed between the nitrogen of the pyridine ring moiety of the 5 and 6 series with OH group of SER280. Also, a metal coordination between the methoxy benzene moiety of compound 6e and Mg2+ is also observed, explaining the SAR of these compounds to MtGS.
- Dilebo, Kabelo B.,Gumede, Njabulo J.,Mampa, Richard M.,Mangokoana, Dikgale,Matsebatlela, Thabe M.,Moraone, Ngaoko R.,Nxumalo, Winston,Omondi, Bernard
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- A magnetically retrievable copper ionic liquid nanocatalyst for cyclooxidative synthesis of 2-phenylquinazolin-4(3: H)-ones
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In the present work, we report the design and fabrication of a copper-containing ionic liquid supported magnetic nanocatalyst via a convenient and straightforward synthetic approach for the formation of 2-phenylquinazolin-4(3H)-ones using o-aminobenzamide and benzaldehydes as the reaction partners. The successful formation and properties of the as-prepared catalyst have been thoroughly investigated using diverse physico-chemical techniques including FT-IR, XRD, FE-SEM, TEM, ICP, VSM, BET and TGA. Using this nanocatalytic system, a variety of 2-phenylquinazolin-4(3H)-ones are synthesized in excellent yields with operational ease and short reaction times in an environmentally preferable solvent under open air and without using any external oxidizing agent. Besides, the catalyst possessed facile magnetic recoverability and remarkable reusability for six consecutive runs without any appreciable decrease in the catalytic efficiency.
- Gupta, Radhika,Arora, Gunjan,Yadav, Priya,Dixit, Ranjana,Srivastava, Anju,Sharma, Rakesh Kumar
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p. 890 - 898
(2021/02/03)
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- Three-Component Couplings among Heteroarenes, Difluorocyclopropenes, and Water via C-H Activation
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Three-component couplings have been realized for efficiently constructing various nitrogen-containing skeletons via C-H activation, where difluorocyclopropenes have been first identified as coupling partners. Many substrates including sp2 and sp3 C-H substrates were well tolerated, furnishing the corresponding products in good yields. Furthermore, a catalyst-dependent reaction was also developed, enabling divergent construction of two different frameworks. The application value of these reactions was demonstrated in gram-scale experiments with as little as 1 mol % catalyst.
- Liu, Xuexin,Chen, Jian,Yang, Chunyan,Wu, Zhouping,Li, Zhiyang,Shi, Yuesen,Huang, Tianle,Yang, Zhongzhen,Wu, Yong
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supporting information
p. 6831 - 6835
(2021/09/08)
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- Antioxidant and ros inhibitory activities of heterocyclic 2-aryl-4(3h)-quinazolinone derivatives
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Background: Antioxidants are small molecules that prevent or delay the process of oxidations caused by highly reactive free radicals. These molecules are known for their ability to protect various cellular architecture and other biomolecules from oxidative stress and free radicals. Thus, antioxidants play a key role in the prevention of oxidative damages caused by highly reactive free radicals. Methods: In the present study, a series of previously synthesized heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 were screened for antioxidant activity by employing in vitro DPPH and superoxide anion radical scavenging activities. ROS inhibitory activities were also evaluated by serum-opsonized zymosan activated whole blood phagocytes and isolated neutrophils. Cytotoxicity studies were carried out by employing an MTT assay against the 3T3 cell line. Results: Most of the 2-aryl-4(3H)-quinazolinone derivatives showed potent antioxidant activities in superoxide anion radical scavenging assay with IC50 value ranging between 0.57 μM-48.93 μM, as compared to positive control quercetin dihydrate (IC50 = 94.1 ± 1.1 μM ). Compounds 5, 6, and 14 showed excellent activity in DPPH assay. Compounds 5-8, 12-15, 17, and 20 showed promising activities in the ROS inhibition assay. All compounds were found to be non-cytotoxic against the 3T3 cell line. Structure antioxidant activity has been established. Conclusion: It can be concluded that most of the heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 are identified as promising antioxidant agents that are capable of fighting against free radicals and oxidative stress. Thus, they can serve as a lead towards treating oxidative stress and related pathologies.
- Choudhary, Muhammad Iqbal,Khan, Khalid Mohammed,Perveen, Shahida,Saad, Syed Muhammad
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p. 806 - 815
(2021/11/17)
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- A Green, Scalable, One-Minute Synthesis of Benzimidazoles
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Herein is reported a substantially improved synthesis of 2-substituted benzimidazoles by condensation of 1,2-diaminoarenes and aldehydes using methanol as the reaction medium. The developed method afforded moderate to excellent yields (33-96percent) at am
- Elumalai, Vijayaragavan,Hansen, Jorn H.
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supporting information
p. 547 - 552
(2020/03/27)
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- Palladium-catalyzed oxidative homocoupling of 2-arylquinazolinones
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Pd-catalyzed oxidative homocoupling of 2-arylquinazolinones was successfully developed for the direct construction of biaryls via C[sbnd]H bond activation. New well-defined structure that possessed two quinazolinone units was obtained with high efficiency
- Feng, Yadong,Wu, Zhengping,Chen, Ting,Fu, Qi,You, Qihua,Shen, Jinhai,Cui, Xiuling
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supporting information
p. 3263 - 3266
(2020/05/06)
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- A Metal- and Ligand-Free Synthesis of Quinazolin-4(3H)-ones via a Bu4NI/TBHP-Mediated Oxidative Cleavage of the Olefinic C=C Bond
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Abstract: A metal and ligand-free protocol has been developed for the synthesis of quinazolin-4(3H)-ones in moderate to good yields from o-aminobenzamide and alkenes via a Bu4NI/TBHP-mediated oxidative cleavage of the C=C bond in alkenes.
- Gollamudi, P.,Inkollu, B.,Karasala, B. K.,Vidavalur, S.
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p. 1446 - 1454
(2020/10/02)
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- Nanoporous Cu doped ZnS nanoparticles an efficient photo catalyst for the chemoselective synthesis of 2-substituted azoles via C-N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence in visible light
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ZnS and Cu:ZnS nanoparticles were prepared by aqueous chemical method and characterized by several analytical tools. Nanoparticles have an average size of about ~ 18 nm and possess highly open mesopores, moderate surface area, and uniform morphology. UV–vis spectra designate that doping of Cu shifted the optical response of the ZnS nanoparticles in to a visible region. These Cu:ZnS nanoparticles were employed as a photocatalyst for chemoselective synthesis of 2-substituted azoles by the reaction of benzyl bromides and 1,2-Diaminobenzene or 2-Mercaptoaniline in visible light. Analogous experiments confirmed that the reaction were proceeds through one pot C–N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence. The enhanced catalytic activity by doping could be attributed to the presence of trapping level generated by copper doping which augments the relaxation time of electron and holes so that they are easily available for the reaction. The method was also applicable for the synthesis of quinazolin-4(3H)-ones.
- Dandia, Anshu,Bansal, Sarika,Sharma, Ruchi,Kumar Mahawar, Dinesh,Rathore, Kuldeep S.,Lal Meena, Mohan,Parewa, Vijay
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- A novel magnetically separable laccase-mediator catalyst system for the aerobic oxidation of alcohols and 2-substituted-2,3-dihydroquinazolin-4(1H)-ones under mild conditions
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In this study, a magnetically reusable artificial metalloenzyme has been constructed by co-immobilization of palladium nanoparticles as a strong oxidizing catalyst and laccase as an oxygen-activating enzyme into the cavities of magnetic mesocellular foams
- Shokri, Zahra,Azimi, Nahid,Moradi, Sirvan,Rostami, Amin
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- Design and synthesis of a versatile cooperative catalytic aerobic oxidation system with co-immobilization of palladium nanoparticles and laccase into the cavities of MCF
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We have designed a versatile reusable cooperative catalyst oxidation system, consisting of palladium nanoparticles and laccase with unprecedented reactivity. This biohybrid catalyst was synthesized by the stepwise immobilization of laccase as an enzyme and Pd as a nanometallic component into the same cavity of siliceous mesocellular foams (MCF). MCF and nanobiohybrid catalyst were characterized by BET, SAXS, SEM, EDX elemental mapping, ICP-OES, TEM, TGA, FT-IR, and XPS techniques and the stepwise immobilization of laccase enzyme and Pd onto MCF was evaluated through several compelling electrochemical studies. The present catalytic system exhibits high activity toward (i) aerobic oxidation of alcohols to the corresponding carbonyl compounds, (ii) aerobic oxidation of cyclohexanol and cyclohexanone to phenol and (iii) aerobic dehydrogenation of important N-heteocyclic compounds (tetrahydro quinazolines, quinazolonones, pyrazolines and 1,4-diydropyridines) in the presence of catalytic amount of hydroquinone (HQ) as mediator in phosphate buffer (0.1 M, pH 4.5, 4 mL)/THF (4%, 1 mL) as solvent under mild conditions. The immobilization of both oxygen-activating catalyst (laccase) and oxidizing catalyst (Pd) onto the same support makes the present catalyst system superior to other currently available heterogeneous palladium based catalytic aerobic oxidation systems.
- Moradi, Sirvan,Shokri, Zahra,Ghorashi, Nadya,Navaee, Aso,Rostami, Amin
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p. 305 - 319
(2020/01/21)
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- Quinazoline-4(3H)-one derivatives as novel and potent inhibitors of soluble epoxide hydrolase: Design, synthesis and biological evaluation
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Inhibition of soluble epoxide hydrolase (sEH) is considered as a promising target to reduce blood pressure, improve insulin sensitivity, and decrease inflammation. In this study, a series of some novel quinazoline-4(3H)-one derivatives (3a-t) with varying steric and electronic properties was designed, synthesized and evaluated as sEH Inhibitors. Most of the synthesized compounds had similar inhibitory activity to the commercial reference inhibitor, 12-(3-adamantan-1-ylureido)dodecanoic acid, and amongst them, 4-chloro-N-(4-(4-oxo-3,4-dihydroquinazoline-2-yl)phenyl)benzamide (3g) was identified as the most active sEH inhibitor (IC50 = 0.5 nM), about 2-fold more potent compared to the reference inhibitor. The results of molecular modeling followed by biological studies indicate that a quinazolinone ring serves as a suitable scaffold to develop novel small molecule candidates to inhibit sEH and the nature of substituent on the amide moiety has a moderate effect on the activity.
- Hejazi, Leila,Rezaee, Elham,Tabatabai, Sayyed Abbas
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- Method for photocatalytic synthesis of quinazolinone compound in aqueous phase (by machine translation)
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The method comprises the following steps: taking the compound of the formula (I) and the compound of the formula (II) as a solvent, adding a photocatalyst and a phase transfer catalyst to obtain the quinazolinone compound (III) under the condition of alkali and visible light. Compared with the prior art, the method not only can be applied to a large amount of functional groups, has high yield, few byproducts, and is simple and safe to operate, low in cost and environment-friendly. Wherein R is hydrogen or R1 Is H, C1 - C4 alkoxy, halogen or nitro; R2 Is H, substituted or unsubstituted phenyl, 2 - pyridyl or 2 - thienyl; the substituted phenyl is phenyl substituted by amino, nitro, C1 - C4 alkyl or C1 - C4 alkoxy. (by machine translation)
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Paragraph 0030; 0031; 0032; 0033; 0038; 0039
(2020/11/22)
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- Method for synthesizing quinazolinone compound by photo-catalyzing alcohol oxidation in water phase
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The invention discloses a method for synthesizing a quinazolinone compound by photo-catalyzing alcohol oxidation in a water phase, which comprises the following steps: by taking a compound shown as aformula (I) and a compound shown as a formula (II) as raw materials and water as a solvent, adding a visible light catalyst, and reacting under the conditions of alkali and visible light to obtain a quinazolinone compound (III). The method for preparing the quinazolinone compound is environmentally friendly, easy and convenient to operate, safe, cheap and efficient. Compared with the prior art, the method is applicable to a large number of functional groups, high in yield, few in byproducts, simple and safe to operate, low in cost and environment-friendly; wherein R1 is H, C1-C4 alkoxy, halogen or nitro; and R2 is H, substituted or unsubstituted phenyl, 2-pyridyl, 2-thienyl or 5-methylfuryl.
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Paragraph 0028-0033
(2020/10/29)
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- Discovery of Quinazolin-4(3 H)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation
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NLRP3 inflammasome is an important therapeutic target for a number of human diseases. Herein, computationally designed series of quinazolin-4(3H)-ones were synthesized using iodine-catalyzed coupling of arylalkynes (or styrenes) with O-aminobenzamides. The key event in this transformation involves the oxidative cleavage of the C-C triple/double bond and the release of formaldehyde. The reaction relies on the C-N bond formation along with the C-C bond cleavage under metal-free conditions. The nitro-substituted quinazolin-4(3H)-one 2k inhibited NLRP3 inflammasome (IC50 5 μM) via the suppression of IL-1β release from ATP-stimulated J774A.1 cells.
- Abdullaha, Mohd,Mohammed, Shabber,Ali, Mehboob,Kumar, Ajay,Vishwakarma, Ram A.,Bharate, Sandip B.
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p. 5129 - 5140
(2019/04/16)
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- Metal-Ligand Cooperative Approach to Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3 H)-ones under Mild Aerobic Conditions
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A simple metal-ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple and easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) (L1,2), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3H)-ones were synthesized in moderate to good isolated yields via dehydrogenative coupling reactions of various inexpensive and easily available starting materials under aerobic conditions. A few control experiments and deuterium labeling studies were carried out to understand the mechanism of the dehydrogenative coupling reactions, which indicate that both copper and the coordinated azo-aromatic ligand participate in a cooperative manner during the catalytic cycle.
- Das, Siuli,Sinha, Suman,Samanta, Deepannita,Mondal, Rakesh,Chakraborty, Gargi,Branda?, Paula,Paul, Nanda D.
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p. 10160 - 10171
(2019/08/20)
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- Palladium Catalyzed Cross-Dehydrogenative Coupling/Annulation Reaction: A Practical and Efficient Approach to Hydroxyisoindolo[1,2-b]quinazolinone
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The palladium-catalyzed cross-dehydrogenative coupling (CDC) followed by an intramolecular cyclization between arylquinazolinones and aldehydes has been described. This viable transformation provides a variety of novel substituted hydroxyisoindolo[1,2-b]quinazolinone compounds in moderate to good yields. Additionally, the reaction is performed with toluene in place of benzaldehyde by using an excess amount of tert-butyl hydroperoxide (TBHP) as the oxidant in good yield.
- Dabiri, Minoo,Lehi, Noushin Farajinia,Movahed, Siyavash Kazemi,Khavasi, Hamid Reza
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p. 2933 - 2940
(2019/05/15)
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- Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability
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Herein, we report chemoselective trifluoroethylation routes of unmasked 2-arylquinazolin-4(3H)-ones using mesityl(2,2,2-trifluoroethyl)iodonium triflate at room temperature. Homologous C-, O-, and N-functionalized subclasses are accessed in a straightforward manner with a wide substrate scope. These chemoselective branching events are driven by Pd-catalyzed ortho-selective C-H activation at the pendant aryl ring and base-promoted reactivity modulation of the amide group, leveraging the intrinsic directing capability and competing pronucleophilicity of the quinazolin-4(3H)-one framework. Furthermore, outstanding photostability of the quinazolin-4(3H)-one family associated with nonradiative decay is presented.
- Maiti, Saikat,Kim, Jaeshin,Park, Jae-Heon,Nam, Dongsik,Lee, Jae Bin,Kim, Ye-Jin,Kee, Jung-Min,Seo, Jeong Kon,Myung, Kyungjae,Rohde, Jan-Uwe,Choe, Wonyoung,Kwon, Oh-Hoon,Hong, Sung You
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supporting information
p. 6737 - 6751
(2019/06/04)
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- Cink4T, a quinazolinone-based dual inhibitor of Cdk4 and tubulin polymerization, identified via ligand-based virtual screening, for efficient anticancer therapy
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Inhibition of cyclin dependent kinase 4 (Cdk4) prevents cancer cells from entering the early G0/G1 phase of the cell division cycle whereas inhibiting tubulin polymerization blocks cancer cells’ ability to undergo mitosis (M) late in the cell cycle. We had reported earlier that two non-planar and relatively non-toxic fascaplysin derivatives, an indole and a tryptoline, inhibit Cdk4 with IC50 values of 6.2 and 10 μM, respectively. Serendipitously, we had also found that they inhibited tubulin polymerization. The molecules were efficacious in mouse tumor models. We have now identified Cink4T in a 59-compound quinazolinone library, designed on the basis of ligand-based virtual screening, as a compound that inhibits Cdk4 and tubulin. Its IC50 value for Cdk4 inhibition is 0.47 μM and >50 μM for inhibition of Cdk1, Cdk2, Cdk6, Cdk9. Cink4T inhibits tubulin polymerization with an IC50 of 0.6 μM. Molecular modelling studies on Cink4T with Cdk4 and tubulin crystal structures lend support to these observations. Cancer cell cycle analyses confirm that Cink4T blocks cells at both G0/G1 and M phases as it should if it were to inhibit both Cdk4 and tubulin polymerization. Our results show, for the very first time, that virtual screening can be used to design novel inhibitors that can potently block two crucial phases of the cell division cycle.
- Sonawane, Vinay,Mohd Siddique, Mohd Usman,Jadav, Surender Singh,Sinha, Barij Nayan,Jayaprakash, Venkatesan,Chaudhuri, Bhabatosh
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p. 115 - 132
(2019/01/23)
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- Efficient and selective microwave-assisted copper-catalyzed synthesis of quinazolinone derivatives in aqueous
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Microwave-assisted copper-catalyzed cascade reactions between 2-halobenzoic acids and amidines to synthesize quinazolinone derivatives in water are reported. A variety of target products were obtained in good to excellent yields up to 94%. Its application was performed by the synthesis of 4-(1H-benzo[d]imidazol-2-ylthio)-6-methoxypteridine, which displayed significant anti-proliferation effect.
- Ke, Fang,Liu, Caiqin,Zhang, Peng,Xu, Jianhua,Chen, Xiaole
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supporting information
p. 3089 - 3098
(2018/12/04)
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- Copper (II)-supported polyethylenimine-functionalized magnetic graphene oxide as a catalyst for the green synthesis of 2-arylquinazolin-4(3H)-ones
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A novel copper (II) catalyst supported on polyethylenimine-functionalized magnetic graphene oxide (denoted Cu@PEI-MGO) has been developed and applied for the cyclization of benzylacetamide with 2-aminobenzamide to afford 2-arylquinazolin-4(3H)-ones in acetonitrile as an inexpensive, non-toxic and reusable solvent medium. Cu@PEI-MGO was characterized by transmission electron microscopy, scanning electron microscopy, thermo-gravimetric analysis, and Fourier-transform infra-red spectroscopy.
- Sayahi, Mohammad Hosein,Bahadorikhalili, Saeed,Saghanezhad, Seyyed Jafar,Mahdavi, Mohammad
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p. 5241 - 5253
(2018/04/10)
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- Method for synthesizing 2-phenyl quinazolinone compound from diphenyl acetylene compound as raw material
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The invention discloses a method for synthesizing a 2-phenyl quinazolinone compound from a diphenyl acetylene compound as raw material. The method comprises the following step: under coactions of a palladium catalyst, ligand and oxygen, enabling a diphenyl acetylene compound and 2-aminobenzene formamide as raw materials to react, thereby obtaining the 2-phenyl quinazolinone compound, wherein the reaction temperature is 60-110 DEG C; the reaction equation is as shown in the specification, in the formula, R is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, nitryl or methoxyl. The method has the beneficial effects that the raw material, namely the diphenyl acetylene compound, is cheap and easy to obtain, so that the method is relatively economic; the preparation process is simple and convenient to operate, and the obtained product is easy to treat and applicable to large-scale industrial production; no high temperature or high pressure is needed, and reaction conditions are gentle; the reaction time is short, the reaction is efficient, the yield is high, and relatively high reaction efficiency can be achieved after the reaction is amplified.
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Paragraph 0087-0089
(2018/07/06)
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- Synthesis, in silico pharmacokinetic profile and anti-cholinesterase activity of quinazolin-4(3h)-one derivatives
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We have carried out synthesis and biological evaluation of various quinazolin-4(3H)-one derivatives as potent cholinesterase (AChE/BChE) inhibitors. In vitro assay results revealed that all compounds exhibited inhibitory activity against both cholinesterase enzymes (AChE and BChE) and in few cases this activity was comparable to that of standard galantamine drug. Among all, the compounds 3j with 3-methoxy-4- hydroxy groups attached to phenyl ring at C-2 position showed the highest inhibition activity with IC50 values of 4.2±0.13 μM and 12.7±1.44 μM for AChE and BChE, respectively. The compound 3c with chloro group at para position of the phenyl ring was found to be the second most potent cholinesterase inhibitor, displaying an IC50 value of 6.1±1.06 μM (AChE) and 13.8±0.74 μM (BChE). Preliminary in silico pharmacokinetic studies showed that, with the exception of a few compounds, all others have a good pharmacokinetic profile. Analysis of molecular descriptors and drug likeliness properties by using the tool Molinspiration server showed that all synthesized compounds are in good agreement with Lipinski Rules of five. The synthesized compounds can be used as structural foundation for the preparation of new potent cholinesterase inhibitors.
- Sarfraz, Muhammad,Sultana, Nargis,Tariq, Muhammad I.
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p. 1035 - 1041
(2019/04/05)
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- Phosphorous acid functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment for one-pot C-C and C-N bond formation reactions
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The preparation and application of fiber catalysts have attracted much attention. However, research on the effect of the micro-environment of fiber catalysts on the catalytic activities though of special importance is limited. In this work, a novel strategy for the synthesis of phosphoric acid-functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment by hydrophobic groups for one-pot C-C and C-N bond formation reactions is reported. The special hydrophobic surface micro-environment of the fiber catalysts is proven to promote the catalytic activities impressively in cyclocondensation of β-ketoesters with 2-aminobenzamides, the Knoevenagel condensation as well as the multi-component Biginelli reactions in green solvents. Both the surface synergy of the catalytic sites and hydrophobic auxiliary groups (benzyl or n-butyl) in the surface of fiber catalysts and interface acceleration in reaction medium play an important role in the highly efficient promotion of catalytic activity. Thereby a surface synergistic mechanism is proposed to explain the micro-environment effect. In addition, the fiber catalysts could be simply separated from the reaction system using tweezers and directly used in the next cycle without further treatment. Importantly, even after 10 reaction cycles in water or ethanol, there is no significant loss in their catalytic activity. The results indicate that the phosphoric acid functionalized fibers show green and sustainable potential for industrial production.
- Xu, Gang,Wang, Lu,Li, Mengmeng,Tao, Minli,Zhang, Wenqin
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supporting information
p. 5818 - 5830
(2017/12/26)
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- Toluene and derivatives oxidation process for preparing 4 (3 H) - quinazolinone derivatives
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The invention relates to a method for preparing a 4(3H)-quinazolinone derivative through a toluene and derivative oxidation one-pot process. The method comprises the following steps: 1, reacting toluene or a derivative thereof with tert-butyl hydroperoxide at 60-80DEG C under the action of a first catalyst and sodium dihydrogen phosphate for 18-24h to obtain an aldehyde and alcohol mixture; 2, adding a Lewis acid catalyst, 2-aminobenzamide and a solvent into the aldehyde and alcohol mixture obtained in step 1, heating to 100-120DEG C, and reacting for 10-12h; and 3, cooling a solution obtained in step 2 to room temperature, filtering, washing, and drying to obtain the 4(3H)-quinazolinone derivative product. Compared with the prior art, the method provided by the invention has the advantages of concise reaction process, simple post-treatment, environmental protection, easily available raw materials, and high comprehensive yield.
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Paragraph 0066-0068; 0112-0116
(2017/09/26)
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- Design, Synthesis, and Pharmacological Characterization of N-(4-(2 (6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)yl)ethyl)phenyl)quinazolin-4-amine Derivatives: Novel Inhibitors Reversing P-Glycoprotein-Mediated Multidrug Resistance
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P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a principal obstacle for successful cancer chemotherapy. A novel P-gp inhibitor with a quinazoline scaffold, 12k, was considered to be the most promising for in-depth study. 12k possessed high potency (EC50 = 57.9 ± 3.5 nM), low cytotoxicity, and long duration of activity in reversing doxorubicin (DOX) resistance in K562/A02 cells. 12k also boosted the potency of other MDR-related cytotoxic agents with different structures, increased accumulation of DOX, blocked P-gp-mediated Rh123 efflux, and suppressed P-gp ATPase activity in K562/A02 MDR cells. However, 12k did not have any effects on CYP3A4 activity or P-gp expression. In particular, 12k had a good half-life and oral bioavailability and displayed no influence on DOX metabolism to obviate the side effects closely related to increased plasma concentrations of cytotoxic agents in vivo.
- Qiu, Qianqian,Liu, Baomin,Cui, Jian,Li, Zheng,Deng, Xin,Qiang, Hao,Li, Jieming,Liao, Chen,Zhang, Bo,Shi, Wei,Pan, Miaobo,Huang, Wenlong,Qian, Hai
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p. 3289 - 3302
(2017/05/05)
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- Potential anti-proliferative agents from 1,4-benzoxazinone-quinazolin-4(3H)-one templates
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A novel synthetic protocol has been developed for the synthesis of 1,4-benzoxazinone-acetylphenylallyl quinazolin-4(3H)-one hybrids 7a–n by employing Pd-catalyzed C[sbnd]H arylation in presence of 5–10% phosphine ligand in good to excellent yields and evaluated for their anti-proliferative activity against three cancer cell lines such as A549 (lung), HeLa (cervical), MDA-MB-231 (breast). Compounds 7d, 7f, 7l and 7n exhibited promising anti-proliferative activity with GI50 values ranging from 0.37 to 2.73 μM respectively against A549, HeLa, and MDA-MB-231, while compound 7f showed significant activity against MDA-MB-231 with GI50 value 0.58 μM, 7j showed significant activity against A549 with GI50 value 0.32 μM and 7l showed significant activity against HeLa with GI50 value 0.37 μM. This is the first report on the synthesis and in vitro anti-proliferative evaluation of 1,4-benzoxazinone-acetylphenylallyl quinazolin-4(3H)-one hybrids.
- Bollu, Rajitha,Banu, Saleha,Kasaboina, Suresh,Bantu, Rajashaker,Nagarapu, Lingaiah,Polepalli, Sowjanya,Jain, Nishant
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p. 5481 - 5484
(2017/11/03)
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- Efficient construction of N-heterocycles from benzylic ethers/alcohols and o-substituted anilines without using any catalyst and additive
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A novel method for the synthesis of N-heterocycles from benzylic ethers/alcohols with o-substituted aniline without using any catalyst and additive is developed. This protocol involves C-O bond cleavage of benzylic ethers, N-benzylation, and benzylic C-H amidation in one pot, the tandem oxidation-cyclization transformation may open the door for the easy generation of N-heterocycles.
- Chen, Xiuling,Qi, Hongxue,Wu, Shaofeng,Liu, Leng,Wen, Jianhui,Li, Wanxi,Guo, Fang,Bian, Yongjun,Li, Jun
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- One-Pot Cascade Synthesis of Quinazolin-4(3H)-ones via Nickel-Catalyzed Dehydrogenative Coupling of o-Aminobenzamides with Alcohols
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In this paper, we report a general, efficient, and environmentally benign method for the one-pot cascade synthesis of quinazolin-4(3H)-ones via acceptorless dehydrogenative coupling of o-aminobenzamide with alcohols catalyzed by a simple Ni(II) catalyst, [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinazolin-4(3H)-ones were synthesized in high yields starting from readily available benzyl alcohols and o-aminobenzamides. Several controlled reactions along with deuterium labeling studies were carried out to establish the acceptorless dehydrogenative nature of the reactions.
- Parua, Seuli,Das, Siuli,Sikari, Rina,Sinha, Suman,Paul, Nanda D.
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p. 7165 - 7175
(2017/07/26)
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- Electron transfer-induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones
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A series of 2-substituted 2,3-dihydroquinazolin- 4(1H)-ones were oxidized to quinazolin-4(3H)-ones using tetrabutylammonium peroxydisulfate. The rate and the outcome of the reaction are dependent on the type and nature of 2-substitution. An electron transfer mechanism is proposed for this study, which is supported by the retention or elimination of 2-substitution during the oxidation process.
- Memarian, Hamid Reza,Ghahremani, Saeideh
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p. 403 - 408
(2017/06/30)
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- Synthesis and biological investigation of 2,4-substituted quinazolines as highly potent inhibitors of breast cancer resistance protein (ABCG2)
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Expression of ABCG2, a member of the ABC transporter superfamily, has been correlated to the clinical outcome of multiple cancers and is often associated with the occurrence of multidrug resistance (MDR) in chemotherapy. Inhibition of the transport protein by potent and selective inhibitors might be a way to treat cancer more efficiently and improve the therapy of cancer patients. Recently we reported the synthesis of new inhibitors based on a quinazoline scaffold. In the present study more structural variations were explored. Compounds with 3,4-dimethoxy groups and meta or para nitro substituents were found to be highly potent inhibitors of ABCG2. The most potent compound was more than five-fold more potent than Ko143, one of the best inhibitors of ABCG2. To determine the new compounds selectivity toward ABCG2 their inhibitory effects on ABCB1 and ABCC1 were also investigated identifying selective as well as broadspectrum inhibitors. Furthermore, intrinsic cytotoxicity and efficacy regarding the reversal of multidrug resistance toward SN-38 and mitoxantrone were explored. The most potent compounds were able to reverse the resistance toward the cytostatic agents with EC50 values below 20 nM. Additionally, the type of interaction between inhibitors and the ABCG2 substrate Hoechst 33342 was investigated yielding competitive and non-competitive interactions suggesting different modes of binding. Finally the effect of the derivatives on vanadate-sensitive ATPase activity of ABCG2 was determined. According to the different effects on ATPase activity we conclude the existence of different binding sites. This study provides the structural requirements for high potency inhibition and elucidates the interaction with ABCG2 setting the basis for further studies.
- Krapf, Michael K.,Gallus, Jennifer,Wiese, Michael
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p. 587 - 611
(2017/08/26)
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- Quinazoline derivatives as selective CYP1B1 inhibitors
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CYP1B1 is implicated to have a role in the development of breast, ovarian, renal, skin and lung carcinomas. It has been suggested that identification of potent and specific CYP1B1 inhibitors can lead to a novel treatment of cancer. Flavonoids have a compact rigid skeleton which fit precisely within the binding cavity of CYP1B1. Systematic isosteric replacement of flavonoid ‘O’ atom with ‘N’ atom led to the prediction that a ‘quinazoline’ scaffold could be the basis for designing potential CYP1B1 inhibitors. A total of 20 quinazoline analogs were synthesized and screened for CYP1B1 and CYP1A1 inhibition in Sacchrosomes. IC50 determinations of six compounds with capability of inhibiting CYP1B1 identified quinazolines 5c and 5h as the best candidates for CYP1B1 inhibition, with IC50 values in the nM range. Further selectivity studies with homologous CYPs, belonging to the CYP1, CYP2 and CYP3 family of enzymes, showed that the compounds are likely to be free from critical drug-drug interaction liability. Molecular modelling studies were performed to rationalize the observed enzymatic inhibitions. Further biological studies in live yeast and human cells, harboring CYP1A1 and CYP1B1 enzymes, have illustrated the most potent compounds' cellular permeability and capability of potently inhibiting CYP1B1 enzyme expressed within live cells.
- Mohd Siddique, Mohd Usman,McCann, Glen J.P.,Sonawane, Vinay R.,Horley, Neill,Gatchie, Linda,Joshi, Prashant,Bharate, Sandip B.,Jayaprakash, Venkatesan,Sinha, Barij N.,Chaudhuri, Bhabatosh
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p. 320 - 327
(2017/03/10)
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- Pd-Catalyzed regioselective C-H halogenation of quinazolinones and benzoxazinones
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A Pd-catalyzed ortho-selective halogenation of benzoxazinone and quinazolinone scaffolds has been described employing N-halosuccinimide as both a halogen source and an oxidant reagent via C-H bond activation. This transformation shows high chemo- and regioselectivities and demonstrates a broad range of benzoxazinone and quinazolinone substrates with different functional groups and has been scaled up to the gram level.
- Dabiri, Minoo,Farajinia Lehi, Noushin,Kazemi Movahed, Siyavash,Khavasi, Hamid Reza
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supporting information
p. 6264 - 6268
(2017/08/02)
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- Synthesis and structure–activity relationship study of novel quinazolinone-based inhibitors of MurA
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MurA is an intracellular bacterial enzyme that is essential for peptidoglycan biosynthesis, and is therefore an important target for antibacterial drug discovery. We report the synthesis, in silico studies and extensive structure–activity relationships of a series of quinazolinone-based inhibitors of MurA from Escherichia coli. 3-Benzyloxyphenylquinazolinones showed promising inhibitory potencies against MurA, in the low micromolar range, with an IC50 of 8?μM for the most potent derivative (58). Furthermore, furan-substituted quinazolinones (38, 46) showed promising antibacterial activities, with MICs from 1?μg/mL to 8?μg/mL, concomitant with their MurA inhibitory potencies. These data represent an important step towards the development of novel antimicrobial agents to combat increasing bacterial resistance.
- Hrast, Martina,Ro?man, Kaja,Juki?, Marko,Patin, Delphine,Gobec, Stanislav,Sova, Matej
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supporting information
p. 3529 - 3533
(2017/07/07)
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- Quinazolinone derivatives: Synthesis and comparison of inhibitory mechanisms on α-glucosidase
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In this study, eight quinazolinone derivatives were designed and synthesized. Their inhibitory activities on α-glucosidase were assessed in vitro. Two compounds: 2-(4-chlorophenyl)-quinazolin-4(3H)-one (CQ) and 2-(4-bromophenyl)-quinazolin-4(3H)-one (BQ) were found to be potent inhibitors of α-glucosidase with IC50values of 12.5 ± 0.1 μM and 15.6 ± 0.2 μM, respectively. Spectroscopy methods were performed to analyze the inhibitory mechanisms of both compounds on α-glucosidase. The results revealed that they reversibly inhibited α-glucosidase in a non-competitive manner. CQ and BQ could statically quench the fluorescence spectra by formation of an inhibitor-α-glucosidase complex. The interaction between CQ and α-glucosidase depended on hydrogen bonds, electrostatic and hydrophobic force, while the driving force of the binding between BQ and the enzyme was hydrophobic. The docking results showed that BQ was less active than CQ against α-glucosidase because of its weaker interaction with the enzyme. In brief, the quinazolinone derivatives identified in this work were potentially promising candidates for developing as novel anti-diabetic agents.
- Wei, Mankun,Chai, Wei-Ming,Wang, Rui,Yang, Qin,Deng, Zhihong,Peng, Yiyuan
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p. 1303 - 1308
(2017/02/10)
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- Ligand-Free Copper-Manganese Spinel Oxide-Catalyzed Tandem One-Pot C–H Amidation and N-Arylation of Benzylamines: A Facile Access to 2-Arylquinazolin-4(3H)-ones
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An efficient ligand-free copper-manganese (Cu-Mn) spinel oxide-catalyzed direct tandem C?H oxygenation and N-arylation of benzylamines has been developed. The method has been utilized for the synthesis of medicinally important 2-arylquinazolin-4(3H)-ones. Salient features of this method include recyclable catalyst, no ligand, excellent product yields, shorter reaction times and a broad substrate scope. (Figure presented.).
- Sharma, Rohit,Vishwakarma, Ram A.,Bharate, Sandip B.
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supporting information
p. 3027 - 3033
(2016/10/09)
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- One-Pot Copper(I)-Catalyzed Ligand/Base-Free Tandem Cyclooxidative Synthesis of Quinazolinones
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A novel and efficient Cu(I)-catalyzed ligand- and base-free multipathway domino strategy has been developed for the synthesis of 2-substituted quinazolinones. The reaction utilizes 2-bromobenzamide and multiform substrates such as aldehydes, alcohols, and methyl arenes for a one-pot protocol, whereas TMSN3 is used as a nitrogen source. A wide range of substrate scope, functional group tolerance, and operational simplicity are synthetically useful features.
- Upadhyaya, Kapil,Thakur, Ravi Kumar,Shukla, Sanjeev K.,Tripathi, Rama Pati
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p. 5046 - 5055
(2016/07/06)
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- Bimetallic Cu–Mn-Catalyzed Synthesis of 2-Arylquinazolin-4(3H)-ones: Aqueous Ammonia as Source of a Ring Nitrogen Atom
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A new method for the synthesis of 2-arylquinazolin-4(3H)-ones that involves a three-component coupling reaction of 2-bromobenzamide, aryl aldehydes, and aqueous ammonia has been developed. This protocol employs Cu–Mn spinel oxide as a heterogeneous catalyst and does not require the presence of a ligand or external oxidant. Key features of the reaction include a recyclable catalyst, ligand-free conditions, and a wide scope of possible substrates. The mechanism begins with the replacement of the bromine atom with NH2from aqueous ammonia followed by imine formation, intramolecular ring cyclization (C–N bond formation), and aromatization.
- Sharma, Rohit,Vishwakarma, Ram A.,Bharate, Sandip B.
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p. 5227 - 5233
(2016/11/13)
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- Quinazolinones-Phenylquinoxaline hybrids with unsaturation/saturation linkers as novel anti-proliferative agents
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A new series of novel quinazolinones with allylphenyl quinoxaline hybrids 9a-n were efficiently synthesized in good yields by the reaction of 3-allyl-2-methylquinazolin-4(3H)-one (5a-n) with bromophenyl)quinoxaline (8) utilizing Pd catalyzed Heck-cross coupling and evaluated for anti-proliferative activity against four cancer cell lines such as HeLa (cervical), MIAPACA (pancreatic), MDA-MB-231 (breast) and IMR32 (neuroblastoma). Compounds 9a, 9e, 9g and 9h exhibited promising anti-proliferative activity with GI50 values ranging from 0.06 to 0.2 μM against four cell lines, while compounds 9e and 9k showed significant activity against HeLa and MIAPACA cell lines and compounds 9b, 9d, 9h and 9j showed selective potency against IMR32 and MDA-MB-231 cell lines. This is the first report on the synthesis and in vitro anti-proliferative evaluation of E-2-(4-substituted)-3-(3-(4-(quinoxalin-2-yl)phenyl)allyl)quinazolin-4(3H)-ones (9a-n). Docking results indicate a sign of good correlation between experimental activity and calculated binding affinity (dock score), suggesting that these compounds could act as promising DNA intercalates.
- Palem, Jyothsna Devi,Alugubelli, Gopi Reddy,Bantu, Rajashaker,Nagarapu, Lingaiah,Polepalli, Sowjanya,Jain, S. Nishanth,Bathini, Raju,Manga, Vijjulatha
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p. 3014 - 3018
(2016/06/13)
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- Iron nitrate/TEMPO-catalyzed aerobic oxidative synthesis of quinazolinones from alcohols and 2-aminobenzamides with air as the oxidant
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A highly efficient, iron nitrate/TEMPO-catalyzed approach for the synthesis of quinazolinones has been achieved via a one-pot, tandem aerobic oxidative cyclization of primary alcohols with 2-aminobenzamides. This practical reaction tolerates a broad scope of substrates and could afford a variety of desirable products in good to excellent yields with air as the terminal green oxidant. Thus, the present synthetic protocol provides an efficient and concise strategy for the synthesis of quinazolinones.
- Hu, Yongke,Chen, Lei,Li, Bindong
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p. 65196 - 65204
(2016/07/21)
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- Iron-based metal-organic framework, Fe(BTC): An effective dual-functional catalyst for oxidative cyclization of bisnaphthols and tandem synthesis of quinazolin-4(3H)-ones
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An iron-based metal-organic framework [Fe(BTC) (BTC: 1,3,5-benzenetricarboxylate)] has been shown to be an active and heterogeneous catalyst for both oxidative cyclization of methylenebisnaphthols and a modern tandem process (an in situ oxidation-aminal formation-oxidation sequence). Such a potential catalytic utility of Fe(BTC) makes it quite attractive for sustainable industrial chemistry.
- Oveisi, Ali Reza,Khorramabadi-Zad, Ahmad,Daliran, Saba
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p. 1136 - 1142
(2016/01/16)
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- Mechanistic insights into a catalyst-free method to construct quinazolinones through multiple oxidative cyclization
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A novel one-pot benign oxidative cyclization of alcohols with 2-aminobenzamides was successfully developed without catalyst to afford the quinazolinones under O2. This one-pot protocol involved oxidations and cyclizations to construct the skeleton of quinazolinones through possibly three kinds of distinct reaction mechanisms.
- Wang, Zhen-Zhen,Tang, Yu
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p. 1330 - 1336
(2017/02/15)
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- Synthesis of 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones catalyzed by graphene oxide nanosheets in an aqueous medium: "on-water" synthesis accompanied by carbocatalysis and selective C-C bond cleavage
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Graphene oxide (GO) nanosheet catalyzed new and straightforward strategies for the construction of 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones starting from anthranilamide (2-aminobenzamide) and an aldehyde/ketone in aqueous medium at room temperature have been realized. This catalyst is also found to be efficient for the expedient construction of quinazolin-4(3H)-ones starting from anthranilamide and a β-ketoester/1,3-diketone following selective C-C bond cleavage of the β-ketoester/1,3-diketone at an elevated temperature under metal and oxidant free conditions.
- Kausar, Nazia,Roy, Indranil,Chattopadhyay, Dipankar,Das, Asish R.
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p. 22320 - 22330
(2016/03/15)
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