- UV-Light-Induced Dehydrogenative N -Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides
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A simple, mild, green, and efficient method for the synthesis of 2-aminobenzamides is highly desirable. Herein, we report the development of an efficient, one-pot strategy starting from 2-aminobenzaldehydes and amines with acetic acid in ethyl acetate/acetone using irradiation with UV light for the synthesis of 2-aminobenzamides in high yields; 32 examples proceeded successfully by this photo-induced protocol in up to 92% yield. The reaction was also readily achieved on a gram scale. The utility of the 2-aminobenzamide building block in organic synthesis was shown by their use in the preparation of quinazolinone derivatives. The method was applied to amino acid derivatives as the amine component, which smoothly gave N-(2-aminobenzoyl)acetate derivatives at room temperature. Finally, a plausible mechanism is proposed.
- Deng, Wei,Kambe, Nobuaki,Qiu, Renhua,Tang, Niu,Xiang, Jiannan,Yang, Tianbao,Yin, Shuang-Feng,Zeng, Dishu
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supporting information
(2022/03/17)
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- Palladium(0)-catalysed regioselective cyclisations of 2-amino(tosyl) benzamides/sulphonamides: The stereoselective synthesis of 3-ylidene-[1,4]benzodiazepin-5-ones/benzo[f][1,2,5]thiadiazepine-1,1-dioxides
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The Pd(0) catalysed cyclisation reactions betweentert-butyl propargyl carbonates and 2-aminotosyl benzamides or sulphonamides deliver 1,4-benzodiazepin-5-ones or sultam derivatives, key components of many biologically active compounds. But 2-amino benzamides/sulphonamides require propargyl carbonates substituted at acetylenic carbon to undergo the reaction resulting in the stereoselective formation of the said products.
- Mondal, Debasmita,Pal, Gargi,Chowdhury, Chinmay
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supporting information
p. 5462 - 5465
(2021/06/09)
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- One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts
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A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.
- Faggyas, Réka J.,McGrory, Rochelle,Sutherland, Andrew
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supporting information
p. 6127 - 6140
(2021/07/21)
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- Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic
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A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 μM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 μM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated.
- Sherafati, Maedeh,Mirzazadeh, Roghieh,Barzegari, Ebrahim,Mohammadi-Khanaposhtani, Maryam,Azizian, Homa,Sadegh Asgari, Mohammad,Hosseini, Samanesadat,Zabihi, Ebrahim,Mojtabavi, Somayeh,Ali Faramarzi, Mohammad,Mahdavi, Mohammad,Larijani, Bagher,Rastegar, Hossein,Hamedifar, Haleh,Hamed Hajimiri, Mir
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- Efficient synthesis of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives catalyzed by functionalized nanoporous silica
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An efficient and facile method has been developed for the synthesis of various 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives, via a three-component reaction of 2-amino-N-(R)-benzamide derivatives with 2-formylbenzoic acid using sulfonic acid functionalized nanoporous silica as an efficient catalyst in ethanol under reflux. High yield of the desired products, reusability of the catalyst, and effortless workup step without using chromatography are the advantages of this method. Graphic abstract: [Figure not available: see fulltext.]
- Rayatzadeh, Ayeh,Haghipour, Sirous
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p. 103 - 107
(2021/02/05)
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- Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives
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A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.
- Ansari, Samira,Asgari, Mohammad Sadegh,Biglar, Mahmood,Esfahani, Ensieh Nasli,Hamedifar, Haleh,Larijani, Bagher,Mahdavi, Mohammad,Mohammadi-Khanaposhtani, Maryam,Rastegar, Hossein,Tas, Recep,Taslimi, Parham
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- Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one
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Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.
- Liu, Mingzhu,Wei, Yu,Xu, Liang
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supporting information
(2021/10/06)
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- N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones
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N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.
- Ding, Chengcheng,Li, Shichen,Ma, Chen,Ren, Jianing,Wang, Yishou
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p. 16848 - 16857
(2021/12/06)
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- Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions
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A series of 2,3-dihydroquinazoline-4(1H)-one derivatives have been synthesized via one-pot three-component reaction using isatoic anhydrides, amines and aldehydes (or ketones) catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media and operational simplicity are the main highlights. Furthermore, the catalyst can be recovered and reused without evident loss of reactivity. This method provides a green and much improved protocol over the existing methods.
- Yang, Yang,Fu, Renzhong,Liu, Yang,Cai, Jing,Zeng, Xiaojun
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- Regioselective Br?nsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones
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A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N′-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one in good to excellent yield with complete regioselectivity. This protocol tolerates a great variety of functional groups and thus provides a simple and step-efficient method for pyrroloquinazolinone synthesis.
- Banerjee, Prabal,Kaur, Navpreet,Singh, Priyanka
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p. 3393 - 3406
(2020/03/23)
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- Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
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Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
- Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
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supporting information
p. 5435 - 5441
(2020/08/03)
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- Corrigendum to “Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions” [Tetrahedron Lett. 76/27 (2020) 131312] (Tetrahedron (2020) 76(27), (S004040202030466X), (10.1016/j.tet.2020.131312))
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The authors regret the following errors: 1. In page 1, “Additionally, 2,3-dihydroquinazolin-4(1H). -one derivatives can easily…” should be changed to “Additionally, 2,3-dihydroquinazolin-4(1H)-one derivatives can easily…” 2. In page 1, “… numerous protocols have been developed recently for the synthesis using catalysts including acidic reagents [21], [?] [29] lewis acids [30–36],…” should be changed to “… numerous protocols have been developed recently for the synthesis using catalysts including acidic reagents [21–29], lewis acids [30–36],…” 3. In page 1, “… alternative methods to perform organic. synthesis under environmentally benign conditions is in…” should be changed to “… alternative methods to perform organic synthesis under environmentally benign conditions is in…” 4. In page 2, “… condensation, which were. readily available based on our previous publicationsn…” should be changed to “… condensation, which were readily available based on our previous publications…” 5. In page 3, “… while bringing down the catalyst loading to 1 mol % led. to a reduction in the yield to…” should be changed to “… while bringing down the catalyst loading to 1 mol % led to a reduction in the yield to…” 6. In page 3, “… transformation to different substituted isatoic. anhydrides was performed.” should be changed to “… transformation to different substituted isatoic anhydrides was performed.” 7. In page 3, “… easily separated from the. reaction mixture via simple centrifugation…” should be changed to “… easily separated from the reaction mixture via simple centrifugation…” 8. The chemical structure 4a-4g should be changed in Table 2 as below: Table 2. HPAIL catalyzed three-component condensation of isatoic anhydrides, amines and aldehydes (or ketones).a [Figure presented] The authors would like to apologise for any inconvenience caused.
- Cai, Jing,Fu, Renzhong,Liu, Yang,Yang, Yang,Zeng, Xiaojun
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- Novel quinazolin–sulfonamid derivatives: synthesis, characterization, biological evaluation, and molecular docking studies
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In the design of novel drugs, the formation of hybrid molecules via the combination of several pharmacophores can give rise to compounds with interesting biochemical profiles. A series of novel quinazolin–sulfonamid derivatives (9a–m) were synthesized, characterized and evaluated for their in vitro antidiabetic, anticholinergics, and antiepileptic activity. These synthesized novel quinazolin–sulfonamid derivatives (9a–m) were found to be effective inhibitor molecules for the α-glycosidase, human carbonic anhydrase I and II (hCA I and hCA II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzyme, with Ki values in the range of 100.62 ± 13.68–327.94 ± 58.21 nM for α-glycosidase, 1.03 ± 0.11–14.87 ± 2.63 nM for hCA I, 1.83 ± 0.24–15.86 ± 2.57 nM for hCA II, 30.12 ± 3.81–102.16 ± 13.87 nM for BChE, and 26.16 ± 3.63–88.52 ± 20.11 nM for AChE, respectively. In the last step, molecular docking calculations were made to compare biological activities of molecules against enzymes which are achethylcholinesterase, butyrylcholinesterase and α-glycosidase. Communicated by Ramaswamy H. Sarma.
- Sepehri, Nima,Mohammadi-Khanaposhtani, Maryam,Asemanipoor, Nafise,Hosseini, Samanesadat,Biglar, Mahmood,Larijani, Bagher,Mahdavi, Mohammad,Hamedifar, Haleh,Taslimi, Parham,Sadeghian, Nastaran,Norizadehtazehkand, Mostafa,Gulcin, Ilhami
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- 2-(2-chloro-4-methylphenyl) quinazoline-4 (3H)-one compound and medical application thereof
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The invention discloses a 2-(2-chloro-4-methylphenyl) quinazoline-4 (3H)-one compound shown as formula (I) and a preparation method thereof and medical application thereof in sedative hypnotic, anticonvulsant, antidepressant, anxiolytic and other drugs.
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Paragraph 0070; 0074-0076
(2019/08/06)
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- Anthranilic amide and imidazobenzothiadiazole compounds disrupt: Mycobacterium tuberculosis membrane potential
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A family of compounds typified by an anthranilic amide 1 was identified from a whole-cell screening effort targeted at identifying compounds that disrupt pH homeostasis in Mycobacterium tuberculosis. 1 demonstrated bactericidal activity against non-replicating M. tuberculosis in pH 4.5 buffer (MBC4.5 = 6.3 μM). Exploration of the structure-activity relations failed to simplify the scaffold. The antitubercular activity proved dependent on the lipophilicity and planarity of the molecule and directly correlated with mammalian cytotoxicity. Further studies revealed a pH-dependent correlation between the family's disruption of M. tuberculosis membrane potential and antitubercular activity, with active compounds causing a drop in membrane potential at concentrations below their MBC4.5. A second compound family, identified in the same screening effort and typified by imidazo(4,5-e)(2,1,3)benzothiadiazole 2, provided a contrasting profile. As with 1, structure-activity profiling of 2 (MBC4.5 = 25 μM) failed to minimize the initial scaffold, mammalian cytotoxicity was observed for a majority of the active compounds, and many of the active compounds disrupted M. tuberculosis membrane potential. However, unlike the anthranilic amide compounds, the benzothiadiazole compounds disrupted M. tuberculosis membrane potential primarily at concentrations above the MBC4.5 in a pH-independent fashion. These differences suggest an alternative mechanism of action for the benzothiadiazole compounds. As a result, while the cytotoxicity of the anthranilic amides limits their utility to tool compounds, benzothiadiazole 2 presents an attractive target for more focused SAR exploration.
- Smith, Jake,Wescott, Heather,Early, Julie,Mullen, Steven,Guzman, Junitta,Odingo, Joshua,Lamar, Jason,Parish, Tanya
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supporting information
p. 934 - 945
(2019/06/27)
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- A facile synthesis of (Z)-1, 6-disubstituted-7H-benzo[b][1,5]diazonin-7-one derivatives via arylation-allylation-RCM pathway of anthranilamide and isatoic anhydride
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A facile and efficient method has been developed for the synthesis of (Z)-6-allyl-1-phenyl-1,2,5,6-tetrahydro-7H-benzo[b][1,5]diazonin-7-one and (Z)-1,6-diphenyl-1,2,5,6-tetrahydro-7H-benzo[b][1,5]diazonin-7-one from anthranilamide via N-arylation/N-allylation and from isatoic anhydride via ring opening/N-arylation/N-allylation followed by ring closing metathesis using Grubbs-II catalyst as a key step. Grubbs-II catalyst was found to be superior over Grubbs-I catalyst in terms of reaction time and yield of the product, and the routes developed were suitable to synthesize benzo fused nine membered nitrogen heterocycles. The requirement of diallylated substrates with protected amine and amide nitrogen is suitable for RCM has been established for the synthesis of diazoninone derivatives.
- Novanna, Motakatla,Kannadasan, Sathananthan,Shanmugam, Ponnusamy
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supporting information
(2019/09/30)
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- Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
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Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.
- Senadi, Gopal Chandru,Kudale, Vishal Suresh,Wang, Jeh-Jeng
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supporting information
p. 979 - 985
(2019/03/12)
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- Sulfur-Promoted Synthesis of 2-Aroylquinazolin-4(3H)-ones by Oxidative Condensation of Anthranilamide and Acetophenones
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A sulfur-promoted three-component reaction of isatoic anhydride, primary aliphatic or aromatic amines, and acetophenones leading to densely substituted 3-substituted 2-aroylquinazolin-4(3H)-ones is reported. The key step involves a cascade reaction of selective oxidation of the methyl group of the acetophenones, followed by a condensation with anthranilamides. The scope of the reaction is applicable to the synthesis of tryptanthrin and various 3-unsubstituted 2-aroylquinazolin-4(3H)-ones. (Figure presented.).
- Nguyen, Thanh Binh,Hou, Jing-ya,Retailleau, Pascal
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p. 3337 - 3341
(2019/06/13)
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- INHIBITORS OF OPLOPHORUS LUCIFERASE-DERIVED BIOLUMINESCENT COMPLEXES
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Compounds that may selectively inhibit Oplophorus luciferase-derived bioluminescent complexes, e.g., NanoBiT? bioluminescent complex, are disclosed as well as compositions and kits comprising the compounds, and methods of using the compounds. The compounds are of formula (I) wherein R1-R4 and p and q are as defined in the claims.
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Paragraph 00175; 00183-00184; 00186; 00188-00189; 00210
(2019/12/25)
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- An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2-Benzodiazaborininones from Boronic Acids and Anthranilamides
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An efficient Ni/Pd catalyzed chemoselective synthesis of 1,3,2-benzodiazaborininones from boronic acids and anthranilamide has been developed. This protocol allows for the rapid and straightforward access to a wide range of 1,3,2-benzodiazaborininones at roomtemperature with excellent functional group tolerance. (Figure presented.).
- Wang, Hao-Jie,Zhang, Mo,Li, Wen-Jing,Ni, Yu,Lin, Jin,Zhang, Zhan-Hui
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p. 5018 - 5024
(2019/11/03)
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- Thermo-Promoted Reactions of Anthranils with Carboxylic Acids, Amines, Phenols, and Malononitrile under Catalyst-Free Conditions
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A convenient and atom-economical procedure for the thermo-promoted reactions of anthranil with different substrates was developed. The catalyst-free process affords various useful building blocks with good to moderate yields. This chemistry enables several step- and cost-effective approaches for biologically interesting molecules and provides an efficient platform for the investigation of untapped reactions at high temperature.
- Jiang, Jing,Cai, Xin,Hu, Yanwei,Liu, Xuejun,Chen, Xiaodong,Wang, Shun-Yi,Zhang, Yinan,Zhang, Shilei
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p. 2022 - 2031
(2019/05/16)
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- Palladium-catalysed regioselective: N -arylation of anthranilamides: A tandem route for dibenzodiazepinone synthesis
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A palladium-catalyzed domino approach to the synthesis of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepinones from 2-aminobenzamides and 1,2-dihaloarenes has been developed. Our strategy integrating double N-arylations (inter- and intra-molecular) of 2-aminobenzamides with 1,2-dihaloarenes under palladium-catalyzed conditions is clearly distinct from the current literature available for the synthesis of dibenzodiazepinones. Unlike a previous report described for regioselective N-arylation of 2-aminobenzamide at the amine group, our mechanistic studies support the regioselective N-arylation of 2-aminobenzamide occurring first primarily at the amide group. The translational application of our protocol may be demonstrated in the synthesis of a marketed drug, clozapine.
- Laha, Joydev K.,Manral, Neelam,Hunjan, Mandeep Kaur
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p. 7339 - 7343
(2019/05/24)
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- NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides
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An efficient transformation of 2-aminobenzamides to 1,2,3-benzotriazin-4(3H)-ones in the presence of sodium nitrite (NaNO2) and Iodine (I2) is described. The reaction is proposed to proceed via formation of nitrosyl halide that induces nitrosylation of the amino group of 2-aminobenzamide leading to diazotization followed by intramolecular cyclization.
- Barak, Dinesh S.,Mukhopadhyay, Sushobhan,Dahatonde, Dipak J.,Batra, Sanjay
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supporting information
p. 248 - 251
(2019/01/04)
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- Comprehensive Synthesis of Amino Acid-Derived Thiazole Peptidomimetic Analogues to Understand the Enigmatic Drug/Substrate-Binding Site of P-Glycoprotein
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A novel set of 64 analogues based on our lead compound 1 was designed and synthesized with an initial objective of understanding the structural requirements of ligands binding to a highly perplexing substrate-binding site of P-glycoprotein (P-gp) and their effect on modulating the ATPase function of the efflux pump. Compound 1, a stimulator of P-gp ATPase activity, was transformed to ATPase inhibitory compounds 39, 53, and 109. The ATPase inhibition by these compounds was predominantly contributed by the presence of a cyclohexyl group in lieu of the 2-aminobenzophenone moiety of 1. The 4,4-difluorocyclohexyl analogues, 53 and 109, inhibited the photolabeling by [125I]-IAAP, with IC50 values of 0.1 and 0.76 μM, respectively. Selected compounds were shown to reverse paclitaxel resistance in HEK293 cells overexpressing P-gp and were selective toward P-gp over CYP3A4. Induced-fit docking highlighted a plausible binding pattern of inhibitory compounds in the putative-binding pocket of P-gp. The current study underscores the stringent requirement by P-gp to bind to chemically similar molecules.
- Patel, Bhargav A.,Abel, Biebele,Barbuti, Anna Maria,Velagapudi, Uday Kiran,Chen, Zhe-Sheng,Ambudkar, Suresh V.,Talele, Tanaji T.
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p. 834 - 864
(2018/02/17)
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- Ionic liquid supported on magnetic nanoparticles as a novel reusable nanocatalyst for the efficient synthesis of tetracyclic quinazoline compounds
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A magnetic ionic liquid supported on γ-Fe2O3 nanocatalyst was synthesized successfully and characterized by Fourier transform infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, differential scanning calorimetry, X-ray diffraction and scanning electron microscopy. The resulting nano-Fe3O4-supported, ionic liquid was an efficient catalyst for preparation of a series of tetracyclic quinazoline compounds by three components reaction of a mixture of isatoic anhydride and amine with ninhydrin in PEG and the desired products were obtained in good to excellent yields. High efficiency, waste-free, mild reaction conditions, effortless magnetic recovery and reusability up to four continuous cycles are the noteworthy features of the currently employed heterogeneous catalytic system.
- Ghorbani-Choghamarani, Arash,Taherinia, Zahra,Nikoorazm, Mohsen
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p. 6591 - 6604
(2018/07/03)
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- Transition-metal-catalyst-free synthesis of anthranilic acid derivatives by transfer hydrogenative coupling of 2-nitroaryl methanols with alcohols/amines
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By using a transfer hydrogenative coupling strategy, we herein describe a new method for the efficient synthesis of anthranilic acid derivatives, a significantly important class of compounds with extensive applications in organic synthesis and the discovery of bioactive molecules, from 2-nitroaryl methanols and readily available alcohols/amines. The synthesis proceeds with the merits of no need for a transition metal catalyst, operational simplicity, broad substrate scope, good functional tolerance, and high step efficiency, which offers a useful alternative to access anthranilic acid derivatives.
- Zhang, Shudi,Tan, Zhenda,Xiong, Biao,Jiang, Huan Feng,Zhang, Min
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supporting information
p. 531 - 535
(2018/02/07)
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- Exploring (bio)catalytic activities of structurally characterised Cu(ii) and Mn(iii) complexes: Histidine recognition and photocatalytic application of Cu(ii) complex and derived CuO nano-cubes
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Structurally characterised two polymeric complexes of Cu(ii) (3) and Mn(iii) (4) of the ligand L (2-(((2-(phenylamino)ethyl)imino)methyl)phenol) have been explored for catecholase-like activity, fluorescence recognition of histidine and catalytic activity towards coupling of aryl iodides with benzamide, leading to N-arylbenzamides. CuO nano-cubes (NCs) prepared by thermal decomposition of the Cu(ii) complex function as photocatalysts for the degradation of methylene blue. Cube-like morphology of CuO nanocrystal and flake-shaped micrometer order Cu(ii) complex have been established from the field emissive scanning electron microscopy (FESEM) images.
- Kumari, Babli,Kundu, Samapti,Ghosh, Kajari,Banerjee, Mahuya,Pradhan, Swapan Kumar,Islam, Sk. Manirul,Brand?o, Paula,Félix, Vítor,Das, Debasis
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supporting information
p. 14008 - 14016
(2018/10/20)
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- Quinazolin-4(3H)-ones and 5,6-dihydropyrimidin-4(3H)-ones from β-aminoamides and orthoesters
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Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110?C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.
- Gavin, Joshua T.,Annor-Gyamfi, Joel K.,Bunce, Richard A.
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- Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones
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A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.
- Qian, Chun,Liu, Kui,Tao, Shou-Wei,Zhang, Fang-Ling,Zhu, Yong-Ming,Yang, Shi-Lin
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p. 9201 - 9209
(2018/07/13)
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- The second aryl quinazoline compound, its preparation method and medical use thereof and comprising the pharmaceutical composition (by machine translation)
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The invention relates to a I shown by following a kind of quinazoline ketone compound or its pharmaceutically acceptable salt, preparation method thereof, and for preparing tumor, antibacterial, anti-HIV, sedative and hypnotic, anticonvulsant, anti-tuberculosis, anti-Parkinson's syndrome, anti-inflammatory, antipyretic, regulating cardiovascular and regulating cell enzyme active function of the use of such drugs. (by machine translation)
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Paragraph 0064; 0069-0071
(2018/03/23)
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- Method used for preparing amides via catalysis of halogenated aromatic hydrocarbons, amines, and carbon monoxide carbonylation with precious metal
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The invention discloses a method used for preparing amides via catalysis of halogenated aromatic hydrocarbons, amines, and carbon monoxide carbonylation with precious metal. According to the method, palladium acetate and triphenyl phosphine are taken as catalysts; a super strong alkali system is composed of potassium hydroxide and dimethyl sulphoxide, p-benzoquinone is taken as an oxidizing agent, carbon monoxide gas is taken as a carbonyl source, aniline is taken as a solvent, iodobenzene is taken as a substrate, carbonylation of iodobenzene into azophenyl benzamide at room temperature under normal pressure is realized. The method is high in conversion rate; reaction conditions are mild; less environment pollution is caused; the method is beneficial for large scale industrialized production, and promising application prospect and economic benefits are achieved.
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Paragraph 0019; 0059; 0060
(2017/10/07)
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- Preparation method of anthranilate and amide compounds
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The invention discloses a preparation method of anthranilate and amide compounds. The method comprises the following steps: adding an aromatic compound containing adjacent hydroxymethyl and nitro substituent groups, an alcohol or an amine and a solvent into a reactor, adding an alkali as a promoter, introducing an inert gas, carrying out a stirring reaction at 100-110 DEG C for 16-20 h, and carrying out separation and purification to obtain the anthranilate or amide compounds. The preparation method has the advantages of simple synthesis steps, safety in operation, non-toxicity and low price of raw materials, high yield of the final product, and facilitation of industrial production.
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Paragraph 0094; 0095; 0096; 0097; 0098; 0099; 0100-0102
(2017/12/09)
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- Chemoselective: N -arylation of aminobenzamides via copper catalysed Chan-Evans-Lam reactions
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Chemoselective N-arylation of unprotected aminobenzamides was achieved via Cu-catalysed Chan-Evans-Lam cross-coupling with aryl boronic acids for the first time. Simple copper catalysts enable the selective arylation of amino groups in ortho/meta/para-aminobenzamides under open-flask conditions. The reactions were scalable and compatible with a wide range of functional groups.
- Liu, Shuai,Zu, Weisai,Zhang, Jinli,Xu, Liang
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supporting information
p. 9288 - 9292
(2017/11/23)
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- Synthesis and properties of 1,2-dihydro-4(3H)-quinazolinones
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We modified the preparative-scale method for the synthesis of 2-aryl 1,2-dihydro-4(3H)-quinazolinone derivatives obtained in high yields by the reaction of new and commercially available aromatic aldehydes with anthranilic acid amides. A series of quinazolinone derivatives possessing anticancer and antiparasitic activities, as well as capable of preventing the progress of neurodegenerative diseases were characterized. There are grounds for clinical trials of these substances in order to select compounds being promising for clinical application.
- Khachatryan,Belus,Misyurin,Baryshnikova,Kolotaev,Matevosyan
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p. 1044 - 1058
(2017/10/31)
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- Dihydropteridin-one derivatives or pharmaceutically acceptable salts thereof, preparation method thereof and pharmaceutical composition for use in preventing or treating PI3 kinase related diseases
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The present invention relates to dihydropteridin-one derivatives or pharmaceutically acceptable salts thereof, a preparation method thereof, and a pharmaceutical composition comprising the same as an effective component for preventing or treating PI3 kinase-related diseases. According to the present invention, the dihydropteridin-one derivatives have excellent selective inhibitory effects on PI3 kinase, and thus may be beneficially used in preventing or treating PI3 kinase-related diseases such as the following: cancers including blood cancer, ovarian cancer, cervical cancer, breast cancer, large intestine cancer, liver cancer, stomach cancer, pancreatic cancer, colon cancer, periotoneal cancer, skin cancer, bladder cancer, prostate cancer, lung cancer, osteosarcoma, fibrous tumor, and brain tumor; autoimmune diseases including rheumatoid arthritis, systemic lupus erythematosus, multiple sclerosis, type 1 diabetes, hyperthyroidism, myasthenia gravis, Crohnandprime;s disease, ankylosing spondylitis, psoriasis, pernicious anemia, and Sjogrenandprime;s syndrome; and respiratory diseases including chronic obstructive pulmonary disease (COPD), rhinitis, asthma, chronic bronchitis, chronic pulmonary inflammatory diseases, silicosis, pulmonary sarcoidosis, pleuritis, alveolitis, vasculitis, emphysema, pneumonia, and bronchiectasis.COPYRIGHT KIPO 2017
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Paragraph 0256-0259
(2017/09/12)
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- COMPOUNDS WHICH HAVE A PROTECTIVE ACTIVITY WITH RESPECT TO THE ACTION OF TOXINS AND OF VIRUSES WITH AN INTRACELLULAR MODE OF ACTION
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The subject matter of the present invention is novel families of compounds which are aromatic amine, imine, aminoadamantane and benzodiazepine derivatives, medicaments comprising same and the use thereof as inhibitors of the toxic effects of toxins with intracellular activity, such as, for example, ricin, and of viruses that use the internalization pathway for infecting cells.
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Paragraph 0267; 0268; 0269; 0270; 0277
(2016/04/19)
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- SUBSTITUTED AMINOPYRIMIDINE COMPOUNDS AND METHODS OF USE
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The invention relates to the preparation and use of new aminopyrimidine derivatives as drug candidates in free form or in pharmaceutically acceptable salt form and formulations thereof for the modulation of a disorder or disease which is mediated by the activity of the PI3K enzymes. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of disorders or diseases, such as disorders of immunity and inflammation in which PI3K enzymes play a role in leukocyte function, and hyperproliferative disorders associated with PI3K activity, including but not restricted to leukemias and solid tumors, in mammals, especially humans.
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Paragraph 346
(2016/10/04)
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- Substituted aminopyrimidine compound and usage method and application thereof
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The present invention relates to a substituted aminopyrimidine compound and a usage method and application thereof, and in particular to application of the novel aminopyrimidine compound and free-form salts or pharmaceutically acceptable salts and preparations thereof as the medicaments for the treatment of PI3-kinase abnormality-related disorder or diseases. The invention also relates to the pharmaceutical compositions comprising the compound, and application of the pharmaceutical compositions to the treatment of mammals, particularly for the treatment of PI3-kinase abnormality-related human disorder or diseases, such as treatment of PI3-kinase regulated immune and inflammatory diseases, wherein PI3-kinase plays a major role in leukocyte function, and the treatment of of PI3- kinase-related proliferative diseases including but not limited to leukemia and solid tumors.
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Paragraph 0607; 0608; 0609
(2017/07/20)
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- Deep eutectic solvent mediated synthesis of quinazolinones and dihydroquinazolinones: Synthesis of natural products and drugs
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A mild and greener protocol was developed to synthesize substituted quinazolinones and dihydroquinazolinones via deep eutectic solvent (DES) mediated cyclization with a series of aliphatic, aromatic, and heteroaromatic aldehydes in good to excellent yields. This greener strategy was further utilised to synthesize various quinazolinone natural products and drugs.
- Ghosh, Suman Kr,Nagarajan, Rajagopal
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p. 27378 - 27387
(2016/04/04)
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- An efficient metal-free synthesis of 2-amino-substituted-4(3H)-quinazolinones
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2-Amino-substituted-4(3H)-quinazolinones have been synthesized via an efficient metal-free reaction between 2-aminobenzamide derivatives and carbonimidic dibromides. The reaction proceeds in the presence of K2CO3 affording cyclized products in good to excellent yields.
- Mirza, Behrooz
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p. 146 - 147
(2015/12/23)
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- Reaction of benzyl alcohols, isatoic anhydride, and primary amines mediated by I2/K2CO3 in water: A new and green approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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An efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones proceeding via a three-component reaction between benzyl alcohols, isatoic anhydride, and primary amines in the presence of iodine and potassium carbonate is reported. This protocol allows the straightforward preparation of the titled products using readily available benzyl alcohols instead of unstable aldehydes under mild oxidative conditions.
- Azimi, Seyedeh Bahareh,Azizian, Javad
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p. 181 - 184
(2015/12/30)
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- An efficient four-step approach toward fused triazino[1,6-a] quinazolines
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Herein, we describe a simple, four-step process for the preparation of 1,2,3-triazino[1,6-a]quinazolin-13-ones. This method involves ring-opening, quinazoline-forming condensation, reduction, diazotization accompanied by rapid intramolecular cyclization in the last step afforded the desired products with structurally complex heterocyclic core in excellent to high yields.
- Sayahi, Mohammad Hosein,Baghersaei, Shirin,Goli, Fereshteh,Moghimi, Setareh,Mahdavi, Mohammad,Firoozpour, Loghman,Shafiee, Abbas,Foroumadi, Alireza
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p. 189 - 192
(2016/05/09)
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- CuBr/Et3N-Promoted Reactions of 2-Aminobenzamides and Isothiocyanates: Efficient Synthesis of Novel Quinazolin-4(3H)-ones
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A series of novel quinazolin-4(3H)-one derivatives were efficiently synthesized starting from isatoic anhydride. First, reaction of isatoic anhydride and amines in H2O at room temperature afforded 2-aminobenzamides. Then, CuBr/Et3N promoted reaction of 2-aminobenzamides and different aryl isothiocyanates in DMF at 80° afforded the title compounds in good yield.
- Mahdavi, Mohammad,Asadi, Mehdi,Khoshbakht, Mahsa,Saeedi, Mina,Bayat, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
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p. 378 - 383
(2016/06/01)
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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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- OXAZINE DERIVATIVE AND PHARMACEUTICAL USE THEREOF
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PROBLEM TO BE SOLVED: To provide a compound that specifically inhibits the signal transmission of an IL-23 receptor uncompetitively with IL-23 without inhibiting phosphoenzyme activity of janus kinases. SOLUTION: The present invention provides an oxazine derivative represented by the following formula or a pharmacologically acceptable salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0094; 0095; 0100
(2016/10/07)
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- Synthesis of N -Heteropolycyclic Compounds Including Quinazolinone Skeleton Using Friedel-Crafts Alkylation
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A simple method to synthesize N-heteropolycyclic quinazolinones was developed including Knoevenagel condensation of quinazolines and aldehydes and Friedel-Craft alkylation as key steps. Knoevenagel reaction of 2-methyl-3-phenylquinazolin-4(3H)-one proceeded smoothly under a basic condition and subsequent Friedel-Craft alkylation with Bronsted acid gave the N-heteropolycyclic quinazolinones in good yields. Furthermore, these new polycyclic compounds were converted into organic molecules having a long π-conjugation system by treatment of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to utilize them as organic dyes. GRAPHICAL ABSTRACT.
- Oh, Bu Keun,Ko, Eun Bi,Han, Jin Wook,Oh, Chang Ho
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supporting information
p. 768 - 776
(2015/10/29)
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- Scaffold identification of a new class of potent and selective BCRP inhibitors
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We recently reported the synthesis and quantitative structure-activity relationships of a new breast cancer resistance protein (BCRP) inhibitor class. In the study presented herein, we investigated the possibility to better define the scaffold of this compound class by removing or modifying the aromatic ring A with various substituents selected on the basis of their electronic and lipophilic properties. The results show that this aromatic ring is important, but not essential, for activity. Many of the selected substituents led to compounds with low activity, but in some cases activity was retained. Among these, a phenolic hydroxy group proved to impart as much potency to the molecule as a hydroxyethyl side chain, initially considered necessary for activity. This derivative is one of the most active compounds in this class, maintaining an inhibitory activity similar to that of the reference compound; it is also selective for BCRP.
- Marighetti, Federico,Steggemann, Kerstin,Karbaum, Maria,Wiese, Michael
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p. 742 - 751
(2015/04/14)
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- Novel β-carboline-quinazolinone hybrid as an inhibitor of Leishmania donovani trypanothione reductase: Synthesis, molecular docking and bioevaluation
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Trypanothione reductase (TR) is a vital enzyme in the trypanothione based redox metabolism of trypanosomatid parasites. It is one of the few chemically validated targets for Leishmania. Herein, we report the synthesis of novel β-carboline-quinazolinone hybrids that are able to inhibit Leishmania donovani TR (LdTR) and subsequently inhibit cell growth. A molecular modeling approach based on docking studies and subsequent binding free energy estimation was performed in the active site of LdTR to understand their possible binding sites. With the enzymatic assay on LdTR with compounds, we were able to identify six hit compounds (8j-8o) that were all found to be the competitive inhibitors of TR with Ki in the range of 0.8-9.2 μM. The whole-cell screening assay highlighted the analogues 8k, 8l and 8n as the most active compounds with IC50 of 4.4, 6.0 and 4.3 μM, respectively, along with an adequate selectivity index (SI) of >91, 36 and 24, respectively. This journal is
- Chauhan, Shikha S.,Pandey, Shashi,Shivahare, Rahul,Ramalingam, Karthik,Krishna, Shagun,Vishwakarma, Preeti,Siddiqi,Gupta, Suman,Goyal, Neena,Chauhan, Prem M. S.
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supporting information
p. 351 - 356
(2015/03/18)
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- I2-catalyzed aerobic oxidative C(sp3)-H amination/C-N cleavage of tertiary amine: Synthesis of quinazolines and quinazolinones
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An iodine-catalyzed oxidative C(sp3)-H amination/C-N cleavage of tertiary amines couducted under an oxygen atmosphere has been developed and affords a route to quinazolines and quinazolinones in good to excellent yields via a domino ring annulation. The method is metal-free, peroxide-free, and operationally simple to implement with a wide scope of substrates and represents a new avenue for multiple C-N bond formations.
- Yan, Yizhe,Xu, Ying,Niu, Bin,Xie, Huifang,Liu, Yanqi
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p. 5581 - 5587
(2015/06/16)
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- Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones
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A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.
- Bao, Yajie,Yan, Yizhe,Xu, Kun,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
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p. 4736 - 4742
(2015/05/13)
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