- (E)-2-(hydroxystyryl)-3-phenylquinazolin-4(3H)-ones: Synthesis, photochemical and luminescent properties
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The new (E)-2-(hydroxyarilethenyl)-3-phenylquinazolin-4(3H)-ones with various substituents in phenyl fragment were synthesized. The effect of electron donor and acceptor substituents (±M) in quinazolinones on luminescence intensity and dual emission in 55
- Kim, Grigory A.,Ovchinnikova, Irina G.,Nosova, Emiliya V.,Rusinov, Gennady L.,Charushina, Valery N.
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- Styryl quinazolinones as potential inducers of myeloid differentiation via upregulation of C/EBPα
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The CCAAT enhancer-binding protein α (C/EBPα) plays an important role in myeloid cell differentiation and in the enhancement of C/EBPα expression/activity, which can lead to granulocytic differentiation in acute myeloid leukemia (AML) cells. We found that styryl quinazolinones induce upregulation of C/EBPα expression, and thereby induce myeloid differentiation in human myeloid leukemia cell lines. We screened a series of active styryl quinazolinones and evaluated the structure–activity relationship (SAR) of these small molecules in inducing C/EBPα expression—thereby prompting the leukemic cells to differentiate. We observed that compound 78 causes differentiation at 3 μM concentration, while 1 induces differentiation at 10 μM concentration. We also observed an increase in the expression of neutrophil differentiation marker CD11b upon treatment with 78. Both the C/EBPα and C/EBPε levels were found to be upregulated by treatment with 78. These SAR findings are inspiration to develop further modified styryl quinazolinones, in the path of this novel differentiation therapy, which can contribute to the care of patients with AML.
- Sridhar, Radhakrishnan,Takei, Hisashi,Syed, Riyaz,Kobayashi, Ikei S.,Hui, Liu Bee,Kamal, Ahmed,Tenen, Daniel G.,Kobayashi, Susumu S.
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- Development of novel Schiff base fluorophores for selective detection of Cu2+ ions in seawater using test strips
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A novel Schiff bases of 2-((2-aminophenylimino)methyl)-3-phenyl-4(3H)-quinazolinone (3a), 2-((2-aminophenylimino)methyl)-3-(4-tolyl)-4(3H)-quinazolinone (3b), and 2-((2-aminophenylimino)methyl)-3-(4-anisyl)-4(3H)-quinazolinone (3c) were synthesized and ch
- El-Sakka, Sahar S.,El-Shalakany, E.,Kamel, Rasha M.,Soliman, M. H. A.
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- A novel superparamagnetic powerful guanidine-functionalized γ-Fe2O3based sulfonic acid recyclable and efficient heterogeneous catalyst for microwave-assisted rapid synthesis of quinazolin-4(3H)-one derivatives in Green media
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The novel organic-inorganic nanohybrid superparamagnetic (γ-Fe2O3@CPTMS-guanidine@SO3H) nanocatalyst modified with sulfonic acid represents an efficient and green catalyst for the one-pot synthesis of quinazolin-4(3H)-one derivativesviathree-component condensation reaction between anthranilic acid, acetic anhydride and different amines under microwave irradiation and solvent-free conditions (4a-q). XRD, FT-IR, FE-SEM, TGA, VSM and EDX were used to characterize this new magnetic organocatalyst. Outstanding performance, short response time (15-30 min), simple operation, easy work-up procedure, and avoidance of toxic catalysts can be regarded as its significant advantages. Moreover, it can be easily separated from the reaction solution through magnetic decantation using an external magnet, and recycled at least six times without notable reduction in its activity.
- Foroughifar, Naser,Khajeh-Amiri, Alireza,Norouzi, Fateme Haji,Pasdar, Hoda
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p. 29948 - 29959
(2021/10/20)
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- Metal-free C-H methylation and acetylation of heteroarenes with PEG-400
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The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.
- Kudale, Vishal Suresh,Wang, Jeh-Jeng
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p. 3506 - 3511
(2020/06/25)
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- Screening of natural deep eutectic solvents for green synthesis of 2-methyl-3-substituted quinazolinones and microwave-assisted synthesis of 3-aryl quinazolinones in ethanol
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In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1: 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.
- Komar, Mario,Konjarevi?, Anastazija,Molnar, Maja
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- Preparation of 4(3H)-quinazolinones from aryldiazonium salt, nitriles and 2-aminobenzoate via a cascade annulation
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One-pot synthesis of 3-aryl-4(3H)-quinazolinones has been realized through a cascade annulation. Reaction of aryldiazonium salt with a nitrile provides in situ generation of a reactive nitrilium ion, which is attacked by the amino group of 2-aminobenzoate followed by cyclization to deliver the desired product. This strategy offers a convenient and easy access to a wide range of functionalized quinazolinone.
- Ramanathan, Mani,Hsu, Ming-Tsung,Liu, Shiuh-Tzung
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p. 791 - 796
(2019/01/08)
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- Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues
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A general metal-free oxidative cyclization process has been developed for the synthesis of quinazolinones, benzothiadiazines and quinazolines. By this protocol, a range of substituted 2-aminobenzamides, 2-aminobenzenesulfonamide and 2-(aminomethyl)anilines react with various alcohols, leading to the desired annulated products smoothly. This protocol features many advantages as broad substrate scope, mild reaction conditions, low environmental pollution, high atom-economy and good to excellent yields.
- Sun, Jinwei,Tao, Tao,Xu, Dan,Cao, Hui,Kong, Qinggang,Wang, Xinyu,Liu, Yun,Zhao, Jianglin,Wang, Yi,Pan, Yi
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p. 2099 - 2102
(2018/05/04)
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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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- Synthesis, photochemical and luminescent properties of ortho-hydroxystyrylquinazolinone-linked benzocrown ethers
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Photoinduced transformations of (E)-2-(2-hydroxystyryl)quinazolinone-linked benzo[15(18)]crown-5(6) ethers in solutions have been studied by using UV–vis absorption and NMR spectroscopy. These crown ethers were found to have dual emission at 520 and 650 nm, associated with proton-transfer tautomer emission (ESIPT-luminescence) as a rare case of excited-state proton-transfer reaction in the non-pseudocyclic chromophoric systems. It was established also, that the organic bases affect the luminescence intensity of solutions of these compounds in the 550–650-nm wavelength range. An X-ray crystallography analysis of molecular structures of crown ethers and their complexes in crystals has been carried out. The fact of reversible photo/thermal E-Z isomerization in DMF and Et3N for these macroheterocyclic compounds has been confirmed. An opportunity to control the photochemical isomerization rate of quinazolinone 2-(hydroxyphenyl)ethenyl derivatives by changing pH of the medium has been demonstrated.
- Ovchinnikova, Irina G.,Kim, Grigory A.,Matochkina, Eugene G.,Kodess, Mikhail I.,Slepukhin, Pavel A.,Kovalev, Igor S.,Nosova, Emilia V.,Rusinov, Gennady L.,Charushin, Valery N.
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- Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation
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A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted both as a solid CO source and a reductant. Notably, methaqualone as a sedative and hypnotic medication can be prepared easily in 68% yield (4b) under our conditions as well.
- Peng, Jin-Bao,Geng, Hui-Qing,Wang, Wei,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
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- Expeditious synthesis and spectroscopic characterization of 2-methyl-3-substituted-quinazolin-4(3H)-one derivatives
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Quinazoline and quinazolinone derivatives are well-known bioactive heterocycles owing to their therapeutic diversity and extensive medicinal application in drug design and pharmaceutics. A series of 2-methyl-3-substituted quinazolin-4(3H)-one derivatives 8a-q was herein synthesized from synthetic conversion of anthranilic acid to 2-methyl-4H-3,1-benzoxazi-4-one, 7 which was subsequently transformed to the targeted 2,3-disubstituted quinazolin-4(3H)-one derivatives 8a-q by reacting with some notable amino-containing moieties via an ameliorable pathway. The catalyst-free synthesis was successful achieved by careful reaction optimization study using solvent choice and reaction temperature variability as key parameters. The chemical structures of the synthesized compounds were confirmed by IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as analytical data.
- Ajani, Olayinka O.,Audu, Oluwatosin Y.,Germann, Markus W.,Bello, Babatunde L.
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p. 562 - 574
(2017/05/26)
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- A facile synthesis of quinazolinone derivatives through Vilsmeier intermediate
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The reaction of ethyl 2-aminobenzoate with different substituted amide compounds led to cyclization through Vilsmeier intermediate in dry dichloromethane and ambient temperature, affording the 4(3H)-quinazolinone derivatives with higher yields. The struct
- Mohammed, Shireen,Khalid, Maher
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- A simple one pot synthesis of novel tricyclic quinazolinones
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Synthesis of a series of tricyclic quinazolinones have been accomplished starting from anthranilamide and 1,3-cyclic dione promoted by TsOH·H2O The protocol presented herein based on retro-Dieckmann type reaction, leading to incorporation of dione as an acyclic unit into the product. Simple reaction conditions, broad scope, excellent yields are the advantages of this protocol. Further, this methodology is extended to the synthesis of pyridopyrimidinones and benzimidazopyridines.
- Bingi, Chiranjeevi,Kola, Kaushik Yadav,Kale, Ashok,Nanubolu, Jagadeesh Babu,Atmakur, Krishnaiah
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supporting information
p. 1071 - 1074
(2017/03/31)
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- A quinazoline compound and its synthesis method
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The invention discloses a synthetic method of a quinazolinone compound. The method can be used for preparing the quinazolinone compound by carrying out reaction at a proper temperature and time by taking a 2-aminobenzamide derivative and a 1, 3-diketone compound as raw materials, taking chiral Bronsted acid or Lewis acid as a catalyst and water and biodegradable ethyl lactate and polyethylene glycol as a mixed solvent. The synthetic method of the quinazolinone compound provided by the invention is mild in reaction condition, low in cost, environment-friendly, high in yield and suitable for industrial production.
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Paragraph 0068-0079
(2017/11/16)
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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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- Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives
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We developed a copper-catalyzed tandem reaction of 2-aminobenzamides with tertiary amines for the formation of quinazolinone derivatives. The strategy includes two steps (cyclization and coupling) performed in one pot. A number of substrates reacted well under standard conditions to give the corresponding quinazolinone derivatives in moderate to good yields.
- Xu, Wei,Zhu, Xiao-Rui,Qian, Peng-Cheng,Zhang, Xing-Guo,Deng, Chen-Liang
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p. 2851 - 2857
(2016/12/16)
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- Compounds for modulating TRPV3 function
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The present application relates to compounds and methods for treating pain and other conditions related to TRPV3.
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Page/Page column 147-148
(2016/11/24)
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- Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization
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In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4 gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmet
- Hirai, Motohiro,Terada, Shumpei,Yoshida, Hiroaki,Ebine, Kenki,Hirata, Tomoaki,Kitagawa, Osamu
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p. 5700 - 5703
(2016/11/17)
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- FeCl3-catalyzed tandem condensation/intramolecular nucleophilic addition/C-C bond cleavage: A concise synthesis of 2-substitued quinazolinones from 2-aminobenzamides and 1,3-diketones in aqueous media
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A concise approach for the synthesis of 2-substituted quinazolinones using an iron-catalyzed tandem reaction of 2-aminobenzamides with acyclic or cyclic 1,3-diketones via condensation, intramolecular nucleophilic addition, C-C bond cleavage in an aqueous solution of poly(ethylene glycol) under oxidant-free conditions has been developed.
- Shen, Guanshuo,Zhou, Haifeng,Sui, Yuebo,Liu, Qixing,Zou, Kun
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supporting information
p. 587 - 590
(2016/01/20)
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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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p. 768 - 776
(2015/10/29)
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- Inhibitors of filovirus entry into host cells
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Organic compounds showing the ability to inhibit viral glycoprotein (GP)-mediated entry of a filovirus into a host cell are disclosed. The disclosed filovirus entry inhibitor compounds are useful for treating, preventing, or reducing the spread of infecti
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Page/Page column 24; 57; 58
(2015/09/22)
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- Br?nsted acid-catalyzed selective C-C bond cleavage of 1,3-diketones: A facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate
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A facile and green approach was developed for the synthesis of 4(3H)-quinazolinones by using camphorsulfonic acid as a catalyst in an aqueous solution of biodegradable ethyl lactate. Various 2-aryl-, 2-alkyl-, and 2-(4-oxoalkyl)quinazolinones were obtained by cyclization of 2-aminobenzamides with a wide range of acyclic or cyclic 1,3-diketones via C-C bond cleavage in satisfactory to excellent yields.
- Shen, Guanshuo,Zhou, Haifeng,Du, Peng,Liu, Sensheng,Zou, Kun,Uozumi, Yasuhiro
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p. 85646 - 85651
(2015/11/03)
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- Reversible P(III)/P(V) redox: Catalytic aza-Wittig reaction for the synthesis of 4(3H)-quinazolinones and the natural product vasicinone
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The catalytic aza-Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by-product triphenylphosphine oxide (Ph 3PO) was reduced in situ to triphenylphosphine (Ph3P) with good chemselectivity so that the aza-Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3H)-quinazolinones and the natural product (S)-vasicinone in high yields, by using a catalytic amount of triphenylphosphine (5%) and the tetramethyldisiloxane/titanium tetraisopropoxide [TMDS/Ti(O-i-Pr)4] reductant system (81-95% yields and >99% ee).
- Wang, Long,Wang, Ying,Chen, Min,Ding, Ming-Wu
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p. 1098 - 1104
(2014/04/03)
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- Synthesis, photochemical and luminescent properties of (E)-2-(2-hydroxyarylethylene)-3-phenylquinazolin-4(3H)-ones
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Photoinduced transformations of 2-styrylquinazolinones in solutions were studied using absorption and NMR spectroscopy methods. A possibility of control of the photochemical isomerization rate of quinazolinone 2-(hydroxyaryl)ethenyl derivatives by changin
- Ovchinnikova,Kim,Matochkina,Kodess,Barykin,E?tsov,Nosova,Rusinov,Charushin
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p. 2467 - 2477
(2015/08/03)
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- Pentafluorophenylammonium triflate: An efficient, practical and environmental friendly catalyst for synthesis of quinazolin-4(3H)-ones
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An efficient, solvent-free, clean and facile synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from cyclocondensation of 2-aminobenzamides with orthoesters catalyzed by pentafluorophenylammonium triflate under microwave irradiation conditions is descri
- Montazeri, Naser,Pourshamsian, Khalil,Rahgol, Mehdi,Bayazi, Masoud
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experimental part
p. 5361 - 5364
(2012/10/18)
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- Synthesis of 2,3-disubstituted-4(3H)-quinazolinones using hy-zeolite as reusable catalyst under microwave irradiation
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A new heterogeneous catalytic method to synthesize to various 4(3H)-quinazolinone derevatives, using an inexpensive and eco-friendly attractive solid catalyst, zeolite, under solvent-free and microwave irradiation conditions is described. The catalyst activity results suggest that the methodology adopted offers several advantages such as mild reaction conditions, low loading of catalyst, good yields, short reaction time and operational simplicity.
- Montazeri, Naser,Pourshamsian, Khalil,Fomani, Arsalan,Kalantarian, Seyd Jafar
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experimental part
p. 2805 - 2807
(2012/08/28)
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- Synthesis of 3-substituted and 2,3-disubstituted quinazolinones via Cu-catalyzed aryl amidation
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CuI/4-hydroxy-l-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide takes place at 80 °C, affording 3-substituted quinazolinones directly. Under these conditions other amides that were tested only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via HMDS/ZnCl2 mediated condensative cyclization.
- Xu, Lanting,Jiang, Yongwen,Ma, Dawei
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supporting information; experimental part
p. 1150 - 1153
(2012/03/27)
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- Functionalized carbodiimide mediated synthesis of 2,3-disubstituted quinazolin-4(3 H)-ones via the tandem strategy of C-nucleophilic addition and intramolecular NH-substitution cyclization
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A facile synthesis of quinazolin-4(3H)-ones possessing carbon substituents at positions 2 and 3 has been developed. Key to the synthesis is a tandem strategy involving introduction of a 2-substituent and construction of the quinazolinone framework via C-nucleophilic addition to the carbodiimide cumulenic carbon followed by intramolecular nucleophilic substitution by the newly formed NH moiety at the proximal ester group.
- Nakano, Hayato,Kutsumura, Noriki,Saito, Takao
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supporting information
p. 3179 - 3184
(2012/11/14)
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- An efficient one-pot access to quinazolinone derivatives using TiO 2 nanoparticles as catalyst: Synthesis and vasorelaxant activity evaluation
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A variety of quinazolinone derivatives were successfully synthesized, via a three-component condensation reaction between anthranilic acid, acetic anhydride, and amines. This process was accomplished in the presence of catalytic amount of titanium dioxide
- Khalafi-Nezhad, Ali,Haghighi, Saghar Mowlazadeh,Purkhosrow, Azar,Panahi, Farhad
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experimental part
p. 920 - 924
(2012/06/15)
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- Synthesis and photophysical properties of 2-Styrylquinazolin-4-ones
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Trans-2-Styryl-substituted 3H-, 3-phenyl-, and 3-naphthylquinazolin-4-ones and their 6,7-difl uoro derivatives were synthesized by condensation of appropriate 2-methylquinazolin-4-ones with aromatic aldehydes or by the transformation of the heterocycle of 2-methyl-3,1-benzoxazin-4-one under the action of benzylidenephenylamines. Pleiades Publishing, Ltd., 2011.
- Trashakhova,Nosova,Valova,Slepukhin,Lipunova,Charushin
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scheme or table
p. 753 - 761
(2011/08/22)
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- Synthesis of 3h-quinazolin-4-ones and 4h-3,1-benzoxazin-4-ones via benzylic oxidation and oxidative dehydrogenation using potassium iodide-tert-butyl hydroperoxide
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A simple and elegant method for benzylic activation was demonstrated employing the potassium iodide/tert-butyl hydrogen peroxide catalytic system. This methodology was further extended for the synthesis of biologically important heterocycles namely, 3H-quinazolin-4-ones and 4H-3,1-benzoxazin-4-ones including mecloqualone and etaqualone which are important quinazolinone-based drugs used for the treatment of insomnia in good yields.
- Kumar, R. Arun,Maheswari, C. Uma,Ghantasala, Satheesh,Jyothi,Reddy, K. Rajender
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p. 401 - 410
(2011/04/18)
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- Ultrasound promoted and ionic liquid catalyzed cyclocondensation reaction for the synthesis of 4(3H)-quinazolinones
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4(3H)-Quinazolinones were synthesized in high yields by one-pot three-component condensation of anthranilic acid, carboxylic acid and aniline in the presence of ionic liquid such as 1-n-butyl-3-methylimidazolium tetrafluoroborate (BMImBF4) as c
- Pawar, Omprakash B.,Chavan, Fulchand R.,Sakate, Sachin S.,Shinde, Narayan D.
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experimental part
p. 69 - 71
(2010/09/05)
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- Compounds for modulating TRPV3 function
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The present application relates to compounds and methods for treating pain and other conditions related to TRPV3.
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Page/Page column 47
(2010/11/28)
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- Synthesis and structure-activity relationships of vasicine analogues as bronchodilatory agents
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The series of vasicine (1) analogues, an alkaloid from Adhatoda vasica Nees., were synthesized with changes in A, B or C rings. Compounds 3-19 were evaluated for in vitro bronchodilatory activity using isolated guinea pig tracheal chain. Compounds 3-8 were also synthesized in good yields using microwave-mediated synthesis under solvent free conditions. Compounds 5 and 8 with seven-member C ring were more active than etofylline and caused 100% relaxation of both the histamine and acetylcholine pre-contracted guinea pig tracheal chain. The structure-activity relationship studies showed that the quinazoline and oxo functionalities were essential for activity. The compounds without C ring and instead having aliphatic and phenyl substitutions in B ring showed relaxation against histamine pre-contracted tracheal chain only, 2-methyl substituted analogues, 12 and 13, being most active with 100% relaxation effect. Birkhaeuser Boston 2006.
- Mahindroo, Neeraj,Ahmed, Zabeer,Bhagat, Asha,Bedi, Kasturi Lal,Khajuria, Ravi Kant,Kapoor, Vijay Kumar,Dhar, Kanaya Lal
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p. 347 - 368
(2007/10/03)
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- Montmorillonite K-10 catalysed solvent-free synthesis of 2,3-disubstituted-4(3H)quinazolinones under microwave irradiation
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An efficient and rapid synthesis of 2,3-disubstituted-4(3H)quinazolinones by condensation of 2-aminobenzamide (substituted anthraniamides) with orthoesters in the presence of K-10 clay under solvent free conditions using microwave irradiation or classical heating is described.
- Dabiri,Salehi,Mohammadi, Ali A.,Baghbanzadeh,Kozehgiry, Gh.
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p. 570 - 572
(2007/10/03)
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- A convenient synthesis of substituted quinazolin-4(3H)-ones under microwave and solvent-free conditions
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A clean and facile synthesis of the title compounds is achieved from cyclocondensation of 2-aminobenzamides with orthoesters catalyzed by SiO 2/H2SO4 in dry and microwave conditions.
- Montazeri, Nasser,Rad-Moghadam, Kurosh
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p. 2533 - 2536
(2007/10/03)
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- A novel route to the niementowski reaction
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The Niementowski reaction has been extended to synthesize 3-substituted/2,3-disubstituted-4(3H)quinazolinones instead of the 2-substituted derivatives. The methodology is environmentally benign and completely eliminates the need of solvent from the reaction. Neat reactants were cyclocondensed under microwaves to afford, in good yield, the desired product in less irradiation time as compared to the classical technique. The reaction time was reduced from hours to minutes along with yield enhancement. The rate enhancement and high yield are attributed to the coupling of solvent-free conditions with microwaves.
- Kidwai, Mazaahir,Rastogi, Shweta,Mohan, Richa,Ruby
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p. 365 - 369
(2007/10/03)
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- Atropisomeric quinazolin-4-one derivatives are potent noncompetitive α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists
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Piriqualone (1) was found to be an antagonist of AMPA receptors. Structure-activity optimization was conducted on each of the three rings in 1 to afford a series of potent and selective antagonists. The sterically crowded environment surrounding the N-3 aryl group provided sufficient thermal stability for atropisomers to be isolated. Separation of these atropisomers resulted in the identification of (+)-38 (CP-465,022), a compound that binds to the AMPA receptor with high affinity (IC50 = 36 nM) and displays potent anticonvulsant activity.
- Welch,Ewing,Huang,Menniti,Pagnozzi,Kelly,Seymour,Guanowsky,Guhan,Guinn,Critchett,Lazzaro,Ganong,DeVries,Staigers,Chenard
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p. 177 - 181
(2007/10/03)
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- One-pot Synthesis of Substituted Quinazolin-4(3H)-ones under Microwave Irradiation
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Synthesis of the title compounds by cyclocondensation of anthranilic acid, formic acid (or orthoesters) and an amine in one pot under microwave irradiation takes place in a few minutes.
- Rad-Moghadam, Kurosh,Khajavi, Mohammad S.
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p. 702 - 703
(2007/10/03)
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- 4(3H)-Quinazolinones from the reaction of N-arylnitrilium salts with isocyanates
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N-Arylnitrilium salts 1 react with isocyanates 2 to give salts 3 of 4(3H)-quinazolinones 4, from which compounds 4 can be obtained with base. A metathesis of an isocyanate with a nitrilium salt is reported.
- Al-Talib,Jochims,Hamed,Wang,Ismail
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p. 697 - 701
(2007/10/02)
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- Synthesis and Anticonvulsant Activity of Some New 2-Substituted 3-Aryl-4(3H)-quinazolinones
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A series of 4(3H)-quinazolinones structurally related to 2-methyl-3-o-tolyl-4(3H)-quinazolinone (methaqualone, 3) were synthesized and evaluated for anticonvulsant activity.Preliminary screening of these compounds revealed that 2--3-aryl-4(3H)-quinazolinones 6l and 8i, 8k, and 8p-r having a single ortho substituent on the 3-aryl group had the most promising anticonvulsant activity.Compounds 6l and 8i possessing 3-o-tolyl and 3-o-chlorophenyl groups, respectively, showed good protection against MES- and scMet-induced seizures, combined with relatively low neurotoxicity after intraperitoneal administration in mice.They also exhibited low toxicity in tests for determining the mean hypnotic dose (HD50) and the median lethal dose (LD50).Although these compounds were markedly more potent as anticonvulsants when administered orally in mice and rats, they were also more neurotoxic.This neurotoxicity was particularly acute in oral tests with rats. which resulted in marginal protective indices.In drug differentiation tests, compound 6l was ineffective against seizures induced by bicuculline, picrotoxin, and strychnine, while 8i showed some protection against picrotoxin-induced seizures.
- Wolfe, James F.,Rathman, Terry L.,Sleevi, Mark C.,Campbell, James A.,Greenwood, Thomas D.
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p. 161 - 166
(2007/10/02)
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- Synthesis and Rearrangement of 4-Imino-4H-3,1-benzoxazines
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N-Acylanthranilamides react with dibromotriphenylphosphorane in the presence of triethylamine as HBr captor to give 4-imino-4H-3,1-benzoxazines in good yields.If the reaction is carried out without acid acceptor, N-acetylanthranilamides yield 2-methyl-4-q
- Mazurkiewicz, Roman
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p. 973 - 980
(2007/10/02)
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- One-Pot Synthesis of 2,3-Disubstituted Quinazolin-4-ones
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Whereas the condensation of N-acetylanthranilic acid (1a) with methyl and phenyl isothiocyanates (2) affords the corresponding 3-substituted 2-methylquinazolin-4-ones (7, R1=Me), N-benzoylanthranilic acid (1b) reacts with these isothiocyanates to give 2-phenyl-3,1-benzoxazin-4-one (5b: R1=Ph) and N-substituted o-benzoylaminobenzamide (6: R1=R2=Ph), respectively.
- Ashare, Ram,Mukerjee, Arya K.
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p. 1180 - 1181
(2007/10/02)
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