- A highly efficient method for the synthesis of novel 1'H-spiro[indene-2,2'-quinazoline]-1,3,4'(3'H)-trione derivatives
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A series of novel ninhydrin-derived spiro-quinazolinone derivatives in moderate to good yields have been synthesised through a ferric chloride catalysed reaction in 1,2-dichloroethane.
- Sadat-Ebrahimi, Seyed Esmail,Irannezhad, Soroor,Moghimi, Setareh,Yahya-Meymandi, Azadeh,Mahdavi, Mohammad,Shafiee, Abbas,Foroumadi, Alireza
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- Synthesis, crystal and molecular structure, DFT, vibrational spectroscopic, hirshfeld surfaces analyses and molecular docking of a novel compound N-(3-((1-(5-bromo-2-(pyrrolidin-1-yl)phenyl)-5-oxo-[1,2,4]triazolo[4,3-a]quinazolin-4(5H)-yl)methyl)phenyl)-2
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The N-(3-((1-(5-bromo-2-(pyrrolidin-1-yl)phenyl)-5-oxo-[1,2,4]triazolo[4,3-a]quinazolin- 4(5H)-yl)methyl)phenyl)-2-thiomorpholinoacetamide is a novel compound having the [1,2,4]triazolo[4,3-a]quinazolinone. It was synthesized by nine steps and confirmed b
- Chen, Dong-Mei,Chen, Yu-Mei,Liao, Tian-Hui,Liao, Wei-Ke,Wang, Zhong-Yuan,Ye, Wen-Jun,Zhao, Chun-Shen,Zhou, Zhi-Xu
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- Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives
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Twenty 2,3-disubstituted quinazolin-4(3H)-one derivatives 1–20 were successfully synthesized in moderate to good yields (25–82%). Their syntheses were based on a one pot tandem ring opening procedure followed by iodine-catalyzed oxidative cyclization of isatoic anhydride with aldehydes, using water as the only solvent under both classical and microwave irradiation conditions. Cytotoxicity assays of the prepared compounds against three human cancer cell lines (HeLa, MCF-7, and A549) indicated that 2, 3, and 20 possessed moderate activities against MCF-7 cells (IC50 = 47.2 μM, 43.9 μM, and 44.9 μM, respectively). Good cytotoxic activities against A549 cells were observed for 3 and 8 with IC50 values of 30.7 μM and 29.8 μM, respectively, which were comparable to the positive control, 5-fluorouracil (5-FU, IC50 = 27.9 μM). Furthermore, compound 4 exhibited slightly stronger activity (IC50 = 23.6 μM) than the positive control 5-FU against the A549 cell line.
- Bui, Hue Thi Buu,Do, Kiep Minh,Nguyen, Huy Tran Duc,Mai, Hieu Van,Danh, Thanh La Duc,Tran, De Quang,Morita, Hiroyuki
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supporting information
(2021/09/08)
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- Synthesis and biological evaluation of quinoline-quinazolinones for antimicrobial and antileishmanial potential
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In an attempt to find a new class of antimicrobial and antileishmanial agents, a series of twenty-three quinoline-quinazolinones were prepared via reaction of 8-hydroxy/methoxyquinoline-2-carbaldehyde with various substituted aminobenzamides. These compounds were screened for their antimicrobial activity against Gram-positive bacteria (B. subtilis), Gram-negative bacteria (E. coli and P. putida) and fungus (C. viswanathii) and antileishmanial activity against promastigotes of L. donovani. Compound 28k exhibited highest activity against B. subtilis with an IC50 of 0.17±0.07 M while compound 28j exhibited highest activity against promastigotes of L. donovani with an IC50 of 6±0.0 M.
- Tiwari, Shweta,Kirar, Seema,Banerjee, Uttam Chand,Babu, Neerupudi Kishore,Singh, Sushma,Singh, Inder Pal
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p. 1251 - 1258
(2020/12/04)
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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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- Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
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A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
- Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
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p. 3160 - 3170
(2019/08/07)
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- Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides
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An efficient, practical approach to the copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-one derivatives is described. The preparation involves treatment of benzyl amines with benzyl anthranilamides in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide (TBAB).
- Foroumadi, Parham,Lotfi, Vahid,Mahdavi, Mohammad,Moghimi, Setareh,Soheilizad, Mehdi,Kianmehr, Ebrahim,Firoozpour, Loghman,Asadipour, Ali,Foroumadi, Alireza
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p. 267 - 271
(2018/10/15)
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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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- 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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- 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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- 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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p. 351 - 356
(2015/03/18)
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- Synthesis and anticancer activity of N -substituted 2-arylquinazolinones bearing trans -stilbene scaffold
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A novel series of 2-arylquinazolinones 7a-o bearing trans-stilbene moiety were designed, synthesized, and evaluated against human breast cancer cell lines including human breast adenocarcinoma (MCF-7 and MDA-MB-231) and human ductal breast epithelial tumor (T-47D). Among the tested compounds, the sec-butyl derivative 7h showed the best profile of activity (IC50 5 μM) against all cell lines, being 2-fold more potent than standard drug, etoposide. Our investigation revealed that the cytotoxic activity was significantly affected by N3-alkyl substituents. Furthermore, the morphological analysis by acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that the prototype compound 7h can induce apoptosis in MCF-7 and MDA-MB-231 cells.
- Mahdavi, Mohammad,Pedrood, Keyvan,Safavi, Maliheh,Saeedi, Mina,Pordeli, Mahboobeh,Ardestani, Sussan Kabudanian,Emami, Saeed,Adib, Mehdi,Foroumadi, Alireza,Shafiee, Abbas
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p. 492 - 499
(2015/04/14)
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- Solvent-free synthesis of novel benzodiazepine derivatives by a three-component base-catalysed reaction of isatoic anhydride, a primary amine and chloroacetyl chloride
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Heating isatoic anhydride with a series of primary amines at 150 °C under solvent-free conditions yielded 2-amino-N-alkylbenzamides which, in the same pot, reacted readily with chloroacetyl chloride in the presence of poly(dimethylaminoethyl acrylamide)-modified magnetic nanoparticles (MNP@PDMA), a base catalyst, to give 4-alkyl-1,4-benzodiazepine-2,5-diones in good yields without formation of by-products.
- Seydey, Mohsen Khalilpour,Rezaei, Zahra,Homami, Seyed Saied
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p. 286 - 288
(2015/06/02)
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- An efficient one pot synthesis of 2-amino quinazolin-4(3H)-one derivative via MCR strategy
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A novel multi-component reaction strategy was developed for the construction of important building blocks, 2-amino 3-substituted quinazolinone derivatives from isatoic anhydride and amine with electrophilic cyanating compound, N-cyano-4-methyl-N-phenylbenzenesulfonamide (NCTS). The quinazolinone synthesis proceeds via a sequential series of reactions such as nucleophilic attack of the amine group on the carbonyl group of isatoic anhydride followed ring opening and subsequent decarboxylation, nucleophilic attack of amine to nitrile, followed by heterocyclization.
- Narayana Murthy,Nikumbh, Satish P.,Praveen Kumar,Vaikunta Rao,Raghunadh, Akula
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supporting information
p. 5767 - 5770
(2015/09/29)
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- Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives
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A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux. Graphical abstract: [Figure not available: see fulltext.]
- Asadi, Mehdi,Masoomi, Shiva,Ebrahimi, Seyed Mostafa,Mahdavi, Mohammad,Saeedi, Mina,Shafiee, Abbas,Foroumadi, Alireza
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p. 497 - 504
(2014/03/21)
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- Vilsmeier Reagent: An efficient reagent for the transformation of 2-aminobenzamides into quinazolin-4(3 h)-one derivatives
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Clean and easy preparation of quinazolin-4(3H)-one derivatives using 2-aminobenzamides and Vilsmeier reagent is described. 2-Aminobenzamides were converted into the corresponding quinazolinones under mild and efficient conditions, in good yields without undesirable by-products.
- Farzipour, Soghra,Saeedi, Mina,Mahdavi, Mohammad,Yavari, Hossein,Mirzahekmati, Mohammadreza,Ghaemi, Nasser,Foroumadi, Alireza,Shafiee, Abbas
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p. 481 - 487
(2014/01/23)
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- Structural optimization of a retrograde trafficking inhibitor that protects cells from infections by human polyoma- and papillomaviruses
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Human polyoma- and papillomaviruses are non-enveloped DNA viruses that cause severe pathologies and mortalities. Under circumstances of immunosuppression, JC polyomavirus causes a fatal demyelinating disease called progressive multifocal leukoencephalopathy (PML) and the BK polyomavirus is the etiological agent of polyomavirus-induced nephropathy and hemorrhagic cystitis. Human papillomavirus type 16, another non-enveloped DNA virus, is associated with the development of cancers in tissues like the uterine cervix and oropharynx. Currently, there are no approved drugs or vaccines to treat or prevent polyomavirus infections. We recently discovered that the small molecule Retro-2cycl, an inhibitor of host retrograde trafficking, blocked infection by several human and monkey polyomaviruses. Here, we report diversity-oriented syntheses of Retro-2cycl and evaluation of the resulting analogs using an assay of human cell infections by JC polyomavirus. We defined structure-activity relationships and also discovered analogs with significantly improved potency as suppressors of human polyoma- and papillomavirus infection in vitro. Our findings represent an advance in the development of drug candidates that can broadly protect humans from non-enveloped DNA viruses and toxins that exploit retrograde trafficking as a means for cell entry.
- Carney, Daniel W.,Nelson, Christian D.S.,Ferris, Bennett D.,Stevens, Julia P.,Lipovsky, Alex,Kazakov, Teymur,Dimaio, Daniel,Atwood, Walter J.,Sello, Jason K.
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p. 4836 - 4847
(2014/10/16)
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- Reaction of isatoic anhydride, amine, and N,N′-dialkyl carbodiimides under solvent-free conditions: New and efficient synthesis of 3-alkyl-2-(alkylamino) quinazolin-4(3H)-ones
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Heating a mixture of isatoic anhydride, amines, and N,N′-dialkyl carbodiimides under solvent-free conditions provided novel 3-alkyl-2- (alkylamino)quinazolin-4(3H)-one derivatives for the first time. The products were obtained in moderate to good yields without formation of any by-products. Copyright
- Asadi, Mehdi,Ebrahimi, Mostafa,Mahdavi, Mohammad,Saeedi, Mina,Ranjbar, Parviz Rashidi,Yazdani, Farshad,Shafiee, Abbas,Foroumadi, Alireza
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supporting information
p. 2385 - 2392
(2013/07/26)
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- Green synthesis of new boron-containing quinazolines: Preparation of benzo[d][1,3,2]diazaborinin-4(1H)-one derivatives
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A series of new boron-containing quinazolinones, benzo[d][1,3,2] diazaborinin-4(1H)-one derivatives, were synthesized by the sequential one-pot reaction of isatoic anhydride, amines, and arylboronic acids in the absence of a catalyst and solvent. Heating isotoic anhydride and amines led to the formation of 2-aminobenzamide intermediates, which reacted easily with boronic acids to obtain the title compounds in good yields. Solvent-free conditions provided a unique procedure because the corresponding products were not obtained using various solvents either under reflux conditions or at room temperature.
- Mahdavi, Mohammad,Asadi, Mehdi,Saeedi, Mina,Tehrani, Maryam Hosseinpour,Mirfazli, Seyedeh Sara,Shafiee, Abbas,Foroumadi, Alireza
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supporting information
p. 2936 - 2942
(2013/09/02)
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- Synthesis of novel 1,4-benzodiazepine-3,5-dione derivatives: Reaction of 2-aminobenzamides under bargellini reaction conditions
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In this paper, we report on a user-friendly synthesis of 1,4-benzodiazepine-3,5-dione derivatives via Bargellini-type reaction. The corresponding products were obtained using various 2-aminobenzamides under Bargellini reaction conditions, in good yields without unfavorable side reaction.
- Mahdavi, Mohammad,Saeedi, Mina,Rezaei, Zahra,Foroumadi, Alireza,Shafiee, Abbas,Asadi, Mehdi,Moghbel, Hooman
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p. 2521 - 2525,5
(2012/12/11)
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- Synthesis and in vitro study of platelet antiaggregant activity of some 4-quinazolinone derivatives
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Some new 4-quinazolinones were prepared. Their antiplatelet activity was evaluated in vitro with respect to aggregation induced by ADP, collagen, arachidonic acid and the platelet serotonin release reaction. Most molecules showed an inhibiting power similar to that of acetylsalicylic acid under the same conditions, and even greater when aggregation was induced by ADP. Reduction of the 4-quinazolinone derivatives to their 1,2,3,4-tetrahydroquinazoline homologues produced an increase in platelet inhibitory action except when ADP is the inductor.
- Gravier,Dupin,Casadebaig,Hou,Boisseau,Bernard
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- Aldose reductase inhibition by 2,4-oxo and thioxo derivatives of 1,2,3,4-tetrahydroquinazoline
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Inhibitors of aldose reductase are believed to be useful for the treatment of diabetic complications.Original acetic acids and their thioxo derivatives have been synthesized and examined for their ability to inhibit aldose reductase in vitro and in vivo.Most were active in vitro on rat lens aldose reductase in the 10-7 molar range.Compound V16, which has a (2'-fluoro-4'-bromo)benzyl substituent on nitrogen N-3 was found in hypergalactosemic rats to be a good inhibitor of galactitol accumulation in sciatic nerves andto prevent cataract formation.
- Billon, Florence,Delchambre, Chantal,Cloarec, Alix,Sartori, Eric,Teulon, Jean-Marie
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p. 121 - 126
(2007/10/02)
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