- 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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- 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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- Method for reducing aromatic nitro into arylamine
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The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.
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Paragraph 0157-0160
(2020/07/15)
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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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- 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; 00226
(2019/12/25)
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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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- 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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- One-Pot, Multistep Reactions for the Modular Synthesis of N, N′-Diarylindazol-3-ones
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The pot-economic synthesis of N,N′-diarylindazol-3-ones has been developed using readily available isatoic anhydrides, aryl amines, and aryl boronic acids. A Cu-catalyzed oxidative C-N cross-coupling and dehydrogenative N-N formation sequence under an air atmosphere affords indazol-3-one derivatives in good to excellent yields. Such process merges well with the preceding decarboxylative amination reaction, resulting in a more modular and straightforward approach.
- Liu, Shuai,Xu, Liang,Wei, Yu
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p. 1596 - 1604
(2019/02/07)
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- Metal-free Reduction of Nitro Aromatics to Amines with B 2 (OH) 4 /H 2 O
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A metal-free reduction of nitro aromatics mediated by diboronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.
- Chen, Danyi,Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Liu, Qixing,Zhang, Kaili,Uozumi, Yasuhiro
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supporting information
p. 1765 - 1768
(2018/06/26)
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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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- Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid
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An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.
- Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Pi, Danwei,Shen, Guanshuo
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p. 3898 - 3904
(2017/06/13)
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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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- 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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- 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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- Identification of potent orally active factor Xa inhibitors based on conjugation strategy and application of predictable fragment recommender system
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Anticoagulant agents have emerged as a promising class of therapeutic drugs for the treatment and prevention of arterial and venous thrombosis. We investigated a series of novel orally active factor Xa inhibitors designed using our previously reported conjugation strategy to boost oral anticoagulant effect. Structural optimization of anthranilamide derivative 3 as a lead compound with installation of phenolic hydroxyl group and extensive exploration of the P1 binding element led to the identification of 5-chloro-N-(5-chloro-2-pyridyl)-3-hydroxy-2-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzamide (33, AS1468240) as a potent factor Xa inhibitor with significant oral anticoagulant activity. We also reported a newly developed Free-Wilson-like fragment recommender system based on the integration of R-group decomposition with collaborative filtering for the structural optimization process.
- Ishihara, Tsukasa,Koga, Yuji,Iwatsuki, Yoshiyuki,Hirayama, Fukushi
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p. 277 - 289
(2015/02/05)
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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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- 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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- Natural surfactant mediated phytosynthesis and solvatochromic fluorescence of 2-aminobenzamide derivatives
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A green synthesis and intriguing solvatochromic behaviour of 2-aminobenzamide derivatives in varying solvents has been investigated. The biomaterial in the form of an aqueous extract of mesocarp of the fruit of the Balanites roxburghii plant as a natural surfactant reaction medium has been employed for phytosynthesis with quantitative yield at 60 °C. The reaction proceeds effortlessly in a short reaction time with easy product formation. The fluorescence property of some synthesized compounds was studied, along with the interesting solvatochromic behaviour of 2-amino-N-benzylbenzamide.
- More, Pallavi,Patil, Amol,Salunkhe, Rajashri
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p. 63039 - 63047
(2015/02/19)
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- One-pot synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion
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An efficient and practical two-step process has been developed for the synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion in one pot. This regioselective procedure could construct a wide range of 2-amino-4(3H)- quinazolinones in moderate to excellent yields. Furthermore, the methodology also had distinct advantages of easily accessible starting materials and operational simplicity. the Partner Organisations 2014.
- Ji, Fei,Lv, Mei-Fang,Yi, Wen-Bin,Cai, Chun
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p. 5766 - 5772
(2014/07/22)
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- Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives
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A series of 2-amino benzoic acid derivatives (1-28) were synthesized and evaluated for their in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. The results of antimicrobial studies indicated that, in general, the synthesized compounds were found to be bacteriostatic and fungistatic in action. QSAR studies performed by the development of one target and multi target models indicated that multi-target model was effective in describing the antimicrobial activity as well demonstrated the effect of structural parameters viz. LUMO, 3χv and W on antimicrobial activity of 2-amino benzoic acid derivatives. Springer Science+Business Media, LLC 2010.
- Mahiwal, Kuldeep,Kumar, Pradeep,Narasimhan, Balasubramanian
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p. 293 - 307
(2012/09/07)
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- Three-component domino synthesis of 2-arylquinazoline-4-amines in one pot by activating an sp3 C-H bond in a nonmetal catalytic oxidation system
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The nonmetal catalytic oxidation system I2/tert-butyl hydroperoxide (TBHP) has been unprecedentedly applied to a three-component domino reaction and simultaneously a simple and efficient protocol has been developed to newly synthesize 2-aryl-N-substitutied quinazoline-4-amines in one pot from isatoic anhydride, aromatic amine, and another amine containing methylene adjacent to nitrogen. This protocol is new and practical because both the electron-donating and -withdrawing groups substituted on amines 2 or 3 can survive and provide the corresponding products in reasonable yields. Iodine is essential to the three-component, one-pot reaction unlike the step-wise procedure. The nonmetal catalytic oxidation system I2/tert-butyl hydroperoxide (TBHP) has been successfully applied to a three-component domino reaction, and a new, simple, efficient protocol has been developed to synthesize 2-aryl-N-substitutied quinazoline-4-amines in one pot from isatoic anhydride, aromatic amine, and another amine containing methylene adjacent to nitrogen. Copyright
- Zeng, Li-Yan,Yi, Wen-Bin,Cai, Chun
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experimental part
p. 559 - 566
(2012/03/08)
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- Synthesis of 3-(aryl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives using heteropolyacids as green, heterogeneous and recyclable catalysts
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Reaction of isatoic anhydride with aniline derivatives gave 2-amino-N-(aryl)benzamides. The latters reacted with phenylisothiocyanate in the presence of heteropolyacids in various solvents which afforded 3-(aryl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives. The effects of various heteropolyacids including Preyssler and Keggin on the yields and reaction times have been investigated.
- Allameh,Heravi,Hashemi,Bamoharram
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scheme or table
p. 131 - 134
(2012/01/02)
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- Synthesis of 3-aryl-2-[hydroxy(diaryl)methyl]-4-oxo-3,4-dihydroquinazolines
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By heating arylamides of N-ethoxalylanthranilic acid in the acetic acid mediun in the presence of triethylamine the corresponding ethyl 3-aryl-4-oxo-3,4-dihydroquinazoline-2-carboxylates were obtained. The latter in the conditions of the Grignard reaction formed 3-aryl-2-[hydroxy-(diaryl)methyl] -4-oxo-3,4-dihydroquinazolines. Pleiades Publishing, Ltd., 2010.
- Shemchuk,Chernykh,Levashov,Sytnik,Shemchuk
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scheme or table
p. 1687 - 1690
(2011/03/19)
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- A regioselective three-component reaction for synthesis of novel 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives
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A ring opening and regioselective three-component reaction of isatoic anhydride, isatins, and aromatic or aliphatic primary amines in the presence of catalytic amount of KAl(SO4)2·12H2O (alum) to yield a novel series of 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione is described.
- Mohammadi, Ali A.,Dabiri,Qaraat
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body text
p. 3804 - 3808
(2009/09/05)
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- Cyclooxygenase-1-selective inhibitors are attractive candidates for analgesics that do not cause gastric damage. Design and in vitro/in vivo evaluation of a benzamide-type cyclooxygenase-1 selective inhibitor
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Although cyclooxygenase-1 (COX-1) inhibition is thought to be a major mechanism of gastric damage by nonsteroidal anti-inflammatory drugs (NSAIDs), some COX-1-selective inhibitors exhibit strong analgesic effects without causing gastric damage. However, it is not clear whether their analgesic effects are attributable to COX-1-inhibitory activity or other bioactivities. Here, we report that N-(5-amino-2-pyridinyl)-4-(trifluoromethyl)benzamide (18f, TFAP), which has a structure clearly different from those of currently available COX-1-selective inhibitors, is a potent COX-1-selective inhibitor (COX-1 IC 50 = 0.80 ± 0.05 μM, COX-2 IC50 = 210 ± 10 μM). This compound causes little gastric damage in rats even at an oral dose of 300 mg/kg, though it has an analgesic effect at as low a dose as 10 mg/kg. Our results show that COX-1-selective inhibitors can be analgesic agents without causing gastric damage.
- Kakuta, Hiroki,Zheng, Xiaoxia,Oda, Hiroyuki,Harada, Shun,Sugimoto, Yukio,Sasaki, Kenji,Tai, Akihiro
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p. 2400 - 2411
(2008/12/22)
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- The use of formamidine protection for the derivatization of aminobenzoic acids
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(Chemical Equation Presented) N,N-Dimethylformamidine and novel N,N-diisopropylformamidine protecting groups were used to carry out a one-pot conversion of aminobenzoic acids into the corresponding amides. General conditions for an in situ transformation of aminobenzoic acids and their heterocyclic analogues into the corresponding formamidine-protected acid chlorides were developed. These chlorides were used in reactions with amines, including poorly reactive anilines. The protected amides were then smoothly deprotected by heating with ethylenediamine derivatives, resulting in a general procedure for the one-pot transformation of aminobenzoic acids into their amides. Our one-pot procedure was successfully applied to the preparation of several compounds of pharmaceutical interest.
- Zhichkin, Paul E.,Peterson, Lisa H.,Beer, Catherine M.,Rennells, W. Martin
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supporting information; experimental part
p. 8954 - 8959
(2009/04/11)
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- An efficient synthesis of quinazoline-2,4-dione derivatives with the aid of a low-valent titanium reagent
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A facile synthetic method using low-valent titanium reagent (TiCl4/Zn system) to promote the novel reductive cyclization of 2-nitrobenzamides and triphosgene is described. Sequentially, a series of quinazoline-2,4-diones were synthesized in goo
- Shi, Da-Qing,Dou, Guo-Lan,Li, Zheng-Yi,Ni, Sai-Nan,Li, Xiao-Yue,Wang, Xiang-Shan,Wu, Hui,Ji, Shun-Jun
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p. 9764 - 9773
(2008/02/12)
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- Convergent one-pot synthesis of 3-substituted quinazolin-4(3H)-ones under solvent-free conditions
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A convenient method for the synthesis of 3-substituted quinazolin-4(3H)- ones using the convergent reactions of formic acid, a primary amine, and isatoic anhydride under solvent-free conditions and with brief microwave irradiation is described. Copyright Taylor & Francis Group, LLC.
- Rad-Moghadam, Kurosh,Mamghani, Manoochehr,Samavi, Laleh
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p. 2245 - 2252
(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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- Antithrombotic agents
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This application relates to a compound of formula (I), a pharmaceutically acceptable salt of the compound, or a prodrug thereof, as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.
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- Relationships between the chemical structure of substances and their antimycobacterial activity against atypical strains. Part 18. 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and isosteric 3-phenylquinazoline-2,4(1H,3H)-diones
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A series of 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones 2 and 3-phenylquinazoline-2,4(1H,3H)-diones 5 substituted on the phenyl rings were synthesized. The target compounds as well as the intermediates were tested against Mycobacterium tuberculosis, M. kansasii, and M. avium. The replacement of the oxygen atom by nitrogen resulted in a decrease or loss of antimycobacterial activity. 2-[(Ethoxycarbonyl)amino]benzanilides 4 appeared to be inactive. Salicylanilides 1 and 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-diones 2 exhibit significant activity against both M. tuberculosis and nontuberculous mycobacteria (the MICs within the range of 4-250 μmol/l for all compounds). The antimycobacterial activity of the compounds increases with increasing both electron-withdrawing properties and hydrophobicity of the substituent(s) on the phenyl moiety. The antimycobacterial profile of the compounds was analyzed according to the criteria based on vector algebra, such as cosine coefficients. Moreover, salicylanilides 1 exhibit activity against other microorganisms tested by the agar diffusion method.
- Waisser, Karel,Machacek, Milos,Dostal, Hynek,Gregor, Jiri,Kubicova, Lenka,Klimesova, Vera,Kunes, Jiri,Palat Jr., Karel,Hladuvkova, Jana,Kaustova, Jarmila,Moellmann, Ute
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p. 1902 - 1924
(2007/10/03)
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- Synthesis and in vitro study of platelet antiaggregant activity of 1,2,3,4-tetrahydroquinazoline derivatives
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Some original 3-substituted 1,2,3,4-tetrahydroquinazolines were synthesized. Their antiplatelet activity was evaluated in vitro with respect to aggregation induced by the main inducers (ADP, collagen, arachidonic acid), platelet serotonin release reaction and thromboxane A2 synthesis. All these molecules possess an inhibiting power which, compared to that of aspirin in the same conditions, is the same or greater when aggregation is induced by ADP.
- Gravier,Dupin,Casadebaig,Hou,Boisseau,Bernard
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p. 531 - 535
(2007/10/02)
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