- Effects Of 2-Methyl-3-propynylquinazolin-4-(3H)-one On Vascular Reactivity in Isolated Porcine Tail Arteries
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The vascular effects of 2-methyl-3-propynylquinazolin-4-(3H)-one (QUIN) have been studied on isolated porcine tail arteries. QUIN had no effect on resting tension but relaxed, dose-dependently, arteries precontracted with noradrenaline or high-K+/su
- Ojeikere, Odafenkhoa,Usifoh, Cyril,Ebeigbe, Anthony
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- Synthesis and anti-acetylcholinesterase activity of benzotriazinone-triazole systems
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An approach for the construction of benzotriazinone-triazole system is described. The synthesis is based on diazonium chemistry and subsequent intramolecular heteroatom-heteroatom bond formation. The introduction of triazole moiety occurred via click reac
- Moghimi, Setareh,Goli-Garmroodi, Fereshteh,Pilali, Hedieh,Mahdavi, Mohammad,Firoozpour, Loghman,Nadri, Hamid,Moradi, Alireza,Asadipour, Ali,Shafiee, Abbas,Foroumadi, Alireza
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- Synthesis of Novel Isoindolo[2,1-a]quinazolinedione Derivatives Containing a 1,2,3-Triazole Ring System
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A synthesis of isoindolo[2,1-a]quinazolinedione derivatives, coupled with a 1,2,3-triazole ring system, via the reaction of isatoic anhydride, HC=CCH2NH2, and 2-formylbenzoic acid is described, which led to the formation of the isoin
- Esmaeili-Marandi, Fatemeh,Saeedi, Mina,Yavari, Issa,Mahdavi, Mohammad,Shafiee, Abbas
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- Synthesis, in vitro and computational studies of novel glycosyl-1, 2, 3-1H-triazolyl methyl benzamide derivatives as potential α-glucosidase inhibitory activity
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A series of novel glycosyl-1,2,3-1H-triazolyl methyl benzamide analogues were synthesized by the unambiguous strategy and evaluated for α-glucosidase inhibitory activity. Glycosyl benzamide exhibited a dose-dependent inhibition of α-glucosidase activity.
- Shukla, Akhilesh Kumar,Shrivash, Manoj Kumar,Pandey, Anwesh,Pandey, Jyoti
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- Quinazolinone [2, 3 - a] carboline derivative as well as preparation method and application thereof
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The main content of the invention is to provide a new quinazolinone [2, 3 - a] carboline compound as well as a preparation method and application thereof, and has the quinazolinone of the general formula (I) and [2, 3 - a] carboline compounds. A quinazolo
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Paragraph 0054-0057; 0141-0144
(2021/10/11)
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- Design, Synthesis and Biological Evaluation of Novel Anthraniloyl-AMP Mimics as PQS Biosynthesis Inhibitors against Pseudomonas aeruginosa Resistance
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The Pseudomonas quinolone system (PQS) is one of the three major interconnected quorum sensing signaling systems in Pseudomonas aeruginosa. The virulence factors PQS and HHQ activate the transcription regulator PqsR (MvfR), which controls several activiti
- Black, David StC,Das, Theerthankar,Kumar, Naresh,Rice, Scott A.,Sabir, Shekh,Subramoni, Sujatha
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- Glycosyl triazoles as novel insect β-N-acetylhexosaminidase OfHex1 inhibitors: Design, synthesis, molecular docking and MD simulations
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The insect enzyme GH20 β-N-acetyl-D-hexosaminidase OfHex1 represents an important chitinolytic enzyme found in the agricultural pest Ostrinia furnacalis (Guenée) and inhibition of this enzyme has been considered a promising strategy for the development of eco-friendly pesticides. In this article, based on the structure of the catalytic domains of OfHex1, a series of novel glycosyl triazoles were designed and synthesized via Cu-catalyzed azide-alkyne [3+2] cycloaddition reaction. To investigate the potency and selectivity of these glycosyl triazoles, the inhibition activities towards OfHex1 and HsHexB (human β-N-acetylhexosaminidase B) were studied. Particularly compound 17c (OfHex1, Ki = 28.68 μM; HsHexB, Ki > 100 μM) exhibited a suitable activity and selectivity against OfHex1. Furthermore, the possible inhibitory mechanisms of 17c with OfHex1 were studied using molecular docking and MD simulations. The structure-activity relationship results as well as the formed binding patterns may provide promising insights into the further development of novel OfHex1 inhibitors.
- Dong, Lili,Shen, Shengqiang,Chen, Wei,Lu, Huizhe,Xu, Dongdong,Jin, Shuhui,Yang, Qing,Zhang, Jianjun
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p. 2315 - 2322
(2018/12/11)
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- Synthesis and antimicrobial activity of novel 1,2,3-triazole-conjugates of quinazolin-4-ones
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A novel series of diethyl{4-[(4-oxoquinazolin-3(4H)-yl)methyl]-1H-1,2,3-triazol-1-yl}alkylphosphonates 9aa–aj and their respective derivatives substituted at C6 of the quinazolinone moiety with a bromine atom (9ba–bj) or a nitro group (9ca–cj) were synthesized and assessed for the antibacterial activity toward selected Gram-positive and Gram-negative bacteria. Their antifungal activity was also screened. Compound 9ac was found to be the most active against Staphylococcus aureus ATCC 6535 (MIC 0.625 mg/mL, MBC 1.25 mg/mL), phosphonates 9ab–ai showed promising activity against Enterococcus faecalis ATCC 29212 (MIC = 0.625 mg/mL, MBC = 1.25 mg/mL), while compounds 9ac–j appeared the most active toward Pseudomonas aeruginosa ATCC 27853 (MIC = 0.625 mg/mL, MBC = 1.25 mg/mL). Antifungal assays of compounds 9aa–aj, 9ba–bj, and 9ca–cj were conducted on Candida albicans ATCC 10231 and Aspergillus brasiliensis ATCC 16404 and revealed noticeable activity of 9aa–aj (MIC = 1.25 mg/mL).
- G?owacka, Iwona E.,Grzonkowski, Piotr,Lisiecki, Pawe?,Kalinowski, ?ukasz,Piotrowska, Dorota G.
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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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- Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyn-Tethered Indoles to Prepare Rutaecarpine Derivatives
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An efficient method to synthesize rutaecarpine derivatives via the gold-catalyzed selective cyclization of alkyn-tethered indoles under mild conditions is described. The alkyn-tethered indole can undergo 6-exo-dig cyclization by oxidation and sequential gold catalysis, while it goes through 7-endo-dig cyclization by gold catalysis and sequential oxidation. Substrate scope studies reveal that the selectivity of cyclization was controlled by the substrates with sp3 and sp2 hybridization of carbon at the 2 position in quinazolinone. Furthermore, the rutaecarpine scaffold was prepared in 67% yield at gram scale easily in four steps from isatoic anhydride.
- Kong, Xiang-Fei,Zhan, Feng,He, Guo-Xue,Pan, Cheng-Xue,Gu, Chen-Xi,Lu, Ke,Mo, Dong-Liang,Su, Gui-Fa
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p. 2006 - 2017
(2018/02/23)
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- Synthesis of novel glycosyl-1,2,3-1H-triazolyl methyl quinazolin-4(3H)-ones and their effect on GLUT4 translocation
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Cu(OTf)2catalyzed synthesis of propargylated 2,3-dihydroquinazolin-4(1H)-ones has been accomplished from 2-amino-N-propargyl benzamides and aromatic aldehydes under MW irradiation. Next, a series of novel glycosyl triazolyl methyl quinazolin-4(
- Ramakrishna, K. Kumar G.,Thakur, Ravi Kumar,Pasam, Venkata Reddy,Pandey, Jyotsana,Mahar, Rohit,Shukla, Sanjeev K.,Tamrakar, Akhilesh K.,Tripathi, Rama Pati
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p. 187 - 203
(2016/12/23)
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- Synthesis and evaluation of novel quinazolinone-1,2,3-triazoles as inhibitors of lipoxygenase
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This work reports the successful synthesis of quinazolinones carrying triazole derivatives with potent lipoxygenase inhibitory activities. This protocol involves sequential reactions affording novel products in high yields without the need for a tedious w
- Farjadmand, Fatemeh,Arshadi, Hossein,Moghimi, Setareh,Nadri, Hamid,Moradi, Alireza,Eghtedari, Mohammad,Jafarpour, Farnaz,Mahdavi, Mohammad,Shafiee, Abbas,Foroumadi, Alireza
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p. 188 - 191
(2016/06/09)
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- Efficient synthesis of 2-methylenethiazolo[2,3- b ]quinazolinone derivatives
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Substituted o-Amino-N-(prop-2-yn-1-yl) aromatic amides easily reacted with carbon disulfide (CS2) in the presence of potassium hydroxide (KOH) in EtOH under reflux conditions. Cyclization reaction followed by a favored 5-exo-dig ring closure af
- Mahdavi, Mohammad,Bialam, Maryam,Saeedi, Mina,Jafarpour, Farnaz,Foroumadi, Alireza,Shafiee, Abbas
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p. 173 - 176
(2015/03/03)
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- Efficient synthesis of 2-methylenethiazolo[2,3-b]quinazolinone derivatives
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Substituted o-amino-N-(prop-2-yn-1-yl) aromatic amides easily reacted with carbon disulfide (CS2) in the presence of potassium hydroxide (KOH) in EtOH under reflux conditions. Cyclization reaction followed by a favored 5-exo-dig ring closure af
- Mahdavi, Mohammad,Bialam, Maryam,Saeedi, Mina,Jafarpour, Farnaz,Foroumadi, Alireza,Shafiee, Abbas
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- One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines
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An operationally simple, one-pot, two-step cascade method has been developed to afford quinazolino[1,2,3]triazolo[1,4]benzodiazepines. This unique, atom-economical transformation engages five reactive centers (amide, aniline, carbonyl, azide, and alkyne) and employs environmentally benign iodine as a catalyst. The method proceeds via sequential quinazolinone-forming condensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions. Substrate scope, multicomponent examples, and mechanistic insights are discussed.
- Guggenheim, Kathryn G.,Toru, Hannah,Kurth, Mark J.
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p. 3732 - 3735
(2012/09/08)
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- Synthesis of Small Molecules Targeting Multiple DNA Structures using Click Chemistry
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The ability of small molecules to target DNA forms the basis of many clinically used antitumour agents. This study examines the effects of novel 9-aminoacridine carboxamides, synthesised by click chemistry based upon the reactions of either 9-(2-azidoethy
- Howell, Lesley A.,Bowater, Richard A.,O'Connell, Maria A.,Reszka, Anthony P.,Neidle, Stephen,Searcey, Mark
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experimental part
p. 792 - 804
(2012/07/27)
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- Facile, selective, and regiocontrolled synthesis of oxazolines and oxazoles mediated by ZnI2 and FeCl3
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An expedient method for a direct approach to the selective and regiocontrolled synthesis of 2-oxazolines and 2-oxazoles mediated by ZnI 2 and FeCl3 is described. A Lewis acid promoted cyclization of acetylenic amide with various func
- Senadi, Gopal Chandru,Hu, Wan-Ping,Hsiao, Jia-Shing,Vandavasi, Jaya Kishore,Chen, Chung-Yu,Wang, Jeh-Jeng
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supporting information
p. 4478 - 4481
(2012/10/30)
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- Fused bicyclic derivatives of 2,4-diaminopyrimidine as c-Met inhibitors
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The HGF-c-Met signaling axis is an important paracrine mediator of epithelial-mesenchymal cell interactions involving the regulation of multiple cellular activities including cell motility, mitogenesis, morphogenesis, and angiogenesis. Dysregulation of c-Met signaling (e.g., overexpression or increased activation) is associated with the development of a wide range of tumor types; thus, inhibiting the HGF-c-Met pathway is predicted to lead to anti-tumor effects in many cancers. Elaboration of a 2-arylaminopyrimidine scaffold led to a series of potent c-Met inhibitors bearing a C4-2-amino-N-methylbenzamide group. Specifically, a series of C2-benzazepinone analogs demonstrated potent inhibition of c-Met in enzymatic and cellular assays. Kinase selectivity could be tuned by varying the nature of the alkyl group on the benzazepinone nitrogen.
- Weinberg, Linda R.,Albom, Mark S.,Angeles, Thelma S.,Husten, Jean,Lisko, Joseph G.,McHugh, Robert J.,Milkiewicz, Karen L.,Murthy, Seetha,Ott, Gregory R.,Theroff, Jay P.,Tripathy, Rabindranath,Underiner, Ted L.,Zificsak, Craig A.,Dorsey, Bruce D.
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supporting information; experimental part
p. 164 - 167
(2011/03/17)
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- One-pot synthesis of luotonin A and its analogues
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Starting with inexpensive reagents, a self-directed chemical process with the aid of a single metal triflate was readily achieved to concomitantly construct quinazoline and pyrroloquinoline cores to afford the synthesis of luotonin A and its analogues. Am
- Tseng, Ming-Chung,Chu, Yu-Wan,Tsai, Hsiang-Ping,Lin, Chun-Mao,Hwang, Jaulang,Chu, Yen-Ho
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supporting information; experimental part
p. 920 - 923
(2011/04/24)
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- Optimization of the azobenzene scaffold for reductive cleavage by dithionite; development of an azobenzene cleavable linker for proteomic applications
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In this paper we conducted an extensive reactivity study to determine the key structural features that favour the dithionite-triggered reductive cleavage of the azo-arene group. Our stepwise investigation allowed identification of a highly reactive azo-arene structure 25 bearing a carboxylic acid, at the ortho position of the electron-poor arene and an ortho-Oalkyl-resorcinol as the electron-rich arene. Based on this 2(2′-alkoxy-4′-hydroxyphenylazo) benzoic acid (HAZA) scaffold, the orthogonally protected difunctional azo-arene cleavable linker 26 was designed and synthesized. Selective linker deprotection and derivatization was performed by introducing an alkyne reactive group and a biotin affinity tag. This optimized azo-arene cleavable linker led to a total cleavage in less than 10 s with only 1 mM dithionite. Similar results were obtained in biological media.
- Leriche, Geoffray,Budin, Ghyslain,Brino, Laurent,Wagner, Alain
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experimental part
p. 4360 - 4364
(2010/09/20)
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- THERAPEUTIC COMPOUNDS
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Substituted cinnamoyl anthranilate compounds exhibiting anti-fibrotic activity; or derivatives thereof, analogues thereof, pharmaceutically acceptable salts thereof, and metabolites thereof; with the proviso that the compound is not Tranilast.
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Page/Page column 53-54
(2008/06/13)
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- Intramolecular hetero Diels-Alder (Povarov) approach to the synthesis of the alkaloids luotonin A and camptothecin
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(Chemical Equation Presented) Pyrrolo[3,4-b]quinolines can be formed through the coupling of anilines with N-propargylic substituted heterocyclic aldehydes in the presence of mild Lewis acid catalysts (Ln(OTf)3). The coupling proceeds through s
- Twin, Heather,Batey, Robert A.
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p. 4913 - 4916
(2007/10/03)
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- Synthesis of 2-(-2-aminophenyl)-5-methyloxazole
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Ring opening of isatoic anhydride by prop-2-ynylamine yielded the corresponding amide, which was cyclised under basic conditions to give 2-(2-aminophenyl)-5-methyloxazole 5.
- Usifoh,Edema
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- Synthesis and anticonvulsant activity of acetylenic quinazolinone derivatives
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Acetylenic derivatives of quinazolinones and quinazolinediones were synthesized and evaluated for their anticonvulsant activity. Most compounds displayed seizure-antagonizing activity in the maximal electroshock test (MES test) in most cases associated wi
- Usifoh, Cyril O.,Scriba, Gerhard K. E.
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p. 261 - 266
(2007/10/03)
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