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A. I. Markosyan - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and Biological Activity of 2-Mercapto-7,10-Dimethyl-3H-Spiro[Benzo[H]Quinazoline-5,1′-Cyclopentane]-4(6H)-One from Ethyl 4′-Amino-5′,8′-Dimethyl-1′H-Spiro[Cyclopentane-1,2′-Naphthalene]-3′-Carboxylate
Pharmaceutical Chemistry Journal, 2018Co-Authors: N. P. Grigoryan, A. I. Markosyan, A. S. Grigoryan, G. A. Stepanyan, R. S. Sukasyan, R. G. ParonikyanAbstract:A synthetic method for 7,10-dimethyl-2-thioxo-2,3-dihydro-1 H -spiro[benzo[ h ]Quinazoline-5,1′-cyclopentane]- 4(6 H )-one from ethyl 4′-amino-5′,8′-dimethyl-1′- H -spiro[cyclopentane-1,2′-naphthalene]-3′-carboxylate was developed. Reaction of the spirobenzo[ h ]Quinazoline with various alkyl(benzyl) halides synthesized a novel series of spirobenzo[ h ]Quinazolines containing methyl substituents on the benzene ring. The antidepressant, anticonvulsant, and antibacterial activities of the synthesized spirobenzo[ h ]Quinazolines were investigated.
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Synthesis, Conversions, and Anti-Monoamine-Oxidase and Anticonvulsant Activity of Ethyl 4′-Amino-5′,8′-Dimethyl-1′H-Spiro[Cyclohexane-1,2′-Naphthalene]-3′-Carboxylate
Pharmaceutical Chemistry Journal, 2017Co-Authors: N. P. Grigoryan, A. I. Markosyan, R. G. Paronikyan, R. S. SukasyanAbstract:7,10-Dimethyl-2-thioxo-2,3-dihydro-1 H -spiro[benzo[ h ]Quinazoline-5,1′-cyclohexane]-4(6 H )-one was synthesized from ethyl 4′-amino-5′,8′-dimethyl-1′ H -spiro[cyclohexane-1,2′-naphthalene]-3′-carboxylate and reacted with various alkyl(benzyl)halides to afford a new series of benzo[ h ]Quinazolines containing methyl substituents on the benzene ring. The anti-monoamine-oxidase and anticonvulsant activities of the benzo[ h ]Quinazolines were studied.
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Synthesis, antitumor, and anti-monoamine oxidase properties of 2,4,4-trisubstituted triazolobenzo[h]Quinazolines
Pharmaceutical Chemistry Journal, 2010Co-Authors: A. I. Markosyan, R. S. Sukasyan, F. G. Arsenyan, S. V. Dilanyan, I. S. Sarkisyan, B. T. GaribdzhanyanAbstract:The interaction of 1-amino-3-methyl-3-ethyl-3,4-dihydronaphthaline-2-carbonitrile (I) with propanoic acid chloranhyride was used to synthesize the corresponding amidonitrile II, which was then cyclized to form 2,5-diethyl-5-methyl-4-oxo-5,6-dihydrobenzo[ h ]quinazolin-4(3H)-one (III). Interaction of aminonitrile I with triethylorthoformate and carboxylic acid hydrazides yielded 2-substituted 4-methyl-4-ethyl-4,5-dihydrobenzo[ h ][1, 2, 4] triazolo[1,5- c ]Quinazolines (IV-XVIII). The antitumor and anti-monoamine oxidase properties of the compounds obtained were studied.
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Synthesis and biological properties of 3-phenyl-and 3-phenethyl-5-methyl-5-ethyl-4-oxo-3,4,5,6-tetrahydrobenzo[h]Quinazolines
Pharmaceutical Chemistry Journal, 2008Co-Authors: A. I. Markosyan, R. S. Sukasyan, Kh. S. Akalyan, F. G. Arsenyan, B. T. GaribdzhanyanAbstract:The interaction of 3-methyl-3-ethyl-1-amino-2-ethoxycarbonyl-3,4-dihydronaphthaline with phenyl-and phenethylisothiocyanates and subsequent treatment of the reaction mix with alkali led to the formation of the corresponding 3-phenyl-and 3-phenethyl-5-methyl-5-ethyl-4-oxo-2-thioxo-1,2,3,4,5,6-hexahydrobenzo[ h ]Quinazolines (II, III). Condensation of the resulting 2-thioxobenzo[ h ]Quinazolines II and III with halogenides of different structures was used to synthesize 2-sulfanyl-substituted 5-methyl-5-ethyl-4-oxo-3,4,5,6-tetrahydrobenzo[ h ]Quinazolines (IV–XXVII). Reaction of benzo[ h ]Quinazoline II with 2-ethanolamine and 3-propanolamine yielded 5-methyl-5-ethyl-3-phenyl-2-(β-hydroxyethylamino)-and 5-methyl-5-ethyl-3-phenyl-2-(γ-hydroxypropylamino)-4-oxo-3,4,5,6-tetrahydrobenzo[ h ]Quinazolines (XXVIII, XXIX) respectively. The effects of the resulting compounds on brain monoamine oxidase (MAO) activity were studied in in vitro experiments. Most of the compounds were found to inhibit 5-HT deamination. The antitumor activities of these compounds were studied using two models of grafted mouse tumors — Ehrlich ascites carcinoma (EAC) and sarcoma 180. Some of the study compounds had moderate therapeutic effects (suppressing tumor growth by 50–60%, p < 0.05).
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Synthesis of spiro(benzo[h]Quinazoline-5,1′-cyclohexane) derivatives
Chemistry of Heterocyclic Compounds, 1996Co-Authors: A. I. Markosyan, R. A. Kuroyan, S. V. Dilanyan, L. A. ShirkhanyanAbstract:3-p-Methoxyphenyl-4-oxo-2-mercapto-3, 4, 5, 6-tetrahydrospiro(benzo[h]Quinazoline-4,1 ′-cyclohexane) wassynthesized by the reaction of 4-amino-3-ethoxycarbonvl-1, 2-dihydrospiro(naphthalene-2,1 '-cyclohexane) (1) with p-methoxyphenvl isothiocyanate without separation of the thioureido derivative. Amino ester 1 is transformed byacetamide and formamideinto 2-methyl-4-oxo-3, 4, 5, 6-tetrahydrospiro(benzo[h]Quinazoline-5,1 ′-cyclohexane) and 4-oxo-3, 4, 5, 6-tetrahydrospiro(benzo[h]Quinazoline-5,1′-cyclohexane (11), respectively. Alkylation of Quinazoline 11 with methyl iodide results in formation of 3-methyl-4-oxo-3, 4, 5, 6-tetrahydro-spiro (benzo[h]Quinazoline-5,1 ′-cyclohexane). Amino ester 1 reacts with caprolactam with formation of 2, 3 pentamethylene-4-oxo-3, 4, 5, 6-tetrahydrospiro(benzo[h]Quinazoline-5,1′-cyclohexane). 4-Ethoxymethyleneamino-3-ethoxy-carbonyl-1,2-dihydrospiro(naphthalene-2,1′-cyclohexane) was synthesized by the reaction of amino ester 1 with o-formic ester, and was converted into 3-amino-4-oxo-3, 4,5, 6-tetrahydro-spiro(benzo[h]Quinazoline-5,1′-cyclohexane) (VIII) by hydrazine hydrate. AminoQuinazoline VIII is acylated by acid chlorides with formation of 3-acylamino-4-oxo-3,4,5,6-tetrahydrospiro(benzo[h]Quinazoline-5,1′-cyclohexanes) and forms 3-benzyl-ideneamino-4-oxo-3,4,5,6-teirahydrospiro(benzo[h]Quinazoline-5,1′-cyclohexane) with benzaldehyde.
R. S. Sukasyan - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and Biological Activity of 2-Mercapto-7,10-Dimethyl-3H-Spiro[Benzo[H]Quinazoline-5,1′-Cyclopentane]-4(6H)-One from Ethyl 4′-Amino-5′,8′-Dimethyl-1′H-Spiro[Cyclopentane-1,2′-Naphthalene]-3′-Carboxylate
Pharmaceutical Chemistry Journal, 2018Co-Authors: N. P. Grigoryan, A. I. Markosyan, A. S. Grigoryan, G. A. Stepanyan, R. S. Sukasyan, R. G. ParonikyanAbstract:A synthetic method for 7,10-dimethyl-2-thioxo-2,3-dihydro-1 H -spiro[benzo[ h ]Quinazoline-5,1′-cyclopentane]- 4(6 H )-one from ethyl 4′-amino-5′,8′-dimethyl-1′- H -spiro[cyclopentane-1,2′-naphthalene]-3′-carboxylate was developed. Reaction of the spirobenzo[ h ]Quinazoline with various alkyl(benzyl) halides synthesized a novel series of spirobenzo[ h ]Quinazolines containing methyl substituents on the benzene ring. The antidepressant, anticonvulsant, and antibacterial activities of the synthesized spirobenzo[ h ]Quinazolines were investigated.
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Synthesis, Conversions, and Anti-Monoamine-Oxidase and Anticonvulsant Activity of Ethyl 4′-Amino-5′,8′-Dimethyl-1′H-Spiro[Cyclohexane-1,2′-Naphthalene]-3′-Carboxylate
Pharmaceutical Chemistry Journal, 2017Co-Authors: N. P. Grigoryan, A. I. Markosyan, R. G. Paronikyan, R. S. SukasyanAbstract:7,10-Dimethyl-2-thioxo-2,3-dihydro-1 H -spiro[benzo[ h ]Quinazoline-5,1′-cyclohexane]-4(6 H )-one was synthesized from ethyl 4′-amino-5′,8′-dimethyl-1′ H -spiro[cyclohexane-1,2′-naphthalene]-3′-carboxylate and reacted with various alkyl(benzyl)halides to afford a new series of benzo[ h ]Quinazolines containing methyl substituents on the benzene ring. The anti-monoamine-oxidase and anticonvulsant activities of the benzo[ h ]Quinazolines were studied.
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Synthesis, antitumor, and anti-monoamine oxidase properties of 2,4,4-trisubstituted triazolobenzo[h]Quinazolines
Pharmaceutical Chemistry Journal, 2010Co-Authors: A. I. Markosyan, R. S. Sukasyan, F. G. Arsenyan, S. V. Dilanyan, I. S. Sarkisyan, B. T. GaribdzhanyanAbstract:The interaction of 1-amino-3-methyl-3-ethyl-3,4-dihydronaphthaline-2-carbonitrile (I) with propanoic acid chloranhyride was used to synthesize the corresponding amidonitrile II, which was then cyclized to form 2,5-diethyl-5-methyl-4-oxo-5,6-dihydrobenzo[ h ]quinazolin-4(3H)-one (III). Interaction of aminonitrile I with triethylorthoformate and carboxylic acid hydrazides yielded 2-substituted 4-methyl-4-ethyl-4,5-dihydrobenzo[ h ][1, 2, 4] triazolo[1,5- c ]Quinazolines (IV-XVIII). The antitumor and anti-monoamine oxidase properties of the compounds obtained were studied.
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Synthesis and biological properties of 3-phenyl-and 3-phenethyl-5-methyl-5-ethyl-4-oxo-3,4,5,6-tetrahydrobenzo[h]Quinazolines
Pharmaceutical Chemistry Journal, 2008Co-Authors: A. I. Markosyan, R. S. Sukasyan, Kh. S. Akalyan, F. G. Arsenyan, B. T. GaribdzhanyanAbstract:The interaction of 3-methyl-3-ethyl-1-amino-2-ethoxycarbonyl-3,4-dihydronaphthaline with phenyl-and phenethylisothiocyanates and subsequent treatment of the reaction mix with alkali led to the formation of the corresponding 3-phenyl-and 3-phenethyl-5-methyl-5-ethyl-4-oxo-2-thioxo-1,2,3,4,5,6-hexahydrobenzo[ h ]Quinazolines (II, III). Condensation of the resulting 2-thioxobenzo[ h ]Quinazolines II and III with halogenides of different structures was used to synthesize 2-sulfanyl-substituted 5-methyl-5-ethyl-4-oxo-3,4,5,6-tetrahydrobenzo[ h ]Quinazolines (IV–XXVII). Reaction of benzo[ h ]Quinazoline II with 2-ethanolamine and 3-propanolamine yielded 5-methyl-5-ethyl-3-phenyl-2-(β-hydroxyethylamino)-and 5-methyl-5-ethyl-3-phenyl-2-(γ-hydroxypropylamino)-4-oxo-3,4,5,6-tetrahydrobenzo[ h ]Quinazolines (XXVIII, XXIX) respectively. The effects of the resulting compounds on brain monoamine oxidase (MAO) activity were studied in in vitro experiments. Most of the compounds were found to inhibit 5-HT deamination. The antitumor activities of these compounds were studied using two models of grafted mouse tumors — Ehrlich ascites carcinoma (EAC) and sarcoma 180. Some of the study compounds had moderate therapeutic effects (suppressing tumor growth by 50–60%, p < 0.05).
Mohamed Marzouk - One of the best experts on this subject based on the ideXlab platform.
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biological effects of a new set 1 2 4 triazolo 1 5 a Quinazolines on heart rate and blood pressure
Chemistry Central Journal, 2014Co-Authors: Rashad Alsalahi, Kamaleldin Eltahir, Ibrahim A Alswaidan, Nabih Lolak, Mohammed A Hamidaddin, Mohamed MarzoukAbstract:Several Quinazoline and triazole derivatives are reported to possess a wide-range of interesting pharmacological effects. Although various triazoloQuinazoline subclasses having been synthesized and studied, the preparation of 1,2,4-triazolo[1,5-a]Quinazolines as antihypertensive agent is still relatively unexplored. In continuation of our earlier research, we aimed at the synthesis and development of various potent antihypertensive 1,2,4-triazoloQuinazoline derivatives. A new series of 1,2,4-triazolo[1,5-a]Quinazoline derivatives have been synthesized. Their structures were mainly established by spectroscopic methods of analysis (IR, MS, 1H and 13C NMR). Their in vivo antihypertensive activity was evaluated by tail cuff method using Muromachi Blood Pressure Monitor (Model MK 2000) for rats and mice. Some of the tested compounds were found to exhibit valuable effects in terms of heart rate and blood pressure. According to the biological results, some of tested derivatives have abolished completely the tachycardia of the parent compounds and may be studied and modified as potential adrenoblockers and cardiac stimulant. New series of fifteen 1,2,4-triazolo[1,5-a]Quinazolines were synthesized by convenient methodology from four key molecules, whereby their structures were established by advanced spectroscopic analyses. Some lead compounds have abolished completely the tachycardia of the parent compounds, that may be examined as potent adrenoblockers and some other compounds seem to be a cardiac stimulant or may be modified to enhance their hypotensive activity.
Gordon W Rewcastle - One of the best experts on this subject based on the ideXlab platform.
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tyrosine kinase inhibitors 15 4 phenylamino Quinazoline and 4 phenylamino pyrido d pyrimidine acrylamides as irreversible inhibitors of the atp binding site of the epidermal growth factor receptor
Journal of Medicinal Chemistry, 1999Co-Authors: Jeff B Smaill, Gordon W Rewcastle, Alexander J Bridges, Hairong Zhou, William A. Denny, Brian D Palmer, Dennis Joseph Mcnamara, Ellen Myra Dobrusin, H Hollis D Showalter, Thomas R WintersAbstract:A series of 6- and 7-acrylamide derivatives of the 4-(phenylamino)Quinazoline and -pyridopyrimidine classes of epidermal growth factor receptor (EGFR) inhibitors were prepared from the corresponding amino compounds by reaction with either acryloyl chloride/base or acrylic acid/1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. All of the 6-acrylamides, but only the parent Quinazoline 7-acrylamide, were irreversible inhibitors of the isolated enzyme, confirming that the former are better-positioned, when bound to the enzyme, to react with the critical cysteine-773. Quinazoline, pyrido[3,4-d]pyrimidine, and pyrido[3,2-d]pyrimidine 6-acrylamides were all irreversible inhibitors and showed similar high potencies in the enzyme assay (likely due to titration of the available enzyme). However the pyrido[3,2-d]pyrimidine analogues were 2−6-fold less potent than the others in a cellular autophosphorylation assay for EGFR in A431 cells. The Quinazolines were generally less potent overall toward inhibition...
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tyrosine kinase inhibitors 5 synthesis and structure activity relationships for 4 phenylmethyl amino and 4 phenylamino Quinazolines as potent adenosine 5 triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth facto
Journal of Medicinal Chemistry, 1995Co-Authors: Gordon W Rewcastle, Alexander J Bridges, Hairong Zhou, Donna Reynolds Cody, William A. Denny, Amy McmichaelAbstract:: A series of 4-substituted Quinazolines and related compounds have been prepared and evaluated for their ability to inhibit the tyrosine kinase activity of the epidermal growth factor receptor on a phospholipase C-gamma 1-derived substrate. The results show a narrow structure-activity relationship (SAR) for the basic ring system, with Quinazoline being the preferred chromophore and benzylamino and anilino the preferred side chains. In the 4-anilino series, substitution on the 3-position of the phenyl ring with small lipophilic electron-withdrawing groups provided analogues with enhanced potency. Two series of compounds [4-(phenylmethyl)amino and 4-(3-bromophenyl)amino] were studied to determine SARs for Quinazoline substituents. In the more active 4-(3-bromophenyl)amino series, electron-donating groups (NH2, OMe) at the 6- or 7-position increased activity, in a pattern consistent with a requirement for high electron density in the vicinity of the 8-position of the Quinazoline ring. The 6,7-dimethoxy derivatives were the most effective in both series, with the 4-(3-bromophenyl)amino derivative (3) having an IC50 of 0.029 nM, making it by far the most potent reported inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor enzyme.
Thierry Besson - One of the best experts on this subject based on the ideXlab platform.
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Novel synthesis of angular thiazolo[5,4-f] and [4,5-h]Quinazolines, preparation of their linear thiazolo[4,5-g] and [5,4-g]Quinazoline analogs
Tetrahedron, 2013Co-Authors: Damien Hedou, Rémi Guillon, Charlotte Lecointe, Cedric Logé, Elizabeth Chosson, Thierry BessonAbstract:Synthesis of 9-oxo-8,9-dihydrothiazolo[5,4-f]Quinazoline-2-carbonitrile (1) or 6-oxo-6,7-dihydrothiazolo[4,5-h]Quinazoline-2-carbonitrile (2) was reinvestigated with the ambition of varying the position of the thiazole ring linked to the quinazolin-4-one moiety, in order to synthesize two novel linear tricyclic 8-oxo-7,8-dihydrothiazolo[4,5-g]Quinazoline-2-carbonitrile (3) and 8-oxo-7,8-dihydrothiazolo[5,4-g]Quinazoline-2-carbonitrile (4). The routes described in this paper open the door to various substitutions and transformations for an access to libraries of potent biologically active heterocyclic compounds.
