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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.
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Microwave-assisted synthesis of bioactive Quinazolines and quinazolinones.
Combinatorial Chemistry & High Throughput Screening, 2007Co-Authors: Thierry Besson, Elizabeth ChossonAbstract:This paper aims to review recent developments in the synthesis of Quinazolines and quinazolinone derivatives under conditions that include the application of microwave heating in the ring forming step. Recently, two reviews on the synthesis and chemistry of natural and synthetic Quinazolines and quinazolinones have been published. This review high- lights significant examples where microwave heating has been either synthetically enabling or has provided a key advan- tage over conventional thermal methods. Wherever possible, this review will focus on chemistry carried out using mono- mode systems and well-designed type of instrumentation. The review is grouped according to the main heterocycle types in order of increasing complexity; commencing with Quinazolines and their derivatives. The microwave-assisted synthesis of Quinazolines and quinazolinones will be classified and based on the substitution patterns of the ring system. Syntheses of heterocyclic systems of particular biological or commercial interest are emphasized.
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Novel 6-substituted benzothiazol-2-yl indolo[1,2-c]Quinazolines and benzimidazo[1,2-c]Quinazolines
Tetrahedron, 2003Co-Authors: Stéphane Frère, Valérie Thiéry, Christian Bailly, Thierry BessonAbstract:The synthetic route to and a preliminary biological evaluation of novel indolo[1,2-c]Quinazolines (8) and benzimidazo[1,2-c]Quinazolines (9) are described. The products were obtained by condensation of the appropriate diamines (e.g. 2-(2-aminophenyl)indole or 2-(2-aminophenyl)benzimidazole) with 2-cyanobenzothiazoles. This work further demonstrates the general applicability of microwaves for a facile and rapid access to original heterocycles with potential pharmaceutical value.
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 and psychotropic activity of 5-cyclohexyl-5-methyl-2-sulfanyl-3,4,5,6-tetrahydrobenzo[h]quinazolin-4-one
Pharmaceutical Chemistry Journal, 2011Co-Authors: N. P. Grigoryan, A. I. Markosyan, R. G. Paronikyan, L. A. Tarzyan, R. S. SukasyanAbstract:Ethyl 2-cyano-3-cyclohexyl-3-methyl-4-phenylbutanoate was synthesized from ethyl (2 Z )-2-cyano-3cyclohexylbut-2-enoate using a Grignard reagent. It was shown that the reaction occurred exclusively at the ethylene bond. Because this cyanoester contained two asymmetric centers, PMR spectra showed two diastereoisomeric forms. These were cyclized in the presence of conc. H_2SO_4 into ethyl 4-amino-2-cyclohexyl-2-methyl-1,2-dihydronaphthalenecarboxylate, which was used to synthesize benzo[ h ]Quinazolines, alkyl-substituted benzo[ h ]Quinazolines, triazole, and tetrazole.
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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).
Edward E Korshin - One of the best experts on this subject based on the ideXlab platform.
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an expedient synthesis of 5 substituted imidazo 1 2 c Quinazolines
Synthesis, 2012Co-Authors: Edward E Korshin, Leila A Sabirova, Yakov A LevinAbstract:An efficient three-step synthesis of 5-substituted 2,3-dihydroimidazo[1,2- c ]Quinazolines and imidazo[1,2- c ]Quinazolines was elaborated. 2-(2-Aminophenyl)-4,5-dihydro-1 H -imidazole, prepared by phosphorus pentasulfide catalyzed condensation of 2-aminobenzonitrile with ethylenediamine, smoothly reacted with aldehydes to give the corresponding 2,3,5,6-tetrahydroimidazo[1,2- c ]Quinazolines. The CH–NH fragments of the latter were subjected to selective oxidative dehydrogenation with one equivalent of potassium permanganate on silica gel to give 2,3-dihydroimidazo[1,2- c ]Quinazolines. With two equivalents of potassium permanganate on silica gel, a one-pot exhaustive dehydrogenation to imidazo[1,2- c ]Quinazolines was accomplished.
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 and psychotropic activity of 5-cyclohexyl-5-methyl-2-sulfanyl-3,4,5,6-tetrahydrobenzo[h]quinazolin-4-one
Pharmaceutical Chemistry Journal, 2011Co-Authors: N. P. Grigoryan, A. I. Markosyan, R. G. Paronikyan, L. A. Tarzyan, R. S. SukasyanAbstract:Ethyl 2-cyano-3-cyclohexyl-3-methyl-4-phenylbutanoate was synthesized from ethyl (2 Z )-2-cyano-3cyclohexylbut-2-enoate using a Grignard reagent. It was shown that the reaction occurred exclusively at the ethylene bond. Because this cyanoester contained two asymmetric centers, PMR spectra showed two diastereoisomeric forms. These were cyclized in the presence of conc. H_2SO_4 into ethyl 4-amino-2-cyclohexyl-2-methyl-1,2-dihydronaphthalenecarboxylate, which was used to synthesize benzo[ h ]Quinazolines, alkyl-substituted benzo[ h ]Quinazolines, triazole, and tetrazole.
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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.
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.
