Synthesis of New 2-Thio-[1,2,4]triazolo[1,5-c]quinazoline Derivatives and Its Antimicrobial Activity

Antipenko, Lyudmila; Karpenko, Alexander V.; Коваленко, С. И.; Katsev, Andrey M.; Komarovska‐Porokhnyavets, Olena; Novikov, V. A.; Chekotilo, Aleksey

doi:10.1248/cpb.57.580

Cited by 73 publications

(57 citation statements)

References 13 publications

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“…C Synthesis of 3-amino-6-(9-arylidene-3-methyl-5-phenyl-6,7,8,9-tetrahydro-[1,2,4]triazolo [3,4- (8) A mixture of Compound 3 (0.01 mol), 2-chlorobenzaldehyde (0.01 mol), malononitrile (0.01 mol) and ammonium acetate ( 0.01 mol) in alcoholic solution of NaOH was heated under reflux for 6 h, cooled to room -temp, neutralized with dil HCl until precipitation. The product was filtered, collected and recrystallized from ethanol to give compound 8.…”

Section: Synthesis Of 3-(9-arylidene-3-methyl-mentioning

confidence: 99%

“…Quinazoline derivatives, which belong to the N-containing heterocyclic compounds, have caused universal concerns due to their biopharmaceutical activities. Researchers have already determined many therapeutic activities of quinazoline derivatives, including anticancer [1][2][3][4] , antiinflammatory 5,6 , antibacterial [7][8][9][10] , analgesic 5,9 , antiviral 11 , anticytotoxic 12 , antispasm 9,13 , antituberculosis 14 , antioxidant 15 , antimalarial 16 , antihypertension 17 , antiobesity 18 , antipsychotic 19 , anti-diabetics 20 , etc. Medicinal chemists synthesized quinazoline derivatives with different biological activities by installing various active groups to the quinazoline moiety.…”

Section: Introductionmentioning

confidence: 99%

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Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

2017

Chem Sci Trans

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Abstract:The present study deals with the synthesis and reactions of 4-aryl-8-arylidene-3,4,5,6,7,8-hexahydroquinazoline-2-thiol (1). Hydrazinolysis of compound 1 yielded hexahydroquinazolinyl hydrazine 2. Acetylation of compound 2 yielded [1,2,4] triazolo [3,4-b] quinazoline derivative 3. The reaction of compound 2 with diethyl oxalate and ethyl acetoacetate afforded hexahydro quinazolin-2-yl-hydrazinyl-2-oxoacetate 9 and hexahydroquinazolin-2-yl-3-oxobutane hydrazide 10. Treatment of compound 1 with chloroacetyl chloride gave tetrahydro-2H-thiazolo [2,3-b] quinazolin-3(5H)-one 13 which was used as a key for the synthesis of a series of heterocyclic compounds (14-19). The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data. The antioxidant activities of some new synthesized compounds have been screened. Compounds 2, 3, 12, 13, 15, 16 and 19 showed antioxidant activity using the DPPH method.

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Section: Synthesis Of 3-(9-arylidene-3-methyl-mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

2017

Chem Sci Trans

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“…Researchers have already determined many therapeutic activities of quinazoline derivatives, including anticancer [3][4][5][6], antiinflammation [7,8], antibacterial [9][10][11][12], antivirus [13], anticytotoxin [14], antispasm [15], antituberculosis [16], antioxident [17], antimalarial [18], antihypertension [19], antiobesity [20], antipsychotic [21] and antidiabetes [22], etc.…”

mentioning

confidence: 99%

Design, Synthesis and Molecular Properties Prediction of Novel Quinazoline Derivatives as Potent Antibacterial Agents

Eswararao¹,

Venkataramireddy²,

Srinivasareddy³

et al. 2017

Asian J. Chem.

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confidence: 99%

“…Moreover, water may play the role of a nucleophile in hydrolytic cleavage reactions. In this case the reaction proceeds for 1 h and needs acidic catalysis [1,6]. It has been noted that cleavage of the pyridine cycle of 2-aryl- [1,2,4]triazolo [1,5-c]quinazoline is insufficiently known in spite of potentially bioactive products of this transformation.…”

mentioning

confidence: 99%

Hydrolytic cleavage of the pyrimidine ring in 2-aryl-[1,2,4]triazole[1,5-c]quinazolines: physico-chemical properties and the hypoglycemic activity of the compounds synthesized

et al. 2015

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Recent publication describes hydrolytic cleavage of azole and azine condensed cycles under the action of nucleophiles [1,3,6, 4,9,11,12,15,17,20,25,26,28,29]. It is known that kinetics of the reactions mentioned depends on basic properties of nucleophilic reagents. Strong nucleophiles (hydroxides and alkoxides of alkaline metals, hydrazine hydrate) easily react with the given substrates in the water or alcohol-water medium for 1 h and form products with high yields [4,15,20,25,26,28,29]. Moreover, water may play the role of a nucleophile in hydrolytic cleavage reactions. In this case the reaction proceeds for 1 h and needs acidic catalysis [1,6]. It has been noted that cleavage of the pyridine cycle of 2-aryl-[1,2,4]triazolo[1,5-c]quinazoline is insufficiently known in spite of potentially bioactive products of this transformation. In addition, products of the reactions mentioned may take a worth place in the process of development of approaches for forming new heterocyclic systems and drug discovery [2,8,13,18,19, 23,24].Moreover, we found reports where the hypoglycemic activity of derivatives of 1,2,4-triazole were described. Thus, A.K.Mohammed Iqbal and co-authors discussed in their research the hypoglycemic and hypolipidemic action of novel compounds, which molecules contained the thiazolidone fragment attached to the triazole cycle via phenoxyethenthiol "linker" groups [14]. 4-Methyl-3-(R-phenyl-,1-methyl-1Н-indol-4(5)-yl)-5-(R-phenyl-)-4H-1,2,4-triazoles as selective inhibitors of 11β-hydroxysteroid dehydrogenase 1 were described as prospective glucose-lowering agents by Susan D. Aster and co-authors [7], and "ELI LILLY and COMPANY" applied for patent series of 2-R 1 -4-R 2 -5-alkaryl-(alkheteryl-, aryl-(heteryl-) oxy-, aryl-(heteryl-)thio-, aryl-(heteryl-)amino-)-2,4-dihydro-3H-1,2,4-triazol-3-ones(thiones) with high affinity to nuclear hormonal receptors. They may be used for treating diabetes, cardiovascular disorders, obesity, Xsyndrome and gastrointestinal disorders [21, 22], etc.Thus, the aims of the present research were to study the peculiarities of the given type of the reaction, elucidation of the effect of o-, m-, p-substituted aryl moiety in position 2 of [1,2,4]triazolo [1,5-c]quinazolines on the process of the pyrimidine cycle hydrolytic cleavage, as well as the hypoglycemic action of the compounds synthesized.experimental part 1. Chemistry 1.1. General method. Melting points were determined in open capillary tubes and were uncorrected. The ele-

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Synthesis of New 2-Thio-[1,2,4]triazolo[1,5-c]quinazoline Derivatives and Its Antimicrobial Activity

Cited by 73 publications

References 13 publications

Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

Design, Synthesis and Molecular Properties Prediction of Novel Quinazoline Derivatives as Potent Antibacterial Agents

Hydrolytic cleavage of the pyrimidine ring in 2-aryl-[1,2,4]triazole[1,5-c]quinazolines: physico-chemical properties and the hypoglycemic activity of the compounds synthesized

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