Synthesis of novel 5,6,7,8,9,10-hexahydropyrimido[4,5-b]quinoline derivatives for antimicrobial and anti-oxidant evaluation

Autor: Rasha S. Gouhar, Mohsen M. Kamel, Wael S. I. Abou-Elmagd, Dina H. El-Ghonamy, Magdy I. El-Zahar
Rok vydání: 2016
Předmět:
Zdroj: Research on Chemical Intermediates. 43:1301-1327
ISSN: 1568-5675
0922-6168
DOI: 10.1007/s11164-016-2699-0
Popis: Because of the well-known chemotherapeutic activity of pyrimidoquinolines, a new series of the title compounds were synthesized and biologically screened for their antimicrobial and anti-oxidant activities. The intermediate compound, 2-amino-1-cyclohexyl-4-(3,4-dimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (2), was prepared and allowed to react with oxalyl chloride to give the corresponding strategic starting material, 10-cyclohexyl-5-(3,4-dimethoxyphenyl)-4-oxo-3,4,5,6,7,8,9,10-octahydropyrimido[4,5-b]quinoline-2-carbonyl chloride 3. Compound 3 underwent diverse reactions with amines to give the corresponding carboxylic amides 4, with alcohols to give the carboxylic esters 5 and with hydrazine to give the carbohydrazide 8. Compound 8 reacted with aldoses to give the corresponding polyhydroxy(-)alkyl Schiff bases 9, which upon reaction with thioglycolic acid afforded the thiazolidinone-C-acyclic nucleosides 10. Several other pyrimidoquinolines incorporated to oxadiazole, iminothiazolidinones and thiadiazoles were synthesized starting from the 2-carbohydrazide derivative 8. Most of the newly prepared derivatives showed considerable antimicrobial activity against Gram +ve and Gram −ve bacteria and anti-oxidant activity.
Databáze: OpenAIRE
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