Synthesis and in vitro cytotoxic evaluation of some novel hexahydroquinoline derivatives containing benzofuran moiety
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- 作者：Eman M. Mohi El-Deen ; Manal M. Anwar…
- 关键词：1 ; 4 ; 5 ; 6 ; 7 ; 8 ; Hexahydroquinoline ; Benzofuran ; Carbohydrazide derivative ; Substituted pyrazoles ; HepG ; 2 cells
- 刊名：Research on Chemical Intermediates
- 出版年：2016
- 出版时间：March 2016
- 年：2016
- 卷：42
- 期：3
- 页码：1863-1883
- 全文大小：665 KB
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42.K. Berg-Schulz, U. Huber, D. Sprenger, Patent WO 2005080341 A1 (2005) - 作者单位：Eman M. Mohi El-Deen (1)
Manal M. Anwar (1)
Sherifa M. Hasabelnaby (2)
1. Department of Therapeutical Chemistry, National Research Centre, Dokki, Cairo, 12311, Egypt
2. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Helwan University, Helwan, Cairo, 11795, Egypt - 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Catalysis
Physical Chemistry
Inorganic Chemistry - 出版者：Springer Netherlands
- ISSN：1568-5675
文摘
A series of new ethyl 4-(2-(benzofuran-2-yl)-4-substituted-1,4,5,6,7,8-hexahydroquinolin-1-yl)-benzoate 3a–c was synthesized by Michael condensation of benzofuran chalcones 1a–c and cyclohexanone to give 2-(2-benzofuranyl)-4-substituted-5,6,7,8-tetrahydro-4-H -chromene 2a–c, followed by reaction of the latter with ethyl 4-aminobenzoate. Condensation of 3a–c with different amines afforded the corresponding amides 4a–e. On the other hand, upon treatment compounds 3a–c with hydrazine hydrate gave the benzohydrazide derivatives 5a–c. The reaction of compounds 5a–c with different thio/isocyanate gave the corresponding thiosemicarbazide and semicarbazide derivatives 6a–c. Meanwhile compounds 5a–c were reacted with ethyl cyanoacetate and different β-dicarbonyl compounds such as acetyl acetone, ethyl acetoacetate, and diethyl malonate to afford pyrazolyl derivatives 7a, b; 8a, b; 9a, b; and 10a–c, respectively. Moreover, 5a–c were reacted with carbon disulfide to synthesize the corresponding oxadiazolyl derivatives 11a–c, while their condensation with different aromatic aldehydes gave the corresponding Schiff bases 12a–d. Cytotoxic evaluation of some of the newly synthesized compounds against human hepatocellular carcinoma cell lines (HepG-2) revealed that the tested compounds produce promising inhibitory effect against the growth of HepG-2 cells with IC50 values ranged from 11.9 to 19.3 µg/mL.