Lewis base-catalyzed synthesis of highly functionalized spirooxindole-pyranopyrazoles and their in vitro anticancer studies

被引：18
|
作者：
Asif, Mohd [1 ]
Aqil, Farrukh [2 ,3 ]
Alasmary, Fatmah Ali [4 ]
Almalki, Amani Salem [4 ]
Khan, Abdul Rahman [1 ]
Nasibullah, Malik [1 ]
机构：
[1] Integral Univ, Dept Chem, Lucknow 226026, UP, India
[2] Univ Louisville, UofL Hlth Brown Canc Ctr, Louisville, KY 40202 USA
[3] Univ Louisville, Dept Med, Louisville, KY 40202 USA
[4] King Saud Univ, Coll Sci, Chem Dept, Riyadh 11451, Saudi Arabia
来源：
MEDICINAL CHEMISTRY RESEARCH | 2023年 / 32卷 / 05期
关键词：
Anticancer activity; Knoevenagel condensation; Michael addition; Multicomponent reactions; Pyranopyrazole; Spirooxindole; INTESTINAL-ABSORPTION; PERMEABILITY; CACO-2; OXINDOLE;
D O I：
10.1007/s00044-023-03053-7
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Herein, the one-step, multi-component reaction (MCR) of a series of spirooxindole-pyranopyrazole derivatives (5a-g), via a Knoevenagel condensation and Michael addition cascade, under mild and green reaction conditions, is reported. The newly synthesized derivatives were screened for in vitro anti-cancer activity against 60 human cancer cell lines at the National Cancer Institute (NCI), USA. We found that compounds 5c, 5d, and 5g showed good activity against the HOP-92 (lung cancer), UO-31 (renal cancer), KM-12, SW-620 (colon cancer), and HS578T (breast cancer) cell lines. Compound 5c showed 43.19 and 21.18% growth inhibition at 10 mu M for HOP-92 and UO-31 cell lines, respectively, while compound 5g showed 82.02% growth inhibition for the KM12 cell line at the same concentration. Therefore, the compound 5g could be further derivatized as a futuristic lead molecule for colorectal cancer.
引用
收藏
页码：1001 / 1015
页数：15
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