Abstract
Indole-based compounds 30-63 were synthesized by the multi-component 1,3-dipolar cycloaddition reaction of 1-alkyl-3,5-bis(arylidene)-4-piperidones 11-25 with azomethine ylides (generated by the condensation of isatins 26-28 with sarcosine 29). The single crystal X-ray studies of 46 and 48 supported the regio- and stereoselectivity of the reaction. Most of the synthesized spiro-indoles exhibited potent antitumor properties against the HeLa (cervical cancer) cell line through in vitro sulfo-rhodamine-B bioassay, higher than that of cisplatin. Only compound 54 showed bio-potency against the HepG2 (hepatocellular cancer) cell line, comparable to that of doxorubicin hydrochloride (standard reference). 3D-Pharmacophore and 2D-QSAR studies were used to validate the observed biological data and determine the most important parameters controlling activity. The estimated bio-properties from the computational studies showed high approximations to the experimental data.
Original language | English (US) |
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Pages (from-to) | 45434-45451 |
Number of pages | 18 |
Journal | RSC Advances |
Volume | 6 |
Issue number | 51 |
DOIs | |
State | Published - 2016 |
ASJC Scopus subject areas
- General Chemistry
- General Chemical Engineering