Synthesis and biological evaluation of potent benzoselenophene and heteroaromatic analogues of (S)-1-(chloromethyl)-8-methoxy-2,3-dihydro-1H-benzo[e]indol-5-ol (seco-MCBI)
| Autor: | Dongyeol Lim, Rashmi Dubey, Ganesh A. Sable, Amol Mhetre, Heekyoung Yang, Kyoungmin Lee, Hangeun Lee, Do-Hyun Nam, Eppakayala Sreedhar |
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| Rok vydání: | 2019 |
| Předmět: |
Chemistry
Stereochemistry General Chemical Engineering Substituent Biological activity 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Cell culture Potency Cancer cell lines 0210 nano-technology Cytotoxicity Biological evaluation Conjugate |
| Zdroj: | RSC Advances. 9:29023-29036 |
| ISSN: | 2046-2069 |
| Popis: | A diverse series of compounds (18a–x) were synthesized from (S)-1-(chloromethyl)-8-methoxy-2,3-dihydro-1H-benzo[e]indol-5-ol (seco-MCBI) and benzoselenophene or heteroaromatic acids. These new compounds were evaluated for their cytotoxicity against the human gastric NCI-N87 and human ovarian SK-OV3 cancer cell lines. The incorporation of a methoxy substituent at the C-7 position of the seco-CBI unit enhances the cytotoxicity through its additional van der Waals interaction and gave a much higher potency than the corresponding seco-CBI-based analogues. Similarly, the seco-MCBI-benzoselenophene conjugates (18h–x) exhibited substitution effects on biological activity, and the N-butyramido and N-methylthiopropanamido analogues are highly potent, possessing >77- and >24-fold better activity than seco-MCBI-TMI for the SK-OV3 and NCI-N87 cell lines, respectively. |
| Databáze: | OpenAIRE |
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