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Title: | Synthesis and cytotoxicity of novel 2,2'-Bis- and 2,2',2''-Tris-indolyl- methanes-based bengacarboline analogs |
Authors: | Pingaew R. Prachayasittikul S. Ruchirawat S. Prachayasittikul V. |
Keywords: | antineoplastic agent bis indolylmethane carboline derivative doxorubicin etoposide silicic acid tris indolylmethane tungstosilicic acid hydrate unclassified drug addition reaction article cell strain HepG2 cell survival controlled study cytotoxicity drug structure drug synthesis elimination reaction Friedel Crafts reaction human human cell IC 50 Antineoplastic Agents Carbolines Cell Survival Dose-Response Relationship, Drug Etoposide Hep G2 Cells Humans Indoles Inhibitory Concentration 50 Molecular Structure |
Issue Date: | 2012 |
Abstract: | Tungstosilicic acid hydrate was employed as an efficient catalyst for the synthesis of bisindolylmethanes 4 using the Friedel-Crafts reaction of N-sulfonyl tryptamine 5 with various aromatic aldehydes, except 3-formylindole. In the excluding case, tris-indolylmethane 7 was formed via a sequential addition-elimination-addition process. The bioactivity test revealed that the phenolic hydroxyl group plays an important role in cytotoxicity; it demonstrated that ortho- and para-hydroxy bis-indolylmethane (BIM) analogs (4b and 4d) displayed cytotoxic potency toward HepG2 (human hepatocellular liver carcinoma cell line) and MOLT-3 (human lymphoblastic leukemia cell line) cancer cell lines. Significantly, both analogs showed slightly higher inhibitory efficacy than the control drug, etoposide, in HepG2 cells, and the analog 4d exhibited the most potent activity against MOLT-3 cell lines, with an IC50 value of 1.62 μg/mL. |
URI: | https://ir.swu.ac.th/jspui/handle/123456789/14328 https://www.scopus.com/inward/record.uri?eid=2-s2.0-84864915962&doi=10.1007%2fs12272-012-0601-1&partnerID=40&md5=cd874f5e13565eacb3e914a762be1583 |
ISSN: | 2536269 |
Appears in Collections: | Scopus 1983-2021 |
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