Publication: Synthesis and cytotoxicity of novel 2,2'-Bis- and 2,2',2''-Tris-indolyl- methanes-based bengacarboline analogs
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Issued Date
2012
Resource Type
File Type
application/pdf
ISSN
2536269
Other identifier(s)
2-s2.0-84864915962
Rights Holder(s)
มหาวิทยาลัยศรีนครินทรวิโรฒ
Bibliographic Citation
Archives of Pharmacal Research. Vol 35, No.6 (2012), p.949-954
Suggested Citation
Pingaew R., Prachayasittikul S., Ruchirawat S., Prachayasittikul V. Synthesis and cytotoxicity of novel 2,2'-Bis- and 2,2',2''-Tris-indolyl- methanes-based bengacarboline analogs. Archives of Pharmacal Research. Vol 35, No.6 (2012), p.949-954. doi:10.1007/s12272-012-0601-1 Retrieved from: https://hdl.handle.net/20.500.14740/7038
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.
Subject(s)
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
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