Publication: Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4- tetrahydroisoquinoline thiosemicarbazone derivatives
Issued Date
2013-01-01
Resource Type
ISSN
15548120
10542523
10542523
Other identifier(s)
2-s2.0-84872013061
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Mahidol University
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SCOPUS
Bibliographic Citation
Medicinal Chemistry Research. Vol.22, No.1 (2013), 267-277
Suggested Citation
Ratchanok Pingaew, Supaluk Prachayasittikul, Somsak Ruchirawat, Virapong Prachayasittikul Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4- tetrahydroisoquinoline thiosemicarbazone derivatives. Medicinal Chemistry Research. Vol.22, No.1 (2013), 267-277. doi:10.1007/s00044-012-0025-y Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/31565
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Title
Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4- tetrahydroisoquinoline thiosemicarbazone derivatives
Abstract
The modified Pictet-Spengler reaction of phenylethylbenzene sulfonamide with a commercially available glyoxal to construct 1-benzoyl- and 1-acetyl-1,2,3,4-tetrahydroisoquinolines 9a-n has been reported. The reaction could be accomplished, regardless of the oxygenation pattern on the aromatic ring, leading to the N-sulfonyltetrahydroisoquinoline analogs which are versatile intermediates for the synthesis of new thiosemicarbazone analogs of 1,2,3,4-tetrahydroisoquinoline. Bioactivity test revealed that most thiosemicarbazones displayed cytotoxic potency against MOLT-3 cell lines with an IC50less than 20 μg/mL. Significantly, the thiosemicarbazone analog of 1-acetyltetrahydroisoquinoline 9j was the most potent cytotoxic compound against HuCCA-1, HepG2, and MOLT-3 cells. This study provides the novel lead molecules for further development. © 2012 Springer Science+Business Media, LLC.