Publication: Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4- tetrahydroisoquinoline thiosemicarbazone derivatives
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Issued Date
2013
Resource Type
File Type
application/pdf
ISSN
10542523
Other identifier(s)
2-s2.0-84872013061
Rights Holder(s)
มหาวิทยาลัยศรีนครินทรวิโรฒ
Bibliographic Citation
Medicinal Chemistry Research. Vol 22, No.1 (2013), p.267-277
Suggested Citation
Pingaew R., Prachayasittikul S., Ruchirawat S., Prachayasittikul V. Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4- tetrahydroisoquinoline thiosemicarbazone derivatives. Medicinal Chemistry Research. Vol 22, No.1 (2013), p.267-277. doi:10.1007/s00044-012-0025-y Retrieved from: https://hdl.handle.net/20.500.14740/6792
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 IC50 less 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.
Subject(s)
1 acetyl 6,7 dimethoxy n 4 methoxybenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 acetyl 6,7 dimethoxy n 4 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 acetyl n 3 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 acetyl n 4 methoxybenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 acetyl n 4 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl 6,7 dimethoxy n 4 chlorobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl 6,7 dimethoxy n 4 methoxybenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl 6,7 dimethoxy n 4 methylbenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl 6,7 dimethoxy n 4 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl n 4 methoxybenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl n 4 methylbenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl n 4 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
Antineoplastic agent
Doxorubicin
Etoposide
Thiosemicarbazone derivative
Unclassified drug
Antineoplastic activity
Article
Controlled study
Cytotoxicity
Drug activity
Drug potency
Drug synthesis
Human
Human cell
IC 50
Oxygenation
Pictet Spengler reaction
1 acetyl 6,7 dimethoxy n 4 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 acetyl n 3 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 acetyl n 4 methoxybenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 acetyl n 4 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl 6,7 dimethoxy n 4 chlorobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl 6,7 dimethoxy n 4 methoxybenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl 6,7 dimethoxy n 4 methylbenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl 6,7 dimethoxy n 4 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl n 4 methoxybenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl n 4 methylbenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
1 benzoyl n 4 nitrobenzenesulfonyl 1,2,3,4 tetrahydroisoquinoline thiosemicarbazone
Antineoplastic agent
Doxorubicin
Etoposide
Thiosemicarbazone derivative
Unclassified drug
Antineoplastic activity
Article
Controlled study
Cytotoxicity
Drug activity
Drug potency
Drug synthesis
Human
Human cell
IC 50
Oxygenation
Pictet Spengler reaction