New method for chloroamidation of olefins. Application in the synthesis of N-glycopeptides and anticancer agents.
Chloroamidation of olefins using a new reagent system (COCl)2-AgNO3-CH3CN was observed. Various glycals with this reagent system produce 2-chloro-1-acetamido sugars in good yields which, in turn, were converted to free amino derivatives and various glycopeptides. The acetamido sugar derivatives and free amines were found to be promising anticancer agents against the U-87 malignant glyoma (a brain tumor) cell line with IC-50=1 nm-22 microM, and they were found to be far less cytotoxic against a normal human embryonic kidney cell line.
Rawal
Girish K
GK
Department of Chemistry, Indian Institute of Technology, Kanpur-208016, India.
Kumar
Amit
A
Tawar
Urmila
U
Vankar
Yashwant D
YD
D000107:Acetylation; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D002700:Chloramines / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure
D000475:Alkenes; D000970:Antineoplastic Agents; D002700:Chloramines; D006020:Glycopeptides