title: An efficient one-pot synthesis of benzothiazolo-4β-anilino-podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity.
abstract: An efficient one-pot iodination methodology for the synthesis of benzothiazolo-4β-anilino-podophyllotoxin (5a-h) and benzothiazolo-4β-anilino-4-O-demethylepipodophyllotoxin (6a-h) congeners has been successfully developed by using zirconium tetrachloride/sodium iodide. Interestingly, this protocol demonstrates enhancement of stereoselectivity apart from the improvement in the yields in comparison to previous methods reported for such related podophyllotoxin derivatives. These compounds have been designed and synthesized using association strategy by coupling of 4β-podophyllotoxin and 4β-demethylepipodophyllotoxin with a variety of substituted aminoaryl benzothiazoles. Some of the representative compounds have been evaluated for their cytotoxicity against selected human cancer cell lines and DNA topoisomerase-II inhibition activity.
authors.affiliation: Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 607, India. ahmedkamal@iict.res.in
authors.forename: Ahmed
authors.initials: A
authors.lastname: Kamal
authors.forename: B Ashwini
authors.initials: BA
authors.lastname: Kumar
authors.forename: Paidakula
authors.initials: P
authors.lastname: Suresh
authors.forename: Nagula
authors.initials: N
authors.lastname: Shankaraiah
authors.forename: M Shiva
authors.initials: MS
authors.lastname: Kumar
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000627:therapeutic use / Q000633:toxicity; D052160:Benzothiazoles / Q000737:chemistry*; D045744:Cell Line, Tumor; D002712:Chlorides / Q000737:chemistry; D004250:DNA Topoisomerases, Type II / Q000737:chemistry* / Q000378:metabolism; D054879:Halogenation; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D011034:Podophyllotoxin / Q000737:chemistry* / Q000627:therapeutic use / Q000633:toxicity; D059005:Topoisomerase II Inhibitors / Q000138:chemical synthesis* / Q000627:therapeutic use / Q000633:toxicity; D015040:Zirconium / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D052160:Benzothiazoles; D002712:Chlorides; D059005:Topoisomerase II Inhibitors; D015040:Zirconium; D004250:DNA Topoisomerases, Type II; D011034:Podophyllotoxin; C429984:zirconium chloride