Synthesis of 3,3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity.
A simple and highly efficient method has been developed for the synthesis of 3,3-diindolyl oxyindoles by the reaction of indoles with isatin or 5-fluoro isatin using a catalytic amount (5 mol%) of FeCl(3) at room temperature in a short reaction time in high yields. All these compounds were evaluated against a panel of five human cancer lines and most of them showed potent cytotoxicity. Compound 4b showed IC(50) of 4.7 and 5 microM against SK-N-SH and DU-145 cell lines, respectively, whereas 4c, 4d, 4f and 4k showed IC(50) of 2.2, 1.2, 3.6 and 3.6 microM, respectively, against DU-145 cell line. Interestingly, some of the compounds are selectively potent in prostate cancer (DU-145) with IC(50) values of 1.2-19.6 microM.
Kamal
Ahmed
A
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, India. ahmedkamal@iict.res.in
Srikanth
Y V V
YV
Khan
M Naseer A
MN
Shaik
Thokhir Basha
TB
Ashraf
Md
M
D045744:Cell Line, Tumor; D002712:Chlorides / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D005290:Ferric Compounds / Q000737:chemistry*; D006801:Humans; D066298:In Vitro Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50
D002712:Chlorides; D005290:Ferric Compounds; D007211:Indoles; C024555:ferric chloride