Synthesis of novel 1,2,3-triazole tagged pyrazolo[3,4-b]pyridine derivatives and their cytotoxic activity

  • Bioorg Med Chem Lett. 2014 Feb 1;24(3):746-9. doi: 10.1016/j.bmcl.2013.12.107.
Chavva Kurumurthy  1 ,  Banda Veeraswamy  1 ,  Pillalamarri Sambasiva Rao  1 ,  Gautham Santhosh Kumar  1 ,  Pamulaparthy Shanthan Rao  1 ,  Velaturu Loka Reddy  2 ,  Janapala Venkateswara Rao  2 ,  Banda Narsaiah  3
Affiliations
  • 1. Fluoro Organic Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India.
  • 2. Biology division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 607, India.
  • 3. Fluoro Organic Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India. Electronic address: [email protected].
PMID: 24424132 DOI: 10.1016/j.bmcl.2013.12.107
Abstract

A series of novel 1,2,3-triazole tagged pyrazolo[3,4-b]pyridine derivatives 3 and 4 were prepared respectively starting from 6-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-amine 1 via selective N-propargylation, followed by reaction with diverse substituted alkyl/perfluoroalkyl/aryl/aryl amide azides under Sharpless conditions. All the synthesized compounds 3 and 4 were screened for cytotoxic activity against four human Cancer cell lines such as U937, THP-1, HL60 and B16-F10. Compounds 3e, 4g, 4i and 4j which showed promising activity have been identified.

Keywords
1,2,3-Triazoles; Cytotoxic activity; Propargylation; Pyrazolo[3,4-b]pyridine; Sharpless conditions.