Synthesis and biological evaluation of novel alkyl amide functionalized trifluoromethyl substituted pyrazolo[3,4-b]pyridine derivatives as potential anticancer agents.
A series of novel alkyl amide functionalized trifluoromethyl substituted pyrazolo[3,4-b]pyridine derivatives 5, 6 and 7 were prepared starting from 6-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-amine 3 via selective N-alkylation, followed by reaction with different primary aliphatic amines, cyclic secondary amines or l-amino acids under different set of conditions. All the synthesized compounds 5, 6 and 7 were screened for anticancer activity against four cancer cell lines such as A549-Lung cancer (CCL-185), MCF7-Breast cancer (HTB-22), DU145-Prostate cancer (HTB-81) and HeLa-Cervical cancer (CCL-2). The compounds 5i and 6e are found to have promising bioactivity at micro molar concentration.
Fluoroorganic Division, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
K
K
Chavva
S
S
Pillalamarri
V
V
Banda
S
S
Gautham
J
J
Gaddamedi
P
P
Yedla
C G
CG
Kumar
N
N
Banda
D000478:Alkylation; D000577:Amides / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D054879:Halogenation; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
C478081:1H-pyrazolo(3,4-b)pyridine; D000577:Amides; D000970:Antineoplastic Agents; D011720:Pyrazoles; D011725:Pyridines
Alkylation; Anticancer activity; Cyclic secondary amines; Primary aliphatic amines; Pyrazolo[3,4-b]pyridine; l-Amino acids