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Synthesis of Novel Pyrido[3′,2′:4,5]furo[3,2‐ d ]pyrimidine Derivatives and Their Cytotoxic Activity
Author(s) -
Naresh Kumar R.,
Malla Reddy G.,
Nagendar P.,
Kurumurthy C.,
Shanthan Rao P.,
Karnewar Santosh,
Kotamraju Srigiridhar,
Narsaiah B.
Publication year - 2014
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1833
Subject(s) - chemistry , pyrimidine , carbohydrazide , pyridine , trifluoromethyl , hydrate , cytotoxic t cell , hydrazine (antidepressant) , medicinal chemistry , alkylation , stereochemistry , organic chemistry , catalysis , biochemistry , alkyl , chromatography , in vitro
The 3‐amino‐6‐(trifluoromethyl)furo[2,3‐ b ]pyridine‐2‐carbohydrazide ( 5 ) was prepared from 3‐cyano‐6‐trifluoromethyl‐2(1 H )pyridone ( 2 ) in series of steps via selective O ‐alkylation , Thorpe–Ziegler cyclization followed by reaction with hydrazine hydrate. The 2‐carbohydrazide ( 5 ) was further reacted with aliphatic acids under different reaction temperatures to form a series of novel N ‐acylfuro[2,3‐ b ]pyridine‐2‐carbohydrazide ( 6 ) and pyrido[3′,2′:4,5]furo[3,2‐ d ]pyrimidine derivatives ( 7 ). All the compounds 6 and 7 were screened for cytotoxic activity against breast carcinoma MD Anderson‐Metastatic Breast (MDA‐MB) 231 (aggressive) cell lines at 10 µM concentration. Compounds 6a , 6b , and 6c showed promising activity.