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Synthesis of Functionalized H ‐[1]Benzopyrano[2,3‐ b ]pyridines by the Friedländer Approach: Antimycobacterial and Antimicrobial Profile
Author(s) -
Haveliwala Dhaval D.,
Kamdar Nimesh R.,
Mistry Prashant T.,
Patel Saurabh K.
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200121
Subject(s) - chemistry , malononitrile , antimycobacterial , acetophenone , pyridine , antimicrobial , staphylococcus aureus , candida albicans , stereochemistry , escherichia coli , potency , mycobacterium tuberculosis , medicinal chemistry , in vitro , organic chemistry , microbiology and biotechnology , bacteria , biochemistry , tuberculosis , catalysis , medicine , pathology , biology , gene , genetics
A series of functionalized H ‐[1]benzopyrano[2,3‐ b ]pyridine derivatives were synthesized by the Friedländer reaction of 2‐amino‐4‐oxo‐4 H ‐chromene‐3‐carbonitriles 1 with malononitrile, ethyl cyanoacetate, or acetophenone ( Scheme ). The synthesized compounds 2 – 4 were screened for their in vitro activity against antitubercular, antibacterial, and antifungal species ( Fig., Table ). Among the synthesized compounds, 3c and 4f were the most active with 99% inhibition against Mycobacterium tuberculosis H 37 Rv , while compounds 2f, 3f , and 4d exhibited 69%, 63%, and 61% inhibition, respectively. The 4‐amino‐7,9‐dibromo‐1,5‐dihydro‐2,5‐dioxo‐2 H ‐chromeno[2,3‐ b ]pyridine‐3‐carbonitrile ( 3b ) showed the most potent antibacterial activity against Escherichia coli and Pseudomonas aeruginosa. Several chromeno[2,3‐ b ]pyridine derivatives showed equal or more potency against Staphylococcus aureus and Candida albicans.