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Ultrasound assisted, synthesis of N ‐(7‐(R)‐2‐oxa‐8‐azabicyclo[4.2.0]octan‐8‐yl)isonicotinamide derivatives and their biological evaluation
Author(s) -
Chavan Pravin,
Salve Amol,
Jadhav Shivaji,
Pansare Dattatraya,
Rai Megha
Publication year - 2020
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.3860
Subject(s) - azetidine , chemistry , dihydropyran , antibacterial activity , catalysis , cycloaddition , proton nmr , antimicrobial , staphylococcus aureus , stereochemistry , combinatorial chemistry , organic chemistry , bacteria , biology , genetics
In this study, new series of azetidine derivatives were synthesized ( 4a‐n ) from isoniazide ( 1 ), Aromatic aldehydes ( 2a‐n ), dihydropyran ( 3 ) using SnCl 2 catalyst, via one pot multicomponent reaction/cycloaddition reaction. The synthesized azetidine derivatives were characterized by IR, 1 H NMR and 13 C NMR and have been screened for antimicrobial, antituberculosis and anti‐inflammatory activities. In relation to Staphylococcus aureus (ATCC 25923) promising antibacterial activity was shown, compounds 4e and 4k , followed by compounds 4h , 4n , 4f , 4g and 4l . The synthesized azetidine derivatives, 4a , 4e , 4j and 4m (with zone 12 mm) displayed antituberculosis activity. But its lower potential than, the standard streptomycin (with zone 18 mm). Further 4d compound alone displayed similar activity.