TY - JOUR
T1 - Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds
T2 - A new class of antimicrobials and antioxidants
AU - Rangaswamy, Javarappa
AU - Kumar, Honnaiah Vijay
AU - Harini, Salakatte Thammaiah
AU - Naik, Nagaraja
N1 - Publisher Copyright:
© 2014 King Saud University
PY - 2017/5
Y1 - 2017/5
N2 - A new class of functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds (4a–q) was synthesized by a four step reaction in good yields. Initially, o-alkyl derivative of salicyaldehyde (1) readily furnished corresponding 2-acetyl benzofuran (2) on treatment with potassium tert-butoxide (t-BuOK) in the presence of molecular sieves. Further, Claisen–Schmidt condensation reaction with 4-methoxy benzaldehyde and hydrazine hydrate followed by coupling of benzoyl chlorides afforded target compounds (4a–q). Representative of the synthesized compounds was characterized by IR, 1H NMR, 13C NMR, mass, elemental analysis and evaluated for antimicrobial and antioxidant activities. The results gathered are allowed to conclude that, all newly synthesized analogues exhibit a certain degree of antimicrobial and antioxidant activities. Among the analogues, compounds (4h) and (4j) showed an excellent antimicrobial activity in the well plate method. Meanwhile, compounds (4e–f), (4l) and (4p) showed good antioxidant activity, whereas compound (4g) and (4q) displayed dominant antioxidant efficacy compared to standard butylated hydroxy anisole (BHA).
AB - A new class of functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds (4a–q) was synthesized by a four step reaction in good yields. Initially, o-alkyl derivative of salicyaldehyde (1) readily furnished corresponding 2-acetyl benzofuran (2) on treatment with potassium tert-butoxide (t-BuOK) in the presence of molecular sieves. Further, Claisen–Schmidt condensation reaction with 4-methoxy benzaldehyde and hydrazine hydrate followed by coupling of benzoyl chlorides afforded target compounds (4a–q). Representative of the synthesized compounds was characterized by IR, 1H NMR, 13C NMR, mass, elemental analysis and evaluated for antimicrobial and antioxidant activities. The results gathered are allowed to conclude that, all newly synthesized analogues exhibit a certain degree of antimicrobial and antioxidant activities. Among the analogues, compounds (4h) and (4j) showed an excellent antimicrobial activity in the well plate method. Meanwhile, compounds (4e–f), (4l) and (4p) showed good antioxidant activity, whereas compound (4g) and (4q) displayed dominant antioxidant efficacy compared to standard butylated hydroxy anisole (BHA).
KW - Antimicrobial activity
KW - Antioxidant activity
KW - Benzofuran
KW - Benzoyl chlorides
KW - Free radicals
KW - Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds
UR - http://www.scopus.com/inward/record.url?scp=84887097545&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84887097545&partnerID=8YFLogxK
U2 - 10.1016/j.arabjc.2013.10.012
DO - 10.1016/j.arabjc.2013.10.012
M3 - Article
AN - SCOPUS:84887097545
SN - 1878-5352
VL - 10
SP - S2685-S2696
JO - Arabian Journal of Chemistry
JF - Arabian Journal of Chemistry
ER -