TY - JOUR
T1 - Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives
T2 - As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility
AU - Rangaswamy, Javarappa
AU - Vijay Kumar, Honnaiah
AU - Harini, Salakatte Thammaiah
AU - Naik, Nagaraja
PY - 2012/7/15
Y1 - 2012/7/15
N2 - In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively.
AB - In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively.
KW - Antimicrobial activity
KW - Antioxidant activity
KW - Benzofuran based 1,3,5-substituted pyrazole analogues
KW - Substituted anilines
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U2 - 10.1016/j.bmcl.2012.05.061
DO - 10.1016/j.bmcl.2012.05.061
M3 - Article
C2 - 22695127
AN - SCOPUS:84863440889
SN - 0960-894X
VL - 22
SP - 4773
EP - 4777
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 14
ER -