TY - JOUR
T1 - Synthesis of BF3 catalyzed Mannich derivatives with excellent ee from phenylpropanolamine, study of their antimicrobial activity and molecular docking
AU - Chennakesava Rao, K.
AU - Easwaramoorthi, K.
AU - Arun, Y.
AU - Balachandran, C.
AU - Muralidhara Rao, K. S.
AU - Govindhan, M.
AU - Emi, Nobuhiko
AU - Prakasam, T.
AU - Perumal, P. T.
N1 - Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.
PY - 2015/10/1
Y1 - 2015/10/1
N2 - Antimicrobial agents 4a-g and 5a-g with very good potency were synthesized with 100% ee from phenylpropanolamine (norephedrine) by BF3 catalyzed three components one pot Mannich reaction in good yields. Obtained compounds were characterized using spectral techniques. Antimicrobial study of these compounds revealed a good to very high potential activity against tested microbes when compared to standard antimicrobial drugs streptomycin and ketoconazole. These synthesized compounds exhibited significant minimum inhibitory concentration (MIC) values against Gram positive and Gram negative bacteria. Amongst compound 4b, 4c, 4d, 4e, 5a, and 5e exhibited very high potent MIC values against tested twelve bacteria and three fungi when compared to control. When subjected to molecular docking, in silico studies revealed significant binding energies ranging from -7.06 to -8.90 kcal/mol for all obtained compounds towards target receptor DNA topoisomerase IV and amongst compounds 4b and 4d have shown maximum binding energies 8.70 and 8.90 kcal/mol, respectively.
AB - Antimicrobial agents 4a-g and 5a-g with very good potency were synthesized with 100% ee from phenylpropanolamine (norephedrine) by BF3 catalyzed three components one pot Mannich reaction in good yields. Obtained compounds were characterized using spectral techniques. Antimicrobial study of these compounds revealed a good to very high potential activity against tested microbes when compared to standard antimicrobial drugs streptomycin and ketoconazole. These synthesized compounds exhibited significant minimum inhibitory concentration (MIC) values against Gram positive and Gram negative bacteria. Amongst compound 4b, 4c, 4d, 4e, 5a, and 5e exhibited very high potent MIC values against tested twelve bacteria and three fungi when compared to control. When subjected to molecular docking, in silico studies revealed significant binding energies ranging from -7.06 to -8.90 kcal/mol for all obtained compounds towards target receptor DNA topoisomerase IV and amongst compounds 4b and 4d have shown maximum binding energies 8.70 and 8.90 kcal/mol, respectively.
KW - DNA topoisomerase IV
KW - Lewis acid catalyzed Mannich reaction
KW - Minimum inhibitory concentration
KW - Phenylpropanolamine
KW - Zone of inhibition
UR - http://www.scopus.com/inward/record.url?scp=84945455343&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2015.07.096
DO - 10.1016/j.bmcl.2015.07.096
M3 - Article
C2 - 26296475
AN - SCOPUS:84945455343
SN - 0960-894X
VL - 25
SP - 4232
EP - 4238
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 19
ER -