TY - JOUR
T1 - New 2-benzylsulfanyl-nicotinic acid based 1,3,4-oxadiazoles
T2 - Their synthesis and biological evaluation
AU - Patel, Navin B.
AU - Purohit, Amit C.
AU - Rajani, Dhanji P.
AU - Moo-Puc, Rosa
AU - Rivera, Gildardo
N1 - Funding Information:
The authors are thankful to Department of Chemistry, VNSGU, Surat for providing necessary research facilities, Sajjan India Ltd for providing some free chemical samples and NCI, Bethesda, MD, USA for performing the antitumor screening. One of the authors Amit C. Purohit is also thankful to Maa Foundation for providing research scholarship. We also thank CDRI Lucknow for elemental analysis and SAIF Chandigarh for spectral analysis of the compounds.
PY - 2013/4
Y1 - 2013/4
N2 - A novel series of 5-(2-benzylsulfanyl-pyridin-3-yl)-2-(substituted)- sulfanyl-1,3,4-oxadiazoles 6a-j were synthesized from key intermediate 5-(2-benzylsulfanyl-pyridin-3-yl)-3H-[1,3,4]oxadiazole-2-thione 5. Nucleophilic substitution reactions with different electrophiles (E+), such as haloacetate and haloalkyl groups, were performed to get target compounds 6a-j. Compounds were characterized by NMR, mass, IR spectra and C, H, N analyses. All compounds were evaluated for their antimicrobial and antimycobacterial activities; selected analogs were screened for their anticancer activity on 60 tumor cell lines at single dose 1.00-5 M. Unfortunately, none of the compounds showed a significant antitumor activity on 60 human tumor cell lines. However, compounds 6g and 6f with benzothiazole moiety (12.5 and 25 μg/ml) showed promising activity against Escherichia coli compared to ampicillin; compounds 6d, 6j bearing triazole and morpholine, respectively, showed promising antitubercular activity (25 μg/ml) compared to rifampicin.
AB - A novel series of 5-(2-benzylsulfanyl-pyridin-3-yl)-2-(substituted)- sulfanyl-1,3,4-oxadiazoles 6a-j were synthesized from key intermediate 5-(2-benzylsulfanyl-pyridin-3-yl)-3H-[1,3,4]oxadiazole-2-thione 5. Nucleophilic substitution reactions with different electrophiles (E+), such as haloacetate and haloalkyl groups, were performed to get target compounds 6a-j. Compounds were characterized by NMR, mass, IR spectra and C, H, N analyses. All compounds were evaluated for their antimicrobial and antimycobacterial activities; selected analogs were screened for their anticancer activity on 60 tumor cell lines at single dose 1.00-5 M. Unfortunately, none of the compounds showed a significant antitumor activity on 60 human tumor cell lines. However, compounds 6g and 6f with benzothiazole moiety (12.5 and 25 μg/ml) showed promising activity against Escherichia coli compared to ampicillin; compounds 6d, 6j bearing triazole and morpholine, respectively, showed promising antitubercular activity (25 μg/ml) compared to rifampicin.
KW - 1,3,4-Oxadiazoles
KW - 2-Benzylsulfanyl-nicotinic acid
KW - Antimicrobial
KW - Antitubercular activity
UR - http://www.scopus.com/inward/record.url?scp=84874146224&partnerID=8YFLogxK
U2 - 10.1016/j.ejmech.2012.12.055
DO - 10.1016/j.ejmech.2012.12.055
M3 - Artículo
SN - 0223-5234
VL - 62
SP - 677
EP - 687
JO - European Journal of Medicinal Chemistry
JF - European Journal of Medicinal Chemistry
ER -