In:
Archiv der Pharmazie, Wiley, Vol. 352, No. 12 ( 2019-12)
Abstract:
A series of new N ‐aryl/aralkyl derivatives of 2‐methyl‐2‐{5‐(4‐chlorophenyl)‐1,3,4‐oxadiazole‐2ylthiol}acetamide were synthesized by successive conversions of 4‐chlorobenzoic acid ( a ) into ethyl 4‐chlorobenzoate ( 1 ), 4‐chlorobenzoylhydrazide ( 2 ) and 5‐(4‐chlorophenyl)‐1,3,4‐oxadiazole‐2‐thiol ( 3 ), respectively. The required array of compounds ( 6a–n ) was obtained by the reaction of 1,3,4‐oxadiazole ( 3 ) with various electrophiles ( 5a–n ) in the presence of DMF ( N , N ‐dimethylformamide) and sodium hydroxide at room temperature. The structural determination of these compounds was done by infrared, 1 H‐NMR (nuclear magnetic resonance), 13 C‐NMR, electron ionization mass spectrometry, and high‐resolution electron ionization mass spectrometry analyses. All compounds were evaluated for their α‐glucosidase inhibitory potential. Compounds 6a, 6c–e, 6g , and 6i were found to be promising inhibitors of α‐glucosidase with IC 50 values of 81.72 ± 1.18, 52.73 ± 1.16, 62.62 ± 1.15, 56.34 ± 1.17, 86.35 ± 1.17, 52.63 ± 1.16 µM, respectively. Molecular modeling and ADME (absorption, distribution, metabolism, excretion) predictions supported the findings. The current synthesized library of compounds was achieved by utilizing very common raw materials in such a way that the synthesized compounds may prove to be promising drug leads.
Type of Medium:
Online Resource
ISSN:
0365-6233
,
1521-4184
DOI:
10.1002/ardp.v352.12
DOI:
10.1002/ardp.201900095
Language:
English
Publisher:
Wiley
Publication Date:
2019
detail.hit.zdb_id:
1496815-0
SSG:
15,3
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