About Bioline  All Journals  Testimonials  Membership  News

Tropical Journal of Pharmaceutical Research
Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, Nigeria
ISSN: 1596-5996
EISSN: 1596-5996
Vol. 16, No. 5, 2017, pp. 1157-1165
Bioline Code: pr17148
Full paper language: English
Document type: Research Article
Document available free of charge

Tropical Journal of Pharmaceutical Research, Vol. 16, No. 5, 2017, pp. 1157-1165

 en Synthesis and molecular docking of new hydrazones derived from ethyl isonipecotate and their biological activities
Munir, A; Aziz-ur-Rehman; Abbasi, MA; Siddiqui, SZ; Nasir, A; Khan, SG; Rasool, S & Shah, SAA


Purpose: To investigate the antibacterial and α-glucosidase inhibitory activities of hydrazone derivatives (8a-h) of ethyl isonipecotate.
Methods: The reaction of ethyl isonipecotate (2) with 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1) in an aqueous basic medium yielded ethyl 1-[(3,5-dichloro-2-hydroxyphenyl)sulfonyl]piperidin-4-carboxylate (3). Compound 3 was subsequently converted to ethyl 1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carboxylate (5) via O-alkylation. Compound 5 on reaction with hydrated hydrazine yielded 1-[(3,5-dichloro-2-ethoxyphenyl)sulfonyl]piperidin-4-carbohyrazide (6) in MeOH. Target compounds 8a-h were synthesized by stirring 6 with different aromatic aldehydes (7a-h) in MeOH. All the synthesized compounds were structurally elucidated by proton nuclear magnetic resonance (1H-NMR), electron impact mass spectrometry (EI-MS) and infrared (IR) spectroscopy. For antibacterial activity, solutions of the synthesized compounds were mixed with bacterial strains, and the change in absorbance before and after incubation was determined. For enzyme inhibitory activity, change in the absorbance of mixtures of synthesized compounds and enzyme before and after incubation with substrate was determined.
Results: The target compounds were synthesized in appreciable yields and well characterized by spectral data analysis. Salmonella typhi check for this species in other resources was inhibited by 8e (MIC 8.00 ± 0.54 μM), Escherichia coli check for this species in other resources by 8f (8.21 ± 0.83 μM), Bacillus subtilis check for this species in other resources by 8c (8.56 ± 0.63 μM) and Staphylococcus aureus check for this species in other resources by 8c (8.86 ± 0.29 μM). Two compounds, 8e and 8d, were very effective inhibitors of α-glucosidase with IC50 values of 40.62 ± 0.07 and 48.64 ± 0.08 μM, respectively.
Conclusion: Low IC50 values of the synthesized compounds against α-glucosidase demonstrates their potential in type-2 diabetes treatment. Furthermore, these compounds exhibit substantial antibacterial activity against the bacterial strains tested.

Antibacterial activity; α-Glucosidase inhibition; Ethyl isonipecotate; Hydrazones

© Copyright 2017 - Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria.
Alternative site location:

Home Faq Resources Email Bioline
© Bioline International, 1989 - 2024, Site last up-dated on 01-Sep-2022.
Site created and maintained by the Reference Center on Environmental Information, CRIA, Brazil
System hosted by the Google Cloud Platform, GCP, Brazil