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Synthesis, pharmacological screening and computational analysis of some 2-(1H-Indol-3-yl)-N'-((un)substituted phenylmethylidene) acetohydrazides and 2-(1H-Indol-3-yl)-N'-((un)substituted benzoyl/2- thienylcarbonyl)acetohydrazides.

Authors :
Rubab, Kaniz
Abbasi, Muhammad Athar
Rehman, Aziz-ur
Siddiqui, Sabahat Zahra
Shah, Syed Adnan Ali
Ashraf, Muhammad
Ain, Qurat-ul
Ahmad, Irshad
Lodhi, Muhammad Arif
Ghufran, Mehreen
Shahid, Muhammad
Fatima, Hina
Source :
Pakistan Journal of Pharmaceutical Sciences; Jul2017, Vol. 30 Issue 4, p1263-1274, 12p, 8 Diagrams, 1 Chart
Publication Year :
2017

Abstract

The undertaken research was initiated by transforming 2-(1H-Indol-3-yl)acetic acid (1) in catalytic amount of sulfuric acid and ethanol to ethyl 2-(1H-Indol-3-yl)acetate (2), which was then reacted with hydrazine monohydrate in methanol to form 2-(1H-Indol-3-yl)acetohydrazide (3). Further, The reaction scheme was designed into two pathways where, first pathway involved The reaction of 3 with substituted aromatic aldehydes (4a-o) in methanol with few drops of glacial acetic acid to generate 2-(1H-Indol-3-yl)-N-[(un)substitutedphenylmethylidene]acetohydrazides (5a-o) and in second pathway 3 was reacted with acyl halides (6a-e) in basic aqueous medium (pH 9-10) to afford 2-(1H-Indol-3-yl)- N-[(un)substitutedbenzoyl/2-thienylcarbonyl]acetohydrazides (7a-e). All The synthesized derivatives were characterized by IR, EI-MS and <superscript>1</superscript>H-NMR spectral techniques and evaluated for their anti-bacterial potentials against Gram positive and Gram negative bacterial strains and it was found that compounds 7a-d exhibited antibacterial activities very close to standard Ciprofloxacin. The synthesized derivatives demonstrated moderate to weak antienzymatic potential against α-Glucosidase and Butyrylcholinesterase (BChE) where, compounds 7c and 5c exhibited comparatively better inhibition against these enzymes respectively. Compounds 7a, 7d and 7e showed excellent antienzymatic potentials against Lipoxygenase (LOX) and their IC50 values were much lower than the reference standard Baicalein. Enzyme inhibitory activities were also supported by computational docking results. Compounds 5c, 7a, 7b and 7c also showed low values of % hemolytic activity as well, showing that these molecules were not toxic, indicating that these molecules can be utilized as potential therapeutic agents against inflammatory ailments. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
1011601X
Volume :
30
Issue :
4
Database :
Supplemental Index
Journal :
Pakistan Journal of Pharmaceutical Sciences
Publication Type :
Academic Journal
Accession number :
123792149