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 | [Pakistan Journal of Pharmaceutical Sciences • 2017]

Author(s):

1. Kaniz Rubab: Department of Chemistry, Government College University,Lahore,Pakistan

2. Muhammad Athar Abbasi: Department of Chemistry, Government College University,Lahore,Pakistan

3. Aziz-ur-Rehman: Department of Chemistry, Government College University,Lahore,Pakistan

4. Sabahat Zahra Siddiqui: Department of Chemistry, Government College University,Lahore,Pakistan

5. Syed Adnan Ali Shah: Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia; Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

6. Muhammad Ashraf: Department of Chemistry, The Islamia University of Bahawalpur,Bahawalpur,Pakistan

7. Qurat-ul-Ain: Department of Chemistry, The Islamia University of Bahawalpur,Bahawalpur,Pakistan

8. Irshad Ahmad: Department of Pharmacy; The Islamia University of Bahawalpur,Bahawalpur,Pakistan

9. Muhammad Arif Lodhi: Department of Biochemistry, Abdul Wali Khan University,Mardan,Pakistan

10. Mehreen Ghufran: Department of Biochemistry, Abdul Wali Khan University,Mardan,Pakistan

11. Muhammad Shahid: Department of Biochemistry, University of Agriculture,Faisalabad,Pakistan

12. Hina Fatima: Department of Biochemistry, University of Agriculture,Faisalabad,Pakistan

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 1H-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 a-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.

Page(s): 1263-1274

DOI: DOI not available

Published: Journal: Pakistan Journal of Pharmaceutical Sciences, Volume: 30, Issue: 4, Year: 2017

Keywords:

Antibacterial activity , 21HIndol3ylNunsubstituted phenylmethylideneacetohydrazides , 21HIndol3ylN unsubstituted benzoyl2thienylcarbonylacetohydrazides , Antienzymatic activity , age Hemolytic activity and Computational docking

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