Citation: Ahmed Kamaal, Dubey Balkrishna, Nadeem Sayyed, Shrivastava Birendra, Sharma Pankaj. p-TSA-catalyzed one-pot synthesis and docking studies of some 5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives as anticonvulsant agents[J]. Chinese Chemical Letters, ;2016, 27(5): 721-725. doi: 10.1016/j.cclet.2016.01.053 shu

p-TSA-catalyzed one-pot synthesis and docking studies of some 5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives as anticonvulsant agents

a.
Department of Pharmaceutical Chemistry, TIT College of Pharmacy, Anand Nagar, Bhopal 462021, Madhya Pradesh, India
b.
Department of Pharmacology, Technocrats Institute of Technology-Pharmacy, Anand Nagar, Bhopal, Madhya Pradesh 462021, India
c.
School of Pharmaceutical Sciences, Jaipur National University, Jaipur Rajasthan, India

Corresponding author: Ahmed Kamaal, kamaal2kamaal@gmail.com
Received Date: 8 April 2015
Revised Date: 2 October 2015
Accepted Date: 6 January 2016
Available Online: 5 May 2016

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The present work describes a facile, one-pot three component environment friendly, green synthesis of a series of 5-(4-methoxyphenyl)-7,7-dimethyl-10-phenyl-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives 8(a-n). 1,3-indanedione, aryl-aldehyde and enaminone was thoroughly ground in the presence of catalytic amount of p-toluene sulfonic acid (p-TSA) to give the titled compounds in good yields. All the synthesized derivatives were evaluated for their anticonvulsant activity using the maximal electroshock (MES) method with phenytoin as a standard drug along with their neurotoxicity effect. Derivatives 8b, 8e and 8k exhibited significant anticonvulsant activity (P<0.001). The neurotoxicity study clearly revealed that all the tested compounds are non-toxic at a dose of 40 mg/kg. The molecular modeling studies also predicted good binding interactions of most active molecules with the serotonin 5-HT_2A receptor. Therefore, it can be safely concluded that synthesized derivatives 8(a-n) would represent useful leads for further investigation in the development of a new class of anticonvulsant agents.
- 5H-Indeno[1,2-b]quinoline,
- One pot,
- p-toluene sulfonic acid (p-TSA),
- Anticonvulsant activity,
- Molecular docking
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