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p-TSA catalyzed synthesis of 4-aryl-2,7,7-trimethyl-5-oxo-N-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides derivatives as CNS active agents and molecular docking studies | Abstract

Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

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Abstract

p-TSA catalyzed synthesis of 4-aryl-2,7,7-trimethyl-5-oxo-N-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides derivatives as CNS active agents and molecular docking studies

Author(s): Kamaal Ahmed, Amit K. Jain, Balkrishna Dubey, Birendra Shrivastava, Pankaj Sharma and Sayyed Nadeem

A facile and efficient synthetic route to 4-aryl-2,7,7-trimethyl-5-oxo-N-phenyl-1,4,5,6,7,8-hexahydroquinoline-3- carboxamides has been developed via four-component condensation reactions of aldehydes, dimedone, acetoacetanilide and ammonium acetate in the presence of p-toluenesulfonic acid (p-TSA) catalyst in ethanol at ambient temperature through grinding. Simple work-up procedure, environmentally friendly, inexpensive and nontoxic catalyst, rapid reaction along with excellent product yields is the significant features of this practical method. Some hexahydroquinolines derivatives have been designed (7a-f) based on the in silico docking studies using the crystal structure of A1 adenosine receptor (PDB ID: 3QAK) employing GLIDE v5 standard docking program (Schrodinger Inc.). All the designed compounds showed binding affinities as well as interactions with all the crucial amino acid residues on par with the reference standard (Fluoxetine). Compounds which were predicted to have good binding affinity (docking score) were considered for further MDA and histological studies


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