Synthesis, evaluation, and molecular properties prediction of substituted cinnamoylpiperazine derivatives as potential antinociceptive and anticonvulsive agents

Synthesis, evaluation, and molecular properties prediction of substituted cinnamoylpiperazine derivatives as potential antinociceptive and anticonvulsive agents

A series of novel cinnamoylpiperazine derivatives ( 5a – 5l ) were synthesized as potential antinociceptive, and anticonvulsive agents. Various heterocyclic systems like piperidine, morpholine, piperazine, and N-arylpiperazine were combined with cinnamoyl or methylenedioxy cinnamoyl moieties to obta...

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Bibliographic Details
Published in:Medicinal chemistry research Vol. 27; no. 6; pp. 1599 - 1608
Main Authors: Prasanthi, Gummalla, Prasad, Kvsrg, Bharathi, Koganti
Format: Journal Article
Language:English
Published: New York Springer US 01-06-2018
Springer Nature B.V
Subjects:
Anticonvulsants
Bioavailability
Biochemistry
Biomedical and Life Sciences
Biomedicine
Capsaicin
Cell Biology
Chemical synthesis
Derivatives
Molecular chains
Molecular properties
Morpholine
Original Research
Pain perception
Pentylenetetrazole
Pharmacology/Toxicology
Piperazine
Piperidine
drug-likeness
anticonvulsant activity
Capsaicin-induced nociception
Cinnamoylpiperazines
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Summary:A series of novel cinnamoylpiperazine derivatives ( 5a – 5l ) were synthesized as potential antinociceptive, and anticonvulsive agents. Various heterocyclic systems like piperidine, morpholine, piperazine, and N-arylpiperazine were combined with cinnamoyl or methylenedioxy cinnamoyl moieties to obtain a series of constrained analogs of cinnamides. Of these, compound 5e possessing 4-fluorophenyl substitution on the piperazine ring exhibited good antinociceptive activity in capsaicin and formalin-induced nociception methods, and also significant anticonvulsant activity in pentylenetetrazole and maximal electroshock-induced seizure methods. Further, all the derivatives were studied for molecular and preadmet properties. The activities of compound 5e were supported by molecular and preadmet properties for its in silico oral bioavailability and drug-likeness.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-018-2175-z