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Journal of Zhejiang University SCIENCE B 2007 Vol.8 No.1 P.45~55


Microwave-assisted synthesis, anticonvulsant activity and quantum mechanical modelling of N-(4-bromo-3-methylphenyl) semicarbazones

Author(s):  SHALINI Mehta, YOGEESWARI Perumal, SRIRAM Dharmarajan, INDUJA Sridharan

Affiliation(s):  Medicinal Chemistry Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science, Pilani-333031, India

Corresponding email(s):   pyogee@bits-pilani.ac.in

Key Words:  Anticonvulsants, Aryl semicarbazones, Quantum mechanics (QM), Molecular orbital surfaces

SHALINI Mehta, YOGEESWARI Perumal, SRIRAM Dharmarajan, INDUJA Sridharan. Microwave-assisted synthesis, anticonvulsant activity and quantum mechanical modelling of N-(4-bromo-3-methylphenyl) semicarbazones[J]. Journal of Zhejiang University Science B, 2007, 8(1): 45~55.

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author="SHALINI Mehta, YOGEESWARI Perumal, SRIRAM Dharmarajan, INDUJA Sridharan",
journal="Journal of Zhejiang University Science B",
publisher="Zhejiang University Press & Springer",

%0 Journal Article
%T Microwave-assisted synthesis, anticonvulsant activity and quantum mechanical modelling of N-(4-bromo-3-methylphenyl) semicarbazones
%A SRIRAM Dharmarajan
%A INDUJA Sridharan
%J Journal of Zhejiang University SCIENCE B
%V 8
%N 1
%P 45~55
%@ 1673-1581
%D 2007
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2007.B0045

T1 - Microwave-assisted synthesis, anticonvulsant activity and quantum mechanical modelling of N-(4-bromo-3-methylphenyl) semicarbazones
A1 - SHALINI Mehta
A1 - SRIRAM Dharmarajan
A1 - INDUJA Sridharan
J0 - Journal of Zhejiang University Science B
VL - 8
IS - 1
SP - 45
EP - 55
%@ 1673-1581
Y1 - 2007
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.2007.B0045

Objective: To study the effect of halo substitution on disubstituted aryl semicarbazones on the anticonvulsant potential and model the activity based on quantum mechanics. Methods: A series of twenty-six compounds of N4-(4-bromo-3-methylphenyl) semicarbazones were synthesized and evaluated for the anticonvulsant activity in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure threshold tests. Some potential compounds were also tested in the subcutaneous strychnine (scSTY) and subcutaneous picrotoxin (scPIC) seizure threshold tests. The synthesized compounds were tested for behavioral impairment and CNS (central nervous system) depression in mice. Quantum mechanical modelling was carried out on these compounds to gain understanding on the structural features essential for activity. Results: Some compounds possessed broad spectrum anticonvulsant activity as indicated by their effect in pentylenetetrazole, strychnine, picrotoxin and maximal electroshock seizures models in resemblance to other aryl semicarbazone derivatives reported earlier. The higher the difference in HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy levels was, the greater was the activity profile. Conclusion: The pharmacophoric requirements for compounds to exhibit anticonvulsant activity that includes one aryl unit in proximity to a hydrogen donor-acceptor domain and an electron donor have been justified with the molecular orbital surface analysis of the synthesized compounds.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article


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