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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Research Article

New Route to Synthesize Fluorine Substituted Lamotrigine Drug Analogues as an Anti-Inflammatory Agent

Author(s): Mohammad Makki, Dina A. Bakhotmah*, Reda M. Abdel-Rahman and Fisal M. Aqlan

Volume 15, Issue 1, 2018

Page: [116 - 125] Pages: 10

DOI: 10.2174/1570179414666170509151123

Price: $65


Aim and Objective: Lamotrigine antiepileptic drug, 3,5-diamino-6-(2',3'-dichlorophenyl)-1,2,4- triazine is used to treat epilepsy and bipolar disorder, lamotrigine is also effective in treating some diabetic neuropath. Recently, interest has focused on the synthesis of new lamotrigine analogues in view of their biocidal effects. This investigation focused on synthesis of novel fluorine substituted lamotrigine drug analogues using an efficient and environmental friendly process.

Materials and Methods: Synthetic route to fluorinated lamotrigine analogues was furnished by aminolysis and ammionlysis of 6-(2'-amino-5'-fluorophenyl)-3-thioxo-1,2,4-triazin-5(2H,4H)one. The structures of the targets compounds have been deduced upon their elemental analysis and spectral data (UV, IR, 1HNMR, 13CNMR and Mass spectroscopy). The anti-inflammatory activities of the synthesized compounds are also evaluated.

Results: The acute anti-inflammatory activity of the synthesis fluorine substituted lamotrigine analogues was evaluated and showed various anti-inflammatory effects at tested condition. Thus, compounds rich in fluorine showed higher activity in comparison with compounds lethal of fluorine atoms. In addition, compound with - COCF3 exhibited a higher activity over compounds with aromatic –CF. Furthermore, the higher number of fluorine atoms tend to a higher number of enzyme receptors involved in the inflammatory process.

Conclusion: The present study described a simple and new route to synthesize some new fluorine substituted lamotrigine analogues starting from 3-thioxo-1,2,4-triazin-5-one through a simple nucleophilic displacement of SH and OH by amino groups. In addition, this study tends to search for new fluorinated lamotrigine analogues as anti-inflammatory agents. The obtained results revealed that compounds binding to -CF3 are more active in comparison with compound with aromatic –CF.

Keywords: Aminolysis, amminolysis, fluorinated 1, 2, 4-triazine, triazinone, anti-inflammatory activities, drug analogues.

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