Synthesis and Single Crystal X‐Ray Structure of New (2E)‐2‐[3‐(1H‐Imidazol‐1‐yl)‐1‐phenylpropylidene]‐N‐phenylhydrazinecarboxamide

Mohamed I Attia,Omar A Al-Deeb,Aida A El-Azzouny,Maha S Almutairi,Hoong-Kun Fun,Hazem A Ghabbour

doi:10.1155/2013/515309

Mohamed I Attia, Omar A Al-Deeb + Show 4 more

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https://doi.org/10.1155/2013/515309

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Abstract

Synthesis, spectroscopic characterization and X‐ray crystal structure of a new (2E)‐2‐[3‐(1H‐imidazol‐1‐yl)‐1‐phenylpropylidene]‐N‐phenylhydrazinecarboxamide (4) are reported. The stereochemistry of the title compound 4, C19H19N5O, about the imine bond [1.296 (4) Å] was assigned to have (E)‐configuration. In the urea moiety, the N–H entities are trans to each other, and one of these forms is an intramolecular N–H⋯H hydrogen bond. The compound crystallizes in the monoclinic space group P21/c with a = 5.8093 (2) Å, b = 20.5575 (6) Å, c = 14.0355 (5) Å, α = 90.00°, β = 97.365° (2), γ = 90.00°, V = 1662.36 (10) Å3, and Z = 4. The molecules are packed in crystal structure by weak intermolecular hydrogen interactions.

Highlights

Epilepsy is the most prevalent neurological disorder, affecting nearly 50 million of mankind [1]
Despite significant advances that have been made in epilepsy research, estimates suggest that convulsions in about 30% of epileptics are still inadequately controlled by the available antiepileptic medications [2]
We report a synthetic pathway to achieve arylsemicarbazones incorporating imidazole moiety as hybrid structures which can be screened as new anticonvulsant leads

Summary

Introduction

Epilepsy is the most prevalent neurological disorder, affecting nearly 50 million of mankind [1]. Despite significant advances that have been made in epilepsy research, estimates suggest that convulsions in about 30% of epileptics are still inadequately controlled by the available antiepileptic medications [2]. The patients often suffer side effects from the currently used antiepileptics, such as nausea, headache, anorexia, hepatotoxicity, gingival hyperplasia, and hirsutism [3,4,5]. There is a substantial demand for the development of more effective and safer antiepileptic therapies. Nafimidone (I) and danzimol (II) (Figure 1) are two representatives of this class of anticonvulsants that are independently discovered. We report a synthetic pathway to achieve arylsemicarbazones incorporating imidazole moiety as hybrid structures which can be screened as new anticonvulsant leads. The (E)-configuration of the title compound 4, namely, (2E)-2-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]N-phenylhydrazinecarboxamide (4), was established via its single crystal X-ray structure

Experimental

Results and Discussion

Conclusion