Synthesis of Newer Indolyl/ Phenothiazinyl Substituted 2-Oxo/ Thiobarbituric Acid Derivatives as Potent Anticonvulsant Agents

Abstract

2-Amino-5-(heteroarylmethylene)-1,3,4-oxadiazoles/thiadiazoles 7-10 were synthesized by cyclisation of 1-(heteroarylacetyl)semicarbazides/thiosemicarbazides 3-6. 5-(2'-Heteroarylmethylene-5'-aminomethylene-1',3,'4'- oxadiazol-2'-yl/thiadiazol-2'-yl)-2-oxo/thiobarbituric acids 11-18 were synthesized by condensation of compounds 7-10 at the 5th position of 2-oxo/thiobarbituric acids. The newly synthesized compounds showed anticonvulsant activity ranging from 50-90% (seizures protection). Compound 18 (5-(2'-phenothiazinylmethylene-5'-aminomethylene-1',3',4'-thiadiazol-2'- yl)-2-thiobarbituric acid) showed maximum activity being more potent than the reference drug phenytoin sodium (CAS 630-93-3).

Synthesis of some new mono, bis-indolo[1, 2-c]quinazolines: evaluation of their antimicrobial studies

“…All 2-(2-arylideneaminophenyl)indole intermediates (1-10) and precursor A exhibit characteristic IR absorption bands in the regions 3330-3400cm -1 and 1540-1560cm -1 indicative of -NH stretching and bending vibrations of indole ring, respectively. 30 The formation of intermediate azomethines (1)(2)(3)(4)(5)(6)(7)(8)(9)(10) disappearance of peaks at 1680-1695 cm -1 for -CHO and 3380-3440 cm -1 for -NH 2 of starting materials and at the same time appearance of band at 1610-1635 cm -1 which is characteristic for -CH=N group. 31 The formation of title compounds (11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were confirmed by the disappearance of the absorption maxima at 3330-3400 cm -1 , which are ascribed to the vibrations of NH group of the indole ring; at the same time the appearance of a new maximum at 1360-1380 cm -1 , which is characteristic for indolo [1,2-c] quinazoline ring with a tertiary nitrogen atom, appears.…”

“…3,4 Due to the structural similarity of indole nuclei with some naturally occurring compounds such as serotonin, tryptamine, hinckdentine A, they can easily interact with biomolecules of the living systems. 5,6 Heterocycles bearing an indole moiety are reported to show a broad spectrum of pharmacological and medicinal properties such as anti-inflammatory, 7,8 anticonvulsant, 9 antimicrobial, 10,11 antimalarial, 12,13 anticancer 14,15 and many other activities.…”

“…Procedure for preparation of mono-2-(2-arylideneamino phenyl) indoles (1)(2)(3)(4)(5)(6)(7)(8)(9)(10) To a solution of precursor 2-(2-aminophenyl)indole (A, 0.416 g, 2 mmol for 1-8 and 0.832 g, 4 mmol for 9-10) in 20-40 mL of ethanol, 2 mmol of Ar-CHO/ CHO-Ar-CHO and few drops of acetic acid was added with vigorous stirring. The reaction mixture was then refluxed for 3 h. After cooling, the deposited solid product was collected by filtration and recrystalized from an ethanol/ dichloromethane-methanol mixture.…”

Synthesis of Some New Heterocyclic Compounds Containing Indole Moeity

“…Therefore Indole derivatives have captured the attention of organic synthetic chemists. Furthermore, indole and its analogs possess a wide spectrum of biological activities such as anti-inflammatory, 1,2 anti-microbial [3][4][5] , anti-bacterial, 6,7 anticonvulsant [8][9][10][11] and cardiovascular 12,13 effect. Indole is a popular component of fragrances and the precursors of many pharmaceuticals.…”

Synthesis of New 2-Substituted Phenyl-1H-Indoles via Fischer Indole Reaction

“…Indole derivatives are used as neuroprotective agent affecting oxidative stress 4 , neurotransmitter serotonin 5 (5-HT 5-hydroxytriptamine) involved in various physiological functions such as appetite, sleep, body temperature, indolodioxane is found to be active hypertensive agent 6 , INF55 is an inhibitor of NorA efflux pump in the human pathogenic bacterium staphylococcus aureus 7 . Different indole derivatives like tryptans are used as antimigrain and anti-inflammatory [8][9] , anticonvulsant 10 , antimicrobial 11 , antimalarial 12 and anticancer 13 . During the past 100 years, considerable attention had been directed towards the synthesis and functionalization of compounds containing the indole skeleton.…”