Synthesis, antimicrobial and anti-inflammatory activities of some new N-substituted sulphonyl indole-3-heterocyclic derivatives

A series of I-substituted sulfonyl indole -3-pyrazolines [4a-j and 5-a-j] and isoxazolines [6a-j] were prepared and tested for their antimicrobial and anti-inflammatory activities. The preparation of compounds 4-6a-j was achieved by treatment of the corresponding chalcones 3a-j with hydrazine hydrate in absolute ethanol, hydrazine hydrate in the presence of glacial acetic acid, and with hydroxylamine hydrochloride in absolute ethanol. The purified products were screened for their antimicrobial activity towards Gram positive, Gram negative bacteria and fungi and also for their anti-inflammatory activity using the carrageenan-induced rat paw oedema. Evaluation of the compounds revealed remarkable antibacterial activity reflected by their ability to inhibit Gram positive and Gram negative bacteria, and also revealed remarkable anti-inflammatory activity reflected by their ability to reduce the carrageenan-induced inflammation in rats

Synthesis and antimicrobial activity of some new heterocycles derived from 1-Benzylindole-3-carboxaldehyde

1-BENZYLINDOLE-3-CARBOXALDEYDE [1] reacted with 2- cyanoaceto-hydrazide to give the pyrazoline derivative 3. its reaction with 3-amino-5-pyrazolinone either in acidic or basic medium gave pyrazoline derivatives 10 and 11, respectively. reaction of 3 with phosphorus oxychloride yielded the 5-choloropyrazoline derivative 4 which was heterocylized in the reaction with hydrazine hydrate, phenylhydrazine or thiourea to give the condensed pyrazolopyrazoles 6 and 7 and pyrazolopyrimidine 9, respectively. on the other hand, cyclization of 10 with malononitrile and 11 with arylidenemaio-nonitrile gave the corresponding pyranopyrazole derivatives 12 and 17a,b, respectively. Compound 14 was obtained via the reaction of 12 with benzene-sulphonyl chloride. Moreover, pyrazole 18, 19, pyrimidine 20, 21 and pyridine 22, 23 derivatives were prepared through cyclization of 1-benzyl-3-indolylidene malononitrile 13 with different amino compounds. The newly synthesized compounds 3-17 showed in vitro potent antifungal activity only towards Candida albicans at MIC 20 and 25 micro g compared with the reference drug Nystatin which showed MIC at 0.3 micro g. They showed slight activities towards gram-negative and gram positive bacteria under test

Vilsmeier - Haack reaction cyclizatlon of N-substituted -3- acetyl indole phenyl hydrazones and their reactions

New 1-phenyl -3- [N-Substitutcd indol- 3-yl] [1H] pyrazolc -4-carboxaldehydes 4a-c were synthesized in 80-85% yield via Vilsmeier - Haack reaction cyclization of N-substitutcd -3- acetyl indole phenyl hydrazones using 2.5 equivalent ratio of phosphrous oxychloride and dimethyl formamide. Reaction of compounds 4a-c with urea, thiourea and different compounds, namely ethyl acetoacetate, acetyl acetone and ethyl cyanoacctatc gave the corresponding pyrimidinc-2-one and pyrimidine-2-thionc derivatives 5a,b-13a,b. Moreover, condensation of compounds 4a-c with active methylene groups of different compounds, namely malononitrile, ethyl cyanoacetate and 2-cyanoacetohydrazide under different conditions led to the formation of pyridine derivatives 15a,b,c-21a,b

Synthesis of 1-benzyl and 1-benzoyl -3-indole derivatives with expected antimicrobial activity

Schiff's bases 2[a,b] were prepared via the reaction of 1-substituted indole-3-carboxaldehydes 1[a,b] with p-methoxyaniline in glacial acetic acid. Electrophilic addition of hydrogen bromide to compounds 2 [a,b] gave 3[a,b], which were reacted with hydrazine hydrate to yield the hydrazino derivatives 4[a,b]. Cyclization of the latter compounds using carbon disulphide and 1,2-dibromoethane gave triazolidine and triazine derivatives 5[a,b] and 6[a,b], respectively. Also, reaction of compounds 2[a,b] with thiosalicylic acid and thioglycolic acid led to the formation of benzothiazinone and thiazolidinone derivatives 7[a,b] and 8[a,b], respectively. Condensation of 8[a,b] with various arylaldehydes gave 9[a,b]-11[a,b] which condensed with hydrazine hydrate and cyclized to afford the fused pyrazolo [3,4-d] thiazole derivatives 12[a,b]-14[a,b]. Moreover, reaction of 8[a,b] with paraformal-dehyde and secondary amines, namely morpholine and N-methyl piperazine gave the corresponding Mannich's products 15[a,b] and 16[a,b], respectively. The newly synthesized compounds were investigated for their antimicrobial activity against Gram-negative and Gram-positive bacteria and Fungi using Naldixic acid, Itraconazole and Nystatin as reference drugs. Some of the synthesized compounds showed high and moderate activity against various tested bacterial and fungal strains. MIC of the highly biological active compounds was also investigated

Synthesis and biological evaluation of 1,2,4 triazole and 1,3,4-Oxa-and Thiadiazoles derivatives

The alkaline hydrolysis with dimethylsulfate and potassium hydroxide of coumarin-6-derivatives [Ia-d] yielded 3-propenoic acid derivatives [IIa-d] which in turn were reached with thionyl chloride in toluene to give carbonyl chloride derivatives [IIa-d]. The latter compounds condensed with thiosemicarbazide in dioxane to give carbonylthiosemicarbazide derivatives [IVa-d], respectively. Cyclization of IVa-d, using sodium hydroxide yielded 5-mercapto- 1,2,4-triazol-3-yl-derivatives [Va-d]. Cyclodehydration of IVa-d using ortho-phosphoric acid or dicyclohexylcarbodiimide [DCC] led to the formation of the corresponding 5-amino-1,3,4-thia and oxadiazol-2-derivatives [VIa-d] and [VIIa-d], respectively. The antimicrobial and antiaflatoxigenic activities of Va-d, VIa-d were also evaluated

Synthesis, antimicrobial and anti-aflatoxigenic activities of new coumarin derivatives

Coumarin-6 sulfonyl chloride [I] reacted with m- or p- aminoacetophenone to give sulfonamide derivatives [IIa, b], which in turn were condensed with semicarbazide to give semicarbazone derivatives [IIIa and IVa], respectively. Also, the sulfonamides [IIa, b], reacted with thiosemicarbazide to give thiosemicarbazone derivatives [IIIb and IVb]. Oxidative cyclization of semicarbazones [IIIa and IVa] or thiosemicarbazones [IIIb and IVb] using thionylchloride led to the formation of 4-substituted-, 1,2,3- thiadiazoles [Va and VIb] using selenium dioxide led to the formation of 4-substituted-1,2,3-selenadiazoles [Vb and VIb], respectively. Also, 4-[6-nitrocoumarin-3-sulfonamido-N-[m- or p- phenylene]]-1,2,3-thiadiazoles [XIa and XIIa] and 1,2,3-selenadiazoles [XIb and XIb] were prepared. The antimicrobial and antiaflatoxigenic activities of thiadiazoles and selenadiazoles were also investigated