PHARMACIE GLOBALE INTERNATIONAL JOURNAL OF COMPREHENSIVE PHARMACY SYNTHESIS AND EVALUATION OF SOME NEW QUINOLINE AND PYRIDO[2,3-b]INDOLE DERIVATIVES (original) (raw)
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Research: SYNTHESIS AND EVALUATION OF SOME NEW QUINOLINE AND PYRIDO[2,3-B]INDOLE DERIVATIVES
Reaction of aryl compounds containing primary amine with acetic anhydride gave the compound 1(a-f) and 4(a-f). Which on further treatment with Vilsmeier–Haack reagent (DMF+ POCl3) gave the fused pyridine ring by cyclization, which gave compound 2-chloroquinoline-3-carbaldehyde 2a-f and 2-chloro-9H-pyrido [2,3-b]indole-3-carbaldehyde 5a-f respectively. These compounds were containing the free aldehyde group in their structure which form schiff base on treatment with the different substituted aniline this was because off the presence of primary amine group. These compounds were containing quinoline (3a-f) and pyrido indole (6a-f) with schiff base (substituted –N-((2-chloroquinolin-3-yl) methylene)benzenamine 3a-f and substituted –N-((2-chloro-9H-pyrido[2,3-b]indol-3-yl) methylene)benzenamine 6a-f) which showed antimicrobial activity due to the presence of these potent groups in their structure.
2008
[1,4]Diazepino[2,3-h]quinolone carboxylic acid 3 and its benzo-homolog tetrahydroquino[7,8-b]benzodiazepine-3-carboxylic acid 5 were prepared via PPAcatalyzed thermal lactamization of the respective 8-amino-7-substituted-1,4-dihydroquinoline-3-carboxylic acid derivatives 8, 10. The latter compounds were obtained by reduction of their 8-nitro-7-substituted-1,4-dihydroquinoline-3-carboxylic acid precursors 7, 9 which, in turn, were prepared by reaction of 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydroquinoline-3-carboxylic acid (6) with each of β-alanine and anthranilic acid. All intermediates and target compounds were characterized using elemental analysis, NMR, IR and MS spectral data. The prepared targets and the intermediates have shown interesting antibacterial activity mainly against Gram positive strains. In particular, compound 8 showed good activity against S. aureus (MIC = 0.39 µg/mL) and B. subtilis (MIC = 0.78 µg/mL). Compounds 5a and 9 have also displayed good antifungal activity against C. albicans (MIC = 1.56 µg/mL and 0.78 µg/mL, respectively
Bulletin of Pharmaceutical Sciences. Assiut
Vilsmeier formylation of acetanilide I followed by treatment with hydroxylamine produced 2-chloroquinoline-3-carbonitrile II that was condensed with different amines to give 2substituted aminoquinolines-3-carbonitriles III. Treatment of II with thiourea yielded 2mercaptoquinoline-3-carbonitrile IV, which was converted to its potassium salt V that was condensed with some chloroacetate esters to produce 2-substituted thioquinoline-3carbonitriles VI. Hydrazinolysis of II or IV gave 1H-pyrazolo[3,4-b]quinolin-3-ylamine VII. Condensation of VII with different aryl aldehydes resulted in the corresponding imines VIII. Treatment of VII with p-chloro-benzoyl chloride afforded the amide IX. Some of the synthesized compounds were evaluated for their antibacterial and antifungal activity.
Acta Pharmaceutica, 2010
Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivativesStarting from 1-benzyl- (2a) and 1-benzoyl-3-bromoacetyl indoles (2b) new heterocyclic, 2-thioxoimidazolidine (4a, b), imidazolidine-2,4-dione (5a, b), pyrano(2,3-d)imida-zole (8a, band9a, b), 2-substituted quinoxaline (11a, b-17a, b) and triazolo(4,3-a)quinoxaline derivatives (18a, band19a, b) were synthesized and evaluated for their antimicrobial and anticancer activities. Antimicrobial activity screening performed with concentrations of 0.88, 0.44 and 0.22 μg mm-2showed that 3-(1-substituted indol-3-yl)quinoxalin-2(1H)ones (11a, b) and 2-(4-methyl piperazin-1-yl)-3-(1-substituted indol-3-yl) quinoxalines (15a, b) were the most active of all the tested compounds towardsP. aeruginosa, B. cereusandS. aureuscompared to the reference drugs cefotaxime and piperacillin, while 2-chloro-3-(1-substituted indol-3-yl)quinoxalines (12a, b) were the most active against C.albicanscompared to th...
Synthesis and Antimicrobial Activities of New Indolyl -Pyrimidine Derivatives
2011
The purpose of research was to synthesize a series of new indolyl-pyrimidine-5carbonitriles 2-5 from compound 1.The reaction of 2a with ethylcyanoacetate and aromatic aldehydes in presences of excess ammonium acetate gives 6 a-c while condensation with aromatic aldehydes produces chalcones 7a-c via the Claisen condensation .Structure of the synthesized compounds was confirmed by means of their IR, 1 H-NMR spectral data and elemental analysis .The antimicrobial testing of the synthesized compounds were evaluated. Some of the prepared compounds, 2-(1H-indol-3-yl)-4, 6-dioxo-6, 11-dihydro-4H-pyrimido [2, 1-b] quinazoline-3-carbonitrile 3 and 2-hydrazino-4-(1H-indol-3-yl)-6-oxo-1,6dihydropyrimidine-5-carbonitrile 4 showed high antibacterial activity. Melting points of the synthesized compounds were determined by open end capillary tube method in Boetius melting point microscope and are uncorrected. The purity of the compounds was checked using precoated TLC plates (Merck 60 F254) using chloroform: methanol (3:1) solvent system. The structures of the compounds were characterized by Beckman Infrared Spectrophotometer PU9712 using KBr discs. The structures of the compounds were elucidated by 1 H NMR (Proton Nuclear Magnetic Resonance). The molecular weights of compound were determined by SSQ7000 mass spectrometer at 70 eV. 1 H NMR spectra were recorded on JoelEX270MHz spectrometer using TMS as internal standard. All the new compounds gave satisfactory analytical results (within 0.4 of the theoretical values). All the synthesized compounds (1-7) were purified by successive recrystallization. The purity of the synthesized compounds was checked by performing TLC. The structures of the synthesized compounds were determined on the basis of their FTIR and 1 HNMR data. In accordance with the data obtained from antimicrobial activity, most of the synthesized compounds have shown moderate activity against the tested bacteria while compounds 2-(1H-indol-3-yl)-4, 6-dioxo-6, 11-dihydro-4H-pyrimido [2, 1-b]quinazoline-3-carbonitrile (3) and 2-hydrazino-4-(1H-indol-3-yl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile (4) showed high antibacterial acivity. Only compounds 1,3,4,7a,7 b and 7c are active against C.albicans.
Archiv der Pharmazie, 2002
The synthesis and in vitro antimicrobial evaluation of several quinoline and pyrimidoquinoline derivatives are described. Treatment of 7-substituted quinolin-2(1H)-one-3-carboxylic acids 2 a-c with phosphoryl chloride or thionyl chloride gave rise to the 7-substituted 2-chloroquinoline-3-carboxylic acids 3 a-c and 7-substituted 2-chloro-3-chlorocarbonylquinolines 5 a-c respectively. The 2-chloro function in compounds 3 a-c was replaced by 2-aminothiazole or 2-aminopyridine to give 2-(thiazol-2-yl)aminoquinoline-3-carboxylic acids 4 a-c or 2-(pyrid-2-yl)aminoquinoline-3-carboxylic acids 4 d-f. Treatment of 5 a-c with the same heterocyclic amines at room temperature furnished the corresponding 7-substituted 2-chloro-3-heterylaminocarbonylquinolines 6 a-f. The tetracyclic 9-substituted thiazolo[3Ј,2Ј:1,2]pyrimido[4,5-b]quinolin-5-ones 7 a-c and 10-substituted pyrido[1Ј,2Ј:1,2]pyrimido[4,5-b]quinolin-6-ones 7 d-f were synthesized by heating 5 a-c with the heterocyclic amines in toluene or by heating 6 a-f under reflux in dimethylformamide. The products were evaluated in vitro for potential antimicrobial activity.
6-Substituted Indolo[1,2- c ]quinazolines as New Antimicrobial Agents
Archiv der Pharmazie, 2009
A series of 2-o-arylidineaminophenylindoles and their cyclic derivatives (indolo[1,2-c]quinazolines) were synthesized. The reactions occurred under relatively mild conditions and afforded the desired product in good yields. Molecular structures of the synthesized compounds were confirmed by IR, 1 H-NMR, 13 C-NMR, MS spectra, and elemental analyses. Furthermore, all the final products were screened for in-vitro antibacterial activity against three Gram-positive and three Gram-negative bacteria and also tested for their inhibitory action against three strains of fungi. Compound IIc showed potent activity against all the bacterial (except S. typhimurium) and fungal strains. Especially, compounds IIi and IIj which have isoquinolyl and pyridyl substituents displayed potent antibacterial as well as antifungal activities compared to those of the respective standard drugs Ampicillin and Ketoconazole.
A series of 3-substituted 6-methoxy-1H-pyrazolo [3,4-b]quinoline derivatives was synthesized by treating 6-methoxy-1H-pyrazolo[3,4-b]quinolin-3-amine (6) with different acid anhydrides including succinic anhydride, maleic anhydride and phthalic anhydride. Also, a series of 3-hetero aryl-2-chloro-6-methoxyquinolines was prepared through 1,3-dipolar cycloaddition of different bi-nucleophiles including hydrazine hydrate, hydroxylamine hydrochloride, thiourea, guanidine hydrochloride, urea and metformin hydrochloride to the chalcone derivative 3-(2-chloro-6-methoxy-quinolin-3-yl)-1-(4-methoxyphenyl)prop-2-en-1-one. Structural identifications of all products were reported and the new compounds were screened for their in vitro antimicrobial activity against Strep-tococcus pneumonia and Bacillus subtilis as examples for Gram-positive bacteria, Pseudomonas aerug-inosa and Escherichia coli as examples for Gram-negative bacteria, and Aspergillus fumigatus, Syncephalastrum racemosum, Geotriucum candidum and Candida albicans as representative examples of fungi. The majority of tested compounds showed moderate activities against a wide range of the selected organisms. Among the tested compounds, pyrimidine derivatives 16 and 17 showed the highest antimicrobial activity against gram-positive strains while the highest activity against E. coli as example for Gram-negative strains was observed in the case of 11 and 17. Compounds 14 and 17 were found to be extremely potent against three of the selected fungal strains.
Journal of the Brazilian Chemical Society, 2010
Uma estratégia conveniente em três etapas é proposta para a síntese de mono e bis-indolo[1,2-c] quinazolinas, a partir de 2-(2-aminofenil)indol e aril aldeídos. Os novos compostos sintetizados foram caracterizados por análise elementar, IV, 1 H RMN, 13 C RMN, e espectrometria de massa. Todos os derivados foram testados para avaliação das suas atividades antibacterial (S. aureus, B. subtilis, S. pyogenes, S. typhimurium, E. coli, K. pneumonia) e antifúngica (A. niger, C. albicans, T. viridae) usando o método cup plate. Dentre os compostos testados, as mono-indolo[1,2-c] quinazolinas (15-18) exibiram boas atividades antibacteriais, enquanto 15 e 18 também mostraram notável atividade antifúngica. Especialmente, 19 e 20 exibiram forte atividade antibacteriana e antifúngica contra todas as cepas testadas. A convenient three-step strategy is proposed for the synthesis of mono and bis-indolo[1,2-c] quinazolines from 2-(2-aminophenyl)indole and various aryl aldehydes. The newly synthesized compounds were characterized by elemental analysis, IR, 1 H NMR, 13 C NMR, and mass spectroscopic investigation. All the derivatives were screened for antibacterial (S. aureus, B. subtilis, S. pyogenes, S. typhimurium, E. coli, K. pneumonia) and antifungal (A. niger, C. albicans, T. viridae) activities by cup plate method. Among the compounds tested, mono-indolo[1,2-c] quinazolines (15-18) exhibited good antibacterial activities while 15 and 18 also showed notable antifungal activity. Especially, 19 and 20 exhibited stronger antibacterial as well as antifungal activity against all tested strains.