Tổng hợp, đặc trưng và đánh giá sinh học của các dẫn xuất thiazole và pyrazole mới của acid quinoline-4-carboxylic như là các tác nhân kháng khuẩn tiềm năng

Springer Science and Business Media LLC - Tập 22 - Trang 3527-3535 - 2012
Abha Bishnoi1, Anil Kumar Tiwari1, Suruchi Singh1, Arun Sethi1, Chandrakant Mani Tripathi2, Bikram Banerjee2
1Department of Chemistry, Lucknow University, Lucknow, India
2Division of Fermentation Technology, Central Drug Research Institute, Lucknow, India

Tóm tắt

Một loạt các heterocyclic dựa trên quinoline đã được chuẩn bị và đánh giá sinh học về khả năng kháng khuẩn tiềm năng của chúng đối với một loạt vi khuẩn gram dương [Staphylococcus aureus (ATCC-9144) và Bacillus subtilis (ATCC-6633)] và vi khuẩn gram âm [Pseudomonas aeruginosa (ATCC-25615) và Escherichia coli (MTCC-739)], cùng với các chủng nấm [Candida albicans (ATCC-24433), Aspergillus niger (MTCC-872) và Aspergillus fumigatus (MTCC-343)] theo các phương pháp đã biết. Tất cả các hợp chất dẫn xuất quinoline đã được chuẩn bị cho thấy hoạt tính kháng khuẩn đáng kể. Một số hợp chất như 4b, 4c và 4a, 4c chứng tỏ có hoạt tính ở nồng độ thấp đối với Sa và Ca, tương ứng, trong khi các hợp chất 4a, 6d và 6b cho thấy tác động ức chế nhẹ hơn đối với các mầm bệnh khác. Cấu trúc của các hợp chất mới tổng hợp được đã được đặc trưng thông qua phân tích nguyên tố, phổ hồng ngoại (IR), 1H-NMR, 13C-NMR và phổ khối.

Từ khóa

#heterocycles; quinoline; antimicrobial activity; bacterial strains; fungal strains; synthesis; characterization

Tài liệu tham khảo

Adhikary PK, Das SK, JrHess BA (1976) Synthesis and antihypertensive activity of some imidazoindole derivatives. J Med Chem 19:1352–1354 Alhaider AA (1986) Antihistamine, anticholinergic and cardiovascular effects of 2-substituted-4-phenylquinoline derivatives. Life Sci 38:601–608 Andreani A, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M (2001) Synthesis and antitubercular activity of imidazo[2,1-b]thiazoles. Eur J Med Chem 36:743–746 Bachir M, Riffaud JP, Lacolle JY, Lemoine J, Almeida AD, Hauziaux P, Danree B (1990) Synthesis and anticonvulsant activity of some 2-(N-substituted glycylamino)-4-methyl thiazoles. Eur J Med Chem 25:71–74 Bakr F, Wahab A, Mohamed SF, Amr AGE, Abdalla MM (2008) Synthesis and reactions of thiosemicarbazides, triazoles, and Schiff bases as antihypertensive α-blocking agents. Monatsh Chem 139:1083–1090 Bauer AW, Kirby M, Sherries JC, Turck M (1966) Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Path 45:493 Bishnoi A, Saxena R, Singh S, Rani A, Joshi MN, Bajpai SK (2009) Synthesis and biological evaluation of a series of 4-(arylamido/imido-alkyl)-5-(arylideno-4-oxo-2- thio-imidazolidinyl)-N-(methyl-phenyl-imino) Acridinium Iodides as Potential Antiviral Agents. Lett Drug Des Discov 6(4):252–257 Bishnoi A, Srivastava K, Singh S, Tripathi CKM (2010) Synthesis of some novel piperazine salts and their antimicrobial property against Escherichia coli and Bacillus subtilis. Der Pharma Chemica 2(5):446–452 Bishnoi A, Srivastava K, Singh S, Tripathi CKM (2011) Facile synthesis of 2′-Phenyl-4′-[3″-(2″-oxo-1″H indolidene)-5′-oxo-imidozolyl]-1′-[{p-1-(4-aryl-1- biphenyl)}]/4-aryl-3-chloro azetidinones: β lactam derivatives as antimicrobes. Eur J Chem 2(3):359–364 Bondock S, Khalifa W, Fadda AA (2007) Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur J Med Chem 42:948–954 Bondock S, Fadaly W, Metwally MA (2010) Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur J Med Chem 45:3692–3701 Charris JE, Lobo GM, Camacho J, Ferrer R, Barazarte A, Domínguez J, Gamboa N, Rodrigues JR, Angel JE (2007) Synthesis and antimalarial activity of (E) 2-(2′-Chloro-3′-Quinolinylmethylidene)-5,7-Dimethoxyindanones. Lett in Drug Design Discov 4:49–54 Conklin JD, Hollifield RD (1970) Studies on the absorption, distribution, and elimination of amiquinsin hydrochloride, a hypotensive drug. Eur J Pharm 10:360–368 El-Sabbagh OI, Baraka MM, Ibrahim SM, Pannecouque C, Andrei G, Snoeck R, Balzarini J, Rashad AA (2009) Synthesis and antiviral activity of new pyrazole and thiazole derivatives. Eur J Med Chem 44:3746–3753 Eswaran S, Adhikari AV, Kumar RA (2010a) New 1,3-oxazolo[4,5-c]quinoline derivatives: synthesis and evaluation of antibacterial and antituberculosis properties. Eur J Med Chem 45:957–966 Eswaran S, Adhikari AV, Chowdhary IH, Pal NK, Thomas KD (2010b) New quinoline derivatives: synthesis and investigation of antibacterial and antituberculosis properties. Eur J Med Chem 45:3374–3383 Fleming FF, Yao L, Ravikumar PCR, Funk L, Shook BC (2010) Nitrile-containing pharmaceuticals: efficacious Role of the Nitrile pharamacophores. J Med Chem 53:7902–7917 Fujimoto S (2007) Promising antitumor activity of a novel quinoline derivative, TAS-103, against fresh clinical specimens of eight types of tumors measured by flow cytometric DNA analysis. Bio Pharm Bull 30:1923–1929 Hans RH, Guantai EM, Lategan C, Smith PJ, Wan B, Franzblau SG, Gut J, Rosenthal JP, Chibale K (2010) Synthesis, antimalarial and antitubercular activity of acetylenic chalcones. Bioorg Med Chem Lett 20:942–944 Holla BS, Poojary KN, Poojary B, Bhat KS, Kumar NS (2005) Synthesis, characterization and antibacterialactivity studies on some fluorine containing quinoline-4-carboxylic acids and their derivatives. Indian J Chem 44B:2114–2119 Jandhyala BS, Grega GJ, Buckley JP (1967) Hypotensive activity of several quinoline derivatives. Arch Int Pharmacodyn Ther 167:126–217 Kaminski K, Obniska J (2008) Design, synthesis, and anticonvulsant activity of N-phenylamino derivatives of 3,3-dialkyl-pyrrolidine-2,5-diones and hexahydro-isoindole-1,3-diones. Bioorg Med Chem 16:4921–4931 Karaman I, Sahin F, Gulluce M, Ogutcu H, Sengul M, Adiguzel A (2003) Antimicrobial activity of aqueous and methanol extracts of Juniperus oxycedrus L. J Ethnopharmacol 85:231–235 Kolavi G, Hegde V, Khazi IA, Gadad P (2006) Synthesis and evaluation of antitubercular activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives. Bioorg Med Chem 14:3069–3080 Kumar S, Bawa S, Drabu S, Gupta H, Machwal L, Kumar R (2011) Synthesis, antidepressant and antifungal evaluation of novel 2-chloro-8-methylquinoline amine derivatives. Eur J Med Chem 46:670–675 Labanauskas L, Kalcas V, Uderenaite E, Gaidelis P, Brukstus A, Dauksas VM (2001) Synthesis of 3-(3,4-dimethoxyphenyl)-1 H-1,2,4-triazole-5-thiol and 2-amino-5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazole derivatives exhibiting anti-inflammatory activity. Pharmazie 56:617–619 Messaoudi S, Sancelme M, Housset VP, Aboab B, Moreau P, Prudhomme M (2004) Synthesis and biological evaluation of oxindoles and benzimidazolinones. Eur J Med Chem 39:453–458 Mullican MD, Wilson MW, Conner DT, Kostlan CR, Schrier DJ, Dyer RD (1993) Design of 5-(3,5-di-tert-butyl-4-hydroxypheny)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles as orally active, nonulcerogenic antiinflammatory agents. J Med Chem 36:1090–1099 Ozdemir A, Zitouni GT, Kaplancikli ZA, Revial G, Guven K (2007) Synthesis and antimicrobial activity of 1-(4-aryl-2-thiazolyl)-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives. Eur J Med Chem 42:403–409 Palit P, Paira P, Hazra A, Banerjee S, Gupta AD, Dastidar SG, Mondal NB (2009) Phase transfer catalyzed synthesis of bis-quinolines: antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial evaluation. Eur J Med Chem 44:845–853 Parekh N, Maheria K, Patel P, Rathod M (2011) Study on antibacterial activity for multidrug resistance stain by using phenyl pyrazolones substituted 3-amino 1h-pyrazolon (3,4-b) quinoline derivative in vitro condition. Int J Pharm Tech Res 3:540–548 Robert M, Josef J, Buchta V, Silva L, Niedbala H, Podeszwa B, Palka A, Majrez-Maniecka K, Oleksyn B, Polanski J (2006) Antifungal properties of new series of quinoline derivatives. Bioorg Med Chem 14:3498–3592 Ryu CK, Lee JY, Jeong SH, Nho JH (2009) Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles. Bioorg Med Chem Lett 19:146–148 Sahm DF, Washington JA (1991) Antibacterial susceptibility tests: dilution methods. In: Ballows A, Hausler WJ Jr, Herrmann KL, Isenberg HD, Shadomy HJ (eds) Manual of Clinical Microbiology, 5th edn. ASM, Washington, DC, p 1105 Sohda T, Mizuno K, Momose Y, Ikeda H, Fujita T, Meguro K (1992) Studies on antidiabetic agents. 11. Novel thiazolidinedione derivatives as potent hypoglycemic and hypolipidemic agents. J Med Chem 35:2617–2626 Song Y, Connor DT, Sercel AD, Sorenson RJ, Doubleday R, Unangst PC, Roth BD, Beylin VG, Gilbertsen RB, Chan K, Schrier DJ, Guglietta A, Bornemeier DA, Dyer RD (1999) Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 2. 1,3,4- and 1,2,4-thiadiazole series. J Med Chem 42:1161–1169 Stawinska MK, Clercq ED, Balzarini J (2009) Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain. Bioorg Med Chem 17:3756–3762 Tempone AG, da Silva AC, Brandt CA, Martinez FS, Borborema SE, da Silveira MA, Jr de Andrade HF (2005) Synthesis and antileishmanial activities of novel 3-substituted quinolines. Antimicro Agents Chemother 49:1076–1080 Veronique I, Veronique S, Coudert P, Seilles E, Couquelet J (1998) Synthesis of new pyrrolo [1,2-d] [1,2,4] triazines and thiazolo [3,4-d] [1,2,4] triazines as immunostimulating agents. Bioorg Med Chem 6:349–354 Vijesh AM, Isloor AM, Prabhu V, Ahmad S, Malladi S (2010) Synthesis, characterization and anti-microbial studies of some novel 2,4-disubstituted thiazoles. Eur J Med Chem 45:5460–5464 Yamato M, Takeuchi Y, Hashigaki K, Ikeda Y, Chag MR, Takeuchi K, Matsuhima M, Tsuruo T, Tashiro T, Tsukagoshi S (1989) Synthesis and antitumor activity of fused tetracyclic quinoline derivatives. J Med Chem 32:1295–1300 Yamato M, Takeuchi Y, Chang MR, Hashigaki K, Tsuruo T, Tashiro T, Tsukagoshi S (1990) Synthesis and antitumor activity of fused quinoline derivatives. Chem Pharm Bull 38:3048–3052