Abstract
With the aim of developing potential antimicrobials, a series of 2-amino-3-cyanopyridines incorporating both sulfur and oxygen as part of the heteroaromatic ring (methyl thiophene, methyl furan) and fused cycloalkane groups were synthesized and characterized by FTIR, 1H-NMR, 13C-NMR, and bases of elemental analysis. All synthesized compounds were evaluated for their in vitro antibacterial and antifungal activity. Antibacterial and antifungal activities of aminocyanopyridines against Pseudomonas aeruginosa ATCC 29212, Bacillus subtilis RSKK 244, Bacillus megaterium (clinical isolate), the gram-positive bacterium Micrococcus luteus NRRLB 4375, and the fungus Candida albicans ATCC 90028 were studied. The relationship between the functional-group variation and the biological activity of the evaluated compounds is discussed.
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Altundas A, Sari N, Colak N, Ögütcü H (2009) Synthesis and biological activity of new of cycloalkylthiophene-Schiff bases and their Cr(III) and Zn(II) complexes. Med Chem Res (doi: 10.1007/s00044-009-9214-8)
Arslan S, Loğoğlu E, Öktemer A (2006) Antimicrobial activity studies on some piperidine and pyrrolidine substituted halogenobenzene derivatives. J Enzyme Inhib Med Chem 21(2):211–214
Baldwin JJ, Engelhart EL, Hirschmann R, Ponticello GS, Atkinson JG, Wasson BK, Sweet CS, Scriabine A (1980) Heterocyclic analogs of the antihypertensive beta.-adrenergic blocking agent (S)-2-[3-(tert-butylamino)-2-hydroxypropoxy]-3-cyanopyridine. J Med Chem 23:65–70
Bermingham A, Derrick JP (2002) The folic acid biosynthesis pathway in bacteria evaluation of potential for antibacterial drug discovery. BioEssays 24:637–648
Budriesi R, Bisi A, Ioan P, Rampa A, Gobbi S, Belluti F, Piazzi L, Valenti P, Chiarini A (2005) 1,4-Dihydropyridine derivatives as calcium channel modulators: the role of 3-methoxyflavone moiety. Bioorg Med Chem 13:3423–3430
Chang CS, Lin YT, Shih SR, Lee CC, Lee YC, Tai CL, Tseng SN (2005) Antipicornavirus activity of pyridyl imidazolidinone derivatives. J Med Chem 48:522–3535
Deo K, Avasthi K, Pratap R, Bakuni DS, Joshi MN (1991) Synthesıs of 2,4-bis(methylthio)-5,7-disubstıtuted-7H-pyrrolo-(2,3-D)pyrimidines and their biological-activity. Indian J Chem Sect B 30:499–503
Elgemeie GEH, Regila HA, Shehata N (1989) Novel syhthesis of condensed 4-(2-thienyl)-and 4-(2-furyl)3-cyano-pyridi-2-(1H)-ones and their conversions into the correponding pyridin-2-(1H)-thione derivatives. Sulfur Lett 9(6):253–264
Fathy NM, Elgemeie GH (1988) Activated nitriles in heterocyclic synthesis—a one-step synthesis of several new pyrimidine, pyridine, and pyrazole derivatives. J Chem Eng Data 33(2):218–219
Fidler DP (1998) Legal issues associated with antimicrobial drug resistance. Emerg Infect Dis 4:169–177
Goldmann S, Stoltefuss J (1991) 1,4-Dihydropyridines-effects of chiralty and conformation on the calcium-antagonist and calcium agonist activities. Angew Chem Int Ed Eng 30:1559–1578
Krauze A, Vitolina R, Zarins G, Pelcers J, Kalme Z, Kimenis A, Dubuns G (1985) Synthesis and cardiovascular activity of substituted 3-cyano-3,4-dihydropyridine-2-thiones and 3-cyanopyridine-2-thiones. Khim Farm Zh 19:540–545
Manna F, Chimenti F, Bolasco A, Bizzarri B, Filippelli W, Fiilppelli A, Gagliardi L (1999) Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines. Eur J Med Chem 34:245–254
Mayler WG (1989) Calcium antagonists. Academic Press, London
Moussa HH, Chabaka LM, Zaki D (1983) Synthesis and evaluation of antifungal properties of a series of the novel 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile and its analogues. Egypt J Chem 26:469–477
Murata T, Shimada M, Sakakibara S, Yoshino T, Masuda T, Shintani T, Sato H, Koriyama Y, Fukushima K, Nunami N, Yamauchi M, Fuchikama K, Komura H, Wanatabe A, Ziegelbauer KB, Bacon KB, Lowinger TB (2004) Synthesis and structure–activity relationships of novel IKK-β inhibitors. Part 3: orally active anti-inflammatory agents. Bioorg Med Chem Lett 14:4019–4022
NCCLS (National Committee for Clinical Laboratory Standards) (1997a) Approved standard M7-A4. NCCLS, Wayne, PA
NCCLS (National Committee for Clinical Laboratory Standards) (1997b) Approved standard M27. NCCLS, Wayne, PA
Sakurai A, Midorikawa H (1968) The cyclization of malononitrile and ketones by ammonium acetate. Bull Chem Soc Jpn 41:430–432
Schramm M, Thomas G, Towart R, Franckowiak G (1983) Novel dihydropyridines with positive inotropic action through activation of Ca2+ channels. Nature 303:535–537
Shevchenko NE (1999) Synthesis of 3-substituted furylethylamines. Chem Heterocycl Compd 35:164–166
Taylor EC Jr, Crovetti AJ (1954) Pyridine 1-oxides. I. Synthesis of some nicotinic acid derivatives. J Org Chem 19:1633–1640
Acknowledgments
The authors thank the Gazi University Scientific Research Fund (Project no. 05/2008-47) for financial support. We also thank Münteha N. Sonuc and Refiye Tekiner for their help with carrying out antibacterial studies.
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Altundas, A., Ayvaz, S. & Logoglu, E. Synthesis and evaluation of a series of aminocyanopyridines as antimicrobial agents. Med Chem Res 20, 1–8 (2011). https://doi.org/10.1007/s00044-009-9273-x
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DOI: https://doi.org/10.1007/s00044-009-9273-x