Synthesis and evaluation of a series of aminocyanopyridines as antimicrobial agents

Medicinal Chemistry Research

Volumn 20, Issue 1, 2011, Pages 1-8

  Altundas, Aliye ^a   Ayvaz, Selcuk ^a   Logoglu, Elif ^a  

^a GAZI UNIVERSITY   (Turkey)

Author keywords

2 Amino 3 cyanopyridines; Antimicrobial agents; Furan; Thiophene

Indexed keywords

2 [(3 METHYLTHIOPHEN 2 YL)METHYLENE]MALONONITRILE; 2 [(5 METHYLFURAN 2 YL)METHYLENE]MALONONITRILE; 2 [(5 METHYLTHIOPHEN 2 YL)METHYLENE]MALONONITRILE; 2 AMINO 5,6,7,8 TETRAHYDRO 4 (3 METHYLTHIOPHEN 2 YL)QUINOLINE 3 CARBONITRILE; 2 AMINO 5,6,7,8 TETRAHYDRO 4 (5 METHYLFURAN 2 YL)QUINOLINE 3 CARBONITRILE; 2 AMINO 5,6,7,8 TETRAHYDRO 4 (5 METHYLTHIOPHEN 2 YL)QUINOLINE 3 CARBONITRILE; 2 AMINO 6,7 DIHYDRO 4 (3 METHYLTHIOPHEN 2 YL) 5H CYCLOPENTA[B]PYRIDINE 3 CARBONITRILE; 2 AMINO 6,7 DIHYDRO 4 (5 METHYLFURAN 2 YL) 5H CYCLOPENTA[B]]PYRIDINE 3 CARBONITRILE; 2 AMINO 6,7 DIHYDRO 4 (5 METHYLTHIOPHEN 2 YL) 5H CYCLOPENTA[B]PYRIDINE 3 CARBONITRILE; 2 AMINO 6,7,8,9 TETRAHYDRO 4 (3 METHYLTHIOPHEN 2 YL) 5H CYCLOHEPTA[B]PYRIDINE 3 CARBONITRILE; 2 AMINO 6,7,8,9 TETRAHYDRO 4 (5 METHYLFURAN 2 YL) 5H CYCLOHEPTA[B]PYRIDINE 3 CARBONITRILE; 2 AMINO 6,7,8,9 TETRAHYDRO 4 (5 METHYLTHIOPHEN 2 YL) 5H CYCLOHEPTA[B]PYRIDINE 3 CARBONITRILE; AMPICILLIN; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; FLUCONAZOLE; GENTAMICIN; KETOCONAZOLE; PENICILLIN G; PYRIDINE DERIVATIVE; TETRACYCLINE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACILLUS MEGATERIUM; BACILLUS SUBTILIS; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROSCOPY; MICROCOCCUS LUTEUS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA;

EID: 79952698862     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-009-9273-x     Document Type: Article

References (22)

1. 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)
2. Arslan S, Loǧoǧlu E, Öktemer A (2006) Antimicrobial activity studies on some piperidine and pyrrolidine substituted halogenobenzene derivatives. J Enzyme Inhib Med Chem 21(2):211-214 (Pubitemid 44083973)
3. 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 (Pubitemid 10192897)
4. Bermingham A, Derrick JP (2002) The folic acid biosynthesis pathway in bacteria evaluation of potential for antibacterial drug discovery. BioEssays 24:637-648 (Pubitemid 34780351)
5. 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 (Pubitemid 40552862)
6. 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
7. Deo K, Avasthi K, Pratap R, Bakuni DS, Joshi MN (1991) Synthesis of 2,4-bis(methylthio)-5,7-disubstituted-7H-pyrrolo-(2,3-D)pyrimidines and their biological-activity. Indian J Chem Sect B 30:499-503
8. 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
9. 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
10. Fidler DP (1998) Legal issues associated with antimicrobial drug resistance. Emerg Infect Dis 4:169-177
11. 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
12. 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
13. 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
14. Mayler WG (1989) Calcium antagonists. Academic Press, London
15. 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
16. 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
17. NCCLS (National Committee for Clinical Laboratory Standards) (1997a) Approved standard M7-A4. NCCLS, Wayne, PA
18. NCCLS (National Committee for Clinical Laboratory Standards) (1997b) Approved standard M27. NCCLS, Wayne, PA
19. Sakurai A, Midorikawa H (1968) The cyclization of malononitrile and ketones by ammonium acetate. Bull Chem Soc Jpn 41:430-432
20. 2+ channels. Nature 303:535-537
21. Shevchenko NE (1999) Synthesis of 3-substituted furylethylamines. Chem Heterocycl Compd 35:164-166
22. Taylor EC Jr, Crovetti AJ (1954) Pyridine 1-oxides. I. Synthesis of some nicotinic acid derivatives. J Org Chem 19:1633-1640