The reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activities

Acta Pharmaceutica

Volumn 58, Issue 4, 2008, Pages 429-444

  Mohareb, Rafat M ^a   El Sharkawy, Karam A ^b   Sherif, Sherif M ^a  

^a CAIRO UNIVERSITY   (Egypt)

^b October University for Modern Sciences and Arts   (Egypt)

Author keywords

Antimicrobial activity; Isoxazole; Pyridazine; Pyridine; Thiophene

Indexed keywords

2 AMINO 4 PHENYL 1,1,3 TRICYANO 6 (2' HYDROXYPHENYL)HEXA 1,3,5 TRIENE; 2 AMINO 4 PHENYLPENTA 1,3 DIENE 1,1,3 TRICARBONITRILE; 2 AMINO 4,6 DIPHENYL 1,1,3 TRICYANOHEXA 1,3,5 TRIENE; 2 [AMINO (2,3 DIHYDRO 3 IMINO 2,5 DIPHENYLPYRIDAZIN 4 YL)METHYLENE]MALONONITRILE; 2 [AMINO [2,3 DIHYDRO 3 IMINO 2 (3 CYANO 4',5',6',7' TETRAHYDROBENZO[B]THIENO 2 YL) 5 PHENYLPYRIDAZIN 4 YL]METHYLENE]MALONONITRILE; 2 [AMINO [2,3 DIHYDRO 3 IMINO 2 (4' CHLOROPHENYL) 5 PHENYLPYRIDAZIN 4 YL]METHYLENE]MALONONITRILE; 2 [AMINO [2,3 DIHYDRO 3 IMINO 2 (ETHYL 4',5',6',7' TETRAHYDROBENZO[B]THIOPHENO 3 CARBOXYLATO 2 YL) 5 PHENYLPYRIDAZIN 4 YL]METHYLENE]MALONONITRILE; 2,4 DIAMINO 5,7 DIPHENYLQUINOLINE 3,8 DICARBONITRILE; 5 (2 PHENYLHYDRAZONO) 2 AMINO 4 PHENYLPENTA 1,3 DIENE 1,1,3 TRICARBONITRILE; 5 (2,4 CHLOROPHENYLHYDRAZONO) 2 AMINO 4 PHENYLPENTA 1,3 DIENE 1,1,3 TRICARBONITRILE; 5 (3' CYANO 4',5',6',7' TETRAHYDROBENZO[B]THIENO 2 HYDRAZONO) 2 AMINO 4 PHENYLPENTA 1,3 DIENE 1,1,3 TRICARBONITRILE; 5 (ETHYL 4',5',6',7' TETRAHYDROBENZO[B]THIOPHENO 3 CARBOXYLATO 2 HYDRAZONO) 2 AMINO 4 PHENYLPENTA 1,3 DIENE 1,1,3 TRICARBONITRILE; ACETOPHENONE; ALDEHYDE; ALPHA CYANO BETA AMINO BETA (2 AMINO 3 CYANO 4,6 DIPHENYLBENZEN 1 YL)ACRYLONITRILE; ALPHA CYANO BETA AMINO BETA (2 AMINO 3 ETHOXYCARBONYL 4,6 DIPHENYLBENZEN 1 YL)ACRYLONITRILE; BETA AMINO ALPHA,GAMMA DICYANOCROTONONITRILE; CYANOMETHYLENE DERIVATIVE; DIAZONIUM COMPOUND; ETHYL 2,4 DIAMINO 5,7 DIPHENYLQUINOLINE 3 NITRILO 8 CARBOXYLATE; HYDRAZINE DERIVATIVE; HYDROXYLAMINE; ISOXAZOLE DERIVATIVE; NITRILE; PYRAZOLE DERIVATIVE; PYRIDAZINE DERIVATIVE; PYRIDINE DERIVATIVE; SULFUR; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BACILLUS SUBTILIS; CANDIDA ALBICANS; CHEMICAL REACTION; CONTROLLED STUDY; CYCLIZATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; POLYMERIZATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 58149166714     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: 10.2478/v10007-008-0030-3     Document Type: Article

References (21)

1. A. Bolognese, G. Correale, M. Manfra, A. Lavecchia, E. Novellino and S. Pepe, Antitumor agents. 5. Synthesis, structure-activity relationships, and biological evaluation of dimethyl-5H-pyridophenoxazin-5-ones, tetrahydro-5H-benzopyridophenoxazin-5-ones, and 5H-benzopyridophenoxazin-5-ones with potent antiproliferative activity, J. Med. Chem. 49 (2006) 5110-5118; DOI: 10.1021/jm0507451.
2. G. Heimer, M. Rivlin-Etzion, I. Bar-Gad, J. A. Goldberg, S. N. Haber and H. Bergman, Dopamine replacement therapy does not restore the full spectrum of normal pallidal activity in the 1-methyl-4-phenyl-1,2,3,6-tetra-hydropyridine primate model of Parkinsonism, J. Neurosci. 26 (2006) 8101-8114; DOI: 10.1523/JNEUROSCI.5140-05.2006.
3. R. Powers, J. C. Copland, K. Germer, K. A. Mercier, V. Ramanathan and P. Revesz, Comparison of protein active site structures for functional annotation of proteins and drug design, Proteins 65 (2006) 124-135; DOI: 10.1002/prot.21092.
4. F. M. Abdelrazek, F. A. Micheal and A. E. Mohamed; Synthesis and molluscicidal activity of some 1,3,4-triaryl-5-chloropyrazole, pyrano[2,3-c]pyrazole, pyrazolylphthalazine and pyrano[2,3--d]thiazole derivatives, Arch. Pharm. (Weinheim) 339 (2006) 305-312; DOI: 10.1002/ardp.200500259.
5. F. M. Abdelrazek and A. D. Fathy, A novel synthesis and molluscicidal activity of some functionally substituted pyridine, pyrido[3,2-c]pyridazine, and pyrido[3,2-c]pyridazino[2′,3′-a]quinazoline derivatives, Arch. Pharm. (Weinheim) 338 (2005) 329-334; DOI: 10.1002/ardp.200400938.
6. S. Alias, R. Andreu, M. A. Cerdan, S. Franco, J. Garin, J. Orduna, P. Romero and B. Villacampa, Synthesis, characterization and optical properties of merocyanines derived from malononitrile dimer, Tetrahedron Lett. 48 (2007) 6539-6542; DOI: 10.1016/j.tetlet.2007.07.048.
7. L. K. Wing, H. A. Behanna, L. J. Van Eldik, D. M. Watterson and R. H. Ralay, De novo and molecular target-independent discovery of orally bioavailable lead compounds for neurological disorders, Curr. Alzheimer Res. 3 (2006) 205-214; DOI: 10.2174/156720506777632844.
8. E. Rozsa, H. Obotka, D. Nagy, T. Farkas, K. Saa, L. Vecsei and J. Toldi, The pentylenetetrazole-iduced acivity in the hippocampus can be inhibited by the conversion of 1-kynurenine to kynurenic acid: an in vitro study, Brain Res. Bull. 76 (2008) 474-479; DOI: 10.1016/j.brainresbull.2007.12.001.
9. E. Szarics, A. Simon, J. Visy, E. Simon-Trompler, Z. Banka, L. Heja, L. G. Harsing, G. Blasco, J. Kardos, L. Jeja, L. G. Harsing, G. Blasco and J. Kardos, Cyclothiazide binding to the GABAA receptor, Neurosci. Lett. 439 (2008) 66-69; DOI: 10.1016/j.neulet.2008.04.092.
10. K. Odlo, J. Hentzen, J. F. Chabert, S. Ducki, O. A. Gani, I. Sylte, M. Skrede, V. A. Florenes and T. V. Hanse, 1,5-Disubstituted 1,2,3-triazole as cis-restricted analogues of combrestastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin, Bioorg. Med. Chem. 16 (2008) 4829-4838; DOI: 10.1016/j.bmc.2008. 03.049.
11. H. Zhao, M. D. Serby, Z. Xin, B. G. Szczepankiewicz, M. Liu, C. Kosogof, B. Liu, L. T. Nelson, E. F. Johnson, S. Wang, T. Pederson, R. J. Gum, J. E. Clampit, D. L. Haasch, C. Abad-Zapatero, E. H. Fry, C. Rondinone, J. M. Trevillyan, H. L. Sham and G. Liu, Discovery of potent highly selective, and orally bioavailable pyridine carboxamide c-Jun NH2-terminal kinase inhibitors, J. Med. Chem. 27 (2006) 4455-4458; DOI: 10.1021/jm0604651.
12. K. Muranaka, A. Sano, S. Ichikawa and A. Mastsuda, Synthesis of Hsp89 inhibitor dimmers as potential antitumer agents, Bioorg. Med. Chem. 16 (2008) 5862-5870; DOI: 10.1016/j.bmc.2008.04.070.
13. A. Burguete, E. Pontiki, D. H. Litina, R. Villar, E. Vicente, B. Solano, S. Ancizu, S. Silanes, I. Aldana, A. Monge, Y. Maruyama, K. Anami and Y. Kotoh, Synthesis and anti-flammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinioxalin-2-yl)-2--propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues, Bioorg. Med. Chem. Lett. 17 (2007) 6439-6443; DOI: 10.1016/j.bmcl.2007.10. 002.
14. Y. Hirokawa, H. Kinoshita, T. Tanaka, T. Nakamura, K. Fujimoto, S. Kashimoto, T. Kojima and S. Kato, Pleuromutilin derivatives having a putine ring. Part 1: new compounds with promising antibacterial activity against resistant Gram-positive pathogens, Bioorg. Med. Chem. Lett. 18 (2008) 3556-3561; DOI: 10.1016/j.bmcl.2008.05.011.
15. A. M. Palmer, B. Grobbel, C. Brehm, P. J. Zimmermann, W. Buhr, M. O Feth, H. C. Holst and W. A. Simon, Preparation of tetrahydroimidazo[2,1-a] isoquinolines and their use as inhibitors of gastric acid secretion, Bioorg. Med. Chem. 15 (2007) 7647-7660; DOI: 10.1016/j.bmc.2007.08.065.
16. R. Leon, C. Rois, J. M. Contelles, M. G. Lopez, A. G. Barcia and M. Villaroya, Synthesis of 6-amino-1,4-dihydropyridines that prevent calcium overload and neuronal death, Eur. J. Med. Chem. 43 (2008) 668-674; DOI: 10.1016/j.ejmech.2007.06.001.
17. J. Z. Yang, Y. Chen, A. M. Zhu, Q. L. Liu and J. Y. Wu, Analyzing diffusion behaviour of methanol/water through MFI membranes by molecular simulation, J. Membrane Sci. 328 (2008) 327-333; DOI: 10.1016/j.memsci.2008,02,059.
18. Y. Z. Povstenko, Fractional radial diffusion ion in a cylinder, J. Mol. Liquids, 137 (2008) 46-50; DOI: 10.1016/j.molliq.2007,03.006.
19. H. Sterk and M. Mittelbach, The relaxational behaviour of nitrile groups, J. Mag. Res. 62 (1985) 175-181; DOI: 10.1016/0022-2364(85)90051- 4.
20. B. P. McKibben, C. H. Cartwright and A. L. Castelhano, Practicle synthesis of tetrasubstituted thiophenes for use in compound libraries, Tetrahedron Lett. 40 (1999) 5471-5474; DOI: 10.1016/S0040-4039(99) 01108-9.
21. P. Milart, J. Wilamowski and J. J. Sepiol, Synthesis of di- and triamino-1,1′:3″,1″-terphenyls from arylethylidene- and arylidenemalonodinitriles, Tetrahedron 54 (1998) 15643-15656; DOI: 10.1016/S0040-4020(98)00978-8.