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Chemical Compound Review

pyridazine     pyridazine

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Disease relevance of pyridazine


High impact information on pyridazine


Biological context of pyridazine

  • The structure-activity relationships in this series were examined by either varying the aryl ring in the 6-position of the pyridazine ring or by modifying the 3-amino side chain [9].
  • Analysis of the enzyme kinetics suggests that the inhibitory action of the pyridazine is similar to that of mycophenolic acid, which involves trapping of a covalent intermediate formed during the conversion of IMP to xanthosine monophosphate [10].
  • Neuropharmacology of a new potential anxiolytic compound, F 2692, 1-(3'-trifluoromethyl phenyl) 1,4-dihydro 3-amino 4-oxo 6-methyl pyridazine. 1. Acute and in vitro effects [11].
  • The pyridazine series 9 showed a maximum in-vitro activity for the p-methoxydrivative 9b, having an IC50 of 17 in MAC 13 and 11 microM in MAC 16 cell lines [12].
  • Studies were extended to assess the mechanistic basis for the enzyme induction by PD and PZ. beta-Naphthoflavone (BNF) caused a 6-fold increase of rGSTA2 mRNA in the liver (100 mg/kg per day, p.o., 3 days), as compared to control, whereas the agent failed to increase mEH mRNA level [13].

Anatomical context of pyridazine


Associations of pyridazine with other chemical compounds

  • By exploring the structure-activity relationship, the potency of the antagonist was increased from a KB of 64 microM for SR 95103 to a KB of 4.7 microM for NCS 281-93 (2-(3-carboxypropyl)-3-amino-4-phenylpropyl-6-phenyl pyridazine) [15].
  • The formation of the stable pyridazine adduct suggested the generation of an electrophilic gamma-thioketo-alpha, beta-unsaturated aldehyde, analogous to that observed during the cytochrome P450-mediated bioactivation of furan [16].
  • FTIR, UV-vis, steady state and time-resolved fluorescence measurements show that harmane (1-methyl-9H-pyrido/3,4-b/indole) interacts with pyrimidine and its isomers pyrazine and pyridazine in its ground and lowest singlet states [17].
  • These results provide evidence that both PD and PZ efficaciously induce mEH and rGSTA2 in the liver with increases in the mRNA levels, while PM is ineffective, and that induction of mEH and rGSTA2 may be mediated through bioactivation of the diazines by P450 2E1 [13].
  • General screening for inhibitors of microvessel growth in vitro in the rat aortic ring assay led to the discovery of a novel series of thiadiazole pyridazine compounds with potential anti-angiogenic activity [18].

Gene context of pyridazine

  • The inhibitor is a pyridazine, which, like mycophenolic acid, exerts uncompetitive inhibition of IMPDH [10].
  • Knowledge of cellular mechanisms and high throughput screens of a pharmacologically focused chemical library allowed the discovery of novel pyridazine-based compounds that are cell permeable ligand modulators of gene regulating protein kinases involved in the induction of iNOS and IL-1 beta in activated glia [19].
  • Novel potent trisubstituted pyridazine inhibitors of p38 MAP (mitogen activated protein) kinase are described that have activity in both cell-based assays of cytokine release and animal models of rheumatoid arthritis [20].
  • Design and synthesis of potent pyridazine inhibitors of p38 MAP kinase [20].
  • Pyridazine derivatives and related compounds. Part 13: Synthesis and antimicrobial activity of some pyridazino[3',4':3,4]pyrazolo[5,1-c]-1,2,4-triazines [21].

Analytical, diagnostic and therapeutic context of pyridazine

  • These results suggest that pyridazine 2h induces analgesia, which is mediated via both opioid and serotonergic mechanisms [22].
  • Copper complexes of pyrazine (1,4-C4H4N2), pyrimidine (1,3-C4H4N2), and pyridazine (1,2-C4H4N2) are produced in laser-vaporization supersonic molecular beams and studied by pulsed-field ionization zero electron kinetic energy (ZEKE) spectroscopy and second-order Moller-Plesset perturbation theory [23].
  • Bioassay of the vasodepressor and cardiostimulatory effects of hydralazine and pyridazine derivative (DL-150) in hypertensive patients [24].


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  3. Effects of 3-[N-(2-chlorobenzyl)amino]-6-(1H-imidazol-1-yl) pyridazine dihydrochloride on various aromatase enzyme systems and experimental breast cancer. Bandoh, K., Ishizuka, Y., Sato, M. Arzneimittel-Forschung. (1995) [Pubmed]
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  6. Novel heterocyclic-fused pyridazinones as potent and selective phosphodiesterase IV inhibitors. Dal Piaz, V., Giovannoni, M.P., Castellana, C., Palacios, J.M., Beleta, J., Doménech, T., Segarra, V. J. Med. Chem. (1997) [Pubmed]
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  10. A novel series of non-nucleoside inhibitors of inosine 5'-monophosphate dehydrogenase with immunosuppressive activity. Franklin, T.J., Morris, W.P., Jacobs, V.N., Culbert, E.J., Heys, C.A., Ward, W.H., Cook, P.N., Jung, F., Plé, P. Biochem. Pharmacol. (1999) [Pubmed]
  11. Neuropharmacology of a new potential anxiolytic compound, F 2692, 1-(3'-trifluoromethyl phenyl) 1,4-dihydro 3-amino 4-oxo 6-methyl pyridazine. 1. Acute and in vitro effects. Assié, M.B., Chopin, P., Stenger, A., Palmier, C., Briley, M. Psychopharmacology (Berl.) (1993) [Pubmed]
  12. Synthesis and evaluation of 5-arylated 2(5H)-furanones and 2-arylated pyridazin-3(2H)-ones as anti-cancer agents. Lattmann, E., Ayuko, W.O., Kinchinaton, D., Langley, C.A., Singh, H., Karimi, L., Tisdale, M.J. J. Pharm. Pharmacol. (2003) [Pubmed]
  13. Differential induction of rat hepatic microsomal epoxide hydrolase and rGSTA2 by diazines: the role of cytochrome P450 2E1-mediated metabolic activation. Cho, M.K., Kim, S.G. Chem. Biol. Interact. (1998) [Pubmed]
  14. Cytostatic activity of pyridazine derivatives. I. In vitro studies on 1-methoxyphenylpyridazine-6-ones. Hładoń, B., Bałoniak, S., Szafarek, P., Zyczyńska-Bałoniak, I. Arch. Immunol. Ther. Exp. (Warsz.) (1980) [Pubmed]
  15. Novel arylaminopyridazine-GABA receptor antagonists examined electrophysiologically in Ascaris suum. Martin, R.J., Sitamze, J.M., Duittoz, A.H., Wermuth, C.G. Eur. J. Pharmacol. (1995) [Pubmed]
  16. Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. O'Donnell, J.P., Dalvie, D.K., Kalgutkar, A.S., Obach, R.S. Drug Metab. Dispos. (2003) [Pubmed]
  17. A spectroscopic study of the molecular interactions of harmane with pyrimidine and other diazines. Muñoz, M.A., Guardado, P., Galán, M., Carmona, C., Balón, M. Biophys. Chem. (2000) [Pubmed]
  18. Synthesis and anti-angiogenic activity of 6-(1,2,4-thiadiazol-5-yl)-3-amino pyridazine derivatives. Bongartz, J.P., Stokbroekx, R., Van der Aa, M., Luyckx, M., Willems, M., Ceusters, M., Meerpoel, L., Smets, G., Jansen, T., Wouters, W., Bowden, C., Valletta, L., Herb, M., Tominovich, R., Tuman, R. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  19. Ligand modulation of glial activation: cell permeable, small molecule inhibitors of serine-threonine protein kinases can block induction of interleukin 1 beta and nitric oxide synthase II. Watterson, D.M., Mirzoeva, S., Guo, L., Whyte, A., Bourguignon, J.J., Hibert, M., Haiech, J., Van Eldik, L.J. Neurochem. Int. (2001) [Pubmed]
  20. Design and synthesis of potent pyridazine inhibitors of p38 MAP kinase. Tamayo, N., Liao, L., Goldberg, M., Powers, D., Tudor, Y.Y., Yu, V., Wong, L.M., Henkle, B., Middleton, S., Syed, R., Harvey, T., Jang, G., Hungate, R., Dominguez, C. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  21. Pyridazine derivatives and related compounds. Part 13: Synthesis and antimicrobial activity of some pyridazino[3',4':3,4]pyrazolo[5,1-c]-1,2,4-triazines. Deeb, A., El-Mariah, F., Hosny, M. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  22. Synthesis and analgesic effects of 3-substituted 4,6-diarylpyridazine derivatives of the arylpiperazine class. Rohet, F., Rubat, C., Coudert, P., Couquelet, J. Bioorg. Med. Chem. (1997) [Pubmed]
  23. Pulsed-field ionization electron spectroscopy and ab initio calculations of copper-diazine complexes. Wang, X., Lee, J.S., Yang, D.S. The Journal of chemical physics. (2006) [Pubmed]
  24. Bioassay of the vasodepressor and cardiostimulatory effects of hydralazine and pyridazine derivative (DL-150) in hypertensive patients. Pasotti, C., Nicrosini, F., Marchetti, M., Manzini, A., Nicolis, F.B. Il Farmaco; edizione pratica. (1976) [Pubmed]
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