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Chemical Compound Review

CINNOLINE     cinnoline

Synonyms: benzodiazine, SureCN3212, SureCN8197, CHEMBL479792, SureCN452420, ...
 
 
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Disease relevance of cinnoline

 

High impact information on cinnoline

  • Thermal cyclization to give a cinnoline from (2-ethynylphenyl)triazenes is proposed to occur through a pericyclic pathway [2].
  • On the basis of the contribution of these pharmacophores to the in vitro potency, they were ranked in the order of 5-isoquinoline > 8-quinoline = 8-quinazoline > 8-isoquinoline > or = cinnoline approximately phthalazine approximately quinoxaline approximately 5-quinoline [3].
  • Structure and biological activity of some 4-amino-3-cinnolinecarboxylic acid derivatives. QSAR analysis of cinnoline derivatives with antibacterial properties [4].
  • Measurement of the kinetics of adsorbed cinnoline by square-wave voltammetry [5].
  • The standard redox reaction rate constant of cinnoline (1,2-benzodiazine) adsorbed to the mercury electrode in 0.9 mol L(-1) KNO(3) buffered to pH 7, 9.2, and 4.65 are k(s)=455+/-110 s(-1), 65+/-25 s(-1), and 300+/-75 s(-1), respectively [5].
 

Anatomical context of cinnoline

 

Associations of cinnoline with other chemical compounds

  • Indolo[3,2-c]cinnolines of type 5, variously substituted either in the indole and in the cinnoline moieties, were prepared in good overall yields, by intramolecular cyclization of indolo derivatives 4 [7].

References

  1. Synthesis and antibacterial activity of substituted 4-arylaminopyrimido[5,4-c]cinnolines. Nargund, L.V., Nargund, K.S. Arzneimittel-Forschung. (1995) [Pubmed]
  2. Deciphering the mechanistic dichotomy in the cyclization of 1-(2-ethynylphenyl)-3,3-dialkyltriazenes: competition between pericyclic and pseudocoarctate pathways. Kimball, D.B., Weakley, T.J., Herges, R., Haley, M.M. J. Am. Chem. Soc. (2002) [Pubmed]
  3. Novel transient receptor potential vanilloid 1 receptor antagonists for the treatment of pain: structure-activity relationships for ureas with quinoline, isoquinoline, quinazoline, phthalazine, quinoxaline, and cinnoline moieties. Gomtsyan, A., Bayburt, E.K., Schmidt, R.G., Zheng, G.Z., Perner, R.J., Didomenico, S., Koenig, J.R., Turner, S., Jinkerson, T., Drizin, I., Hannick, S.M., Macri, B.S., McDonald, H.A., Honore, P., Wismer, C.T., Marsh, K.C., Wetter, J., Stewart, K.D., Oie, T., Jarvis, M.F., Surowy, C.S., Faltynek, C.R., Lee, C.H. J. Med. Chem. (2005) [Pubmed]
  4. Structure and biological activity of some 4-amino-3-cinnolinecarboxylic acid derivatives. QSAR analysis of cinnoline derivatives with antibacterial properties. Brzezińska, E., Stańczak, A., Ochocki, Z. Acta poloniae pharmaceutica. (2003) [Pubmed]
  5. Measurement of the kinetics of adsorbed cinnoline by square-wave voltammetry. Komorsky-Lovrić, S. Analytical and bioanalytical chemistry. (2002) [Pubmed]
  6. Synthesis and action on the central nervous system of some N2-substituted cinnoline derivatives. Stańczak, A., Kwapiszewski, W., Szadowska, A., Pakulska, W. Die Pharmazie. (1994) [Pubmed]
  7. Polycondensed nitrogen heterocycles. Part 27. Indolo[3,2-c]cinnoline. Synthesis and antileukemic activity. Cirrincione, G., Almerico, A.M., Diana, P., Grimaudo, S., Dattolo, G., Aiello, E., Barraja, P., Mingoia, F. Farmaco (1995) [Pubmed]
 
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