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Chemical Compound Review

Thiocarbonyl     methanidylidynesulfanium

Synonyms: sulfidocarbon, Carbon sulfide, AG-E-95875, CHEBI:30253, CTK2A9799, ...
 
 
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Disease relevance of methanidylidynesulfanium

  • Rats were pretreated with 1-methyl-1-phenylbenzoylthiourea (MPBTU), a non-toxic arylthiourea which inhibits the metabolism and toxicity of thiocarbonyl compounds [1].
  • These results can be valuable for the design of new thiocarbonyl-containing drugs against resistant strains of Mycobacterium tuberculosis by a self-activating mechanism [2].
 

High impact information on methanidylidynesulfanium

  • Attractive interactions between a thiocarbonyl group and a pyridinium nucleus, and between a carbonyl group and a pyridinium nucleus have been proven by (1)H and (13)C NMR studies, UV-vis spectral analyses, and X-ray crystallographic analyses of nicotinic amides 1 and 3, and pyridinium salts 2 and 4 [3].
  • The potency of 19 warrants further study and suggests that replacement of the amide carbonyl with a thiocarbonyl may be beneficial for increased TNF-alpha inhibitory action [4].
  • Compound 10, a thiocarbonyl-containing compound, decreased the NADPH oxidase activity of the enzyme (EC50 = 190 microM) and shifted the heme iron spin state toward a low-spin configuration, similar to that of L-thiocitrulline [5].
  • The fact that the structure-activity relationship of these two series was quite similar suggests that a common substructure, such as the 1,2,4-triazole ring with a substituted phenyl ring at the 3 position and a thiocarbonyl moiety at the 1 position, could contribute to the activity [6].
  • For one inhibitor, conversion of one of the carbonyl groups on the cyclobut-3-enedione core to a thiocarbonyl group resulted in a 18-fold increase in potency, and yielded a compound with an IC50 value of 15 microM [7].
 

Biological context of methanidylidynesulfanium

 

Associations of methanidylidynesulfanium with other chemical compounds

 

Gene context of methanidylidynesulfanium

  • We conclude that all 2,3-benzodiazepines studied are effective against various models of experimental epilepsy and the presence of thiocarbonyl groups at the C-4 position of heptatomic ring is able to increase the anticonvulsant effect of these compounds [10].
  • The thiocarbonyl complex [Ru(CPh = CHPh)Cl(CS)(PPh(3))(2)] reacted with HMI and NaOMe without migration to yield [Ru(CPh= CHPh)(kappa(2)-MI)(CS)(PPh(3))(2)], while treatment of [Ru(CH=CHPh)Cl(CO)(2)(PPh(3))(2)] with HMI yielded the monodentate acyl product [Ru{eta(1)-C(=O)CH=CHPh}(kappa(2)-MI)(CO)(PPh(3))(2)] [11].
 

Analytical, diagnostic and therapeutic context of methanidylidynesulfanium

  • Circular dichroism data of the ribozymes containing (4S)U+2 and (2S)U+2, as well as the susceptibility of the thiocarbonyl group to hydrogen peroxide, suggest that a conformational change of U+2 occurs during the domain docking in the cleavage reaction [12].

References

  1. Nephrotoxicity of para-substituted thiobenzamide derivatives in the rat. Traiger, G.J., Gammal, L.M., Cox, D.N., Haschek, W.M. Toxicology (1989) [Pubmed]
  2. Electron transfer kinetics and mechanistic study of the thionicotinamide coordinated to the pentacyanoferrate(III)/(II) complexes: a model system for the in vitro activation of thioamides anti-tuberculosis drugs. Sousa, E.H., Pontes, D.L., Diógenes, I.C., Lopes, L.G., Oliveira, J.S., Basso, L.A., Santos, D.S., Moreira, I.S. J. Inorg. Biochem. (2005) [Pubmed]
  3. Cation-pi interactions of a thiocarbonyl group and a carbonyl group with a pyridinium nucleus. Yamada, S., Misono, T., Tsuzuki, S. J. Am. Chem. Soc. (2004) [Pubmed]
  4. Thiothalidomides: novel isosteric analogues of thalidomide with enhanced TNF-alpha inhibitory activity. Zhu, X., Giordano, T., Yu, Q.S., Holloway, H.W., Perry, T.A., Lahiri, D.K., Brossi, A., Greig, N.H. J. Med. Chem. (2003) [Pubmed]
  5. Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase. Ichimori, K., Stuehr, D.J., Atkinson, R.N., King, S.B. J. Med. Chem. (1999) [Pubmed]
  6. Synthesis and pharmacological activity of triazolo[1,5-a]triazine derivatives inhibiting eosinophilia. Akahoshi, F., Takeda, S., Okada, T., Kajii, M., Nishimura, H., Sugiura, M., Inoue, Y., Fukaya, C., Naito, Y., Imagawa, T., Nakamura, N. J. Med. Chem. (1998) [Pubmed]
  7. Squaric acid-based peptidic inhibitors of matrix metalloprotease-1. Onaran, M.B., Comeau, A.B., Seto, C.T. J. Org. Chem. (2005) [Pubmed]
  8. Biological monitoring of occupational exposure to n-hexane by exhaled air analysis and urinalysis. Periago, J.F., Cardona, A., Marhuenda, D., Roel, J., Villanueva, M., Marti, J., Luna, A. International archives of occupational and environmental health. (1993) [Pubmed]
  9. Muon spectroscopy applied to biological systems: a study of thiyl radicals, RS. Rhodes, C.J., Hinds, C.S., Morris, H., Reid, I.D. Free Radic. Res. (1997) [Pubmed]
  10. Comparative anticonvulsant activity of some 2,3-benzodiazepine derivatives in rodents. De Sarro, G., Ferreri, G., Gareri, P., Russo, E., De Sarro, A., Gitto, R., Chimirri, A. Pharmacol. Biochem. Behav. (2003) [Pubmed]
  11. Sigma-organyl complexes of ruthenium and osmium supported by a mixed-donor ligand. Wilton-Ely, J.D., Honarkhah, S.J., Wang, M., Tocher, D.A., Slawin, A.M. Dalton transactions (Cambridge, England : 2003) (2005) [Pubmed]
  12. Investigation of the recognition of an important uridine in an internal loop of a hairpin ribozyme prepared using post-synthetically modified oligonucleotides. Komatsu, Y., Kumagai, I., Ohtsuka, E. Nucleic Acids Res. (1999) [Pubmed]
 
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