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Chemical Compound Review

AG-F-63986     1,3-dithiolane

Synonyms: ACMC-20ap3t, CHEBI:38079, NSC-193357, AC1L2HCX, LS-63228, ...
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Disease relevance of Dithiolane


High impact information on Dithiolane

  • The similarities in architecture of the E1E2 and E2E3 complexes indicate fundamental similarities in the mechanism of active site coupling involved in the two key stages requiring motion of the swinging lipoyl domain across the annular gap, namely the synthesis of acetyl CoA and regeneration of the dithiolane ring of the lipoyl domain [2].
  • Then, many functional groups such as allyl alcohol, silyl ether, acetate, methyl ether, triphenylmethyl (Tr) ether, 1,3-dithiolane, methyl ester, and tert-butyl ester could survive under these conditions [3].
  • Studies on the biochemical mechanism of dithiolane S-oxygenation in liver, kidney, and lung microsomes suggest that this reaction is catalyzed in a diastereoselective and enantioselective fashion by the flavin-containing monooxygenase and, to a lesser extent, the cytochromes P-450 [4].
  • The dithiolane cephalosporins themselves were stable against hydrolysis by the beta-lactamases tested [5].
  • The dithiolane was not a good antidote in the cultured cell system [6].

Anatomical context of Dithiolane


Associations of Dithiolane with other chemical compounds

  • AIM: To investigate the effect of a group of novel synthetic dithiolane analogs of lignans and a well characterized platelet-activating factor (PAF) receptor antagonist, L659,989 on PAF-receptor binding, IFN-gamma- and lipopolysaccharide (LPS)-induced NO production, and steady-state inducible nitric-oxide synthase (iNOS) mRNA expression [9].

Gene context of Dithiolane


  1. Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition. Park, J.S., Chang, C.T., Schmidt, C.L., Golander, Y., De Clercq, E., Descamps, J., Mertes, M.P. J. Med. Chem. (1980) [Pubmed]
  2. Molecular structure of a 9-MDa icosahedral pyruvate dehydrogenase subcomplex containing the E2 and E3 enzymes using cryoelectron microscopy. Milne, J.L., Wu, X., Borgnia, M.J., Lengyel, J.S., Brooks, B.R., Shi, D., Perham, R.N., Subramaniam, S. J. Biol. Chem. (2006) [Pubmed]
  3. Reaction of the Acetals with TESOTf-Base Combination; Speculation of the Intermediates and Efficient Mixed Acetal Formation. Fujioka, H., Okitsu, T., Sawama, Y., Murata, N., Li, R., Kita, Y. J. Am. Chem. Soc. (2006) [Pubmed]
  4. Enantioselective S-oxygenation of para-methoxyphenyl-1,3-dithiolane by various tissue preparations: effect of estradiol. Cashman, J.R., Olsen, L.D., Lambert, C.E., Presas, M.J. Mol. Pharmacol. (1990) [Pubmed]
  5. Potent cephalosporinase inhibitors: 7 beta-[2-(1, 3-dithiolan-2-ylidene) acetamido] cephalosporins and related compounds. Ohya, S., Miyadera, T., Yamazaki, M. Antimicrob. Agents Chemother. (1982) [Pubmed]
  6. 2,3-Dithioerythritol, a possible new arsenic antidote. Boyd, V.L., Harbell, J.W., O'Connor, R.J., McGown, E.L. Chem. Res. Toxicol. (1989) [Pubmed]
  7. Metabolism of 7-(1,3-dithiolan-2-ylmethyl)-1,3-dimethylxanthine by rat liver microsomes. Diastereoselective metabolism of the 1,3-dithiolane ring. Grosa, G., Caputo, O., Ceruti, M., Biglino, G., Franzone, J.S., Cravanzola, C. Drug Metab. Dispos. (1991) [Pubmed]
  8. Alpha-Lipoic acid-based PPARgamma agonists for treating inflammatory skin diseases. Venkatraman, M.S., Chittiboyina, A., Meingassner, J., Ho, C.I., Varani, J., Ellis, C.N., Avery, M.A., Pershadsingh, H.A., Kurtz, T.W., Benson, S.C. Arch. Dermatol. Res. (2004) [Pubmed]
  9. Dithiolane analogs of lignans inhibit interferon-gamma and lipopolysaccharide-induced nitric oxide production in macrophages. Hussaini, I.M., Zhang, Y.H., Lysiak, J.J., Shen, T.Y. Acta Pharmacol. Sin. (2000) [Pubmed]
  10. Synthesis and pharmacological evaluation of new 1,2-dithiolane based antioxidants. Guillonneau, C., Charton, Y., Ginot, Y.M., Fouquier-d'Hérouël, M.V., Bertrand, M., Lockhart, B., Lestage, P., Goldstein, S. European journal of medicinal chemistry. (2003) [Pubmed]
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