1,2-Dithiolane-3-carboxylic Acid.

Claeson, Göran; Elming, Niels; Tyle, Zdeněk; Caglieris, Albertina

doi:10.3891/acta.chem.scand.09-0178

Cited by 18 publications

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“…Finally, compounds 2-5 were tested as antiproliferative drugs because it has been reported that 1-related derivatives, namely, terazosin and doxazosin, exert apoptotic activity in stroma smooth muscle and epithelial cell populations in prostate tissue. 15 Synthesis of quinazolines 2-5 was accomplished by reaction of the known quinazolinylpiperazine 6 16 with LA (7), 2-(1,2-dithiolan-3-yl)acetic acid (8), 17 1,2-dithiolane-3-carboxylic acid (9), 18 or 2-methoxy-1,4-naphthoquinone (10), respectively (Scheme 1). No attempt was made to obtain the enantiomers of 2-4 because it was reported that stereochemistry is not relevant for the protective effect of LA against oxidative cell damage.…”

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“…Synthesis of quinazolines 2 − 5 was accomplished by reaction of the known quinazolinylpiperazine 6 with LA ( 7 ), 2-(1,2-dithiolan-3-yl)acetic acid ( 8 ), 1,2-dithiolane-3-carboxylic acid ( 9 ), or 2-methoxy-1,4-naphthoquinone ( 10 ), respectively (Scheme ). No attempt was made to obtain the enantiomers of 2 − 4 because it was reported that stereochemistry is not relevant for the protective effect of LA against oxidative cell damage …”

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Design, Synthesis, and Biological Evaluation of Prazosin-Related Derivatives as Multipotent Compounds

et al. 2004

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To combine in the same molecule alpha(1)-adrenoreceptor blocking and antioxidant properties, compounds 2-5 were designed and synthesized. All compounds were effective alpha(1)-adrenoreceptor antagonists and were tested in both functional and binding assays. In addition, compounds 2 and 5 also displayed significant capacity to inhibit intracellular oxidative stress, whereas 3-5 exerted potent antiproliferative activity in lymph node carcinoma of prostate cells.

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Design, Synthesis, and Biological Evaluation of Prazosin-Related Derivatives as Multipotent Compounds

et al. 2004

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“…Bisnor-lipoic acid was synthesized from monomethyl succinate after the method of Kumagaya & Kasuga (I 963). Tetranor-lipoic (I ,2-dithiolane-3-carboxylic) acid was synthesized from y-butyrolactone according to Claeson (1955) as modified by Wladislaw (1957). The D-and L-forms of lipoic acid were prepared by the method of Acker & Wayne (1957).…”

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Characterization of the Growth of Pseudomonas Putida LP on Lipoate and its Analogues: Transport, Oxidation, Sulphur Source, and Enzyme Induction

Shih

Rozo

Wright

et al. 1975

Journal of General Microbiology

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S U M M A R YPseudomonas putida LP, which grows on lipoate, NH,NO, and mineral salts, converts most of the organic substrate to bisnor-lipoate (I ,2-dithiolane-3-propanoic acid) and acetyl-CoA. D-, L-, or ~~-1 i p o a t e serve equally well as carbon and sulphur sources. There was no growth on or bacterial oxidation of the chemicalIy synthesized bisnor-or tetranor-( I ,2-dithiolane-3-carboxylic acid) chain-shortened analogues, but these, as well as lipoate, could supply the sulphur needed for growth when acetate was provided as the sole source of carbon. The uptake of lipoate by the bacterium is very slow and non-inducible, while the uptake of acetate is faster than octanoate. The oxidation of octanoate is more rapid and extensive than that of lipoate. Levels of acyl-CoA synthetase are not affected by the source of carbon, but activities of isocitrate lyase and malate synthase are higher when the cells are grown in acetate, octanoate or lipoate and lower when glucose is the carbon source. The glyoxylate cycle is induced to facilitate utilization of acetyl-CoA derived from lipoate, which is also degraded to water-soluble catabolites that yield the much smaller amount of sulphur required for growth. I N T R O D U C T I O NAlthough the principal biochemical function of lipoic (thioctic) acid in a-keto acid dehydrogenases is understood, little was known concerning the metabolic fate of this compound. An organism identified as Pseudomonasputida LP was isolated and adapted to grow in a synthetic medium, which contained 0.4 % (w/v) lipoic acid as the sole source of carbon, sulphur and energy. One major catabolite was identified as bisnor-lipoic (I ,a-dithiolane-3-propanoic) acid, indicating at least partial P-oxidation of the side chain (Shih, Wright & McCormick, I 972).We have now studied uptake, oxidation and sulphur utilization of lipoic acid and its chainshortened analogues by this lipoate-degrading pseudomonad. To ascertain the existence of pathways for P-oxidation and the glyoxylate cycle in the pseudomonad grown on lipoate, some relevant enzyme activities have also been determined.

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C ₃ S ₂ Ring Systems

1966

Chemistry of Heterocyclic Compounds: A Series of Monographs

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1,2-Dithiolane-3-carboxylic Acid.

Cited by 18 publications

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Design, Synthesis, and Biological Evaluation of Prazosin-Related Derivatives as Multipotent Compounds

Design, Synthesis, and Biological Evaluation of Prazosin-Related Derivatives as Multipotent Compounds

Characterization of the Growth of Pseudomonas Putida LP on Lipoate and its Analogues: Transport, Oxidation, Sulphur Source, and Enzyme Induction

C ₃ S ₂ Ring Systems

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1,2-Dithiolane-3-carboxylic Acid.

Cited by 18 publications

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Design, Synthesis, and Biological Evaluation of Prazosin-Related Derivatives as Multipotent Compounds

Design, Synthesis, and Biological Evaluation of Prazosin-Related Derivatives as Multipotent Compounds

Characterization of the Growth of Pseudomonas Putida LP on Lipoate and its Analogues: Transport, Oxidation, Sulphur Source, and Enzyme Induction

C 3 S 2 Ring Systems

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C ₃ S ₂ Ring Systems