Antimetabolites of coenzyme Q. 17. Improved synthesis of 5-hydroxy-1,4-benzoquinone analogs and their indices

Bogentoft, Conny; Klaudy, Alexander Von; Folkers, Karl

doi:10.1021/jm00281a011

Cited by 14 publications

(2 citation statements)

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“…All chemicals were purchased from either Sigma, Calbiochem, or Alrich except for C-OH-BQ and C-OH-NQ which were synthesized according to previously described procedures (Fieser et al, 1948;Bogentoft et al, 1972) and heptyl coenzyme Q which were gifts from Dr. K. Folkers and Dr. T. H. Porter. Duroquinol (DQH2) was made by reducing duroquinone (DQ) with borohydride in ethanol as described by Ruzicka (Ruzicka and Crane, 1971) and used as a methanol solution saturated at 0°.…”

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confidence: 99%

Inhibition of mitochondrial electron transport by hydroxy-substituted 1,4-quinones

Phelps¹,

Crane²

1975

Biochemistry

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Mitochondrial electron transport from NADH, succinate, or duroquinol to oxygen is inhibited by 5-omega-cyclohexyl-n-pentyl-6-hydroxy-2,3-dimethoxy-1,4-benzoquinone and 2-omega-cyclohexyl-n-pentyl-3-hydroxy-1,4-napthoquinone. Assays of partial electron transport activities indicate a site of inhibition in the region between the site of duroquinol oxidation and cytochrome c reduction. Effects of the inhibitors on cytochrome spectra indicate the principle site of inhibition is between cytochromes of the b group and cytochrome c1. The quinones do not induce increased reduction of the b566 as does antimycin A. The benzoquinone can induce a partial antimycin insensitive bypass of the cytochromes b-c1 region. Uncoupling agents do not affect the extent of inhibition as has been reported for analogous naphthoquinone inhibitors.

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confidence: 99%

Inhibition of mitochondrial electron transport by hydroxy-substituted 1,4-quinones

Phelps¹,

Crane²

1975

Biochemistry

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“…von R-(-)d'-Hydroxymethyllaudanosin (la)4) uber 2a oder von R-(-)-Laudanosin (18b)") ausgehend uber Wa unabhangig synthetisiert wurde, sollte Apfelsaure (19) in optisch aktiver Form entstehen (Abb. lo), deren absol.…”

Section: Ozonolyse Von 4aunclassified

Nachweis der Inversion bei der Umsetzung optisch aktiver 1‐(0‐Hydroxymethyl‐benzyl)‐N‐methyl‐1,2,3,4‐tetrahydroisochinoline zu 3‐Phenylisochromanen

Wiegrebe

Prior

Mayer

1982

Archiv der Pharmazie

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Antimetaboliten des Coenzyms Q. Möglichkeiten ihrer Anwendung als Antimalaria‐Mittel

Porter

Folkers

1974

Angewandte Chemie

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Die Malaria wird auf den Menschen durch den Stich der Anopheles-Mucke ubertragen; der Mensch fungiert als Zwischenwirt und die Mucke als Endwirt fur die Plasmodien. Gegen einige Chemotherapeutica sind die Plasmodien resistent geworden. €in neues Konzept der Malaria-Therapie geht davon aus, daB der Elektronentransport im Stoffwechsel'der Plasmodien durch Antimetaboliten des Coenzyms Q gehemmt wird, das am Elektronentransport maageblich beteiligt ist. Als Coenzym Q bezeichnet man 2.3-Dimethoxy-5-methyl-1.4-benzochinone mit isoprenoiden Ketten wechselnder Lange an C-6. In diesem Fortschrittsbericht wird eine Reihe synthetischer Antimetaboliten vorgestellt und ihre Wirkung in vorliufigen pharmakologischen Tests diskutiert.

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Antimetabolites of coenzyme Q. 17. Improved synthesis of 5-hydroxy-1,4-benzoquinone analogs and their indices

Cited by 14 publications

References 0 publications

Inhibition of mitochondrial electron transport by hydroxy-substituted 1,4-quinones

Inhibition of mitochondrial electron transport by hydroxy-substituted 1,4-quinones

Nachweis der Inversion bei der Umsetzung optisch aktiver 1‐(0‐Hydroxymethyl‐benzyl)‐N‐methyl‐1,2,3,4‐tetrahydroisochinoline zu 3‐Phenylisochromanen

Antimetaboliten des Coenzyms Q. Möglichkeiten ihrer Anwendung als Antimalaria‐Mittel

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