Aziridinomitosenes: A New Class of Antibiotics Related to the Mitomycins

Patrick, James B.; Williams, Robert P.; Meyer, W.E.; Fulmor, W.; Cosulich, Donna B.; Broschard, R. W.; Webb, John S.

doi:10.1021/ja01063a073

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“…10E) . No elimination of the 9a group was observed upon electrolytic reduction of mitomycin B to a semiquinone stage (PATRICK et al, 1964). The spontaneous elimination of the 9a methoxy group, which was previously observed during acid solvolysis of mitomycins (GARRETT, 1963;GARRETT and SCHROEDER, 1964;WEBB et al, 1962), was determined analytically.…”

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confidence: 71%

“…3 A;ALLEN et al, 1964a) and 7-methoxy-1,2-(N-methylaziridino)mitosene ( Fig. 3 B, PATRICK et al, 1964). 7-Methoxymitosene, which is only very remotely related to mitomycins, can be regarded as a monofunctional agent, whereas the other two compounds are bifunctional alkylating agents.…”

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confidence: 91%

“…aureus, 0.5 11-gfml for B. subtilis, and over 150 11-gfml for E. coli (ALLEN et al, 1964a). The inhibitory concentrations of the aziridinomitosenes (PATRICK et al, 1964) and indoloquinones (ALLEN et al, 1964b) have not been released by the manufacturer (Dr. G. R. ALLEN JR., personal communication). …”

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confidence: 99%

“…7-Methoxy-1,2-(N-methylaziridino) mitosene (Fig. 3B) was prepared in 40% yield by reduction and reoxidation of mitomycin B and reported to have bactericidal activity (PATRICK et al, 1964). Unfortunately, however, it was not made available for testing of its in vitro DNA cross-linking activity.…”

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confidence: 99%

“…Unfortunately, however, it was not made available for testing of its in vitro DNA cross-linking activity. No quantitative data were published on the antibiotic activities of three aziridinomitosenes derived from mitomycins A, B, and porfiromycin, but it was stated that surprisingly the activity of the latter compound is much lower than that of the derivatives of mitomycins A and B (PATRICK et al, 1964).After this review was completed, a theoretical paper of MuRAKAMI (1966) was published outlining the possible electronic mechanisms of mitomycin activation and DNA cross-linking. The author postulates that the intermediary semiquinoid form of mitomycin is the active intermediate and that the cross-link includes 0-o of guanine, N_ 4 and 0_ 5 of mitomycin, and N_ 4 of cytosine.…”

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Antibiotics

1967

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AII rights, especially that of tnmslation into foreign languages, reserved. It is also forbidden to reproduce this book, either whole DedicationFor most areas of scientific pursuit, there is usually that rare investigator who has the imagination to conceive ideas, who has faith in his visions, and who has the ability to critically test his concepts in the laboratory. Almost invariably, this scientist also inspires younger men to enthusiastically enter into his research program. To him should go the accolades and the recognitions of the esteem in which he is held. As only a small part of this esteem, we wish to dedicate these books to Professor SELMAN A. W AKSMAN in appreciation of his leadership and contributions in all facets of antibiotic research. PrefaceThe idea for publishing these books on the mechanism of action and on the biosynthesis of antibiotics was born of frustration in our attempts to keep abreast of the literature. Gone were the years when we were able to keep a bibliography on antibiotics and feel confident that we could find everything that was being published on this subject. These fields of investigation were moving forward so rapidly and were encompassing so wide a range of specialized areas in microbiology and chemistry that it was almost impossible to keep abreast of developments. In our naivete and enthusiasm, however, we were unaware that we were toying with an idea that might enmesh us, that we were creating an entity with a life of its own, that we were letting loose a Golom who instead of being our servant would be our master.That we set up ideals for these books is obvious; they would be current guides to developments and information in the areas of mechanism of action and biosynthesis of antibiotics. For almost every subject, we wished to enlist the aid of an investigator who himself had played a part in determining the nature of the phenomena that were being discussed. One concept for the books was that they include only antibiotics for which a definitive, well-documented mechanism of action or biosynthetic pathway was known. Yet, such an approach would not entirely serve the purpose we projected, for it would not encompass all of the information available in these fields of antibiotic investigations and blind searches for the original literature would still have to be made. We therefore chose to include any and all antibiotics about which some pertinent information had been published. It was obvious even at the start that such a compilation, integration, and analysis of information could never be complete unless scientific investigations ceased at the moment the last manuscript was submitted-an end that was neither desirable nor possible. An addendum was therefore included at the end of the volume and left open for the addition of new information until the last pages of the regular articles had been printed.The original concept has also been further expanded as the authors of several papers found it advisable to elaborate on their subject. Some of the articles included discussions...

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Antibiotics

1967

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Die Totalsynthese von (±)‐Mitomycin K

Benbow

Schulte

1992

Angewandte Chemie

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The Total Synthesis of (±)‐Mitomycin K

Benbow

Schulte

1992

Angew. Chem. Int. Ed. Engl.

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Crystal data: (Ph,P),-1, monoclinic. C2/c. u = 14.968(3) A, b = 20.232(4) A, c = 22.336(5) A, fi = 106.41(2)", V = 6488(2) A3, Z = 4, Q~~,~~ = 1.90 gcm-3. p(MoKm) = 2.97 mm-' (transmission factors: 0.84-1 .OO). Refined using 2792 observed reflections [ I > 3 o(r)] to R(F,) = 0.0734 and R,(F,) = 0.0851. All non-hydrogen atoms were refined anisotropically with observed reflections per parameter = 7.086. For (Ph,P),-Z. triclinic, Pi, u =13.037(3) A, b =14.913(3) A, c = 24.041(4) A, x =76.70(2)", fi = 86.90(2)", y = 66.75(2)", V = 4176(2) A', Z = 2, Q~~,~~ = 2.36 gcm-3, p(MoK.) = 4.89 mm-' (transmission factors: 0.58-1 .OO). Refined using 8609 observed reflections [I > 3 ~(01, to R(FJ =0.0423. and R,(Fo) = 0.0539. The carbon atoms of the cation were refined istropically and all other heavy atoms anisotropically, hydrogen atoms were not located. observed reflections per parameter = 11.74. Further details of the crystal structure investigations may be obtained from the Fachinformationszentrum Karlsruhe, Gesellschaft fur wissenschaftlich-technische Information mbH, W-7514 Eggenstein-Leopoldshafen 2 (FRG) on quoting the depository number CSD-56092, the names of the authors, and the journal citation.[S] a)

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Aziridinomitosenes: A New Class of Antibiotics Related to the Mitomycins

Cited by 54 publications

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Antibiotics

Antibiotics

Die Totalsynthese von (±)‐Mitomycin K

The Total Synthesis of (±)‐Mitomycin K

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