Synthesis and Herbicidal Activity of Hydantocidin Analogues: Modification of the Carbonyl Groups in Spirohydantoin

Sano, Hiromi; Mio, Shigeru; Hamura, Masae; Kitagawa, Junko; Shindou, Masahiro; Honma, Toyokuni; Sugai, Soji

doi:10.1271/bbb.59.2247

Cited by 9 publications

(7 citation statements)

References 4 publications

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“…Surprisingly, as for the bacterial enzyme, hydantocidin did not show any significant inhibition of the partially purified plant AdSS activity, in contrast to that observed in the raw extract. On the other hand hadacidin potently inhibited both the wheat germ AdSS activity in a crude extract (IC50, 15 ,uM ± 1) as well as in the enriched fractions (IC50, 24 ,uM + 1), as expected. All these results led us to suspect that hydantocidin could be a prodrug, as recently suggested (42,43 (26).…”

Section: Resultssupporting

confidence: 80%

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The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.

Fonné‐Pfister

Chemla

Ward

et al. 1996

Proc. Natl. Acad. Sci. U.S.A.

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(+)-Hydantocidin, a recently discovered natural spironucleoside with potent herbicidal activity, is shown to be a proherbicide that, after phosphorylation at the 5' position, inhibits adenylosuccinate synthetase, an enzyme involved in de novo purine synthesis. The mode of binding of hydantocidin 5'-monophosphate to the target enzyme was analyzed by determining the crystal structure of the enzyme-inhibitor complex at 2.6-A resolution. It was found that adenylosuccinate synthetase binds the phosphorylated compound in the same fashion as it does adenosine 5'-monophosphate, the natural feedback regulator of this enzyme. This work provides the first crystal structure of a herbicide-target complex reported to date.

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Section: Resultssupporting

confidence: 80%

“…Its intriguing structure and remarkable biological properties have stimulated a considerable amount of synthetic work on the parent compound (9)(10)(11)(12)(13)(14) and its analogues (15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25). The novel injury symptoms it elicits in plants has prompted a detailed investigation of its mode of action.…”

mentioning

confidence: 99%

The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.

Fonné‐Pfister

Chemla

Ward

et al. 1996

Proc. Natl. Acad. Sci. U.S.A.

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“…Sano et al prepared several hydantocidin analogues including modifications on the carbonyl groups of the hydantoin ring [ 89 ]. For example, spiroimidazolidinone 176 was synthesized using a demethyldesulfurization as key step ( Scheme 36 ).…”

Section: Synthesis Of Miscellaneous Spiroheterocyclic Unitsmentioning

confidence: 99%

Synthesis of Spironucleosides: Past and Future Perspectives

2017

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Spironucleosides are a type of conformationally restricted nucleoside analogs in which the anomeric carbon belongs simultaneously to the sugar moiety and to the base unit. This locks the nucleic base in a specific orientation around the N-glycosidic bond, imposing restrictions on the flexibility of the sugar moiety. Anomeric spiro-functionalized nucleosides have gained considerable importance with the discovery of hydantocidin, a natural spironucleoside isolated from fermentation broths of Streptomyces hygroscopicus which exhibits potent herbicidal activity. The biological activity of hydantocidin has prompted considerable synthetic interest in this nucleoside and also in a variety of analogues, since important pharmaceutical leads can be found among modified nucleoside analogues. We present here an overview of the most important advances in the synthesis of spironucleosides.

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“…In some cases, the same compound has been proposed as both herbicidal and pharmaceutical products, although there are no commercial products of either. The microbial product hydantocidin is an example of this (Mandal et al 2005;Sano et al 1995). In this brief review, there is no room to report the many thousands of papers and patents on the potential pharmaceutical uses of herbicides or closely related compounds.…”

Section: Final Thoughtsmentioning

confidence: 99%

Herbicide and Pharmaceutical Relationships

Duke

2010

Weed sci.

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For many years, virtually all pharmaceutical companies had an agrochemical division. This was partly to maximize the benefits of expensive chemical synthesis efforts by searching for many types of useful biological activities. Leads for pharmaceuticals and pesticides often overlap, in some cases leading to similar compounds used for human health and weed management purposes. This review will focus on herbicides and herbicide classes that have potential pharmaceutical properties, both as therapeutic agents that act through human molecular target sites and those that act on infectious agents. An example of the first case is compounds that target plant acetyl coenzyme A carboxylases, inhibiting fatty acid synthesis, and similar compounds used in humans as anti-inflammatory agents. Another such example is the triketone class of compounds that can act both as herbicides and as treatments for the genetic disease tyrosinemia, targeting the same enzyme in both cases. Examples of the second case are the relatively large number of herbicides that have activity against the malaria protozoan (Plasmodiumspp.). It turns out thatPlasmodiumspp. and related disease organisms have an organelle that is apparently analogous to the plant plastid, the apicoplast. Herbicides such as dinitroanilines are active against several protozoan parasites by the same mechanism by which they kill plants, interaction with tubulin to halt cell division and other tubulin-dependent processes. These and other multiple activities of various herbicides and herbicide classes provide perspective on the broad biological activity of herbicides and related compounds.

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Synthesis and Herbicidal Activity of Hydantocidin Analogues: Modification of the Carbonyl Groups in Spirohydantoin

Cited by 9 publications

References 4 publications

The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.

The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.

Synthesis of Spironucleosides: Past and Future Perspectives

Herbicide and Pharmaceutical Relationships

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