Synthesis of (±)-carbocyclic analogue of spirohydantoin nucleoside

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

“…All the diastereomers and deoxy derivatives, except the 5-epimer, were found to be inactive, indicating that the integrity of three hydroxy groups in the sugar part are required to retain the activity.5) In contrast, the carbocyclic analogue showed herbicidal activity when applied to the foliage of weeds at 1000ppm. 4 ) On the other hand, the role of the spirohydantoin ring, which could be responsible for the interaction with a target site in plants, has not been clarified in spite of the synthesis of two analogues; a spirosuccinimide analogue,6) in which an amide nitrogen atom was replaced with a carbon atom, showed herbicidal activity, and a spirodihydrouracil analogue,7) in which a methylene group was inserted at the anomeric position, had no biological activity.…”

“…Our continuous investigation on the structure-herbicidal activity relationship of hydantocidin 1,1) the first naturally occurring spironucleoside, resulted in the synthesis of several analogues of hydantocidin diastereomers,2) deoxy derivatives,3) and carbocyclic nucleosides 4 ) to elucidate the role of the sugar part of the natural product. All the diastereomers and deoxy derivatives, except the 5-epimer, were found to be inactive, indicating that the integrity of three hydroxy groups in the sugar part are required to retain the activity.5) In contrast, the carbocyclic analogue showed herbicidal activity when applied to the foliage of weeds at 1000ppm.…”

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.

“…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.…”

Fluorous parallel synthesis of a hydantoin/thiohydantoin library

“…Aplysinopsins are isolated from marine organisms, and they exhibit cytotoxicity to cancer cells and ability to affect neurotransmitters [35][36][37]. Other hydantoin derivatives also exhibit a broad range of biological activities in medicinal (antitumor, anticovulsant, antimuscarinic, antiulcer, and antiarrythmic) [38][39][40][41][42] and agrochemical (herbicidal and fungicidal) [43][44][45][46][47][48][49] applications. In addition to solution phase synthesis [50][51], solid-phase synthesis of hydantoin has also been reported in the literature [52][53][54][55][56].…”