Isolation, synthesis and antitumor evaluation of spirohydantoin aziridine, a mutagenic metabolite of spirohydantoin mustard

Struck, Robert F.; Kirk, Marion; Rice, Louise S.; Suling, William J.

doi:10.1021/jm00157a039

Cited by 33 publications

(16 citation statements)

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“…Many of the hydantoins containing natural and synthetic products exhibit diverse biological activities, such as antitumor [5], antiarrhythmic [6], anticonvulsant [7], herbicidal [8], and others [9][10][11]. Although hydantoin compounds are studied extensively, there are not many studies about their anticancer properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, DFT calculations and cytotoxic investigation of platinum complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranespiro-5′-hydantoin

Bakalova

Buyukliev

Momekov

2015

Journal of Molecular Structure

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Section: Introductionmentioning

confidence: 99%

Synthesis, DFT calculations and cytotoxic investigation of platinum complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranespiro-5′-hydantoin

Bakalova

Buyukliev

Momekov

2015

Journal of Molecular Structure

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“…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].…”

Section: Introductionmentioning

confidence: 99%

Fluorous parallel synthesis of a hydantoin/thiohydantoin library

Zhang

2005

Mol Divers

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Fluorous tagging strategy is applied to solution-phase parallel synthesis of a library containing hydantoin and thiohydantoin analogs. Two perfluoroalkyl (Rf)-tagged α-amino esters each react with 6 aromatic aldehydes under reductive amination conditions. Twelve amino esters then each react with 10 isocyanates and isothiocyanates in parallel. The resulting 120 ureas and thioureas undergo spontaneous cyclization to form the corresponding hydantoins and thiohydantoins. The intermediate and final product purifications are performed with solid-phase extraction (SPE) over FluoroFlash™ cartridges, no chromatography is required. Using standard instruments and straightforward SPE technique, one chemist accomplished the 120-member library synthesis in less than 5 working days, including starting material synthesis and product analysis.

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“…In particular, hydantoins are used in medicine and agrochemistry as anticonvulsants [1,2], anticancer preparations [3], fungicides [4], and herbicides [5]. On the other hand compounds containing a sulfamide fragment display bacteriostatic, hypoglycemic, diuretic, and herbicidal action [2,[6][7][8].…”

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confidence: 99%

Synthesis and structure of 1,3-dialkyl-4-(sulfonylimino)imidazolidin-2-ones

Газиева

Lozhkin

Кравченко

et al. 2007

Chem Heterocycl Comp

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Keywords: 1-alkylsulfamides, 1,3-dialkyl-4-(alkylaminosulfonylimino)imidazolidin-2-ones, 4,5-dihydroxyimidazolidin-2-ones, 1,3-dimethyl-4-(benzenesulfonylimino)imidazolidin-2-one, X-ray structural analysis.Imidazolidin-2-one derivatives possess a broad spectrum of biological activity. In particular, hydantoins are used in medicine and agrochemistry as anticonvulsants [1, 2], anticancer preparations [3], fungicides [4], and herbicides [5]. On the other hand compounds containing a sulfamide fragment display bacteriostatic, hypoglycemic, diuretic, and herbicidal action [2, 6-8]. For several years the reactions of 4,5-dihydroxyimidazolidin-2-ones (DHI) with ureas and their hetero analogues have been among our scientific interests. Recently as a result of investigations carried out by us on the interaction of 1-alkyl and 1,3-dialkyl-DHI with sulfamide and amides of sulfonic acids, an unusual reaction has been detected [9] leading to 4,4'-sulfonyldiiminobis(1,3-dialkylimidazolidin-2-one) 1 and 4(5)-aryl(or alkyl)-sulfonyliminoimidazolidin-2-one 2, containing both pharmacophoric fragments. We later showed that the reaction of 1,3-dialkyl-DHI with aminoguanidine proceeds analogously with the formation of 1,3-dialkyl-4-guanidinoiminoimidazolidin-2-ones 3 [10]. N N O NSO 2 R 3 R 1 R 2 N N O R 1 NNHCNH 2 R 2 NH N N O R R NSO 2 N N N R O R 2 3 HCl 1 .With the aim of broadening the scope of the discovery, the reaction of 1,3-dialkyl-DHI 4a,b with 1-alkylsulfamides 5a-d under conditions analogous to the conditions of obtaining compounds 2 and 3 (methanol, HCl) (Scheme 1) has been investigated. __________________________________________________________________________________________

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Isolation, synthesis and antitumor evaluation of spirohydantoin aziridine, a mutagenic metabolite of spirohydantoin mustard

Cited by 33 publications

References 0 publications

Synthesis, DFT calculations and cytotoxic investigation of platinum complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranespiro-5′-hydantoin

Synthesis, DFT calculations and cytotoxic investigation of platinum complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranespiro-5′-hydantoin

Fluorous parallel synthesis of a hydantoin/thiohydantoin library

Synthesis and structure of 1,3-dialkyl-4-(sulfonylimino)imidazolidin-2-ones

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