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通过 C-苯甘氨酸衍生物合成新型咪唑烷-2,4-二酮和 2-硫代咪唑烷-4-酮。

Synthesis of new imidazolidin-2,4-dione and 2-thioxoimidazolidin-4-ones via C-phenylglycine derivatives.

机构信息

Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, João Pessoa-PB, CEP 58.051-970, Brazil.

出版信息

Molecules. 2009 Dec 30;15(1):128-37. doi: 10.3390/molecules15010128.

DOI:10.3390/molecules15010128
PMID:20110877
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6257050/
Abstract

Hydantoins and their derivatives constitute a group of pharmaceutical compounds with anticonvulsant and antiarrhythmic properties, and are also used against diabetes. N-3 and C-5 substituted imidazolidines are examples of such products. As such, we have developed a synthesis of 2,4-dione and 2-thioxo-4-one imidazolidinic derivatives by reaction of amino acids with C-phenylglycine, phenyl isocyanate and phenyl isothiocyanate. Four amino-derivatives IG(1-4) and eight imidazolidinic derivatives, IM(1-8), were obtained in yields of 70-74%. The mass, infrared, (1)H and (13)C-NMR spectra of representative products are discussed.

摘要

脒基乙内酰脲及其衍生物是一组具有抗惊厥和抗心律失常特性的药物化合物,也可用于治疗糖尿病。N-3 和 C-5 取代的咪唑烷是此类产品的示例。因此,我们通过氨基酸与 C-苯甘氨酸、苯异氰酸酯和苯异硫氰酸酯的反应,开发了 2,4-二酮和 2-硫代-4-氧代咪唑烷衍生物的合成方法。得到了四个氨基衍生物 IG(1-4)和八个咪唑烷衍生物 IM(1-8),产率为 70-74%。讨论了代表性产物的质量、红外、(1)H 和 (13)C-NMR 谱。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad6a/6257050/016e0b188d3b/molecules-15-00128-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad6a/6257050/abd7dd88d6ea/molecules-15-00128-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad6a/6257050/016e0b188d3b/molecules-15-00128-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad6a/6257050/abd7dd88d6ea/molecules-15-00128-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad6a/6257050/016e0b188d3b/molecules-15-00128-sch002.jpg

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A simple synthesis of 2-thiohydantoins.2-硫代乙内酰脲的简易合成法。
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Novel 5-substituted 2,4-thiazolidinedione and 2,4-oxazolidinedione derivatives as insulin sensitizers with antidiabetic activities.
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