Teroxirone, NSC-296934, alpha-TGT, alpha-TGI, -Drug Synthesis Database

【结构式】

【药物名称】Teroxirone, NSC-296934, alpha-TGT, alpha-TGI

【化学名称】[1(R*),3(R*),5(S*)]-(±)-1,3,5-Tris(oxiranylmethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
　　　　　　(RS,RS,SR)-1,3,5-Tris(2,3-epoxypropyl)-s-triazine-2,4,6(1H,3H,5H)-trione
　　　　　　alpha-1,3,5-Triglycidyl-s-triazinetrione
　　　　　　alpha-Triglycidyl isocyanurate
　　　　　　Triazinetrione triepoxide

【CA登记号】59653-73-5, 59653-74-6 (beta-isomer)

【分子式】C₁₂H₁₅N₃O₆

【分子量】297.26985

【开发单位】Henkel (Originator), National Cancer Institute (Originator), Asta Medica (Licensee)

【药理作用】Oncolytic Drugs

合成路线1

The compound can be prepared in the following way: The reaction of a large excess of epichlorohydrin (II) with cyanuric acid (I) at a temperature above 60 C leads to the 1,3,5-tris(oxiranylmethyl)-substituted derivative (III). Thus, epichlorohydrin functions both as alkylating agent and base. The addition of sodium hydroxide accelerates and completes the hydrogen chloride abstraction after the first step of the reaction. Fractional crystallization of the product gives the alpha and beta stereoisomers.

参考文献中间体

【1】 Budnowski, M.; Preparation and properties of the diastereoisomeic 1,3,5-triglycidyl-s-triazinetriones. Angew Chem 1968, 7, 827.
【2】 Schnegelberger, H.; Budnowski, M. (Henkel KgA); Therapeutic compsns. with a cytostatic action. GB 2044614 .
【3】 Castaner, J.; Serradell, M.N.; Blancafort, P.; Teroxirone. Drugs Fut 1983, 8, 11, 936.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	36210	1,3,5-triazinane-2,4,6-trione		C₃H₃N₃O₃	详情	详情
(II)	13917	(S)-Epichlorohydrin; (2S)-2-(Chloromethyl)oxirane;(S)-(+)-epichlorohydrin	67843-74-7	C₃H₅ClO	详情	详情

Extended Information