Diaziquone, CI-904, NSC-182986, AZQ, -Drug Synthesis Database

【结构式】

【药物名称】Diaziquone, CI-904, NSC-182986, AZQ

【化学名称】Diethyl 2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-dicarbamate
　　　　　　2,5-Diaziridinyl-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone
　　　　　　[2,5-Bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexanediene-1,4-diyl]biscarbamic acid diethyl ester

【CA登记号】57998-68-2

【分子式】C₁₆H₂₀N₄O₆

【分子量】364.361

【开发单位】National Cancer Institute (Originator), MedImmune Oncology (Licensee)

【药理作用】Oncolytic Drugs, DNA-Damaging Drugs

合成路线1

The reaction of chloranil (I) with ethyl carbamate (II) by means of Na in dry benzene gives 2,5-dichloro-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone (III), which is then condensed with aziridine (IV) by means of triethylamine in THF.

参考文献中间体

【1】 Driscoll, J.S.; et al.; Structure-antitumor activity relationships among quinone derivatives. Cancer Chemother Rep 1974, 4, 2, 1.
【2】 Zubrod, C.G.; Rall, D.P.; Anu Rev Pharmacol 1962, 2, 109.
【3】 Kahn, A.H.; Driscoll, J.S.; Potential central nervous system antitumor agents. Azirinylbenzoquinones. 1. J Med Chem 1976, 19, 2, 313-317.
【4】 Driscoll, J.S.; et al. (US Department of Health & Human Services); Aziridinyl quinone anti-transplanted tumor agents. US 4146622 .
【5】 Cabanillas, F.; Blancafort, P.; Serradell, M.N.; Castaner, J.; AZQ. Drugs Fut 1981, 6, 6, 338.

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)	21891	2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzo-1,4-quinone; p-Chloranil	118-75-2	C₆Cl₄O₂	详情	详情
(II)	24199	Ethyl carbamate; Urethane	51-79-6	C₃H₇NO₂	详情	详情
(III)	32193	2,5-Dichloro-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone; Ethyl 2,5-dichloro-4-[(ethoxycarbonyl)amino]-3,6-dioxo-1,4-cyclohexadien-1-ylcarbamate		C₁₂H₁₂Cl₂N₂O₆	详情	详情
(IV)	10151	Ethyleneimine; Aziridine; Azirane	151-56-4	C₂H₅N	详情	详情

Extended Information