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Pimonidazole hydrochloride, Ro-038799

哌莫硝唑 Chemical Name: 1-(2-Nitroimidazol-1-yl)-3-(1-piperidinyl)-2-propanol
CAS No. 70132-51-3, 70132-50-2 (free base)
项目整合开发状态: Phase III
项目研究机构: Roche (Originator)
合成路线:1) By condensation of 2-nitroimidazole (I) with 3-(1-piperidino)propyliene oxide (II) in refluxing ethanol.

合成路线:Hexamethylenebisacetamide is prepared by reacting 1,6-hexanediamine (I) with two moles of acetic acid.
📌 参考资料/链接:
参考文献标题:Preparation of polyacetylalkylenediamines
文献作者:Grimmelikhuysen,J.; Schroeder,A.(Unilever NV)
参考来源:BE 769655; DE 2133458; FR 2100320; GB 1335204

📄 详细内容


合成路线:2) By condensation of 1-(3-chloro 2 hydroxypropyl)-2-nitroimidazole (III) with piperidine (IV) in refluxing methanol.

合成路线:3) By condensation of 1-(2,3-epoxypropyl)-2 nitroimidazole (V) with (IV) in refluxing ethanol.

合成路线:1) The reaction of N1-(4-chlorobenzoyl)-N1-(4-methoxyphenyl)hydrazine (I) [the starting material for the synthesis of indomethacin],with d,l-(2-carboxyethyl-2-phenyl)-4-oxopentanoate (II) under the conditions of Fischer indole synthesis by means of 100% phosphoric acid in toluene at 100 C.d,l-(2-Carboxyethyl-2-phenyl)-4-oxopentanoate (II) is obtained hy treatment of d,l-tropic acid with levulinic acid chloride.

参考文献标题:Method of producing 2-phenyl-2-carboxyethyl ester of 1-p-chlorobenzoyl-5-methoxy-2-methyl-3-indolyl acetic acid
文献作者:Fisnerova,L.; Nemecek,O.
参考来源:CS 194284


合成路线:1) By condensation of 2-nitroimidazole (I) with 3-(1-piperidino)propyliene oxide (II) in refluxing ethanol.

合成路线:2) By condensation of 1-(3-chloro 2 hydroxypropyl)-2-nitroimidazole (III) with piperidine (IV) in refluxing methanol.

合成路线:3) By condensation of 1-(2,3-epoxypropyl)-2 nitroimidazole (V) with (IV) in refluxing ethanol.

参考文献标题:RO-038799
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1986,11(7),580


合成路线:[2H]-Labeled RSU-1069 is synthesized as follows:The condensation of 2-nitroimidazole (I) with 3-chloro-1,2-epoxypropane (II) gives 1-(3-chloro-2-hydroxypropyl)-2-nitroimidazole (III),which is oxidized with CrO3 - H2SO4 in acetone yielding 1-(3-chloro-2-oxopropyl)-2-nitroimidazole (IV).The reduction of (IV) with NaB[2H]4 in ethanol affords 1-(3-chloro-2-hydroxy-2(2H)-propyl)-2-nitroimidazole (V),which is cyclized with NaOH to the corresponding labeled epoxide (VI).Finally,this compound is condensed with aziridine (VII) by means of triethylamine in refluxing ethanol.

合成路线:[2H]-Labeled pimonidazole is synthesized as follows:The condensation of 2-nitroimidazole (I) with 3-chloro-1,2-epoxypropane (II) gives 1-(3-chloro-2-hydroxypropyl)-2-nitroimidazole (III),which is oxidized with CrO3 - H2SO4 in acetone yielding 1-(3-chloro-2-oxopropyl)-2-nitroimidazole (IV).The reduction of (IV) with NaB[2H]4 in ethanol affords 1-(3-chloro-2-hydroxy-2(2H)-propyl)-2-nitroimidazole (V),which is cyclized with NaOH to the corresponding labeled epoxide (VI).Finally,this compound is condensed with piperidine (VII) in refluxing ethanol.
参考文献标题:Labelled compounds of interest as antitumour agents.Part II (1).Synthesis of 2H and 3H isotopomers of RSU 1069 and Ro 03-8799 (pimonidazole)
文献作者:Webb,P.; Threadgill,M.D.
参考来源:J Label Compd Radiopharm 1990,28(3),257


产品链接: CAS No. 70132-51-3››

产品链接: CAS No.70132-50-2››