RSU-1069

1-(1-氮丙啶基)-3-(2-硝基-1H-咪唑-1-基)-2-丙醇Chemical Name: 1-(2-Nitro-1-imidazolyl)-3-(1-aziridino)-2-propanol; 1-(2-Hydroxy-3-aziridinyl-n-propyl)-2-nitroimidazole
CAS No. 88876-88-4
项目整合开发状态: Phase I
项目研究机构: BTG (Originator)
合成路线:By reaction of 1-(2,3-epoxypropyl)-2-nitroimidazole (I) with aziridine (II) in refluxing methanol.
📌 参考资料/链接:
参考文献标题:Aziridino containing nitro imidazoles and pharmaceutical compositions
文献作者:Ahmed,I.; Adams,G.E.; Stratford,I.J.(National Research Development Corp.)
参考来源:EP 0095906; GB 2123816; JP 58225086; US 4596817; US 4631289; US 4757148

📄 详细内容


合成路线:By reaction of 1-(2,3-epoxypropyl)-2-nitroimidazole (I) with aziridine (II) in refluxing methanol.

参考文献标题:RSU-1069
文献作者:Hopkins,S.J.; Castar,J.
参考来源:Drugs Fut 1986,11(6),467


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


合成路线:By reaction of 1-(2,3-epoxypropyl)-2-nitroimidazole (I) with aziridine (II) in refluxing methanol.
参考文献标题:Radiation sensitization and chemopotentation.RSU 1069,a compound more efficient than misonidazole in vitro and un vivo
文献作者:Adams,G.E.; Ahmed,I.; Sheldon,P.W.; Stratford,I.J.
参考来源:Brit J Cancer 1984,49(1),571


产品链接: CAS No. 88876-88-4››