Esorubicin hydrochloride, NSC-267469(free base), IMI-58
依索比星 Chemical Name: 4'-Deoxydoxorubicin hydrochloride; [2S-[2alpha(8R*,10R*),4beta,6beta]]-10-[(4-Aminotetrahydro-6-methyl-2H-pyran-2-yl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione hydrochloride; (8S,10S)-10-[[(2S,4R,6S)-4-[(Aminotetrahydro-6-methyl-2H-pyran-2-yl)oxy]-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione hydrochloride
CAS No. 63950-06-1, 63521-85-7 (free base)
项目整合开发状态: Phase II
项目研究机构: Pfizer (Originator)
合成路线:The sulfonation of methyl N-trifluoroacetyldaunosaminide (I) with mesyl chloride or with 4-bromophenylsulfonyl chloride in pyridine gives the corresponding 4-O-mesyl derivative (II) or 4-O-(4-bromophenylsulfonyl) derivative (IIa); both compounds by reaction with NaI in refluxing butanone yield the 4-iodo compound (III).The hydrogenation of (III) with H2 over Pd/C in methanol,followed by hydrolysis with hot acetic acid yields 4-deoxy-N-trifluoroacetyldaunosaminide (IV),which is esterified with p-nitrobenzoyl chloride in pyridine affording the corresponding p-nitrobenzoyl ester (V).The reaction of (V) with dry HCl in methylene chloride gives 1,4-dideoxy-N-trifluoroacetyldanosaminide (VI),which is condensed with daunomycinone (VII) by means of silver trifluoromethylsulfonate in methylene chloride and hydrolyzed with NaOH to afford 4'-deoxy-daunomycine (VIII).The bromination of (VIII) with Br2 in methanol-dioxane gives 4'-deoxy-14-bromodaunomycine (IX),which is finally hydrolyzed with aqueous sodium formate.
📌 参考资料/链接：
参考文献标题:Novel antitumor glycosides of the anthracycline series and process for their preparation
文献作者:Penco,S.; Arcamone,F.; Di Marco,A.
参考来源:FR 2325659
📄 详细内容
合成路线:The sulfonation of methyl N-trifluoroacetyldaunosaminide (I) with mesyl chloride or with 4-bromophenylsulfonyl chloride in pyridine gives the corresponding 4-O-mesyl derivative (II) or 4-O-(4-bromophenylsulfonyl) derivative (IIa); both compounds by reaction with NaI in refluxing butanone yield the 4-iodo compound (III).The hydrogenation of (III) with H2 over Pd/C in methanol,followed by hydrolysis with hot acetic acid yields 4-deoxy-N-trifluoroacetyldaunosaminide (IV),which is esterified with p-nitrobenzoyl chloride in pyridine affording the corresponding p-nitrobenzoyl ester (V).The reaction of (V) with dry HCl in methylene chloride gives 1,4-dideoxy-N-trifluoroacetyldanosaminide (VI),which is condensed with daunomycinone (VII) by means of silver trifluoromethylsulfonate in methylene chloride and hydrolyzed with NaOH to afford 4'-deoxy-daunomycine (VIII).The bromination of (VIII) with Br2 in methanol-dioxane gives 4'-deoxy-14-bromodaunomycine (IX),which is finally hydrolyzed with aqueous sodium formate.
参考文献标题:Synthesis and antitumor activity of 4'-deoxydaunorubicin and 4'-deoxyadriamycin
文献作者:Arcamone,F.; Penco,S.; Redaelli,S.; Hanessian,S.
参考来源:J Med Chem 1976,191424-25
合成路线:The sulfonation of methyl N-trifluoroacetyldaunosaminide (I) with mesyl chloride or with 4-bromophenylsulfonyl chloride in pyridine gives the corresponding 4-O-mesyl derivative (II) or 4-O-(4-bromophenylsulfonyl) derivative (IIa); both compounds by reaction with NaI in refluxing butanone yield the 4-iodo compound (III).The hydrogenation of (III) with H2 over Pd/C in methanol,followed by hydrolysis with hot acetic acid yields 4-deoxy-N-trifluoroacetyldaunosaminide (IV),which is esterified with p-nitrobenzoyl chloride in pyridine affording the corresponding p-nitrobenzoyl ester (V).The reaction of (V) with dry HCl in methylene chloride gives 1,4-dideoxy-N-trifluoroacetyldanosaminide (VI),which is condensed with daunomycinone (VII) by means of silver trifluoromethylsulfonate in methylene chloride and hydrolyzed with NaOH to afford 4'-deoxy-daunomycine (VIII).The bromination of (VIII) with Br2 in methanol-dioxane gives 4'-deoxy-14-bromodaunomycine (IX),which is finally hydrolyzed with aqueous sodium formate.
参考文献标题:ESORUBICIN HYDROCHLORIDE < Rec INNM; USAN >
文献作者:Robinson,C.P.; Prous,J.; Castar,J.
参考来源:Drugs Fut 1990,15(10),986
产品链接: CAS No. 63950-06-1›› 产品链接: CAS No.63521-85-7››