Motexafin gadolinium, Gadolinium texaphyrin, PCI-0120, GdT2B2, Gd-Tex, Xcytrin
钆,双(乙酰-kO)[9,10-二乙基-20,21-双[2-[2-(2-甲氧基乙氧基)乙氧基]乙氧基]-4,15-二甲基-8,11-亚胺基-3,6:16,13-二硝基-1,18-苯二氮卓二氮环固烯-5,14-二丙醇-kN1,kN18,kN23,kN24,kN25]-,水合物(1:),(PB-7-11-233'2'4)-Chemical Name: (PB-7-11-233'2'4)-Bis(acetato-O)[9,10-diethyl-20,21-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-4,15-dimethyl-8,11-imino-3,6:16,13-dinitrilo-1,18-benzodiazacycloeicosine-5,14-dipropanolato-N1,N18,N23,N24,N25]gadolinium
CAS No. 246252-06-2, 218290-68-7 (deleted CAS), 156436-89-4 (hydrate)
项目整合开发状态: Phase III
项目研究机构: Pharmacyclics (Originator), National Cancer Institute (Codevelopment)
合成路线:The condensation of 3-[2-(acetoxymethyl)-5-(benzyloxycarbonyl)-4-methyl-1H-pyrrol-3-yl]propionic acid methyl ester (VII) with 3,4-diethyl-1H-pyrrole (VIII) by means of Ts-OH in ethanol gives the bis adduct (IX).The reduction of both methoxycarbonyl groups of (IX) with borane/THF complex yields bis-propanol derivative (X),which is debenzylated by hydrogenation with H2 and TEA over Pd/C in THF to afford the dicarboxylic acid (XI).The reduction of (XI) with TFA,triethyl orthoformate and LiOH in methanol/water provides the dialdehyde (XII),which is cyclized with the intermediate phenylenediamine (VI) by means of HCl in methanol to give the pentacyclic compound (XIII).
📌 参考资料/链接：
参考文献标题:Texaphyrin metal complex mediated ester hydrolysis
文献作者:Sessler,J.L.; Hemmi,G.W.; Magda,D.; Miller,R.A.; Ross,K.L.; Wright,M.; Dow,W.C.; Smith,D.A.; Kr醠,V.A.; Iverson,B.; Mody,T.(University of Texas System)
参考来源:WO 9429316
📄 详细内容
合成路线:The intermediate phenylenediamine derivative (VI) has been obtained as follows: The reaction of 2-[2-(2-methoxyethoxy)ethoxy]ethanol (I) with Ts-Cl and NaOH in THF/water gives the tosylate (II),which is condensed with pyrocatechol (III) by means of K2CO3 in methanol,yielding the aryl ether (IV).The nitration of (IV) with HNO3 in acetic acid affords the dinitro derivative (V),which is finally reduced to the target phenylenediamine intermediate (VI) with hydrazine in ethanol catalyzed by Pd/C.
合成路线:The condensation of 3-[2-(acetoxymethyl)-5-(benzyloxycarbonyl)-4-methyl-1H-pyrrol-3-yl]propionic acid methyl ester (VII) with 3,4-diethyl-1H-pyrrole (VIII) by means of Ts-OH in ethanol gives the bis adduct (IX).The reduction of both methoxycarbonyl groups of (IX) with borane/THF complex yields bis-propanol derivative (X),which is debenzylated by hydrogenation with H2 and TEA over Pd/C in THF to afford the dicarboxylic acid (XI).The reduction of (XI) with TFA,triethyl orthoformate and LiOH in methanol/water provides the dialdehyde (XII),which is cyclized with the intermediate phenylenediamine (VI) by means of HCl in methanol to give the pentacyclic compound (XIII).
合成路线:Finally,compound (XIII) is treated with gadolinium triacetate and TEA in methanol and dehydrogenated with air to furnish the target gadolinium complex.
参考文献标题:Radiation sensitization using texaphyrins
文献作者:Sessler,J.L.; Miller,R.A.; Harriman,A.M.(Pharmacyclics,Inc.; University of Texas System)
参考来源:US 5622946
合成路线:The condensation of 3-[2-(acetoxymethyl)-5-(benzyloxycarbonyl)-4-methyl-1H-pyrrol-3-yl]propionic acid methyl ester (VII) with 3,4-diethyl-1H-pyrrole (VIII) by means of Ts-OH in ethanol gives the bis adduct (IX).The reduction of both methoxycarbonyl groups of (IX) with borane/THF complex yields bis-propanol derivative (X),which is debenzylated by hydrogenation with H2 and TEA over Pd/C in THF to afford the dicarboxylic acid (XI).The reduction of (XI) with TFA,triethyl orthoformate and LiOH in methanol/water provides the dialdehyde (XII),which is cyclized with the intermediate phenylenediamine (VI) by means of HCl in methanol to give the pentacyclic compound (XIII).
参考文献标题:Synthesis and structural characterization of lanthanide(III) texaphyrins
文献作者:Sessler,J.L.; et al.
参考来源:Inorg Chem 1993,32(14),3175
产品链接: CAS No. 246252-06-2›› 产品链接: CAS No.156436-89-4››