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【结 构 式】

【分子编号】51698

【品名】dichloroplatinum diammoniate

【CA登记号】

【 分 子 式 】H6Cl2N2Pt

【 分 子 量 】300.04652

【元素组成】H 2.02% Cl 23.63% N 9.34% Pt 65.02%

与该中间体有关的原料药合成路线共 4 条

合成路线1

该中间体在本合成路线中的序号:(I)

The condensation of platinum complex (I) with N-Boc-hexane-1,6-diamine (II) by means of 1 mole of AgNO3 in DMF gives the platinum complex (III), which is deprotected with HCl in methanol/ethanol to yield complex (IV). Finally, platinum complex (I) is condensed with two moles of complex (IV) by means of two moles of AgNO3 in DMF to afford the target trinuclear complex.

1 Valsecchi, M.; Pavesi, P.; Bugatti, C.; Menta, E.; Giuliani, F.C.; Manzotti, C.; Spinelli, S.; Farrell, N. (Roche Diagnostics GmbH); Trinuclear cationic platinum complexes having antitumour activity and pharmaceutical compsns. containing them. EP 0793667; JP 1998509159; WO 9616068 .
2 Valsecchi, M.; Conti, M.; Del Greco, L.; Gubatti, C.; Menta, E.; Giuliani, F.; Manzotti, C.; Spinelli, S.; Farrell, N. (Roche Diagnostics GmbH); Trinuclear cationic platinum complexes having antitumor activity and pharmaceutical compsns. containing them. EP 0753000; JP 1997506633; US 5744497; WO 9526968 .
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) 51698 dichloroplatinum diammoniate H6Cl2N2Pt 详情 详情
(II) 31638 tert-butyl 6-aminohexylcarbamate 51857-17-1 C11H24N2O2 详情 详情
(III) 53506   n/a C11H30ClN4O2Pt 详情 详情
(IV) 53507   n/a C6H22ClN4Pt 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

The title platinum complex was prepared by treatment of cis-dichlorodiaminoplatinum (I) with potassium ethyl xanthate (II).

1 Amtmann, E.; Schilling, G. (Deutsches Krebsforschungszentrum; Ruprecht-Karls-Universitat Heidelberg); Medicament containing platinum complex cpds. and the use thereof. WO 0010543 .
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) 51698 dichloroplatinum diammoniate H6Cl2N2Pt 详情 详情
(II) 29923 o-Ethylxanthic acid potassium salt; Potassium ethyl xanthogenate; potassium 1-(carbodithioatooxy)ethane 140-89-6 C3H5KOS2 详情 详情

合成路线3

该中间体在本合成路线中的序号:(II)

The title compound was obtained by mixing aqueous solutions of sodium cholylglycinate (I) and cis-diamminedichloroplatinum (II) at 80 C.

1 Criado, J.J.; et al.; Synthesis and characterization of the new cytostatic complex cis-diammineplatinum(II)-chlorocholylglycinate. Bioconjugate Chem 1997, 8, 4, 453.
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) 51697 sodium 2-([(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino)acetate C26H42NNaO6 详情 详情
(II) 51698 dichloroplatinum diammoniate H6Cl2N2Pt 详情 详情

合成路线4

该中间体在本合成路线中的序号:(VIII)

Substitution of chlorine with iodine in potassium tetrachloroplatinate (I) by treatment with KI in water results in potassium tetraiodoplatinate (II), which by reaction with cyclohexylamine (III) yields cis-di(cyclohexylamine)diiodoplatinium (IV). Reaction of complex (IV) with HClO4 in H2O/EtOH furnishes dimer (V), which is then treated with NH4OH in H2O affording cis-ammine(cyclohexylamine) diiodoplatinium (VI). Nitration of complex (VI) with AgNO3 in H2O followed by chlorination with HCl gives cis-amminechloro-(cyclohexylamine)platinium (VII) . Alternatively, treatment of cisplatin (VIII) with Et4NCl in dimethylacetamide at 100 °C followed by ion exchange by DOWEX 50WX8 and HCl leads to amminetrichloroplatinum (IX), which is then treated with KCl, giving potassium(SP-4-2)-amminetrichloroplatinate (X). Subsequent reaction of compound (X) with cyclohexylamine (III) in the presence of NaI in water furnishes (SP-4-3)-amminechloro(cyclohexanamine)iodoplatinum (XI), which by subsequent nitration and chlorination with AgNO3 in water and treatment with HCl affords complex (VII) . Then, compound (VII) is submitted to hydroxylation with H2O2 in water to give (OC-6-43)-amminedichloro(cyclohexylamine)dihydroxyplatinum (XII), which is finally acetylated with Ac2O in CH2Cl2 .

1 Khokhar, A.R., Deng, Y., Al-Baker, S., Yoshida, M., Siddik, Z.H. Synthesis and antitumor activity of ammine/amine platinum (II) and (IV) complexes. J Inorg Biochem 1993, 51(3): 677-87.
2 Ciandomenico, C.M., Abrams, M.J., Murrer, B.A. et al. Carboxylation of kinetically inert platinum (IV) hydroxy complexes. An entr.acte.ee into orally active platinum (IV) antitumor agents. Inorg Chem 1995, 34(5): 1015-21.
3 Abrams, M.J., Giandomenico, C.M., Murrer, B.A., Vollano, J.F. (Johnson Matthey plc). Pt(IV) complexes. AU 8928971, EP 0328274, JP 1989294684.
4 Abrams, M.J., Giandomenico, C., Murrer, B.A., Vollano, J.F. (Johnson &Johnson). Pt(IV) complexes. US 5072011.
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) 51693 dipotassium tetrachloroplatinate(2-);potassium tetrachloroplatinate(II);potassium tetrachloroplatinate 10025-99-7 Cl4K2Pt 详情 详情
(II) 51694 dipotassium tetraiodoplatinate(2-);potassium tetraiodoplatinate(II);Potassium tetraiodoplatinate 14708-56-6 I4K2Pt 详情 详情
(III) 17966 cyclohexanamine; cyclohexyl amine; cyclohexylamine 108-91-8 C6H13N 详情 详情
(IV) 69489 cis-di(cyclohexylamine)diiodoplatinium C12H26I2N2Pt 详情 详情
(V) 69490 (cyclohexylamino)platinum(III) iodide C12H26I4N2Pt2 详情 详情
(VI) 69491 cis-ammine(cyclohexylamine)diiodoplatinium C6H16I2N2Pt 详情 详情
(VII) 69492 cis-amminechloro-(cyclohexylamine)platinium C6H16Cl2N2Pt 详情 详情
(VIII) 51698 dichloroplatinum diammoniate H6Cl2N2Pt 详情 详情
(IX) 69493 amminetrichloroplatinum H4Cl3NPt 详情 详情
(X) 69494 potassium (SP-4-2)-amminetrichloroplatinate H3Cl3KNPt 详情 详情
(XI) 69495 (SP-4-3)-amminechloro(cyclohexanamine)iodoplatinum C6H16ClIN2Pt 详情 详情
(XII) 69496 (OC-6-43)-amminedichloro(cyclohexylamine)dihydroxyplatinum C6H18Cl2N2O2Pt 详情 详情
Extended Information