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【结 构 式】

【药物名称】PS-26

【化学名称】1-[3-(3,4-Dichlorophenoxy)propoxy]-5-isopropylbiguanide dihydrochloride

【CA登记号】

【 分 子 式 】C14H23Cl4N5O2

【 分 子 量 】435.18371

【开发单位】Jacobus (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Treatment of Protozoal Diseases, Dihydrofolate Reductase (DHFR) Inhibitors

合成路线1

The reaction of 3,4-dichlorophenol (I) with 1,3-dibromopropane (II) by means of NaOH and tetrabutylammonium hydrogensulfate gives the corresponding phenol ether (III), which is condensed with N-acetylhydroxylamine (IV) by means of NaOH or KOH in an alcoholic solvent to yield the O-substituted acetylhydroxylamine (V). The hydrolysis of (V) with HCl in methanol affords the free O-substituted hydroxylamine (VI), which is finally condensed with N1-cyano-N3-isopropylguanidine (VII) in hot ethyl acetate. The intermediate N1-cyano-N3-isopropylguanidine (VII) has been obtained by reaction of sodium dicyanamide (VIII) with isopropylamine (IX) and HCl in a hot alcoholic solvent.

1 Jensen, N.P.; et al.; Phenoxypropoxybiguanides, prodrugs of DHFR-inhibiting diaminotriazine antimalarials. J Med Chem 2001, 44, 23, 3925.
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) 34044 3,4-Dichlorophenol 95-77-2 C6H4Cl2O 详情 详情
(II) 12581 1,3-Dibromopropane 109-64-8 C3H6Br2 详情 详情
(III) 52210 3-bromopropyl 3,4-dichlorophenyl ether; 4-(3-bromopropoxy)-1,2-dichlorobenzene C9H9BrCl2O 详情 详情
(IV) 23102 N-hydroxyacetamide 546-88-3 C2H5NO2 详情 详情
(V) 52211 N-[3-(3,4-dichlorophenoxy)propoxy]acetamide C11H13Cl2NO3 详情 详情
(VI) 52212 4-[3-(aminooxy)propoxy]-1,2-dichlorobenzene; O-[3-(3,4-dichlorophenoxy)propyl]hydroxylamine C9H11Cl2NO2 详情 详情
(VII) 52213 N-cyano-N'-isopropylguanidine C5H10N4 详情 详情
(VIII) 52214   C2N3Na 详情 详情
(IX) 23933 2-Propanamine; Isopropylamine 75-31-0 C3H9N 详情 详情
Extended Information