Pd-Bacteriopheophorbide, WST-09, Pd-BPheid, Tookad

(1R,5S)-8-甲基-8-氮杂二环[3.2.1]辛-3-基2-甲基丙酸酯Chemical Name: Hydrogen [(22R,7R,8R,17S,18S)-3-[12-acetyl-7-ethyl-22-(methoxycarbonyl)-3,8,13,17-tetramethyl-21-oxo-21,22,7,8,17,18-hexahydrocyclopenta[at]porphyrin-18-yl]propanoato(3-)-kappaN21,kappaN22,kappaN23,kappaN24]palladate(1-); Hydrogen (SP-4-2)-[(3S,4S,13R,14R,21R)-9-acetyl-14-ethyl-13,14-dihydro-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoato(3-)-kappaN23,kappaN24,kappaN25,kappaN26]palladate(1-)
CAS No. 274679-00-4
项目整合开发状态: Phase I/II
项目研究机构: Yeda (Originator)
合成路线:Bacteriochlorophyll a (I) was isolated from the lyophilized bacteria Rhodovolum sulfidophilum.From this,the title compound was obtained by several methods.Hydrolysis of the C-17 ester group and simultaneous demetalation by means of 80% aqueous trifluoroacetic acid provided bacteriopheophorbide (II).This was then complexed with palladium acetate in the presence of sodium ascorbate to produce the title compound.In a related procedure,transmetalation of (I) with palladium acetate in the presence of 6-O-palmitoyl-L-aspartic acid led to the corresponding palladium complex (III),which was then hydrolyzed to the title compound in aqueous trifluoroacetic acid.An alternative method consisted of the initial hydrolysis of the 17-C ester group of (I) by means of the enzyme chlorophyllase to afford acid (IV),and then transmetalation with palladium acetate.

合成路线:Bacteriochlorophyll a (I) is isolated from lyophilized bacteria Rhodovolum sulfidophilum as a mixture of phytyl and geranylgeranyl esters.Demetalation and hydrolysis of (I) with 80% aqueous trifluoroacetic acid furnishes bacteriopheophorbide a (II).Then,complexation of (II) with palladium acetate in the presence of sodium ascorbate gives rise to the title compound.In an alternative method,bacteriochlorophyll a (I) is hydrolyzed by means of chlorophyllase to produce bacteriochlorophyllide (III) along with some bacteriopheophorbide (II).Subsequent transmetalation of (III) with palladium acetate leads to the target palladium complex.