新产品编号:906995
Chemical Name: 3-[7(R)-Ethyl-2(2)-hexyl-12-[1-(heptyloxy)ethyl]-3,8(R),13,17(S)-tetramethyl-2(1),2(3)-dioxo-2(1),2(2),2(3),7,8,18-hexahydro-17H-pyrido[3,4,5-at]porphyrin-18(S)-yl]propionic acid propyl ester
CAS No. 380229-05-0
项目整合开发状态: Preclinical
项目研究机构: Health Research (Originator)
合成路线:Bacteriopurpurin 1 (I) was obtained from the extracts of Rhodobacter sphaeroides,enriched with bacteriochlorophyll a,by treatment with KOH/n-propanol in the presence of air.Subsequent acidification of the propanol solution of (I) produced the propyl ester (II).Opening of the anhydride ring system of (II) with n-hexylamine led to a mixture of regioisomeric amido-acid compounds,which were further converted to the respective amido-esters (III) and (IV) upon treatment with diazomethane.Repeating several times the dissolution of this mixture in THF,followed by evaporation of the solvent,gave rise to the cyclic imide (V).The keto group of (V) was then reduced to alcohol (VI) employing NaBH4 in MeOH.
合成路线:Alcohol (VI) was converted to alkyl bromide (VII) by means of a solution of HBr in HOAc.Subsequent displacement of the bromide ion of (VII) with n-heptanol in the presence of K2CO3 furnished the title heptyl ether.Alternatively,alcohol (VI) was dehydrated to the vinyl bacteriopurpurin (VIII) by a short reflux in ortho-dichlorobenzene.Then,addition of HBr to the vinyl group,followed by treatment with heptyl alcohol,afforded the target compound.
📌 参考资料/链接：
参考文献标题:Long wavelength absorbing bacteriochlorin alkyl ether analogs
文献作者:Pandey,R.K.; Dougherty,T.J.; Potter,W.R.(Health Research,Inc.)
参考来源:EP 1164136; JP 2002020389
📄 详细内容
合成路线:Bacteriopurpurin 1 (I) was obtained from the extracts of Rhodobacter sphaeroides,enriched with bacteriochlorophyll a,by treatment with KOH/n-propanol in the presence of air.Subsequent acidification of the propanol solution of (I) produced the propyl ester (II).Opening of the anhydride ring system of (II) with n-hexylamine led to a mixture of regioisomeric amido-acid compounds,which were further converted to the respective amido-esters (III) and (IV) upon treatment with diazomethane.Repeating several times the dissolution of this mixture in THF,followed by evaporation of the solvent,gave rise to the cyclic imide (V).The keto group of (V) was then reduced to alcohol (VI) employing NaBH4 in MeOH.
合成路线:Alcohol (VI) was converted to alkyl bromide (VII) by means of a solution of HBr in HOAc.Subsequent displacement of the bromide ion of (VII) with n-heptanol in the presence of K2CO3 furnished the title heptyl ether.Alternatively,alcohol (VI) was dehydrated to the vinyl bacteriopurpurin (VIII) by a short reflux in ortho-dichlorobenzene.Then,addition of HBr to the vinyl group,followed by treatment with heptyl alcohol,afforded the target compound.
参考文献标题:Bacteriopurpurinimides: Highly stable and potent photosensitizers for photodynamic therapy
文献作者:Chen,Y.; Graham,A.; Potter,W.; Morgan,J.D.; Vaughan,L.; Bellnier,D.A.; Henderson,B.W.; Oseroff,A.; Dougherty,T.J.; Pandey,R.K.
参考来源:J Med Chem 2002,45(2),255