Selodenoson, RG-14202, DTI-0009
(2S,3S,4R,5R)-5-[6-(环戊基氨基)嘌呤-9-基]-N-乙基-3,4-二羟基四氢呋喃-2-甲酰胺Chemical Name: N6-Cyclopentyl-N5'-ethyladenosine-5'-uronamide
CAS No. 110299-05-3
项目整合开发状态: Phase II
项目研究机构: Aderis (Originator), Fujisawa (Licensee)
合成路线:The title compound is prepared by two methods.Chlorination of 2',3'-O-isopropylideneinosine-5'-uronic acid (I) with SOCl2 in the presence of DMF produces the chloropurine acid chloride (II),which is further converted into the amide (III) upon treatment with ethylamine.Subsequent displacement of the purine 6-chloro group of (III) with cyclopentylamine (IV) furnishes the cyclopentylamino purine (V).Finally,acidic ketal hydrolysis in (IV) gives rise to the target compound.
📌 参考资料/链接：
参考文献标题:N-6 Substd.-5'-(N-substd.carboxamido)adenosines as cardiac vasodilators and antihypertensive agents
文献作者:Olsson,R.A.; Thompson,R.D.(UCB Pharma,Inc.)
参考来源:AU 8544972; EP 0191025; ES 8609359; JP 1986286398; US 5310731; WO 8600310
📄 详细内容
合成路线:Alternatively,the inosine uronic acid (I) is converted to ethyl ester (II) by sequential treatment with thionyl chloride and then ethanol.Subsequent reaction with acetic anhydride in pyridine gives rise to diacetate (III).Chlorination of the inosine ring of (III) to produce (IV) is accomplished by treatment with phosphoryl chloride in the presence of tetraethylammonium chloride.Displacement of the 6-chloro group of (IV) with cyclopentylamine (V) yields amino purine (VI).Finally,aminolysis of the ester groups of (VI) with ethanolic ethylamine leads to the title compound.
参考文献标题:N6-Substd.-5'-oxidized adenosine analogs
文献作者:Hamilton,H.W.; Patt,W.C.(Pfizer Inc.)
参考来源:EP 0222330; JP 1987111996; US 4738954
产品链接: CAS No. 110299-05-3››