GYKI-14166, RGH-2958

(S)-D-苯丙氨酰-N-(4-((氨基亚胺甲基)氨基)-1-甲酰基丁基)-L-脯氨酰胺硫酸盐 (1:1)Chemical Name: D-Phenylalanyl-L-prolyl-L-argininal sulfate (1:1); D-Phenylalanyl-N-[4-guanidino-1(S)-formylbutyl]-L-prolinamide sulfate (1:1)
CAS No. 83997-16-4, 77481-39-1 (diacetate), 77481-38-0 (diHCl), 60503-05-1 (free base)
项目整合开发状态: Biological Testing
项目研究机构: Gedeon Richter (Originator)
合成路线:N2-tert-Butyloxycarbonyl-N5-benzyloxycarbonyl-L-arginine (I) is cyclized by treatment with isobutyloxycarbonyl chloride and N-methylmorpholine to the lactam (II).The tert-butyloxycarbonyl group is removed by hydrochloric acid to give the aminolactam (III),which is coupled with N-benzyloxycarbonyl-D-phenylalanyl-L-proline (IV) using,as in the first step,the mixed anhydride method.The resulting tripeptide lactam (V) is reduced with LiAlH4 to an aldehyde,present as the cyclic alpha-aminoalcohol (VI).Deblocking by hydrogenolysis gives RGH-2958.In solution the aldehyde group is either in the cyclic alpha-aminoalcohol form or is hydrated.