新产品编号:948127
BMS470539二盐酸盐Chemical Name: 1-[1-(Ntau-Methyl-L-histidyl-O-methyl-D-tyrosyl)-4-phenylpiperidin-4-yl]butan-1-one; N1-[2-(4-Butyryl-4-phenylpiperidin-1-yl)-1(R)-(4-methoxybenzyl)-2-oxoethyl]-Ntau-methyl-L-histidinamide
CAS No. 457893-92-4
项目整合开发状态: Preclinical
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The title compound has been synthesized by two related methods.Coupling of N-Boc-L-methylhistidine (I) with D-4-methoxyphenylalanine methyl ester (II) employing EDC/HOBt affords the protected dipeptide (III).Subsequent saponification of the methyl ester (III) leads to carboxylic acid (IV).This is then coupled to 4-butyryl-4-phenylpiperidine (V) to furnish amide (VI).Finally,acidic cleavage of the N-Boc protecting group of (VI) provides the title compound.
📌 参考资料/链接：
参考文献标题:Cpds.useful as modulators of melanocortin receptors and pharmaceutical compsns.comprising same
文献作者:Poindexter,G.S.; Ruediger,E.H.; Ruel,R.; Lawrence,R.M.; Yu,G.; Macor,J.; Morton,G.C.; Thibault,C.; Herpin,T.(Bristol-Myers Squibb Co.)
参考来源:EP 1363631; EP 1363898; WO 0270511; WO 0279146
📄 详细内容
合成路线:The title compound has been synthesized by two related methods.Coupling of N-Boc-L-methylhistidine (I) with D-4-methoxyphenylalanine methyl ester (II) employing EDC/HOBt affords the protected dipeptide (III).Subsequent saponification of the methyl ester (III) leads to carboxylic acid (IV).This is then coupled to 4-butyryl-4-phenylpiperidine (V) to furnish amide (VI).Finally,acidic cleavage of the N-Boc protecting group of (VI) provides the title compound.
参考文献标题:Co-administration of melanocortin receptor agonists and phosphodiesterase inhibitor for treatment of cyclic-AMP associated disorders
文献作者:Macor,J.E.; Carlson,K.E.(Bristol-Myers Squibb Co.)
参考来源:WO 0269905
合成路线:Similarly,N-Boc-D-4-methoxyphenylalanine (I) is coupled to 4-butyryl-4-phenylpiperidine (II),yielding amide (III).After acidic Boc group cleavage in (III),the resultant amine (IV) is acylated by N-Boc-L-methylhistidine (V) to provide the dipeptide amide (VI).The N-Boc protecting group of (VI) is finally removed employing trifluoroacetic acid.
参考文献标题:Discovery of tyrosine-based potent and selective melanocortin-1 receptor small-molecule agonists with anti-inflammatory properties
文献作者:Herpin,T.F.; Yu,G.; Carlson,K.E.; Morton,G.C.; Wu,X.; Kang,L.; Tuerdi,H.; Khanna,A.; Tokarski,J.S.; Lawrence,R.M.; Macor,J.E.
参考来源:J Med Chem 2003,46(7),1123
产品链接: CAS No. 457893-92-4››