CHAP-31
Chemical Name: Cyclo[L-isoleucyl-D-prolyl-2(S)-amino-8-(N-hydroxyamino)-8-oxooctanoyl-O-methyl-D-tyrosyl]; (3S,6R,9S,14aR)-6-[6-(4-Methoxybenzyl)-9-[1(S)-methylpropyl]-1,4,7,10-tetraoxoperhydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-3-yl]hexanohydroxamic acid
CAS No. 221186-64-7
项目整合开发状态: Preclinical
项目研究机构: Japan Energy (Originator)
合成路线:The linear peptide-bound resin (VIII) was prepared by solid-phase synthesis on a Kaiser抯 oxime resin by sequential coupling-deprotection cycles with N-Boc-L-aminosuberic acid omega-benzyl ester (I),N-Boc-D-proline (III),N-Boc-L-isoleucine (V) and N-Boc-4-O-methyl-D-tyrosine (VII) to afford the peptide resins (II),(III),(IV) and (V),respectively.Cleavage of resin (VIII) with concomitant cyclization provided the cyclic tetrapeptide (IX).After hydrogenolysis of the side-chain benzyl ester,the resulting carboxylic acid was coupled to hydroxylamine in the presence of BOP and HOBt to obtain the title hydroxamic acid.
📌 参考资料/链接：
参考文献标题:Novel cyclic tetrapeptide derivs.and medicinal use thereof
文献作者:Mimoto,T.; Komatsu,Y.; Horinouchi,S.; Nishino,N.; Yoshida,M.(Japan Energy Corp.)
参考来源:EP 1010705; WO 9911659
📄 详细内容
合成路线:The linear peptide-bound resin (VIII) was prepared by solid-phase synthesis on a Kaiser抯 oxime resin by sequential coupling-deprotection cycles with N-Boc-L-aminosuberic acid omega-benzyl ester (I),N-Boc-D-proline (III),N-Boc-L-isoleucine (V) and N-Boc-4-O-methyl-D-tyrosine (VII) to afford the peptide resins (II),(III),(IV) and (V),respectively.Cleavage of resin (VIII) with concomitant cyclization provided the cyclic tetrapeptide (IX).After hydrogenolysis of the side-chain benzyl ester,the resulting carboxylic acid was coupled to hydroxylamine in the presence of BOP and HOBt to obtain the title hydroxamic acid.
参考文献标题:Synthesis and activity of Cyl-1 analogs having hydroxamic acid at side chain
文献作者:Tsukamoto,M.; et al.
参考来源:Pept Sci 1998,185