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【结 构 式】

【药物名称】NNC-26-1167

【化学名称】1-[N-[5-Amino-5-methyl-2(E)-hexenoyl]-N-methyl-3-(2-naphthyl)-D-alanyl-N-methyl-3-(2-thienyl)-D-alanyl]-1,2,2-trimethylhydrazine

【CA登记号】232614-78-7

【 分 子 式 】C32H43N5O3S

【 分 子 量 】577.79521

【开发单位】Novo Nordisk (Originator)

【药理作用】ENDOCRINE DRUGS, Pituitary Disorder Therapy, Treatment of Growth Hormone Deficiency, Treatment of Growth Hormone Secretion Disorders, Growth Hormone Secretagogues

合成路线1

The title compound was prepared by stepwise peptide synthesis starting from N-Fmoc-N-methyl-D-thienylalanine (I), which was condensed with trimethyl hydrazine (II) to give hydrazide (III). Removal of the Fmoc protecting group with piperidine in DMF provided amine (IV), which was subsequently coupled with N-methyl-D-naphthylalanine (V) in the presence of EDC and HOAt to furnish the dipeptide hydrazide (VI). After removal of the Fmoc group of (VI) with piperidine, the resulting amine (VII) was coupled with N-Boc-5-amino-5-methylhex-2-enoic acid (VIII), yielding amide (IX). Final deprotection of the Boc group of (IX) using trifluoroacetic acid afforded the title compound.

1 Hansen, B.S.; Ankersen, M.; Nielsen, K.K.; Hansen, T.K.; Raun, K.; Growth hormone secretagogues derived from NN703 with hydrazides as c-terminal. Eur J Med Chem 2000, 35, 5, 487.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 42289 (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(2-thienyl)propionic acid C23H21NO4S 详情 详情
(II) 42290 1,1,2-trimethylhydrazine C3H10N2 详情 详情
(III) 42291 9H-fluoren-9-ylmethyl methyl[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]carbamate C26H29N3O3S 详情 详情
(IV) 42292 (2R)-N,N',N'-trimethyl-2-(methylamino)-3-(2-thienyl)propanohydrazide C11H19N3OS 详情 详情
(V) 42293 (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino]-3-(2-naphthyl)propionic acid C29H25NO4 详情 详情
(VI) 42294 9H-fluoren-9-ylmethyl methyl[(1R)-2-[methyl[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]amino]-1-(2-naphthylmethyl)-2-oxoethyl]carbamate C40H42N4O4S 详情 详情
(VII) 42295 (2R)-N-methyl-2-(methylamino)-3-(2-naphthyl)-N-[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]propanamide C25H32N4O2S 详情 详情
(VIII) 22191 (E)-5-[(tert-butoxycarbonyl)amino]-5-methyl-2-hexenoic acid C12H21NO4 详情 详情
(IX) 42296 tert-butyl (E)-1,1-dimethyl-5-[methyl[(1R)-2-[methyl[(1R)-2-oxo-1-(2-thienylmethyl)-2-(1,2,2-trimethylhydrazino)ethyl]amino]-1-(2-naphthylmethyl)-2-oxoethyl]amino]-5-oxo-3-pentenylcarbamate C37H51N5O5S 详情 详情
Extended Information