SC-alphaalphadelta9, -Drug Synthesis Database

【结构式】

【药物名称】SC-alphaalphadelta9

【化学名称】N-Benzyl-N-[2-(2,5-diphenyloxazol-4-ylcarboxamido)ethyl]-2-(decanamido)glutaramic acid

【CA登记号】

【分子式】C₄₀H₄₈N₄O₆

【分子量】680.85176

【开发单位】University of Pittsburgh (Originator)

【药理作用】Oncolytic Drugs, Apoptosis Inducers, Cell Division Cycle CDC25 Phosphatase Inhibitors, Inhibitors of Signal Transduction Pathways

合成路线1 合成路线2

合成路线1

Protection of L-glutamic acid (I) with allyl alcohol and chlorotrimethylsilane produced the gamma-allyl ester (II). Subsequent treatment of (II) with fluorenylmethoxycarbonyl chloride afforded the N-Fmoc derivative (III). This was coupled to Wang resin using EDC and DMAP to provide the glutamate-coupled resin (IV). Removal of the Fmoc protecting group by means of piperidine gave (V), which was then condensed with decanoyl chloride (VI) yielding amide (VII). The allyl ester was then cleaved by treatment with Pd(PPh3)4 and the resulting carboxylic acid (VIII) was coupled with monoprotected diamine (IX) to furnish diamide (X). Deprotection of the allyl carbamate of (X) provided amine (XI).

参考文献中间体

【1】 Wipf, P.; et al.; Combinatorial synthesis and biological evaluation of library of small-molecule Ser/Thr-protein phosphatase inhibitors. Bioorg Med Chem 1997, 5, 1, 165.
【2】 Lazo, J.S.; Rice, R.L.; Cunningham, A.; Wipf, P. (University of Pittsburgh); Phosphatase inhibitors and methods of use thereof. EP 0959884; US 5700821; WO 9804257 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II), (V)	28269	(2S)-5-(allyloxy)-2-amino-5-oxopentanoic acid		C₈H₁₃NO₄	详情	详情
(III), (IV)	28270	(2S)-5-(allyloxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-oxopentanoic acid		C₂₃H₂₃NO₆	详情	详情
(I)	12005	L-2-Amino propane dicarboxylic acid; (-)-2-Aminoglutaric acid; L-2-Aminopentanoic acid; L-Glutamic acid	56-86-0	C₅H₉NO₄	详情	详情
(V)	28269	(2S)-5-(allyloxy)-2-amino-5-oxopentanoic acid		C₈H₁₃NO₄	详情	详情
(VI)	28271	decanoyl chloride	112-13-0	C₁₀H₁₉ClO	详情	详情
(VII)	28272	(2S)-5-(allyloxy)-2-(decanoylamino)-5-oxopentanoic acid		C₁₈H₃₁NO₅	详情	详情
(VIII)	28273	(2S)-2-(decanoylamino)pentanedioic acid		C₁₅H₂₇NO₅	详情	详情
(IX)	28274	allyl 2-(benzylamino)ethylcarbamate		C₁₃H₁₈N₂O₂	详情	详情
(X)	28275	(2S)-5-[(2-[[(allyloxy)carbonyl]amino]ethyl)(benzyl)amino]-2-(decanoylamino)-5-oxopentanoic acid		C₂₈H₄₃N₃O₆	详情	详情
(XI)	28276	(2S)-5-[(2-aminoethyl)(benzyl)amino]-2-(decanoylamino)-5-oxopentanoic acid		C₂₄H₃₉N₃O₄	详情	详情

合成路线2

Amine (XI) was coupled to isoxazolecarboxylic acid (XII) to give (XIII). which was finally liberated from the resin by cleavage with trifluoroacetic acid in CH2Cl2.

参考文献中间体

【1】 Wipf, P.; et al.; Combinatorial synthesis and biological evaluation of library of small-molecule Ser/Thr-protein phosphatase inhibitors. Bioorg Med Chem 1997, 5, 1, 165.
【2】 Lazo, J.S.; Rice, R.L.; Cunningham, A.; Wipf, P. (University of Pittsburgh); Phosphatase inhibitors and methods of use thereof. EP 0959884; US 5700821; WO 9804257 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XI)	28276	(2S)-5-[(2-aminoethyl)(benzyl)amino]-2-(decanoylamino)-5-oxopentanoic acid	C₂₄H₃₉N₃O₄	详情	详情
(XII)	28277	2,5-diphenyl-1,3-oxazole-4-carboxylic acid	C₁₆H₁₁NO₃	详情	详情
(XIII)	28278	(2S)-5-[benzyl(2-[[(2,5-diphenyl-1,3-oxazol-4-yl)carbonyl]amino]ethyl)amino]-2-(decanoylamino)-5-oxopentanoic acid	C₄₀H₄₈N₄O₆	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)