Alethine, -Drug Synthesis Database

【结构式】

【药物名称】Alethine

【化学名称】　

【CA登记号】646-08-2

【分子式】C₁₀H₂₂N₄O₂S₂

【分子量】294.44044

【开发单位】

【药理作用】0

合成路线1 合成路线2

合成路线1

The reaction of disulfide (I) with sodium azide in DMSO gives the bis azido derivative (II), which is finally reduced with PPh3 in THF/water to afford the target beta-alanine derivative. Alternatively, the condensation of N-(tert-butoxycarbonyl)-beta-alanine (III) with S-acetyl-cysteamine (IV) by means of DCC in ethyl acetate gives the bet-alaninamide (V), which is deacetylated by means of NaOMe in methanol to yield N-[N-(tert-butoxycarbonyl)-beta-alanyl]cysteamine (VI). The dimerization of (VI) by means of I2 in Ac-OH affords the protected cystamine derivative (VII), which is finally deprotected by means of TFA.

参考文献中间体

【1】 Oiry, J.; et al.; Synthesis and radioprotective activity of new cysteamine and cystamine derivatives. J Med Chem 1986, 29, 11, 2217.
【2】 Vogel, K.W.; et al.; Investigating the role of the geminal dimethyl groups of coenzyme A: Synthesis and studies of a didemethyl analogue. Bioorg Med Chem 2000, 8, 10, 2451.

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)	54379	3-chloro-N-[2-({2-[(3-chloropropanoyl)amino]ethyl}disulfanyl)ethyl]propanamide		C₁₀H₁₈Cl₂N₂O₂S₂	详情	详情
(II)	54380	3-azido-N-[2-({2-[(3-azidopropanoyl)amino]ethyl}disulfanyl)ethyl]propanamide		C₁₀H₁₈N₈O₂S₂	详情	详情
(III)	26616	N-(tert-butoxycarbonyl)-beta-alanine	3303-84-2	C₈H₁₅NO₄	详情	详情
(IV)	54381	S-(2-aminoethyl) ethanethioate		C₄H₉NOS	详情	详情
(V)	54382	S-[2-({3-[(tert-butoxycarbonyl)amino]propanoyl}amino)ethyl] ethanethioate		C₁₂H₂₂N₂O₄S	详情	详情
(VI)	54383	tert-butyl 3-oxo-3-[(2-sulfanylethyl)amino]propylcarbamate		C₁₀H₂₀N₂O₃S	详情	详情
(VII)	54384	tert-butyl 18,18-dimethyl-3,12,16-trioxo-17-oxa-7,8-dithia-4,11,15-triazanonadec-1-ylcarbamate		C₂₀H₃₈N₄O₆S₂	详情	详情

合成路线2

Also alternatively, the condensation of benzyloxycarbonyl-beta-alanine (VIII) with dimeric cystamine (IX) by the activated ester method gives the protected cystamine intermediate (X), which is finally deprotected with HBr in acetic acid.

参考文献中间体

【1】 Lednicer, D.; Murray, C.K.; Daughenbaugh, R.J.; Taub, F.E. (Dovetail Technologies Inc.); Novel disulfides and thiol cpds.. JP 2002503700; US 2001008933; US 6414114; WO 9942097; WO 9942116 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	54385	N-Carbobenzoxy-beta-alanine; N-CBZ-beta-alanine; Nbeta-(Benzyloxycarbonyl)-beta-alanine	2304-94-1	C₁₁H₁₃NO₄	详情	详情
(IX)	27502	2-[(2-aminoethyl)disulfanyl]-1-ethanamine	56-17-7	C₄H₁₂N₂S₂	详情	详情
(X)	54386	benzyl 3,12,16-trioxo-18-phenyl-17-oxa-7,8-dithia-4,11,15-triazaoctadec-1-ylcarbamate		C₂₆H₃₄N₄O₆S₂	详情	详情

Extended Information