CAS: 88321-09-9; Ethyl (2S,3S)-3-(((S)-1-(Isopentylamino)-4-Methyl-1-Oxopentan-2-yl)Carbamoyl)Oxirane-2-Carboxylate

该化合物是合成化合物,主要以其作为酶HMG-CoA再生酶的强大抑制剂的作用而著称,这是胆固醇生物合成途径的关键.Loxistatin作为管理超脂性贫血和相关心血管病症的潜在治疗剂,具有这一特征,具有特殊化学结构,有助于其生物活动,典型特征是乳胶环和各种功能组,加强了其与目标酶的互动.Loxistatatin已经研究其药用动力特性,包括吸收,分布,新陈代谢和排泄,这对于了解其功效和安全性能至关重要.此外,它与其他表一样,还可能具有脾性影响,可能影响炎症和内皮功能.然而,与任何制药剂一样,Loxistatin的使用可能与副作用有关,因此需要在临床应用中仔细考虑.进一步的研究将继续探索其充分的治疗潜力和行动机制.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

ECHA物质C&L通报

上下游产品

1-isoamylleucinamideN1-isoamylleucinamide 2-ethyl 3-(4-nitrophenyl) (2S,3S)-oxirane-2,3-dicarboxylate (S)-1-(isopentylamino)-2-amino-4-methyl-1-oxopentan hydr°Chloride 1-amino-3-methylbutaneloxistatin acid (2S,3S)-Oxirane-2,3-dicarboxylic acid 2-(benzyloxy-amide) 3-{[(S)-3-methyl-1-(3-methyl-butylcarbamoyl)-butyl]-amide} (2S,3S)-3-[(S)-3-Methyl-1-(3-methyl-butylcarbamoyl)-butylcarbamoyl]-oxirane-2-carboxylic acid 2-chloro-benzyl ester (R)-2-({(2S,3S)-3-[(S)-3-Methyl-1-(3-methyl-butylcarbamoyl)-butylcarbamoyl]-oxiranecarbonyl}-amino)-3-phenyl-propionic acid methyl ester

合成工艺路线路线简述

  • 915697-62-0 = 88321-09-9
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Water; 2 H,0 °C
    标题:Stereoselective Synthesis Of The Epoxysuccinyl Peptide E-64C
    作者:Lygo,Barry; Et Al
    参考文献:Synlett 日期:2006 卷标:(13) 页码:2063-2066]

    84851-37-6 + 89886-73-7 = 88321-09-9
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide,1-Hydroxybenzotriazole Solvents: Ethyl Acetate; 3 H,0 °C; 12 H,Rt
    标题:Design,Synthesis,And Screen Of Cathepsin K Inhibitors
    作者:Yu,Ying-Ying; Et Al
    参考文献:Chinese Chemical Letters 日期:2013 卷标:24(8) 页码:715-718]

    89886-73-7 = 88321-09-9
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Ethyl Acetate2.1 Solvents: Ethyl Acetate
    标题:An Efficient Synthetic Method For Ethyl (+)-(2S,3S)-3-[(S)-3-Methyl-1-(3-Methylbutylcarbamoyl)Butylcarbamoyl]-2-Oxiranecarboxylate (Est),A New Inhibitor Of Cysteine Proteinases
    作者:Tamai,Masaharu; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1987 卷标:35(3) 页码:1098-104]

    75657-73-7 = 88321-09-9
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol,Ethyl Acetate2.1 Reagents: 4-Methylmorpholine,1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Chloroform2.2 Solvents: Ethyl Acetate,Water
    标题:A New Synthesis Of Peptidyl Epoxysuccinates For Probing Cysteine Protease-Inhibitor P3/s3 Binding Interactions
    作者:Roush,William R.; Et Al
    参考文献:Synthesis 日期:1999 卷标:1500 页码:1500-1504]

    84863-67-2 = 88321-09-9
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Ethyl Acetate2.1 Solvents: Ethyl Acetate
    标题:An Efficient Synthetic Method For Ethyl (+)-(2S,3S)-3-[(S)-3-Methyl-1-(3-Methylbutylcarbamoyl)Butylcarbamoyl]-2-Oxiranecarboxylate (Est),A New Inhibitor Of Cysteine Proteinases
    作者:Tamai,Masaharu; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1987 卷标:35(3) 页码:1098-104]

    915697-61-9 = 88321-09-9
    反应条件:1.1 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Dichloromethane,4-Methylmorpholine2.1 Reagents: M-Chloroperbenzoic Acid Solvents: Chloroform; 50 °C3.1 Reagents: Potassium Hydroxide Solvents: Water; 2 H,0 °C
    标题:Stereoselective Synthesis Of The Epoxysuccinyl Peptide E-64C
    作者:Lygo,Barry; Et Al
    参考文献:Synlett 日期:2006 卷标:(13) 页码:2063-2066]

    13139-15-6 = 88321-09-9
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide,1-Hydroxybenzotriazole Solvents: Ethanol; 1.5 H,3 °C -> 8 °C; 2.5 H,Rt2.1 Reagents: Hydrochloric Acid Solvents: Ethyl Acetate; 2.5 H,Rt3.1 Reagents: Dicyclohexylcarbodiimide,1-Hydroxybenzotriazole Solvents: Ethyl Acetate; 3 H,0 °C; 12 H,Rt
    标题:Design,Synthesis,And Screen Of Cathepsin K Inhibitors
    作者:Yu,Ying-Ying; Et Al
    参考文献:Chinese Chemical Letters 日期:2013 卷标:24(8) 页码:715-718]

    17087-75-1 = 88321-09-9
    反应条件:1.1 Reagents: Sulfuric Acid; 4.5 H,Reflux2.1 Reagents: Potassium Hydroxide Solvents: Water; 1 H,4 °C -> 6 °C; 4 H,Rt3.1 Reagents: Dicyclohexylcarbodiimide,1-Hydroxybenzotriazole Solvents: Ethyl Acetate; 3 H,0 °C; 12 H,Rt
    标题:Design,Synthesis,And Screen Of Cathepsin K Inhibitors
    作者:Yu,Ying-Ying; Et Al
    参考文献:Chinese Chemical Letters 日期:2013 卷标:24(8) 页码:715-718]

    1738-69-8 + 89886-73-7 = 88321-09-9
    反应条件:1.1 Reagents: 4-Methylmorpholine,1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Chloroform1.2 Solvents: Ethyl Acetate,Water2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol,Ethyl Acetate3.1 Reagents: 4-Methylmorpholine,1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Chloroform3.2 Solvents: Ethyl Acetate,Water
    标题:A New Synthesis Of Peptidyl Epoxysuccinates For Probing Cysteine Protease-Inhibitor P3/s3 Binding Interactions
    作者:Roush,William R.; Et Al
    参考文献:Synthesis 日期:1999 卷标:1500 页码:1500-1504]

    174759-66-1 = 88321-09-9
    反应条件:1.1 Reagents: 4-Methylmorpholine,1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Chloroform1.2 Solvents: Ethyl Acetate,Water
    标题:A New Synthesis Of Peptidyl Epoxysuccinates For Probing Cysteine Protease-Inhibitor P3/s3 Binding Interactions
    作者:Roush,William R.; Et Al
    参考文献:Synthesis 日期:1999 卷标:1500 页码:1500-1504]

    84851-37-6 + 100464-19-5 = 88321-09-9
    反应条件:1.1 Solvents: Ethyl Acetate
    标题:An Efficient Synthetic Method For Ethyl (+)-(2S,3S)-3-[(S)-3-Methyl-1-(3-Methylbutylcarbamoyl)Butylcarbamoyl]-2-Oxiranecarboxylate (Est),A New Inhibitor Of Cysteine Proteinases
    作者:Tamai,Masaharu; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1987 卷标:35(3) 页码:1098-104]

    848778-06-3 = 88321-09-9
    反应条件:1.1 Reagents: Lithium Ethoxide Solvents: Ethanol; 10 Min,Rt1.2 Reagents: 4-(Dimethylamino)Pyridine,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Dimethylformamide; 4 H,Rt
    标题:Stereoselective Synthesis Of E-64 And Related Cysteine Proteases Inhibitors From 2,3-Epoxyamides
    作者:Sarabia,Francisco; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2005 卷标:13(5) 页码:1691-1705]

    73890-18-3 = 88321-09-9
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Water; 1 H,4 °C -> 6 °C; 4 H,Rt2.1 Reagents: Dicyclohexylcarbodiimide,1-Hydroxybenzotriazole Solvents: Ethyl Acetate; 3 H,0 °C; 12 H,Rt
    标题:Design,Synthesis,And Screen Of Cathepsin K Inhibitors
    作者:Yu,Ying-Ying; Et Al
    参考文献:Chinese Chemical Letters 日期:2013 卷标:24(8) 页码:715-718]

    84863-67-2 = 88321-09-9
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Ethyl Acetate; 2.5 H,Rt2.1 Reagents: Dicyclohexylcarbodiimide,1-Hydroxybenzotriazole Solvents: Ethyl Acetate; 3 H,0 °C; 12 H,Rt
    标题:Design,Synthesis,And Screen Of Cathepsin K Inhibitors
    作者:Yu,Ying-Ying; Et Al
    参考文献:Chinese Chemical Letters 日期:2013 卷标:24(8) 页码:715-718]

    848778-05-2 = 88321-09-9
    反应条件:1.1 Reagents: 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone Solvents: Benzene; 72 H,Reflux2.1 Reagents: Lithium Ethoxide Solvents: Ethanol; 10 Min,Rt2.2 Reagents: 4-(Dimethylamino)Pyridine,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Dimethylformamide; 4 H,Rt
    标题:Stereoselective Synthesis Of E-64 And Related Cysteine Proteases Inhibitors From 2,3-Epoxyamides
    作者:Sarabia,Francisco; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2005 卷标:13(5) 页码:1691-1705]

    915697-59-5 = 88321-09-9
    反应条件:1.1 Reagents: M-Chloroperbenzoic Acid Solvents: Chloroform; 50 °C2.1 Reagents: Potassium Hydroxide Solvents: Water; 2 H,0 °C
    标题:Stereoselective Synthesis Of The Epoxysuccinyl Peptide E-64C
    作者:Lygo,Barry; Et Al
    参考文献:Synlett 日期:2006 卷标:(13) 页码:2063-2066
📜(2S,3S)-3-(乙氧羰基)环氧乙烷-2-羧酸置于n,N'-二环己基碳二亚胺体系中,用 乙酸乙酯 作为反应溶剂,化学反应 8.0H,反应生成 阿洛司他丁
参考文献:Efficient Synthetic Method For Ethyl (+)-(2S,3S)-3-((S)-3-Methyl-1-(3-Methylbutylcarbamoyl)Butylcarbamoyl)-2-Oxiranecarboxylate (Est),A New Inhibitor Of Cysteine Proteinases.
标题:Efficient Synthetic Method For Ethyl (+)-(2S,3S)-3-((S)-3-Methyl-1-(3-Methylbutylcarbamoyl)Butylcarbamoyl)-2-Oxiranecarboxylate (Est),A New Inhibitor Of Cysteine Proteinases.
摘要:Ethly (+)-(2S,3S)-3-[(S)-3-甲基-1-(3-甲基丁基氨基甲酰基)丁基氨基甲酰基]-2-环氧羧酸酯(est;la)预计将作为治疗肌肉萎缩症的口服药物,因为它对与疾病相关的肌纤维蛋白降解中涉及的半胱氨酸蛋白酶具有强大的抑制活性.通过广泛的研究,旨在开发一种适用于工业应用的新合成方法,发现l-精氨酸可以作为新的高效分离剂,用于获得光学纯的l-反-环氧富马酸(3A),而使用对硝基苯酚的活性酯方法在乙基l-反-环氧富马酸(7A)和l-亮氨酸异戊酰胺(8A)之间的偶联反应中非常有效,因为副产物的反应生成极少.为了检查反-环氧富马酸和亮氨酸部分的立体化学对半胱氨酸蛋白酶抑制活性的贡献,采用类似的方法合成了la的二叠体(lb-D),并测量了la-D对木瓜蛋白酶的灭活速率常数.化合物la,具有l-反-环氧富马酸和l-亮氨酸部分,显示出其中最强的活性.
DOI:10.1248/cpb.35.1098

海关参考信息

专利信息


专利号:US-6350878-B1
优先权日:1998-05-18
标 题 :Intermediates for the synthesis of epothilones and methods for their preparation
发明人：ALTMANN KARL-HEINZ; BAUER ARMIN; SCHINZER DIETER
权利人:NOVARTIS AG
摘要:The invention relates to a method of synthesis for a compound of formula (I),wherein R is a heterocyclyl moiety and X1, X2, X3 and X4 are, independently of each other, protecting groups, which is appropriate for the synthesis of epothilone B and desoxyepothione B.

专利号:US-6576777-B2
优先权日:1996-10-18
标 题:Semi-synthesis of a protected baccatin III compound
发明人：ZAMIR LOLITA; CARON GAETAN
权利人:INST NAT RECH SCIENT
摘要:The present invention relates to a semi-synthetic process to convert a naturally occurring taxane into a suitable starting material for the synthesis of paclitaxel and related compounds. Specifically, the present invention relates to a process for the conversion of 9-dihydro-13-acetylbaccatin III into a 7-protected baccatin III which can then be used as starting material for the synthesis of taxane derivatives such as paclitaxel, docetaxel, cephalomannine and other taxanes structurally related to baccatin III. The method as described uses a preparative scale technique which is amenable to commercial scale-up.

专利号:US-10961273-B2
优先权日:2016-08-16
标 题 :N-carboxyanhydride-based-scale synthesis of elamipretide
发明人：DUNCAN SCOTT M; OUDENES JAN; ANDERSEN MARC W
权利人:STEALTH BIOTHERAPEUTICS CORP
摘要:Disclosed are methods of making elamipretide (MTP-131), a peptide compound with therapeutic potential for treating various mitochondrial myopathies. The synthesis of the peptide can be achieved via the use of N-carboxyanhydride-modified amino acid residues, which increases the efficiency of the synthetic process and the purity of the peptide product generated.

专利号:US-9115179-B2
优先权日:2012-06-22
标题 :Synthesis of beta-turn peptidomimetic cyclic compounds
发明人：LAMA TERESA; PASCAL JEANICK
权利人:MIMETOGEN PHARMACEUTICALS INC
摘要:The present invention relates to methods of preparing β-turn cyclic peptidomimetic compounds and intermediates thereof. Particularly, the present invention relates to a process for the synthesis of β-turn cyclic peptidomimetic compounds of formula I: n nwhere R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L 2 , X, Y and n are as defined in the specification.n n The present invention provides a more efficient route for preparing β-turn cyclic peptidomimetic compounds and intermediates thereof.

专利号:US-9321794-B2
优先权日:2013-12-31
标题:Synthesis of racemic amphetamine derivatives by cuprate addition reaction with aziridine phosphoramidate compounds
发明人：MECKLER HAROLD; GREGG BRIAN THOMAS; YANG JIE
权利人:Chemapotheca LLC
摘要:The invention includes processes for the synthesis of amphetamine, dexamphetamine, methamphetamine, derivatives of these, including their salts, and novel precursors and intermediates obtained thereby, by synthesizing aziridine phosphoramidate compounds in specified solvents at specified temperatures, and then converting to a novel aryl or aryl-alkyl phosphoramidate precursors using an organometallic compound such as a copper salt, where the novel aryl or aryl-alkyl phosphoramidate precursor is then easily converted to the target compounds using known reactions.

专利号:US-9273023-B2
优先权日:2011-11-01
标 题:Modular synthesis of graphene nanoribbons and graphene substructures from oligo-alkynes
发明人：ALABUGIN IGOR; BYERS PHILIP M
权利人:UNIV FLORIDA STATE RES FOUND
摘要:A method for the synthesis of carbon-based structures, particularly graphene substructures and ribbons, from oligo- and poly-alkyne starting materials.

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1: Yao J, Wang J, Xu Y, Guo Q, Sun Y, Liu J, Li S, Guo Y, Wei L. CDK9 inhibition blocks the initiation of PINK1-PRKN-mediated mitophagy by regulating the SIRT1-FOXO3-BNIP3 axis and enhances the therapeutic effects involving mitochondrial dysfunction in hepatocellular carcinoma. Autophagy. 2022 Aug;18(8):1879-1897. doi: 10.1080/15548627.2021.2007027. Epub 2021 Dec 10.
2: Yousefi H, Mashouri L, Okpechi SC, Alahari N, Alahari SK. Repurposing existing drugs for the treatment of COVID-19/SARS-CoV-2 infection: A review describing drug mechanisms of action. Biochem Pharmacol. 2021 Jan;183:114296. doi: 10.1016/j.bcp.2020.114296. Epub 2020 Oct 22.
3: Saberian MS, Moriarty KP, Olmstead AD, Hallgrimson C, Jean F, Nabi IR, Libbrecht MW, Hamarneh G. DEEMD: Drug Efficacy Estimation Against SARS-CoV-2 Based on Cell Morphology With Deep Multiple Instance Learning. IEEE Trans Med Imaging. 2022 Nov;41(11):3128-3145. doi: 10.1109/TMI.2022.3178523. Epub 2022 Oct 27.

合成参考文献


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参考文献:10.1161/01.str.0000227259.15506.24
摘要:Tsubokawa T, Solaroglu I, Yatsushige H, Cahill J, Yata K, Zhang JH. Cathepsin and calpain inhibitor E64d attenuates matrix metalloproteinase-9 activity after focal cerebral ischemia in rats. Stroke. 2006 Jul;37(7):1888–94. doi: 10.1161/01.str.0000227259.15506.24.
参考文献:10.1007/s11524-008-9267-x
摘要:Lippert AM, Fendrich M, Johnson TP. Vicarious Exposure to Terrorist Attacks and Substance Use: Results from an Urban Household Survey. Journal of Urban Health. 2008 Mar 25;85(3):411–27. doi: 10.1007/s11524-008-9267-x.
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