S-Methyl-N_α-(tert-butyloxycarbonyl)-cysteine-N-methoxy-N-methylamide | 144474-29-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-Methyl-N_α-(tert-butyloxycarbonyl)-cysteine-N-methoxy-N-methylamide
• 英文别名: N,O-dimethyl 2(R)-(tert-butoxyformamido)-3-(methylthio)propionohydroxamate；(R)-N-[(1,1-Dimethyl)ethoxycarbonyl]-S-methylcysteine N-methoxy-N-methylamide；tert-butyl N-[(2R)-1-[methoxy(methyl)amino]-3-methylsulfanyl-1-oxopropan-2-yl]carbamate
• CAS: 144474-29-3
• 化学式: C₁₁H₂₂N₂O₄S
• 分子量: 278.373
• InChiKey: NVTDEEZPWFVXGE-QMMMGPOBSA-N

物化性质

• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-Methyl-N_α-(tert-butyloxycarbonyl)-cysteine-N-methoxy-N-methylamide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醚 、 异丙醇 为溶剂， 反应 12.0h， 生成 (threo)-1-Methylthio-2-(N-tert-butyloxycarbonyl)-amino-3-hydroxynonane
  参考文献：
  名称：

  Synthesis of potential inhibitors of the glycosphingolipid biosynthesis

  摘要：

  A synthesis of ceramide analogs 6 and 7 is reported here starting from L-cysteine. Alkylation of 2 and subsequent reduction of the intermediate formed ketone 3 afforded the diastereomeric alcohols 4. Deprotection and acylation of 4 lead to the desired product 6 which is converted to the sulfonium salt 7. Compound 6 is a powerful inhibitor of the glycosphingolipid biosynthesis.

  DOI：

  10.1016/s0040-4020(01)90177-2
• 作为产物：
  描述：

  N-(叔丁氧羰基L)-S-甲基-L-半胱氨酸 、 二甲羟胺盐酸盐 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 S-Methyl-N_α-(tert-butyloxycarbonyl)-cysteine-N-methoxy-N-methylamide
  参考文献：
  名称：

  [EN] HETEROARYL NITRILE COMPOUNDS USEFUL AS INHIBITORS OF CATHEPSIN-S
  [FR] COMPOSÉS D'HÉTÉROARYL-NITRILE UTILES COMME INHIBITEURS DE CATHEPSINE-S

  摘要：

  揭示了具有以下化学式（I）的Cathepsin-S可逆抑制剂化合物，可用于治疗自身免疫和其他疾病。还揭示了含有这些化合物的药物组合物，以及制备和使用这些化合物的方法。

  公开号：

  WO2011109470A1

文献信息

• Peptidyl compounds having MMP and TNF inhibitory activity
  申请人：Darwin Discovery Limited

  公开号：US06090840A1

  公开（公告）日：2000-07-18

  The subject invention concerns mercaptoalkylacyl compounds of formula (I): ##STR1## The compounds of the subject invention can be used to inhibit matrix metalloproteinases and/or TNF.alpha.- and L-selectin sheddase-mediated diseases including degenerative diseases and cancers. The subject invention also concerns methods of using the compounds of the invention to treat or prevent conditions associated with matrix metalloproteinases or that are mediated by TNF.alpha. or L-selectin sheddase.

  本发明涉及公式（I）的巯基烷基酰化合物：##STR1## 本发明的化合物可用于抑制基质金属蛋白酶和/或TNFα和L-选择素剪切酶介导的疾病，包括退行性疾病和癌症。本发明还涉及使用本发明的化合物治疗或预防与基质金属蛋白酶相关的疾病或由TNFα或L-选择素剪切酶介导的疾病的方法。
• Exploration of cathepsin S inhibitors characterized by a triazole P1–P2 amide replacement
  作者：Neil Moss、Zhaoming Xiong、Mike Burke、Derek Cogan、Donghong A. Gao、Kathleen Haverty、Alexander Heim-Riether、Eugene R. Hickey、Raj Nagaraja、Matthew Netherton、Kathy O’Shea、Philip Ramsden、Racheline Schwartz、Daw-Tsun Shih、Yancey Ward、Erick Young、Qing Zhang

  DOI：10.1016/j.bmcl.2012.09.054

  日期：2012.12

  This paper details exploration of a class of triazole-based cathepsin S inhibitors originally reported by Ellman and co-workers. SAR studies involving modifications across the whole inhibitor provide a perspective on the strengths and weaknesses of this class of inhibitors. In addition, we put the unique characteristics of this class of compounds into perspective with other classes of cathepsin S inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.
• PEPTIDYL COMPOUNDS HAVING MMP AND TNF INHIBITORY ACTIVITY
  申请人：Darwin Discovery Limited

  公开号：EP0891329B1

  公开（公告）日：2003-09-17
• ANTIVIRAL PEPTIDE DERIVATIVES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0941233A2

  公开（公告）日：1999-09-15
• Heteroaryl Nitrile Compounds Useful as Inhibitors of Cathepsin-S
  申请人：Burke Michael J.

  公开号：US20130158018A1

  公开（公告）日：2013-06-20

  Disclosed are Cathepsin-S reversible inhibitor compounds of the formula (I) which are useful in the treatment of autoimmune and other diseases. Also disclosed are pharmaceutical compositions containing the same, and methods of making and using the same.