methyl (3S)-4-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate | 1028260-16-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (3S)-4-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1028260-16-3
• 化学式: C₁₀H₂₀N₂O₄
• 分子量: 232.28
• InChiKey: PZWJTKNQFJSDGB-ZETCQYMHSA-N

物化性质

• 沸点：
  351.9±37.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3S)-4-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (S)-methyl 3-(5-chloro-1H-indole-2-carboxamido)-4-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamido)butanoate
  参考文献：
  名称：

  Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors

  摘要：

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.132
• 作为产物：
  描述：

  benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 methyl (3S)-4-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
  参考文献：
  名称：

  Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors

  摘要：

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.132

文献信息

• Synthesis and Evaluation of Boronated Lysine and Bis(carboranylated)γ-Amino Acids as Monomers for Peptide Assembly
  作者：Christophe Morin、Christian Thimon

  DOI：10.1002/ejoc.200400342

  日期：2004.9

  synthesized N-Fmoc amino acid derivatives bearing boronated and carboranylated substituents. Thus, a 1,3,2-dioxaborolane subunit has been introduced on the side chain of Nα-Fmoc-L-lysine, and a bis(carboranylated) γ-amino acid building block has been prepared. As shown by the preparation of a model tetrapeptide, only the latter monomer can be successfully used in peptide synthesis. (© Wiley-VCH Verlag

  我们已经合成了带有硼化和碳化取代基的 N-Fmoc 氨基酸衍生物。因此，在 Nα-Fmoc-L-赖氨酸的侧链上引入了 1,3,2-二氧硼烷亚基，并制备了双（碳酰化）γ-氨基酸结构单元。如模型四肽的制备所示，只有后一种单体才能成功用于肽合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors
  作者：Kenji Yoshikawa、Toshiharu Yoshino、Yoshihiro Yokomizo、Kouichi Uoto、Hiroyuki Naito、Katsuhiro Kawakami、Akiyoshi Mochizuki、Tsutomu Nagata、Makoto Suzuki、Hideyuki Kanno、Makoto Takemura、Toshiharu Ohta

  DOI：10.1016/j.bmcl.2011.01.132

  日期：2011.4

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.