N-[N-[(2S,3S)-3-trans-ethoxycarbonyloxirane-2-carbonyl]-L-phenylalanyl]morpholine

• 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: N-[N-[(2S,3S)-3-trans-ethoxycarbonyloxirane-2-carbonyl]-L-phenylalanyl]morpholine
• 英文别名: ethyl (2S,3S)-3-[[(2S)-1-morpholin-4-yl-1-oxo-3-phenylpropan-2-yl]carbamoyl]oxirane-2-carboxylate
• 化学式: C₁₉H₂₄N₂O₆
• 分子量: 376.409
• InChiKey: NUHKDZNRPTZUIZ-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N^α-(tert-butoxycarbonyl)-L-phenylalanine-N-morpholinamide 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 17.5h， 生成 N-[N-[(2S,3S)-3-trans-ethoxycarbonyloxirane-2-carbonyl]-L-phenylalanyl]morpholine
  参考文献：
  名称：

  Design, synthesis, and screen of cathepsin K inhibitors

  摘要：

  We synthesized a series of epoxysuccinic acid derivatives and evaluated their in vitro cathepsin K inhibitory activity The screening results show that the potency of compounds 9e, 9d, 9p, 9j and 9k (IC50 <= 0.005 mu mol/L) were equal to or greater than that of the lead compound 9a. Less hydrophobic compounds showed weaker potency, which can be explained by the hydrophobic nature of the cathepsin K binding pockets. (C) 2013 Jun-Hai Xiao and Xiao-Hong Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.05.002

文献信息

• Epoxysuccinic acid derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05556853A1

  公开（公告）日：1996-09-17

  A compound of the general formula: ##STR1## wherein R.sup.1 represents a carboxyl group which may optionally be esterified or amidated; R.sup.2 represents a cyclic group which may optionally be substituted or a polar group; n is an integer of 0 to 6; R.sup.3 represents hydrogen or a hydrocarbon residue which may optionally be substituted; R.sup.4 represents (1) a hydrocarbon residue which is substituted by an optionally protected amino group or (2) an alkenyl group; or R.sup.3 and R.sup.4 may be combined with the adjacent nitrogen atom to form a heterocyclic group containing at least two hetero atoms, or a salt thereof. The compound or a salt thereof of the present invention inhibits thiol proteases such as cathepsin L and B and serves well as a prophylactic/therapeutic agent for bone diseases such as osteoporosis.

  一种通式为：##STR1## 的化合物，其中R.sup.1代表羧基，可以选择酯化或酰胺化；R.sup.2代表环状基团，可以选择取代或极性基团；n为0至6的整数；R.sup.3代表氢或可选择取代的烃基残基；R.sup.4代表（1）可选择保护的氨基团取代的可选择取代的烃基残基或（2）烯基基团；或者R.sup.3和R.sup.4可以与相邻的氮原子结合形成含有至少两个杂原子的杂环基团，或其盐。本发明的化合物或其盐抑制巯基蛋白酶如L和B型蛋白酶，并且可作为骨疾病如骨质疏松的预防/治疗剂。
• US5556853A
  申请人：——

  公开号：US5556853A

  公开（公告）日：1996-09-17
• Design, synthesis, and screen of cathepsin K inhibitors
  作者：Ying-Ying Yu、Wei Sun、Lei Dong、Hai-Dong Liu、Dan Jiang、Jun-Hai Xiao、Xiao-Hong Yang、Song Li

  DOI：10.1016/j.cclet.2013.05.002

  日期：2013.8

  We synthesized a series of epoxysuccinic acid derivatives and evaluated their in vitro cathepsin K inhibitory activity The screening results show that the potency of compounds 9e, 9d, 9p, 9j and 9k (IC50 <= 0.005 mu mol/L) were equal to or greater than that of the lead compound 9a. Less hydrophobic compounds showed weaker potency, which can be explained by the hydrophobic nature of the cathepsin K binding pockets. (C) 2013 Jun-Hai Xiao and Xiao-Hong Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.