(R)-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid | 324795-39-3

• 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: (R)-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid
• 英文别名: (2R)-2-(cyclohexylmethyl)-4-morpholin-4-yl-4-oxobutanoic acid
• CAS: 324795-39-3
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: HFMGKJUNLQOLDP-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid 、 4-氨基-1-甲基-4-哌啶甲腈 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-N-(4-cyano-1-methylpiperidin-4-yl)-2-(cyclohexylmethyl)-4-morpholino-4-oxobutanamide
  参考文献：
  名称：

  Identification of a novel class of succinyl-nitrile-based Cathepsin S inhibitors

  摘要：

  The synthesis and in vitro activities of a series of suceinyl-nitrile-based inhibitors of Cathepsin S are described. Several members of this class show nanomolar inhibition of the target enzyme as well as cellular potency. The inhibitors displaying the greatest potency contain N-alkyl substituted piperidine and pyrrolidine rings spiro-fused to the alpha-carbon of the P1 residue. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.046
• 作为产物：
  描述：

  (R)-(+)-2-(环己烷基甲基)丁二酸 1-甲基酯 在 lithium hydroxide 、 水 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (R)-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid
  参考文献：
  名称：

  [EN] INHIBITORS OF CATHEPSIN S
  [FR] INHIBITEURS DE LA CATHEPSINE S

  摘要：

  公开号：

  WO2005034848A3

文献信息

• Succinate derivative compounds useful as cysteine protease inhibitors
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US06313117B1

  公开（公告）日：2001-11-06

  Disclosed are novel succinate derivative compounds of the formula(I)/(Ia): wherein R1, R2, R3, R4, R5, R6, R7, X and A are defined herein. The compounds are useful as inhibitors of cysteine proteases. Also disclosed are methods of using and methods of making such compounds.

  披露了新颖的琥珀酸衍生物化合物，其化学公式为(I)/(Ia): 其中R1, R2, R3, R4, R5, R6, R7, X和A的定义如下。这些化合物作为胱氨酸蛋白酶的抑制剂是有用的。还披露了使用和制造这类化合物的方法。
• Novel succinate derivative compounds useful as cysteine protease inhibitors
  申请人：——

  公开号：US20010041700A1

  公开（公告）日：2001-11-15

  Disclosed are novel succinate derivative compounds of the formula (I)/(Ia): 1 wherein R1, R2, R3, R4, R5, R6, R7, X and A are defined herein. The compounds are useful as inhibitors of cysteine proteases. Also disclosed are methods of using and methods of making such compounds.

  披露了新型琥珀酸衍生物化合物，其化学公式为(I)/(Ia)：1，其中R1、R2、R3、R4、R5、R6、R7、X和A的定义如下。这些化合物可用作胱氨酸蛋白酶的抑制剂。还披露了使用和制造这些化合物的方法。
• Synthesis and SAR of succinamide peptidomimetic inhibitors of cathepsin S
  作者：Arnab K. Chatterjee、Hong Liu、David C. Tully、Jianhua Guo、Robert Epple、Ross Russo、Jennifer Williams、Michael Roberts、Tove Tuntland、Jonathan Chang、Perry Gordon、Thomas Hollenbeck、Christine Tumanut、Jun Li、Jennifer L. Harris

  DOI：10.1016/j.bmcl.2007.02.049

  日期：2007.5

  Peptidic, non-covalent inhibitors of lysosomal cysteine protease cathepsin S (1 and 2) were investigated due to low oral bioavailability, leading to an improved series of peptidomimetic inhibitors. Utilizing phenyl succinamides as the P2 residue increased the oral exposure of this lead series of compounds, while retaining selective inhibition of the cathepsin S isoform. Concurrent investigation of

  由于口服生物利用度低，研究了溶酶体半胱氨酸蛋白酶组织蛋白酶S（1和2）的肽类非共价抑制剂，从而产生了一系列拟肽抑制剂。使用苯基琥珀酰亚胺作为P2残基可增加该先导系列化合物的口腔暴露，同时保留对组织蛋白酶S亚型的选择性抑制作用。对P1和P2亚位点的同时研究导致发现了几种有效的和选择性的组织蛋白酶S抑制剂，这些酶由于消除了饱和脂肪族P2残基而具有良好的药代动力学特性。
• Novel compounds and compositions as cathepsin inhibitors
  申请人：——

  公开号：US20030105099A1

  公开（公告）日：2003-06-05

  The present invention relates to novel cathepsin S inhibitors, the pharmaceutically acceptable salts and N-oxides thereof, their uses as therapeutic agents and the methods of their making.

  本发明涉及新型卡特普西林S抑制剂、其药学上可接受的盐和N-氧化物，它们作为治疗剂的用途以及它们的制备方法。
• [EN] INHIBITORS OF CRUZIPAIN AND OTHER CYSTEINE PROTEASES<br/>[FR] INHIBITEURS DE LA CRUZIPAINE ET AUTRES CYSTEINES PROTEASES
  申请人：INCENTA LTD

  公开号：WO2002057270A1

  公开（公告）日：2002-07-25

  Compounds of general formula (I) or general formula (II) wherein R1, P1, P2, Q, Y, (X)o, (W)n, (V)m, Z and U are as defined in the specification, are inhibitors of cruzipain and other cysteine protease inhibitors and are useful as therapeutic agents, for example in Chagas' disease, or for validating therapeutic target compounds.

  通式(I)或通式(II)的化合物，在规范中定义的R1，P1，P2，Q，Y，(X)o，(W)n，(V)m，Z和U，是cruzipain和其他半胱氨酸蛋白酶抑制剂的抑制剂，并且可用作治疗剂，例如在恶性贫血病中，或用于验证治疗靶点化合物。