(S)-2-(2-Bromo-benzoylamino)-3-(1H-indol-3-yl)-propionic acid | 317321-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(2-Bromo-benzoylamino)-3-(1H-indol-3-yl)-propionic acid
• 英文别名: (2S)-2-[(2-bromobenzoyl)amino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 317321-65-6
• 化学式: C₁₈H₁₅BrN₂O₃
• 分子量: 387.233
• InChiKey: PYLJGABTKOZRCY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-Bromo-benzoylamino)-3-(1H-indol-3-yl)-propionic acid 在 羟胺 作用下， 生成 2-Bromo-N-[(S)-1-hydroxycarbamoyl-2-(1H-indol-3-yl)-ethyl]-benzamide
  参考文献：
  名称：

  N-Benzoyl amino acids as LFA-1/ICAM inhibitors 1: amino acid structure–activity relationship

  摘要：

  The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00084-2
• 作为产物：
  描述：

  2-溴苯甲酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 苯甲醚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-2-(2-Bromo-benzoylamino)-3-(1H-indol-3-yl)-propionic acid
  参考文献：
  名称：

  N-苄基氨基酸作为ICAM / LFA-1抑制剂。第2部分：苯甲酰基部分的结构活性关系。

  摘要：

  邻溴苯甲酰基l-色氨酸1抑制LFA-1与ICAM-1的缔合，其IC（50）为1.7microM。对苯甲酰基部分的结构-活性关系的评估表明，2，6-二取代极大地增强了这类抑制剂的效力。有利于苯甲酰基环和酰胺键之间成90度角的电负性取代产生最有效的化合物。化合物的效力与90度从头算起的能量与给定化合物的整体最小能量之间的差异之间存在很强的相关性。将有利的苯甲酰基取代与L-组氨酸和L-天冬酰胺结合使用，其效价比化合物1高15倍。

  DOI：

  10.1016/j.bmcl.2004.02.046

文献信息

• Hydantoin compounds useful as anti-inflammatory agents
  申请人：——

  公开号：US20020143035A1

  公开（公告）日：2002-10-03

  Compounds having the formula (I): 1 and pharmaceutically-acceptable salts thereof, are useful for treating inflammatory or immune diseases, in which A is a four to seven membered heterocyclic or carbocyclic saturated ring; L and K are O or S; M is N or CH; Y is N or CH; Z is hydrogen, alkyl or substituted alkyl; and R 1 -R 4 are as defined in the specification.

  具有公式(I)的化合物： 1 以及其中A是四至七成员的杂环或碳环饱和环；L和K是O或S；M是N或CH；Y是N或CH；Z是氢、烷基或取代烷基；R 1 -R 4 如说明书定义的药用可接受的盐，用于治疗炎症或免疫疾病。
• Spiro-hydantoin compounds useful as anti-inflammatory agents
  申请人：——

  公开号：US20040009998A1

  公开（公告）日：2004-01-15

  Compounds having the formula (I), and pharmaceutically-acceptable salts, hydrates, enantiomers, and diastereomers, and prodrugs thereof, 1 are useful as inhibitors of LFA-1/ICAM and as anti-inflammatory agents, wherein L and K are O or S; Z is N or CR 4b ; Ar is an optionally-substituted aryl or heteroaryl; G is a linker attached to T or M or is absent; J, M and T are selected to define a three to six membered saturated or partially unsaturated non-aromatic ring; and R 2 R 4a , R 4b , and R 4c are as defined in the specification.

  具有公式(I)的化合物，以及药用可接受的盐、水合物、对映异构体、非对映异构体和前药，可用作LFA-1/ICAM的抑制剂和作为抗炎剂，其中L和K是O或S；Z是N或CR4b；Ar是可选地取代的芳基或杂芳基；G是连接到T或M的连接剂或不存在；J、M和T被选用来定义一个三到六成员的饱和或部分不饱和的非芳香环；R2R4a, R4b, 和R4c如说明书所定义。
• Pyrrolizine compounds useful as anti-inflammatory agents
  申请人：Dhar Murali T. G.

  公开号：US20060052434A1

  公开（公告）日：2006-03-09

  Pyrrolizine compounds having the formula (I), or pharmaceutically-acceptable salts thereof, are effective in treating inflammatory or immune diseases, where A is a four- to seven-membered saturated ring, K is O or S, and R 1 , R 2 , R 3 n, and M are defined in the specification.

  具有化学式(I)的吡咯烷化合物或其药用盐，在治疗炎症性或免疫性疾病方面具有有效性，其中A是一个四至七元饱和环，K是O或S，而R1、R2、R3n和M在规范中有定义。
• Antagonists for treatment of CD/11CD18 adhesion receptor mediated disorders
  申请人：Burdick J. Daniel

  公开号：US20050203135A1

  公开（公告）日：2005-09-15

  Compounds of the general structure D-L-B-(AA), for example (A), that are useful for treating Mac-1 or LFA-1-mediated disorders such as inflammatory disorders, allergies, and autoimmune diseases are provided.

  提供了一些具有一般结构D-L-B-(AA)的化合物，例如(A)，这些化合物对治疗Mac-1或LFA-1介导的疾病如炎症性疾病、过敏和自身免疫疾病是有用的。
• Crystalline forms and process for preparing spiro-hydantoin compounds
  申请人：DelMonte J. Albert

  公开号：US20060074099A1

  公开（公告）日：2006-04-06

  A process is provided for preparing spiro-hydantoin compounds of the formula II wherein Z is N or CR 4b ; K and L are independently O or S; Ar is an optionally substituted aryl or heteroaryl; A 2 is a linker, G′ is a linker; Q is a linker; and R 2 , R 4a , R 4c , and R h are defined in the specification. The process optionally includes the enantiomeric separation of intermediates to allow preparation of enantiomers of the spiro-hydantoin compounds of formula II. Substituted spiro-hydantoin compounds may be prepared from the spiro-hydantoin compounds of formula II. The spiro-hydantoin compound of formula II and the substituted spiro-hydantoin compounds are useful in the treatment of immune or inflammatory diseases. Also, provided are products made by the instant inventive process and crystalline forms (prepared by any process) of the substituted spiro-hydantoin compound, 5-[(5S, 9R)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-thiophene-3-carboxylic acid, including solvates and salts thereof, as well as methods of use thereof. Crystalline forms of certain intermediates are provided.

  提供了一种用于制备公式II中的螺环咪唑烷酮化合物的过程，其中Z为N或CR4b；K和L分别为O或S；Ar为可选择取代的芳基或杂芳基；A2为连接物，G'为连接物；Q为连接物；R2、R4a、R4c和Rh在规范中有定义。该过程可选择包括对中间体进行对映体分离，以便制备公式II中的螺环咪唑烷酮化合物的对映体。可从公式II中的螺环咪唑烷酮化合物制备取代的螺环咪唑烷酮化合物。公式II的螺环咪唑烷酮化合物和取代的螺环咪唑烷酮化合物在治疗免疫或炎症性疾病方面具有用途。还提供了通过即时创新过程制备的产品以及取代的螺环咪唑烷酮化合物5-[(5S, 9R)-9-(4-氰基苯基)-3-(3,5-二氯苯基)-1-甲基-2,4-二氧代-1,3,7-三氮杂螺[4.4]壬-7-基甲基]-噻吩-3-羧酸的结晶形式（通过任何过程制备），包括其溶剂合物和盐，以及其使用方法。提供了某些中间体的结晶形式。