(2-{[(3S)-4-(benzylsulfonyl)-3-methylpiperazin-1-yl]methyl}-4-chlorophenyl)acetic acid | 936098-51-0

• 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: (2-{[(3S)-4-(benzylsulfonyl)-3-methylpiperazin-1-yl]methyl}-4-chlorophenyl)acetic acid
• 英文别名: (S)-2-(2-((4-(benzylsulfonyl)-3-methylpiperazin-1-yl)methyl)-4-chlorophenyl)acetic acid；2-[2-[[(3S)-4-benzylsulfonyl-3-methylpiperazin-1-yl]methyl]-4-chlorophenyl]acetic acid
• CAS: 936098-51-0
• 化学式: C₂₁H₂₅ClN₂O₄S
• 分子量: 436.96
• InChiKey: USELGMAYVJTSGV-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基磺酰胺 、 (2-{[(3S)-4-(benzylsulfonyl)-3-methylpiperazin-1-yl]methyl}-4-chlorophenyl)acetic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以23%的产率得到2-(2-{[(3S)-4-(benzylsulfonyl)-3-methylpiperazin-1-yl]methyl}-4-chlorophenyl)-N-(methylsulfonyl)acetamide
  参考文献：
  名称：

  Zwitterionic CRTh2 Antagonists

  摘要：

  A novel series of zwitterions is reported that contains potent, selective antagonists of the chemoattractant receptor-homologous expressed on Th2 lymphocytes receptor (CRTh2 or DP2). A high quality lead compound 2 was discovered from virtual screening based on the pharmacophore features present in a literature compound 1. Lead optimization through side chain modification and preliminary changes around the acid are disclosed. Optimization of physicochemical properties (log D, MWt, and HBA) allowed maintenance of high CRTh2 potency while achieving low rates of metabolism and minimization of other potential concerns such as hERG channel activity and permeability. A step-change increase in potency was achieved through addition of a single methyl group onto the piperazine ring, which gave high quality compounds suitable for progression into in vivo studies.

  DOI：

  10.1021/jm1014549
• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (2-{[(3S)-4-(benzylsulfonyl)-3-methylpiperazin-1-yl]methyl}-4-chlorophenyl)acetic acid
  参考文献：
  名称：

  Zwitterionic CRTh2 Antagonists

  摘要：

  A novel series of zwitterions is reported that contains potent, selective antagonists of the chemoattractant receptor-homologous expressed on Th2 lymphocytes receptor (CRTh2 or DP2). A high quality lead compound 2 was discovered from virtual screening based on the pharmacophore features present in a literature compound 1. Lead optimization through side chain modification and preliminary changes around the acid are disclosed. Optimization of physicochemical properties (log D, MWt, and HBA) allowed maintenance of high CRTh2 potency while achieving low rates of metabolism and minimization of other potential concerns such as hERG channel activity and permeability. A step-change increase in potency was achieved through addition of a single methyl group onto the piperazine ring, which gave high quality compounds suitable for progression into in vivo studies.

  DOI：

  10.1021/jm1014549

文献信息

• Novel Compounds
  申请人：Luker Timothy

  公开号：US20080255150A1

  公开（公告）日：2008-10-16

  The invention relates to substituted aryl acids as useful pharmaceutical compounds for treating respiratory disorders, pharmaceutical compositions containing them, and processes for their preparation.

  这项发明涉及用作治疗呼吸系统疾病的有用药用化合物的取代芳基酸，包含它们的药用组合物以及它们的制备过程。
• NOVEL COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1948630A2

  公开（公告）日：2008-07-30
• [EN] NOVEL COMPOUNDS<br/>[FR] COMPOSES
  申请人：ASTRAZENECA AB

  公开号：WO2007052023A2

  公开（公告）日：2007-05-10

  [EN] The invention relates to substituted aryl acids as useful pharmaceutical compounds for treating respiratory disorders, pharmaceutical compositions containing them, and processes for their preparation.
  [FR] L'invention concerne des acides d'aryle substitués utilisés comme composés pharmaceutiques utiles dans le traitement de troubles respiratoires, des compositions pharmaceutiques renfermant ceux-ci et des procédés de préparation de ceux-ci.