(S)-2-(benzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid | 1279713-95-9

• 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: (S)-2-(benzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid
• 英文别名: (2S)-2-(1-benzothiophene-2-carbonylamino)-3-(4-hydroxyphenyl)propanoic acid
• CAS: 1279713-95-9
• 化学式: C₁₈H₁₅NO₄S
• 分子量: 341.387
• InChiKey: RCYYJEHKVQJXDD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-酪氨酸 在 高氯酸 、 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-) 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-2-(benzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid
  参考文献：
  名称：

  Small-Molecule Inhibitors of the TLR3/dsRNA Complex

  摘要：

  The protein-RNA interface has been regarded as "undruggable" despite its importance in many biological processes. The toll-like receptor 3 (TLR3)/double-stranded RNA (dsRNA) complex provides an exciting target for a number of infectious diseases and cancers. We describe the development of a series of small-molecule probes that were shown to be competitive inhibitors of dsRNA binding to TLR3 with high affinity and specificity. In a multitude of assays, compound 4a was profiled as a potent antagonist to TLR3 signaling and also repressed the expression of downstream signaling pathways mediated by the TLR3/dsRNA complex, including TNF-alpha and IL-1 beta.

  DOI：

  10.1021/ja111312h

文献信息

• [EN] MODULATORS OF TLR3/DSRNA COMPLEX AND USES THEREOF<br/>[FR] MODULATEURS DU COMPLEXE TLR3/ARNDS ET LEURS UTILISATIONS
  申请人：UNIV COLORADO REGENTS

  公开号：WO2012099785A3

  公开（公告）日：2012-09-27
• US9409880B2
  申请人：——

  公开号：US9409880B2

  公开（公告）日：2016-08-09
• Small-Molecule Inhibitors of the TLR3/dsRNA Complex
  作者：Kui Cheng、Xiaohui Wang、Hang Yin

  DOI：10.1021/ja111312h

  日期：2011.3.23

  The protein-RNA interface has been regarded as "undruggable" despite its importance in many biological processes. The toll-like receptor 3 (TLR3)/double-stranded RNA (dsRNA) complex provides an exciting target for a number of infectious diseases and cancers. We describe the development of a series of small-molecule probes that were shown to be competitive inhibitors of dsRNA binding to TLR3 with high affinity and specificity. In a multitude of assays, compound 4a was profiled as a potent antagonist to TLR3 signaling and also repressed the expression of downstream signaling pathways mediated by the TLR3/dsRNA complex, including TNF-alpha and IL-1 beta.