(S)-2-(5-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid | 1049008-07-2

• 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-(5-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid
• 英文别名: (2S)-2-[(5-fluoro-1-benzothiophene-2-carbonyl)amino]-3-phenylpropanoic acid
• CAS: 1049008-07-2
• 化学式: C₁₈H₁₄FNO₃S
• 分子量: 343.378
• InChiKey: YULWOWYRLISVNC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  94.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-苯丙氨酸 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-(5-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic 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

• MODULATORS OF TLR3/DSRNA COMPLEX AND USES THEREOF
  申请人：Yin Hang

  公开号：US20140094507A1

  公开（公告）日：2014-04-03

  The present invention provides compounds and compositions that can modulate formation of Toll-like receptor 3 (TLR3) and double-stranded RNA (dsRNA) complex, and methods for using the same. In particular, some aspects of the invention provide compounds of the formula: compositions comprising and methods for using the same, where n, Ar 1 , Ar 2 , X 1 , X 2 , X 3 , Z 1 , and Z 2 are those defined herein.

  本发明提供了能够调节Toll样受体3（TLR3）和双链RNA（dsRNA）复合物形成的化合物和组合物以及使用它们的方法。特别地，本发明的某些方面提供了公式的化合物：组合物和使用它们的方法，其中n、Ar1、Ar2、X1、X2、X3、Z1和Z2的定义如本文所述。
• Modulators of TLR3/dsRNA complex and uses thereof
  申请人：Yin Hang

  公开号：US09409880B2

  公开（公告）日：2016-08-09

  The present invention provides compounds and compositions that can modulate formation of Toll-like receptor 3 (TLR3) and double-stranded RNA (dsRNA) complex, and methods for using the same. In particular, some aspects of the invention provide compounds of the formula: compositions comprising and methods for using the same, where n, Ar1, Ar2, X1, X2, X3, Z1, and Z2 are those defined herein.

  本发明提供了可以调节Toll样受体3（TLR3）和双链RNA（dsRNA）复合物形成的化合物和组合物，以及使用它们的方法。特别是，本发明的某些方面提供了公式的化合物：组合物和使用它们的方法，其中n、Ar1、Ar2、X1、X2、X3、Z1和Z2的定义如本文所述。
• 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.