N-[(3-氯-6-氟苯并[b]噻吩-2-基)羰基]-D-苯丙氨酸 | 1279713-77-7

• 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
• 中文名称: N-[(3-氯-6-氟苯并[b]噻吩-2-基)羰基]-D-苯丙氨酸
• 英文名称: CU-CPT 4a
• 英文别名: (R)-2-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid；CU CPT 4a；(2R)-2-[(3-chloro-6-fluoro-1-benzothiophene-2-carbonyl)amino]-3-phenylpropanoic acid
• CAS: 1279713-77-7
• 化学式: C₁₈H₁₃ClFNO₃S
• 分子量: 377.824
• InChiKey: IAASQMCXDRISAV-CYBMUJFWSA-N

物化性质

• 溶解度：
  <37.78mg/ml，溶于 DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 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

安全信息

• 储存条件：
  2-8°C

制备方法与用途

CU-CPT 4a是 Toll 样受体 3 (TLR3)/双链 RNA (dsRNA) 复合物的有效抑制剂，表现出剂量依赖性的抑制效应，其 IC50 值为 3.44 µM[1][2]，能够阻断聚(I:C)诱导的 TLR3 激活。

反应信息

• 作为反应物：
  描述：

  N-[(3-氯-6-氟苯并[b]噻吩-2-基)羰基]-D-苯丙氨酸 、 L-苯基丙氨酸叔丁酯 以gave 4b as a white powder的产率得到(S)-2-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid
  参考文献：
  名称：

  Modulators of TLR3/dsRNA complex and uses thereof

  摘要：

  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。

  公开号：

  US09409880B2
• 作为产物：
  描述：

  D-phenylalanine tert-butyl ester 在 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 12.0h， 生成 N-[(3-氯-6-氟苯并[b]噻吩-2-基)羰基]-D-苯丙氨酸
  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。
• US9409880B2
  申请人：——

  公开号：US9409880B2

  公开（公告）日：2016-08-09
• [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：WO2012099785A2

  公开（公告）日：2012-07-26

  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 (I) compositions comprising and methods for using the same, where n, Ar1, Ar2, X1, X2, X3, Z1, and Z2 are those defined herein.
• 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.
• 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。