3-氯-5,6-二氟-1-苯并噻吩-2-羰酰氯 | 605658-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 3-氯-5,6-二氟-1-苯并噻吩-2-羰酰氯
• 英文名称: 3-chloro-5,6-difluorobenzo[b]thiophene-2-carbonyl chloride
• 英文别名: 3-Chloro-5,6-difluoro-1-benzothiophene-2-carbonyl chloride
• CAS: 605658-32-0
• 化学式: C₉H₂Cl₂F₂OS
• 分子量: 267.083
• InChiKey: JELLQOMTCZUZKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-苯基丙氨酸叔丁酯 、 3-氯-5,6-二氟-1-苯并噻吩-2-羰酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  3,4-二氟肉桂酸 在 吡啶 、 氯化亚砜 作用下， 以 氯苯 为溶剂， 反应 65.0h， 以20%的产率得到3-氯-5,6-二氟-1-苯并噻吩-2-羰酰氯
  参考文献：
  名称：

  DNA Binding Ligands Targeting Drug-Resistant Bacteria:  Structure, Activity, and Pharmacology

  摘要：

  We describe the lead optimization and structure-activity relationship of DNA minor-groove binding ligands, a novel class of antibacterial molecules. These compounds have been shown to target A/T-rich sites within the bacterial genome and, as a result, inhibit DNA replication and RNA transcription. The optimization was focused on N-terminal aromatic heterocycles and C-terminal amines and resulted in compounds with improved in vivo tolerability and excellent in vitro antibacterial potency (MIC greater than or equal to 0.031 mug/mL) against a broad range of Grainpositive pathogens, including drug-resistant strains such as methicillin-resistant Stapylococcus aureus (MRSA), penicillin-resistant Streptococcus pneumoniae (PRSP), and vancomycin-resistant Enterococcus faecalis (VRE). In a first proof-of-concept study, a selected compound (35) showed in vivo efficacy in a mouse peritonitis model against methicillin-sensitive S. aureus infection with an ED50 value of 30 mg/kg.

  DOI：

  10.1021/jm030097a

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。
• THIADIAZOLE DERIVATIVES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：GRIFFIOEN Gerard

  公开号：US20090054410A1

  公开（公告）日：2009-02-26

  This invention provides specifically substituted 1,2,4-thiadiazole derivatives for use in the treatment of an α-synucleopathy such as Parkinson's disease, diffuse Lewy body disease, traumatic brain injury, amyotrophic lateral sclerosis, Niemann-Pick disease, Hallervorden-Spatz syndrome, Down syndrome, neuroaxonal dystrophy, multiple system atrophy and Alzheimer's disease. This invention also provides various methods for producing such substituted 1,2,4-thiadiazole derivatives.
• US8541406B2
  申请人：——

  公开号：US8541406B2

  公开（公告）日：2013-09-24
• US9409880B2
  申请人：——

  公开号：US9409880B2

  公开（公告）日：2016-08-09