3-氨基-苯并[b]噻吩-2-羧酰胺 | 37839-59-1

• 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-氨基-苯并[b]噻吩-2-羧酰胺
• 英文名称: 3-aminobenzo[b]thiophene-2-carboxamide
• 英文别名: 3-amino-benzo[b]thiophene-2-carboxylic acid amide；3-Amino-1-benzothiophene-2-carboxamide
• CAS: 37839-59-1
• 化学式: C₉H₈N₂OS
• mdl: MFCD00834778
• 分子量: 192.241
• InChiKey: LTNWICBPQWPXDK-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C
• 沸点：
  418.7±25.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 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：
  97.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氨基-苯并[b]噻吩-2-羧酰胺 以49%的产率得到
  参考文献：
  名称：

  SCHNELLER S. W.; CLOUGH F. W., HETEROCYCLES , 1975, 3, NO 2, 135-138

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基-苯并[b]噻吩-2-羧酸乙酯 在 hydrazine hydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-氨基-苯并[b]噻吩-2-羧酰胺
  参考文献：
  名称：

  Synthesis and characterization of 1,2,4-triazolo[1,5-a]pyrimidine-2-carboxamide-based compounds targeting the PA-PB1 interface of influenza A virus polymerase

  摘要：

  Influenza viruses (Flu) are responsible for seasonal epidemics causing high rates of morbidity, which can dramatically increase during severe pandemic outbreaks. Antiviral drugs are an indispensable weapon to treat infected people and reduce the impact on human health, nevertheless anti-Flu armamentarium still remains inadequate. In search for new anti-Flu drugs, our group has focused on viral RNA-dependent RNA polymerase (RdRP) developing disruptors of PA-PB1 subunits interface with the best compounds characterized by cycloheptathiophene-3-carboxamide and 1,2,4-triazolo[1,5-a]pyrimidine-2-carboxamide scaffolds. By merging these moieties, two very interesting hybrid compounds were recently identified, starting from which, in this paper, a series of analogues were designed and synthesized. In particular, a thorough exploration of the cycloheptathiophene-3-carboxamide moiety led to acquire important SAR insight and identify new active compounds showing both the ability to inhibit PA-PB1 interaction and viral replication in the micromolar range and at non-toxic concentrations. For few compounds, the ability to efficiently inhibit PA-PB1 subunits interaction did not translate into anti-Flu activity. Chemical/physical properties were investigated for a couple of compounds suggesting that the low solubility of compound 14, due to a strong crystal lattice, may have impaired its antiviral activity. Finally, computational studies performed on compound 23, in which the phenyl ring suitably replaced the cycloheptathiophene, suggested that, in addition to hydrophobic interactions, H-bonds enhanced its binding within the PAC cavity.

  DOI：

  10.1016/j.ejmech.2020.112944

文献信息

• Evolution of the Thienopyridine Class of Inhibitors of IκB Kinase-β:  Part I:  Hit-to-Lead Strategies
  作者：Tina Morwick、Angela Berry、Janice Brickwood、Mario Cardozo、Katrina Catron、Molly DeTuri、Jonathan Emeigh、Carol Homon、Matt Hrapchak、Stephen Jacober、Scott Jakes、Paul Kaplita、Terence A. Kelly、John Ksiazek、Michel Liuzzi、Ronald Magolda、Can Mao、Daniel Marshall、Daniel McNeil、Anthony Prokopowicz、Christopher Sarko、Erika Scouten、Cynthia Sledziona、Sanxing Sun、Jane Watrous、Jiang Ping Wu、Charles L. Cywin

  DOI：10.1021/jm0510979

  日期：2006.5.1

  High-throughput screening is routinely employed as a method for the identification of novel hit structures. Large numbers of active compounds are typically procured in this way and must undergo a rigorous validation process. This process is described in detail for a collection of screening hits identified as inhibitors of I kappa B kinase-beta (IKK beta), a key regulatory enzyme in the nuclear factor-kappa B (NF-kappa B) pathway. From these studies, a promising hit series was selected. Subsequent lead generation activities included the development of a pharmacophore hypothesis and structure-activity relationship (SAR) for the hit series. This led to the exploration of related scaffolds offering additional opportunities, and the various structural classes were comparatively evaluated for enzyme inhibition, selectivity, and drug-like properties. A novel lead series of thienopyridines was thereby established, and this series advanced into lead optimization for further development.
• Schneller,S.W.; Clough,F.W., Heterocycles, 1975, vol. 3, p. 135 - 138
  作者：Schneller,S.W.、Clough,F.W.

  DOI：——

  日期：——
• BECK J. R.; YAHNER J. A., J. ORG. CHEM. <JOCE-AH>, 1976, 41, NO 10, 1733-1734
  作者：BECK J. R.、 YAHNER J. A.

  DOI：——

  日期：——
• HETEROAROMATIC CARBOXAMIDE DERIVATIVES FOR THE TREATMENT OF INFLAMMATION
  申请人：Pharmacia Corporation

  公开号：EP1444010A2

  公开（公告）日：2004-08-11
• METHODS OF TREATING MUSCULAR DYSTROPHY
  申请人：BURKIN Dean

  公开号：US20160030390A1

  公开（公告）日：2016-02-04

  Disclosed herein are α7β1 integrin modulatory agents and methods of using such to treat conditions associated with decreased α7β1 integrin expression or activity, including muscular dystrophy. In one example, methods for treating a subject with muscular dystrophy are disclosed. The methods include administering an effective amount of an α7β1 integrin modulatory agent to the subject with muscular dystrophy, wherein the α7β1 integrin modulatory agent increases α7β1 integrin expression or activity as compared to α7β1 integrin expression or activity prior to treatment, thereby treating the subject with muscular dystrophy. Also disclosed are methods of enhancing muscle regeneration, repair, or maintenance in a subject and methods of enhancing α7β1 integrin expression by use of the disclosed α7β1 integrin modulatory agents. Methods of prospectively preventing or reducing muscle injury or damage in a subject are also disclosed.