2-bromo-N-(2-chloro-4-methylphenyl)propanamide | 1211464-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-N-(2-chloro-4-methylphenyl)propanamide
• CAS: 1211464-21-9
• 化学式: C₁₀H₁₁BrClNO
• 分子量: 276.56
• InChiKey: ULIMURDXVKLIML-UHFFFAOYSA-N

物化性质

• 沸点：
  380.2±37.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(2-chloro-4-methylphenyl)propanamide 在 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-(2-chloro-4-methylphenyl)-2-((1-(4-methoxyphenyl)-1H-benzo[d]imidazol-2-yl)sulfonyl)propanamide
  参考文献：
  名称：

  Host-Directed Inhibitors of Myxoviruses: Synthesis and in Vitro Biochemical Evaluation

  摘要：

  Drugs targeted to viral proteins are highly vulnerable to the development of viral resistance. One little explored approach to the treatment of viral diseases is the development of agents that target host factors required for virus replication. Myxoviruses are predominantly associated with acute disease and, thus, ideally suited for this approach since the necessary treatment time is anticipated to be limited. High-throughput screening previously identified benzimidazole 22407448 with broad antiviral activity against different influenza virus and paramyxovirus strains. Hit to lead chemistry has generated 6p (JMN3-003) with potent antiviral activity against a panel of myxovirus family members exhibiting EC(50) values in the low nanomolar range.

  DOI：

  10.1021/ml200125r
• 作为产物：
  描述：

  2-溴丙酰溴 、 2-氯-4-甲基苯胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到2-bromo-N-(2-chloro-4-methylphenyl)propanamide
  参考文献：
  名称：

  Imidazolyl amide compounds and uses related thereto

  摘要：

  本公开涉及此处披露的抗病毒化合物及其相关用途。在某些实施例中，本公开涉及包含2-((苯并[d]咪唑-2-基)硫基)-N-苯基丙酰胺衍生物、N-苯基-2-((1-苯基-苯并[d]咪唑-2-基)硫基)丙酰胺衍生物或2-((苯并[d]咪唑-2-基)硫基)-N-(2-氯-4-甲基苯基)丙酰胺衍生物的药物组合物。这些衍生物可能被一个或多个取代基取代。通常，药物组合物包括具有化合物I式的化合物，或其盐、前药或酯，其中X、Y和R1至R7如本文所述。

  公开号：

  US09365523B2

文献信息

• Asymmetric synthesis of host-directed inhibitors of myxoviruses
  作者：Terry W Moore、Kasinath Sana、Dan Yan、Pahk Thepchatri、John M Ndungu、Manohar T Saindane、Mark A Lockwood、Michael G Natchus、Dennis C Liotta、Richard K Plemper、James P Snyder、Aiming Sun

  DOI：10.3762/bjoc.9.23

  日期：——

  High-throughput screening (HTS) previously identified benzimidazole 1 (JMN3-003) as a compound with broad antiviral activity against different influenza viruses and paramyxovirus strains. In pursuit of a lead compound from this series for development, we sought to increase both the potency and the aqueous solubility of 1. Lead optimization has achieved compounds with potent antiviral activity against a panel of myxovirus family members (EC₅₀ values in the low nanomolar range) and much improved aqueous solubilities relative to that of 1. Additionally, we have devised a robust synthetic strategy for preparing 1 and congeners in an enantio-enriched fashion, which has allowed us to demonstrate that the (S)-enantiomers are generally 7- to 110-fold more potent than the corresponding (R)-isomers.

  高通量筛选（HTS）先前确定苯并咪唑1（JMN3-003）作为一种具有广谱抗病毒活性的化合物，可对不同流感病毒和副粘病毒株产生作用。为了寻找这一系列化合物中的引导化合物进行开发，我们努力提高1的效力和水溶性。引导优化已经获得了对多种粘病毒家族成员具有强效抗病毒活性的化合物（EC₅₀值在低纳摩尔范围），并且相对于1的水溶性有了显著改善。此外，我们已经设计出了一种稳健的合成策略，用于以对映富集的方式制备1和同系物，这使我们能够证明（S）-对映体通常比相应的（R）-异构体更有效，效力提高了7到110倍。
• IMIDAZOLYL AMIDE COMPOUNDS AND USES RELATED THERETO
  申请人：Emory University

  公开号：EP2691095A2

  公开（公告）日：2014-02-05
• US9365523B2
  申请人：——

  公开号：US9365523B2

  公开（公告）日：2016-06-14
• [EN] IMIDAZOLYL AMIDE COMPOUNDS AND USES RELATED THERETO<br/>[FR] COMPOSÉS D'IMIDAZOLYLAMIDE ET LEURS UTILISATIONS
  申请人：UNIV EMORY

  公开号：WO2012135296A2

  公开（公告）日：2012-10-04

  This disclosure relates to antiviral compounds disclosed herein and uses related thereto. In certain embodiments, the disclosure relates to pharmaceutical compositions comprising 2-((benzo[d]imidazol-2-yl)thio)-N-phenylpropanamide derivatives, N-phenyl-2-((1-phenyl-benzo[d]imidazol-2-yl)thio)propanamide derivatives, or 2-((benzo[d]imidazol-2-yl)thio)-N-(2-chloro-4-methylphenyl)propanamide derivatives. The derivatives may be substituted with one or more substituents. Typically, the pharmaceutical composition comprises a compound of Formula (I), or salt, prodrug, or ester thereof wherein X, Y, and R1 to R7 are described herein.