4-((4-formylphenyl)thio)benzonitrile | 959034-63-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-((4-formylphenyl)thio)benzonitrile
• 英文别名: 4-[4-Cyanothiophenoxy]benzaldehyde；4-(4-formylphenyl)sulfanylbenzonitrile
• CAS: 959034-63-0
• 化学式: C₁₄H₉NOS
• 分子量: 239.298
• InChiKey: BHWLIKHTLOLPIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((4-formylphenyl)thio)benzonitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 4-(4-hydroxymethyl-phenylsulfanyl)-benzonitrile
  参考文献：
  名称：

  Non-basic ligands for aminergic GPCRs: The discovery and development diaryl sulfones as selective, orally bioavailable 5-HT2A receptor antagonists for the treatment of sleep disorders

  摘要：

  Scaffold hopping from a non-basic series of 5-HT2A receptor antagonists developed in-house that possessed reduced activity in vivo enabled the discovery of a novel series of diaryl sulfones that gave excellent occupancy on oral dosing. Not only does this work further demonstrate that oral bioavailability of a given series can be enhanced by improving physicochemical parameters such as log P, but it corroborates the growing evidence that a protonated amine is not essential for affinity at aminergic GPCRs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.090
• 作为产物：
  描述：

  4-巯基苯甲腈 、 对氟苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 19.0h， 以57%的产率得到4-((4-formylphenyl)thio)benzonitrile
  参考文献：
  名称：

  二苯醚苄胺对人类非洲锥虫病的活性。

  摘要：

  昆虫传播的寄生虫布氏锥虫困扰人类和其他动物，引发人类非洲锥虫病，也称为非洲昏睡病。这种疾病对撒哈拉以南非洲地区的人民构成最大威胁。鉴于目前可用药物的高毒性和给药困难，需要一种新的治疗方法。基于已知的人类非洲锥虫病 SAR（结构-活性关系），我们现在描述了许多功能简单的二苯醚类似物，它们对T. b.具有低微摩尔活性 (IC 50 = 0.16–0.96 μM) 。罗得西亚. 最好的化合物对 L6 细胞系 (SI = 750) 表现出良好的选择性，对四种人类细胞系表现出更好的选择性 (SI = 1200)。本文的数据为持续优化抗锥虫二苯醚提供了方向。

  DOI：

  10.1016/j.bioorg.2020.103590

文献信息

• Synthesis and Biological Evaluation of Inhibitors of Botulinum Neurotoxin Metalloprotease
  作者：Peter Wipf、Chenbo Wang、Julia Widom、Filip Petronijevic、James C. Burnett、Jonathan E. Nuss、Sina Bavari、Rick Gussio

  DOI：10.3987/com-08-s(d)8

  日期：——

  Based on the lead therapeutic agent NSC 240898, a new series of heterocyclic inhibitors of the BoNT serotype A metalloprotease has been generated. Highlights of the synthetic sequences include Sonogashira couplings of polysubstituted building blocks and gold-catalyzed indole formations. Preliminary structure-activity relationship studies afford detailed insights into the steric and electrostatic properties of the pharmacophore of this molecular scaffold.
• Activity of diphenyl ether benzyl amines against Human African Trypanosomiasis
  作者：James P. Hagen、Grant Darner、Samuel Anderson、Katie Higgins、Derek A. Leas、Ananya Mitra、Victoria Mashinson、Tasloach Wol、Carlos Vera-Esquivel、Bret Belter、Monica Cal、Marcel Kaiser、Alexander Wallick、Rosalie C. Warner、Paul H. Davis

  DOI：10.1016/j.bioorg.2020.103590

  日期：2020.4

  and other animals, eliciting the disease Human African trypanosomiasis, also known as African sleeping sickness. This disease poses the biggest threat to the people in Sub-Saharan Africa. Given the high toxicity and difficulties with administration of currently available drugs, a novel treatment is needed. Building on known Human African trypanosomiasis SAR (structure–activity relationship), we now

  昆虫传播的寄生虫布氏锥虫困扰人类和其他动物，引发人类非洲锥虫病，也称为非洲昏睡病。这种疾病对撒哈拉以南非洲地区的人民构成最大威胁。鉴于目前可用药物的高毒性和给药困难，需要一种新的治疗方法。基于已知的人类非洲锥虫病 SAR（结构-活性关系），我们现在描述了许多功能简单的二苯醚类似物，它们对T. b.具有低微摩尔活性 (IC 50 = 0.16–0.96 μM) 。罗得西亚. 最好的化合物对 L6 细胞系 (SI = 750) 表现出良好的选择性，对四种人类细胞系表现出更好的选择性 (SI = 1200)。本文的数据为持续优化抗锥虫二苯醚提供了方向。
• Non-basic ligands for aminergic GPCRs: The discovery and development diaryl sulfones as selective, orally bioavailable 5-HT2A receptor antagonists for the treatment of sleep disorders
  作者：Tammy Ladduwahetty、Myra Gilligan、Alexander Humphries、Kevin J. Merchant、Rebecca Fish、George McAlister、Magnus Ivarsson、Maria Dominguez、Desmond O’Connor、Angus M. MacLeod

  DOI：10.1016/j.bmcl.2010.04.090

  日期：2010.6

  Scaffold hopping from a non-basic series of 5-HT2A receptor antagonists developed in-house that possessed reduced activity in vivo enabled the discovery of a novel series of diaryl sulfones that gave excellent occupancy on oral dosing. Not only does this work further demonstrate that oral bioavailability of a given series can be enhanced by improving physicochemical parameters such as log P, but it corroborates the growing evidence that a protonated amine is not essential for affinity at aminergic GPCRs. (C) 2010 Elsevier Ltd. All rights reserved.