1-[(4-chlorophenyl)amino]cyclopentanecarbonitrile | 6340-83-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-[(4-chlorophenyl)amino]cyclopentanecarbonitrile
• 英文别名: 1-(4-chloro-anilino)-cyclopentanecarbonitrile；1-(4-Chlor-anilino)-cyclopentancarbonitril；1-(4-Chlor-anilino)-1-cyan-cyclopentan；1-(4-Chloroanilino)cyclopentane-1-carbonitrile
• CAS: 6340-83-6
• 化学式: C₁₂H₁₃ClN₂
• 分子量: 220.702
• InChiKey: FAJMEWKZJREKSK-UHFFFAOYSA-N

物化性质

• 熔点：
  73 °C
• 沸点：
  406.8±25.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(4-chlorophenyl)amino]cyclopentanecarbonitrile 以 苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Chande, Madhukar S.; Balel, Satish K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 377 - 380

  摘要：

  DOI：
• 作为产物：
  描述：

  氰化钾 、 对氯苯胺 、 环戊酮 以 溶剂黄146 为溶剂， 生成 1-[(4-chlorophenyl)amino]cyclopentanecarbonitrile
  参考文献：
  名称：

  Chande, Madhukar S.; Balel, Satish K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 377 - 380

  摘要：

  DOI：

文献信息

• Synthesis of α-aminonitriles under mild catalytic, metal-free conditions
  作者：Baskar Nammalwar、Chelsea Fortenberry、Richard A. Bunce

  DOI：10.1016/j.tetlet.2013.11.035

  日期：2014.1

  alpha-Aminonitriles have been synthesized by a Strecker synthesis from aldehydes and ketones under mild catalytic, metal-free conditions. Aromatic aldehydes (1 equiv) were reacted with TMSCN (1 equiv) and aromatic and 1 degrees or 2 degrees aliphatic amines (1 equiv) in EtOH containing 3 mol % of NH4Cl to give high yields of alpha-aminonitriles. An alternative to adding NH4Cl as a catalyst involved the use of excess TMSCN (1.2 equiv) to promote the process. The reaction was also successful under microwave conditions using excess TMSCN with no solvent. Ketones similarly reacted with aromatic amines and excess TMSCN under conventional and microwave heating, but 30 mol % of added NH4Cl was required for optimum conversion. (C) 2013 Elsevier Ltd. All rights reserved.
• Discovery of the First‐in‐Class Inhibitors of Hypoxia Up‐Regulated Protein 1 (HYOU1) Suppressing Pathogenic Fibroblast Activation
  作者：Dimitra Papadopoulou、Vasiliki Mavrikaki、Filippos Charalampous、Christos Tzaferis、Martina Samiotaki、Konstantinos D. Papavasileiou、Antreas Afantitis、Niki Karagianni、Maria C. Denis、Julie Sanchez、J. Robert Lane、Zacharias Faidon Brotzakis、Georgios Skretas、Dimitris Georgiadis、Alexios N. Matralis、George Kollias

  DOI：10.1002/anie.202319157

  日期：2024.4.2

  Fibroblasts are key regulators of inflammation, fibrosis, and cancer. Targeting their activation in these complex diseases has emerged as a novel strategy to restore tissue homeostasis. Here, we present a multidisciplinary lead discovery approach to identify and optimize small molecule inhibitors of pathogenic fibroblast activation. The study encompasses medicinal chemistry, molecular phenotyping assays, chemoproteomics, bulk RNA‐sequencing analysis, target validation experiments, and chemical absorption, distribution, metabolism, excretion and toxicity (ADMET)/pharmacokinetic (PK)/in vivo evaluation. The parallel synthesis employed for the production of the new benzamide derivatives enabled us to a) pinpoint key structural elements of the scaffold that provide potent fibroblast‐deactivating effects in cells, b) discriminate atoms or groups that favor or disfavor a desirable ADMET profile, and c) identify metabolic “hot spots”. Furthermore, we report the discovery of the first‐in‐class inhibitor leads for hypoxia up‐regulated protein 1 (HYOU1), a member of the heat shock protein 70 (HSP70) family often associated with cellular stress responses, particularly under hypoxic conditions. Targeting HYOU1 may therefore represent a potentially novel strategy to modulate fibroblast activation and treat chronic inflammatory and fibrotic disorders.