3-Cyclopentylprop-2-enoyl chloride | 208922-42-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 3-Cyclopentylprop-2-enoyl chloride
• CAS: 208922-42-3
• 化学式: C₈H₁₁ClO
• 分子量: 158.628
• InChiKey: IUSFLWRQSGVDDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Cyclopentylprop-2-enoyl chloride 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 生成 2-(2-cyclopentylvinyl)-5-(2-trifluoromethoxyphenyl)-1H-benzimidazole
  参考文献：
  名称：

  Discovery of vinylcycloalkyl-substituted benzimidazole TRPM8 antagonists effective in the treatment of cold allodynia

  摘要：

  Thermosensitive transient receptor potential melastatin 8 (TRPM8) antagonists are considered to be potential therapeutic agents for the treatment of cold hypersensitivity. The discovery of a new class of TRPM8 antagonists that shows in vivo efficacy in the rat chronic constriction injury (CCI)-induced model of neuropathic pain is described. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.060

文献信息

• Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as janus kinase inhibitors
  申请人：Rodgers D. James

  公开号：US20070135461A1

  公开（公告）日：2007-06-14

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯并[2,3-b]吡啶和杂环取代的吡咯并[2,3-b]嘧啶，可以调节雅努斯激酶的活性，并且在治疗与雅努斯激酶活性相关的疾病中具有用处，例如免疫相关疾病、皮肤疾病、髓增生性疾病、癌症和其他疾病。
• HETEROARYL SUBSTITUTED PYRROLO[2,3-b]PYRIDINES AND PYRROLO[2,3-b]PYRIMIDINES AS JANUS KINASE INHIBITORS
  申请人：Rodgers James D.

  公开号：US20090181959A1

  公开（公告）日：2009-07-16

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯并[2,3-b]吡啶和杂环取代的吡咯并[2,3-b]嘧啶，可调节Janus激酶的活性，并可用于治疗与Janus激酶活性相关的疾病，包括免疫相关疾病、皮肤疾病、髓系增生性疾病、癌症和其他疾病。
• Heteroaryl Substituted Pyrrolo[2,3-B] Pyridines And Pyrrolo[2,3-B] Pyrimidines As Janus Kinase Inhibitors
  申请人：Incyte Corporation

  公开号：US20140005210A1

  公开（公告）日：2014-01-02

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯并[2,3-b]吡啶和杂环取代的吡咯并[2,3-b]嘧啶，它们可以调节Janus激酶的活性，并且可用于治疗与Janus激酶活性相关的疾病，例如免疫相关疾病、皮肤疾病、骨髓增生性疾病、癌症和其他疾病。
• Heteroaryl Substituted Pyrrolo[2,3-B]Pyridines And Pyrrolo[2,3-B]Pyrimidines As Janus Kinase Inhibitors
  申请人：Rodgers James D.

  公开号：US20140018374A1

  公开（公告）日：2014-01-16

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯[2,3-b]吡啶和杂环取代的吡咯[2,3-b]嘧啶，其调节Janus激酶的活性，并且在治疗与Janus激酶活性相关的疾病中具有用处，包括但不限于免疫相关性疾病、皮肤疾病、髓样增生性疾病、癌症和其他疾病。
• Fragment-Based Anti-inflammatory Agent Design and Target Identification: Discovery of AF-45 as an IRAK4 Inhibitor to Treat Ulcerative Colitis and Acute Lung Injury
  作者：Yu Zou、Xiemin Wang、Pan Chen、Zhiwei Zheng、Xiaobo Li、Zhichao Chen、Mi Guo、Ying Zhou、Chenhui Sun、Ran Wang、Wufu Zhu、Pengwu Zheng、Won-Jea Cho、Young-Chang Cho、Guang Liang、Qidong Tang

  DOI：10.1021/acs.jmedchem.4c00202

  日期：2024.7.11

  pathway and target IRAK4, a promising target for inflammation and autoimmune diseases. The selectivity of AF-45 targeting IRAK4 was validated by comparing its effects on other kinase/nonkinase proteins. In vivo, AF-45 exhibited a good therapeutic effect on UC and ALI, and favorable PK proprieties. Since there are currently no clinical or preclinical trials for IRAK4 inhibitors to treat UC and ALI, AF-45

  UC 和 ALI 是临床治疗有限的炎症性疾病。在此，我们实验室基于环己胺/环丁胺和抗炎剂的几个片段进行了基于片段的抗炎剂设计。使用 ELISA 和 MTT 测定对 33 种合成化合物进行分析，将 AF-45（对 THP-1 巨噬细胞中的 IL-6/TNF-α 的 IC 50 = 0.53/0.60 μM）确定为最佳分子。通过机制研究和系统性靶点搜索过程，发现 AF-45 可以阻断 NF-κB/MAPK 通路并靶向 IRAK4（炎症和自身免疫性疾病的一个有希望的靶点）。通过比较 AF-45 对其他激酶/非激酶蛋白的影响，验证了 AF-45 靶向 IRAK4 的选择性。在体内，AF-45对UC和ALI表现出良好的治疗效果，并具有良好的PK特性。由于目前尚无 IRAK4 抑制剂治疗 UC 和 ALI 的临床或临床前试验，AF-45 提供了一种新的针对 IRAK4 的先导化合物或候选药物，用于治疗这些疾病。