4-chloro-1-(thiophen-2-yl)-1H-pyrazole | 1198162-01-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-chloro-1-(thiophen-2-yl)-1H-pyrazole
• 英文别名: 4-Chloro-1-thiophen-2-ylpyrazole；4-chloro-1-thiophen-2-ylpyrazole
• CAS: 1198162-01-4
• 化学式: C₇H₅ClN₂S
• 分子量: 184.649
• InChiKey: CTPSXLSBQJAFDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 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：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-1-(thiophen-2-yl)-1H-pyrazole 在 硫酸 、 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and SAR of 2-phenyl-1-sulfonylaminocyclopropane carboxylates as ADAMTS-5 (Aggrecanase-2) inhibitors

  摘要：

  A series of 1-sulfonylaminocyclopropanecarboxylates was synthesized as ADAMTS-5 (Aggrecanase-2) inhibitors. After an intensive investigation of the central cyclopropane core including its absolute stereochemistry and substituents, we found compound 22 with an Agg-2 IC(50) = 7.4 nM, the most potent ADAMTS-5 inhibitor reported so far. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.093
• 作为产物：
  描述：

  噻吩 、 4-氯吡唑 在 亚硝酸特丁酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以81%的产率得到4-chloro-1-(thiophen-2-yl)-1H-pyrazole
  参考文献：
  名称：

  Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst

  摘要：

  一种通过可见光照射在氧化途径下进行噻吩的直接C-H氨化反应被提出，其中噻吩自由基阳离子作为关键中间体。各种噻吩和唑类化合物可以很好地转化为相应的氨化产物，水是唯一的副产物，对环境无害。

  DOI：

  10.1039/c7cc01339f

文献信息

• Visible‐Light‐Induced [4+2] Annulation of Thiophenes and Alkynes to Construct Benzene Rings
  作者：Chunlan Song、Xin Dong、Zhongjie Wang、Kun Liu、Chien‐Wei Chiang、Aiwen Lei

  DOI：10.1002/anie.201905971

  日期：2019.8.26

  The [4+2] annulation represents an elegant and versatile synthetic protocol for the construction of benzene rings. Herein, a strategy for visible-light induced [4+2] annulation of thiophenes and alkynes, to afford benzene rings, is presented. Under simple and mild reaction conditions, the ready availability and structural diversity of thiophenes and alkynes permit the facile synthesis of several substituted

  [4 + 2]环空表示用于苯环构建的优雅且通用的合成方案。在本文中，提出了一种策略，用于可见光诱导的噻吩和炔烃的[4 + 2]环化，以提供苯环。在简单温和的反应条件下，噻吩和炔烃的易得性和结构多样性允许轻松合成数个取代的芳环。有价值的药物和氨基酸也被很好地耐受。此外，DFT计算解释了该反应的高区域选择性。
• Inhibitors of ADAMTS4 or ADAMTS5 for use in preventing or treating cardiac remodeling and chronic heart failure
  申请人：Universitetet i Oslo

  公开号：US10322143B2

  公开（公告）日：2019-06-18

  The present invention provides an inhibitor of an ADAMTS proteoglycanase for use in treating or preventing cardiac remodeling or for use in treating or preventing heart failure in a subject. In particular, the present invention provides an inhibitor of ADAMTS4 or ADAMTS5 for use in treating or preventing cardiac remodeling or chronic heart failure in a subject with cardiac remodeling or with chronic heart failure, or with a condition that may lead to cardiac remodeling and/or chronic heart failure. Also provided is a method of treating or preventing cardiac remodeling or treating or preventing heart failure which method comprises administering to a subject in need thereof a therapeutically effective amount of an inhibitor of an ADAMTS proteoglycanase. Also provided is the use of an inhibitor of an ADAMTS proteoglycanase in the manufacture of a medicament for treating or preventing cardiac remodeling or treating or preventing heart failure.

  本发明提供了一种ADAMTS蛋白聚糖酶抑制剂，用于治疗或预防心脏重塑或用于治疗或预防受试者的心力衰竭。特别是，本发明提供了一种ADAMTS4或ADAMTS5的抑制剂，用于治疗或预防患有心脏重塑或慢性心力衰竭或可能导致心脏重塑和/或慢性心力衰竭的病症的受试者的心脏重塑或慢性心力衰竭。还提供了一种治疗或预防心脏重塑或治疗或预防心衰的方法，该方法包括向有需要的受试者施用治疗有效量的 ADAMTS 蛋白聚糖酶抑制剂。还提供了一种ADAMTS蛋白聚糖酶抑制剂在制造治疗或预防心脏重塑或治疗或预防心衰的药物中的用途。
• INHIBITORS OF ADAMTS4 OR ADAMTS5 FOR USE IN PREVENTING OR TREATING CARDIAC REMODELING AND CHRONIC HEART FAILURE
  申请人：Universitetet i Oslo

  公开号：US20190282606A1

  公开（公告）日：2019-09-19

  The present invention provides an inhibitor of an ADAMTS proteoglycanase for use in treating or preventing cardiac remodeling or for use in treating or preventing heart failure in a subject. In particular, the present invention provides an inhibitor of ADAMTS4 or ADAMTS5 for use in treating or preventing cardiac remodeling or chronic heart failure in a subject with cardiac remodeling or with chronic heart failure, or with a condition that may lead to cardiac remodeling and/or chronic heart failure. Also provided is a method of treating or preventing cardiac remodeling or treating or preventing heart failure which method comprises administering to a subject in need thereof a therapeutically effective amount of an inhibitor of an ADAMTS proteoglycanase. Also provided is the use of an inhibitor of an ADAMTS proteoglycanase in the manufacture of a medicament for treating or preventing cardiac remodeling or treating or preventing heart failure.
• Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst
  作者：Chunlan Song、Hong Yi、Bowen Dou、Yiying Li、Atul K. Singh、Aiwen Lei

  DOI：10.1039/c7cc01339f

  日期：——

  A direct C–H amination of thiophenes was presented via an oxidation pathway under visible-light irradiation, in which the thiophene radical cation serves as the key intermediate. Various thiophenes and azoles could be transformed into the corresponding amination products well, and H₂O was the only byproduct, which is environmentally benign.

  一种通过可见光照射在氧化途径下进行噻吩的直接C-H氨化反应被提出，其中噻吩自由基阳离子作为关键中间体。各种噻吩和唑类化合物可以很好地转化为相应的氨化产物，水是唯一的副产物，对环境无害。
• Synthesis and SAR of 2-phenyl-1-sulfonylaminocyclopropane carboxylates as ADAMTS-5 (Aggrecanase-2) inhibitors
  作者：Makoto Shiozaki、Hiroto Imai、Katsuya Maeda、Tomoya Miura、Katsutaka Yasue、Akira Suma、Masahiro Yokota、Yosuke Ogoshi、Julia Haas、Andrew M. Fryer、Ellen R. Laird、Nicole M. Littmann、Steven W. Andrews、John A. Josey、Takayuki Mimura、Yuichi Shinozaki、Hiromi Yoshiuchi、Takashi Inaba

  DOI：10.1016/j.bmcl.2009.08.093

  日期：2009.11

  A series of 1-sulfonylaminocyclopropanecarboxylates was synthesized as ADAMTS-5 (Aggrecanase-2) inhibitors. After an intensive investigation of the central cyclopropane core including its absolute stereochemistry and substituents, we found compound 22 with an Agg-2 IC(50) = 7.4 nM, the most potent ADAMTS-5 inhibitor reported so far. (c) 2009 Elsevier Ltd. All rights reserved.