4-氟-2(3H)-苯并噻唑酮腙 | 753441-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 4-氟-2(3H)-苯并噻唑酮腙
• 英文名称: 4-fluoro-2-hydrazinylbenzo[d]thiazole
• 英文别名: 4-Fluoro-2-hydrazinyl-1,3-benzothiazole；(4-fluoro-1,3-benzothiazol-2-yl)hydrazine
• CAS: 753441-57-5
• 化学式: C₇H₆FN₃S
• mdl: MFCD04448797
• 分子量: 183.209
• InChiKey: XEGVEMYIOVYRHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 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：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(5-acetylfuran-2-yl)-2-chlorobenzoic acid 、 4-氟-2(3H)-苯并噻唑酮腙 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以5%的产率得到2-chloro-5-(5-(1-(2-(4-fluorobenzothiazol-2-yl)hydrazono)ethyl)-furan-2-yl)benzoic acid
  参考文献：
  名称：

  Discovery of Potent and Selective Benzothiazole Hydrazone Inhibitors of Bcl-X_L

  摘要：

  Developing potent molecules that inhibit Bcl-2 family mediated apoptosis affords opportunities to treat cancers via reactivation of the cell death machinery. We describe the hit-to-lead development of selective Bcl-X-L inhibitors originating from a high-throughput screening campaign. Small structural changes to the hit compound increased binding affinity more than 300-fold (to IC50 < 20 nM). This molecular series exhibits drug-like characteristics, low molecular weights (M-w < 450) and unprecedented selectivity for Bcl-X-L. Surface plasmon resonance experiments afford strong evidence of binding affinity within the hydrophobic groove of Bcl-X-L. Biological experiments using engineered Mcl-1 deficient mouse embryonic fibroblasts (MEFs, reliant only on Bcl-X-L, for survival) and Bax/Bak deficient MEFs (insensitive to selective activation of Bcl-2-driven apoptosis) support a mechanism-based induction of apoptosis. This manuscript describes the first series of selective small-molecule inhibitors of Bcl-X-L and provides promising leads for the development of efficacious therapeutics against solid tumors and chemoresistant cancer cell lines.

  DOI：

  10.1021/jm400556w
• 作为产物：
  描述：

  2-chloro-4-fluoro benzothiazole 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以99%的产率得到4-氟-2(3H)-苯并噻唑酮腙
  参考文献：
  名称：

  Optimization of Benzothiazole and Thiazole Hydrazones as Inhibitors of Schistosome BCL-2

  摘要：

  DOI：

  10.1021/acsinfecdis.0c00700

文献信息

• Process for producing biaryl compound
  申请人：Hagiya Koji

  公开号：US20050096471A1

  公开（公告）日：2005-05-05

  A process for producing a biaryl compound, characterized by reacting an arylhydrazine compound, hydrogen peroxide and an aryl compound. When the reaction is conducted in the presence of a given metal or a compound of the metal or in the presence of a metal oxide obtained by reacting the given metal or a compound of the metal with hydrogen peroxide, then the yield of the biaryl compound is improved.

  一种生产双芳基化合物的工艺，其特征在于使芳基肼化合物、过氧化氢和芳基化合物反应。当反应是在某种金属或金属化合物存在下进行，或在某种金属或金属化合物与过氧化氢反应得到的金属氧化物存在下进行时，双芳基化合物的产率会提高。
• Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers
  作者：Ge Chen、Chunyi Niu、Jianhua Yi、Lin Sun、Hengyi Cao、Yanjia Fang、Taijie Jin、Ying Li、Chunli Lou、Jingwu Kang、Wanguo Wei、Jidong Zhu

  DOI：10.1021/acs.jmedchem.8b01996

  日期：2019.3.28

  Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC2S (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10 Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.
• PROCESS FOR PRODUCING BIARYL COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1473286B1

  公开（公告）日：2009-11-04
• US7554000B2
  申请人：——

  公开号：US7554000B2

  公开（公告）日：2009-06-30
• US8242278B2
  申请人：——

  公开号：US8242278B2

  公开（公告）日：2012-08-14