5-甲氧基-2(3H)-苯并噻唑酮腙 | 80945-74-0

• 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: 5-甲氧基-2(3H)-苯并噻唑酮腙
• 英文名称: 2-hydrazinyl-5-methoxybenzo[d]thiazole
• 英文别名: 2-hydrazino-5-methoxy-benzothiazole；2-Hydrazino-5-methoxy-benzothiazol；2-Hydrazino-5-methoxy-1,3-benzothiazole；(5-methoxy-1,3-benzothiazol-2-yl)hydrazine
• CAS: 80945-74-0
• 化学式: C₈H₉N₃OS
• mdl: MFCD06809778
• 分子量: 195.245
• InChiKey: QIVKJRKJMPQOCD-UHFFFAOYSA-N

物化性质

• 沸点：
  383.7±44.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-甲氧基-2(3H)-苯并噻唑酮腙 在 sulfur 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 6.0h， 生成 1H-Benzoimidazole-2-carboxylic acid N'-(5-methoxy-benzothiazol-2-yl)-hydrazide
  参考文献：
  名称：

  Sharma, Pratibha; Mandloi, Anupam; Pritmani, Shreeya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 11, p. 1289 - 1294

  摘要：

  DOI：
• 作为产物：
  描述：

  2-巯基-5-甲氧基苯并噻唑 在 potassium permanganate 、 potassium carbonate 、 一水合肼 作用下， 生成 5-甲氧基-2(3H)-苯并噻唑酮腙
  参考文献：
  名称：

  具有抗分枝杆菌活性的 N1-杂芳基取代的吡啶-和吡嗪甲脒腙

  摘要：

  制备了一系列脒腙并通过 1 H NMR 和质谱进行表征。这些物质针对结核分枝杆菌、鸟分枝杆菌、胞内分枝杆菌和鲁弗分枝杆菌进行了测试。化合物11-13表现出令人满意的分枝杆菌抑制作用。

  DOI：

  10.1002/ardp.19973300603

文献信息

• [1,2,4]Triazolo[3,4-<i>b</i>]benzothiazole Scaffold as Versatile Nicotinamide Mimic Allowing Nanomolar Inhibition of Different PARP Enzymes
  作者：Sudarshan Murthy、Maria Giulia Nizi、Mirko M. Maksimainen、Serena Massari、Juho Alaviuhkola、Barbara E. Lippok、Chiara Vagaggini、Sven T. Sowa、Albert Galera-Prat、Yashwanth Ashok、Harikanth Venkannagari、Renata Prunskaite-Hyyryläinen、Elena Dreassi、Bernhard Lüscher、Patricia Korn、Oriana Tabarrini、Lari Lehtiö

  DOI：10.1021/acs.jmedchem.2c01460

  日期：2023.1.26

  nicotinamide in the binding pocket of human poly- and mono-ADP-ribosylating enzymes. The binding mode was studied through analogues and cocrystal structures with TNKS2, PARP2, PARP14, and PARP15. Based on the substitution pattern, we were able to identify 3-amino derivatives 21 (OUL243) and 27 (OUL232) as inhibitors of mono-ARTs PARP7, PARP10, PARP11, PARP12, PARP14, and PARP15 at nM potencies, with 27 being

  我们将 [1,2,4] 三唑并 [3,4- b ] 苯并噻唑 (TBT) 报告为一种新的抑制剂支架，它与烟酰胺在人类聚-和单-ADP-核糖基化酶的结合口袋中竞争。通过 TNKS2、PARP2、PARP14 和 PARP15 的类似物和共晶结构研究了结合模式。基于取代模式，我们能够将 3-氨基衍生物21 (OUL243) 和27 (OUL232) 鉴定为 nM 效价的单 ART PARP7、PARP10、PARP11、PARP12、PARP14 和 PARP15 抑制剂，其中27是迄今为止描述的最有效的 PARP10 抑制剂（IC 50为 7.8 nM）和第一个报道的 PARP12 抑制剂。相反，羟基衍生物16(OUL245) 抑制对 PARP2 具有选择性的多 ART。支架不具有固有的细胞毒性，抑制剂可以进入细胞并与靶蛋白结合。这与有利的 ADME 特性一起，证明了 TBT 支架在未来针对
• 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.
• Wel'tman, Ukrainskij Khimicheskij Zhurnal, 1958, vol. 24, p. 351
  作者：Wel'tman

  DOI：——

  日期：——
• US4143097A
  申请人：——

  公开号：US4143097A

  公开（公告）日：1979-03-06
• Sharma, Pratibha; Mandloi, Anupam; Pritmani, Shreeya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 11, p. 1289 - 1294
  作者：Sharma, Pratibha、Mandloi, Anupam、Pritmani, Shreeya

  DOI：——

  日期：——