4,5,6,7-四氢-1,3-苯并噻唑-2-硫醇 | 42937-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4,5,6,7-四氢-1,3-苯并噻唑-2-硫醇
• 英文名称: 4,5,6,7-tetrahydrobenzo[d]thiazole-2-thiol
• 英文别名: 4,5,6,7-tetrahydro-3H-benzothiazole-2-thione；2-mercapto-4,5,6,7-tetrahydrobenzothiazole；2-Mercapto-4,5-dihydro-4H-cyclopenta-thiazol；4,5,6,7-Tetrahydro-1,3-benzothiazole-2-thiol；4,5,6,7-tetrahydro-3H-1,3-benzothiazole-2-thione
• CAS: 42937-91-7
• 化学式: C₇H₉NS₂
• 分子量: 171.287
• InChiKey: AIOFFKHESNBMFU-UHFFFAOYSA-N

物化性质

• 熔点：
  176 °C(Solv: benzene (71-43-2))
• 沸点：
  293.7±23.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5,6,7-四氢-1,3-苯并噻唑-2-硫醇 在 ammonium persulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 bis(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)disulfide
  参考文献：
  名称：

  Development of the First Generation of Disulfide-Based Subtype-Selective and Potent Covalent Pyruvate Dehydrogenase Kinase 1 (PDK1) Inhibitors

  摘要：

  Pyruvate dehydrogenase kinases (PDKs) are overexpressed in most cancer cells and are responsible for aberrant glucose metabolism. We previously described bis(4-morpholinyl thiocarbonyl)-disulfide (JX06, 16) as the first covalent inhibitor of PDK1. Here, on the basis of the scaffold of 16, we identify two novel types of disulfide-based PDK1 inhibitors. The most potent analogue, 3a, effectively inhibits PDK1 both at the molecular (k(mact)/K-i = 4.17 x 10(3) M-1 s(-1)) and the cellular level (down to 0.1 mu M). In contrast to 16, 3a is a potent and subtype-selective inhibitor of PDK1 with >40-fold selectivity for PDK2-4. 3a also significantly alters glucose metabolic pathways in A549 cells by decreasing ECAR and increasing ROS. Moreover, in the xenograft models, 3a shows significant antitumor activity with no negative effect to the mice weight. Collectively, these data demonstrate that 3a may be an excellent lead compound for the treatment of cancer as a first-generation subtype-selective and covalent PDK1 inhibitor.

  DOI：

  10.1021/acs.jmedchem.6b01245
• 作为产物：
  描述：

  2-溴环己酮 生成 4,5,6,7-四氢-1,3-苯并噻唑-2-硫醇
  参考文献：
  名称：

  Erlenmeyer; Simon, Helvetica Chimica Acta, 1942, vol. 25, p. 362

  摘要：

  DOI：

文献信息

• .alpha.-Phenyl-2-(aza)benzothiazolylthioglycolic acids and derivatives
  申请人：American Home Products Corporation

  公开号：US04567267A1

  公开（公告）日：1986-01-28

  Novel .alpha.-phenyl-2-(aza)benzothiazolylthioglycolic acids, derivatives thereof and pharmacologically acceptable salts thereof are disclosed, as well as their use as intermediates in the preparation of 2-substituted-3-hydroxy-thiazolo[2,3-b]-benzothiazolium salts, 2-substituted-thiazolo[2,3-b]benzothiazol-3(2H)-one mesoionic didehydro derivatives, 2-substituted-thiazolo[2',3'-2,3]thiazolo[5,4-b]pyridin-3(2H)-one mesoionic didehydro derivatives and related compounds, and their use as modulators of the immune response.

  新型α-苯基-2-(氮杂)苯并噻唑硫代乙酸及其衍生物和药理学上可接受的盐被披露，以及它们作为2-取代-3-羟基噻唑并[2,3-b]-苯并噻唑盐、2-取代噻唑并[2,3-b]苯并噻唑-3(2H)-酮中间体的用途，2-取代噻唑并[2',3'-2,3]噻唑并[5,4-b]吡啶-3(2H)-酮中间体和相关化合物，以及它们作为免疫应答调节剂的用途。
• Substituted thiazole sulfonamides as antiglaucoma agents
  申请人：Allergan

  公开号：US05519040A1

  公开（公告）日：1996-05-21

  The present invention provides novel carbonic anhydrase inhibitors represented by the structural formula: ##STR1## wherein

  本发明提供了一种新型的碳酸酐酶抑制剂，其结构式如下：##STR1##
• Discovery of Orally Available Retinoic Acid Receptor-Related Orphan Receptor γ-t/Dihydroorotate Dehydrogenase Dual Inhibitors for the Treatment of Refractory Inflammatory Bowel Disease
  作者：Ji-An Chen、Hui Ma、Zehui Liu、Jinlong Tian、Sisi Lu、Wenqing Fang、Shuyin Ze、Weiqiang Lu、Qiong Xie、Jin Huang、Yonghui Wang

  DOI：10.1021/acs.jmedchem.1c01746

  日期：2022.1.13

  Inflammatory bowel disease (IBD) is a multifactorial autoimmune disease, representing a major clinical challenge. Herein, a strategy of dual-targeting approach employing retinoic acid receptor-related orphan receptor γ-t (RORγt) and dihydroorotate dehydrogenase (DHODH) was proposed for the treatment of IBD. Dual RORγt/DHODH inhibitors are expected not only to reduce RORγt-driven Th17 cell differentiation

  炎症性肠病 (IBD) 是一种多因素自身免疫性疾病，是一项重大的临床挑战。在此，提出了一种采用视黄酸受体相关孤儿受体γ-t（RORγt）和二氢乳清酸脱氢酶（DHODH）的双靶向方法治疗IBD的策略。预计双重 RORγt/DHODH 抑制剂不仅可以减少 RORγt 驱动的 Th17 细胞分化，还可以减轻 T 细胞的扩增和活化，从而增强抗炎作用。从 2-氨基苯并噻唑 hit 1开始，一系列 2-氨基四氢苯并噻唑被发现是有效的双重 RORγt/DHODH 抑制剂。化合物14d以 IC 50脱颖而出RORγt 的值为 0.110 μM，DHODH 的值为 0.297 μM。在可接受的小鼠药代动力学特征下，14d表现出显着的体内抗炎活性，并且剂量依赖性地减轻了葡聚糖硫酸钠 (DSS) 诱导的小鼠急性结肠炎的严重程度。总之，本研究为开发治疗 IBD 的治疗剂提供了一个新的框架。
• Modulating the immune response with 2-substituted-3-hydroxythiazolo[2,3-b]b
  申请人：American Home Products Corporation

  公开号：US04275065A1

  公开（公告）日：1981-06-23

  Novel 2-substituted-3-hydroxythiazolo[2,3-b]benzo-(and azabenzo)thiazolium salts, the mesoionic didehydro derivatives thereof and related compounds are disclosed, as well as the use thereof as modulators of the immune response.

  揭示了小说2-取代-3-羟基噻唑并噻唑[2,3-b]苯并（和吡啶苯并）噻唑盐，以及其二脱氢间离子衍生物和相关化合物，以及其作为免疫应答调节剂的用途。
• Inhibitors of mammalian collagenase
  申请人：American Home Products Corporation

  公开号：US04367233A1

  公开（公告）日：1983-01-04

  A method of inhibiting mammalian collagenase by using .alpha.-phenyl-2-(aza)benzothiazolylthioglycolic acids and derivatives thereof, and the pharmaceutically acceptable salts thereof.

  使用.alpha.-苯基-2-(aza)苯并噻唑基巯基乙酸及其衍生物及其药学上可接受的盐，抑制哺乳动物胶原酶的方法。