6-羟基-1,3-苯并噻唑-2(3H)-硫酮 | 74537-63-6

• 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: 6-羟基-1,3-苯并噻唑-2(3H)-硫酮
• 英文名称: 6-hydroxy-2-mercapto-benzothiazole
• 英文别名: 6-hydroxyl-2-mercaptobenzothiazole；2-mercaptobenzo[d]thiazol-6-ol；2-mercaptobenzothiazol-6-ol；2-mercapto-6-hydroxybenzothiazole；6-OH-MBT；6-hydroxy-3H-benzothiazole-2-thione；6-hydroxy-3H-1,3-benzothiazole-2-thione
• CAS: 74537-63-6
• 化学式: C₇H₅NOS₂
• 分子量: 183.255
• InChiKey: SZNXHOMOAFJDRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  2-8℃，保持干燥环境。

反应信息

• 作为反应物：
  描述：

  6-羟基-1,3-苯并噻唑-2(3H)-硫酮 以92的产率得到2-甲基磺酰基-苯并噻唑-6-醇
  参考文献：
  名称：

  6-O-Substituted Benzoxazole and Benzothiazole Compounds and Methods of Inhibiting CSF-1R Signaling

  摘要：

  公开了苯并噻唑化合物和苯并噻唑类化合物的立体异构体、互变异构体、溶剂化物、氧化物、酯和前药及其药学上可接受的盐。还公开了这些化合物的组合物，其可以与至少一种额外的治疗剂一起使用，并与药学上可接受的载体结合使用。这些实施例对于抑制细胞增殖、抑制肿瘤的生长和/或代谢、治疗或预防癌症、治疗或预防退化性骨疾病如类风湿性关节炎以及/或抑制CSF-1R等分子具有用途。

  公开号：

  US20120225861A1
• 作为产物：
  描述：

  6-乙氧基-2-巯基苯并噻唑 在 aluminum (III) chloride 作用下， 生成 6-羟基-1,3-苯并噻唑-2(3H)-硫酮
  参考文献：
  名称：

  Benzothiazole derivatives augment glucose uptake in skeletal muscle cells and stimulate insulin secretion from pancreatic β-cells via AMPK activation

  摘要：

  开发独特的双功能AMPK激活剂（促进葡萄糖摄取和胰岛素分泌增强剂），用于潜在的抗糖尿病治疗。

  DOI：

  10.1039/c4cc03310h

文献信息

• 6-O-SUBSTITUTED BENZOXAZOLE AND BENZOTHIAZOLE COMPOUNDS AND METHODS OF INHIBITING CSF-1R SIGNALING
  申请人：Sutton C James

  公开号：US20080045528A1

  公开（公告）日：2008-02-21

  Benzoxazole and benzothiazole compounds and the stereoisomers, tautomers, solvates, oxides, esters, and prodrugs thereof and pharmaceutically acceptable salts thereof are disclosed. Compositions of the compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier, and uses of the compounds, either alone or in combination with at least one additional therapeutic agent are also disclosed. The embodiments are useful for inhibiting cellular proliferation, inhibiting the growth and/or metathesis of tumors, treating or preventing cancer, treating or preventing degenerating bone diseases such as rheumatoid arthritis, and/or inhibiting molecules such as CSF-1R.

  苯并噁唑和苯并噻唑化合物及其立体异构体、互变异构体、溶剂合物、氧化物、酯类和前药以及其药学上可接受的盐已被披露。所述化合物的组合物，无论是单独使用还是与至少一种额外治疗剂组合，并与药学上可接受的载体一起使用的用途也已被披露。这些实施例可用于抑制细胞增殖，抑制肿瘤的生长和/或交换反应，治疗或预防癌症，治疗或预防类风湿性关节炎等退行性骨病，以及/或抑制CSF-1R等分子。
• Substituted benzothiazoles, benzimidazoles, and benzoxazoles
  申请人：The Upjohn Company

  公开号：US04873346A1

  公开（公告）日：1989-10-10

  The present invention provides certain novel substituted benzothiazoles, benzimidazoles and benzoxazoles which are useful as inhibitors of leukotriene biosynthesis and/or as inhibitors of the action of lipoxygenase and/or as inhibitors of mucus secretion in mammalian metabolism. They are thus employed wherever it is medically necessary or desirable to inhibit these systems.

  本发明提供了一些新颖的取代苯并噻唑、苯并咪唑和苯并噁唑化合物，它们可用作白三烯生物合成的抑制剂和/或脂氧化酶活性的抑制剂和/或哺乳动物代谢中粘液分泌的抑制剂。因此，在医学上需要或希望抑制这些系统的地方可以使用它们。
• Benzothiazoles and benzoxazoles, drugs containing them, their use and
  申请人：Dr. Karl Thomae GmbH

  公开号：US05919807A1

  公开（公告）日：1999-07-06

  The invention relates to benzothiazoles and benzoxazoles of general formula ##STR1## wherein R.sup.1 to R.sup.3, X, Z and n are defined as in claim 1, the enantiomers, diastereomers and salts thereof, particularly the physiologically acceptable acid addition salts thereof which have valuable properties, particularly an inhibitory effect on cholesterol biosynthesis, pharmaceutical compositions containing these compounds, the use thereof and processes for preparing them.

  该发明涉及一般式##STR1##中的苯并噻唑和苯并噁唑，其中R.sup.1至R.sup.3、X、Z和n的定义如权利要求书中所述，其对映异构体、顺异构体和盐，特别是其生理上可接受的酸盐，具有有价值的特性，特别是对胆固醇生物合成具有抑制作用，含有这些化合物的制药组合物，其用途和制备方法。
• A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles
  作者：Lei Zhu、Mingbao Zhang、Miao Dai

  DOI：10.1002/jhet.5570420440

  日期：2005.5

  A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles is described. The key feature of the synthesis is an exclusive ortho-selective nucleophilic aromatic substitution reaction of ortho-haloanilines with potassium/sodium O-ethyl dithiocarbonate under mild conditions. Subsequent intra-molecular cycliza-tion affords 2-mercaptobenzothiazoles in high yields. The 2-mercaptobenzothiazoles are readily

  描述了2-巯基和2-氯苯并噻唑的方便合成。合成的关键特征是在温和条件下邻卤代苯胺与钾/ O-乙基二硫代碳酸氢钠的独家邻位选择性亲核芳族取代反应。随后的分子内环化以高收率提供2-巯基苯并噻唑。用硫酰氯处理后，2-巯基苯并噻唑容易转化为相应的2-氯苯并噻唑。
• Purine Analogues as Amplifiers of Phleomycin. V. Thioethers of Several Heterocyclic Systems with One or Two Rings
  作者：DJ Brown、GW Grigg、Y Iwai、KN McAndrew、T Nagamatsu、Rv Heeswyck

  DOI：10.1071/ch9792713

  日期：——

  Thioethers, appropriate for testing as amplifiers of phleomycin against in vitro cultures of Escherichia coli, are prepared via corresponding thiones in the purine, imidazo[4,5-b(and 4,5-c)]pyridine, pyrazolo[3,4-d]pyrimidine, quinazoline, benzothiazole, benzoxazole, pyrimidine, imidazole, thiazoline, 1,2,4-triazole, s-triazolo[4,3-c(and 1,5-c)]pyrimidine, oxazolo[4,5-b]pyridine, quinoline and 1,3,5-triazine series. Structures are confirmed by N.M.R. spectra. Biological activities are tabulated and discussed in terms of structure.

  硫醚，适合 硫代硫醚 体外培养大肠杆菌的扩增剂、 通过嘌呤、咪唑并[4,5-b(和 4,5-c)]吡啶中的相应硫醚制备、 吡唑并[3,4-d]嘧啶、喹唑啉、苯并噻唑、苯并恶唑、嘧啶、 咪唑、噻唑啉、1,2,4-三唑、s-三唑并[4,3-c（和 1,5-c）]嘧啶、 噁唑并[4,5-b]吡啶、喹啉和 1,3,5-三嗪系列。结构 通过 N.M.R.光谱确认。生物活性表 结构进行了讨论。