5-羟基-1,3-苯并噻唑-2(3H)-硫酮 | 89677-89-4

• 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-羟基-1,3-苯并噻唑-2(3H)-硫酮
• 英文名称: 2-mercaptobenzo[d]thiazol-5-ol
• 英文别名: 5-OH-MBT；5-Hydroxybenzo[d]thiazole-2(3H)-thione；5-hydroxy-3H-1,3-benzothiazole-2-thione
• CAS: 89677-89-4
• 化学式: C₇H₅NOS₂
• 分子量: 183.255
• InChiKey: PYFGEWYBIKHXIY-UHFFFAOYSA-N

物化性质

• 沸点：
  383.8±44.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

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

反应信息

• 作为反应物：
  描述：

  5-羟基-1,3-苯并噻唑-2(3H)-硫酮 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 14.0h， 生成 2-[2-[2-[2-[(2-Methylsulfonyl-1,3-benzothiazol-5-yl)oxy]ethoxy]ethoxy]ethoxy]ethanamine
  参考文献：
  名称：

  使用 Julia-Kocieński 样试剂快速、稳定、化学选择性标记硫醇：一种血清稳定的马来酰亚胺基蛋白质缀合替代品

  摘要：

  已发现在各种缓冲条件下甲基磺酰基苯基恶二唑化合物对半胱氨酸具有精确的化学选择性。此外，所得到的蛋白质偶联物比人血浆中的半胱氨酸-马来酰亚胺偶联物（HSA=人血清白蛋白，MBP-C-HA=麦芽糖结合蛋白）具有更好的稳定性。这种新的硫醇点击反应为生成稳定的蛋白质偶联物和聚乙二醇化蛋白质提供了一种新方法。

  DOI：

  10.1002/anie.201306241
• 作为产物：
  描述：

  2-巯基-5-甲氧基苯并噻唑 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以63%的产率得到5-羟基-1,3-苯并噻唑-2(3H)-硫酮
  参考文献：
  名称：

  使用 Julia-Kocieński 样试剂快速、稳定、化学选择性标记硫醇：一种血清稳定的马来酰亚胺基蛋白质缀合替代品

  摘要：

  已发现在各种缓冲条件下甲基磺酰基苯基恶二唑化合物对半胱氨酸具有精确的化学选择性。此外，所得到的蛋白质偶联物比人血浆中的半胱氨酸-马来酰亚胺偶联物（HSA=人血清白蛋白，MBP-C-HA=麦芽糖结合蛋白）具有更好的稳定性。这种新的硫醇点击反应为生成稳定的蛋白质偶联物和聚乙二醇化蛋白质提供了一种新方法。

  DOI：

  10.1002/anie.201306241

文献信息

• CSF-1R, Inhibitors, Compositions, and Methods of Use
  申请人：Sutton James

  公开号：US20100261679A1

  公开（公告）日：2010-10-14

  Disclosed herein are compounds and their oxides, esters, prodrugs, solvates, and pharmaceutically acceptable salts thereof, 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. 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.

  本文公开了化合物及其氧化物、酯、前药、溶剂化物和其药学上可接受的盐，以及化合物的组合物，可以单独使用或与至少一种其他治疗剂合用，并与药学上可接受的载体一起使用，以及化合物的用途，可以单独使用或与至少一种其他治疗剂合用。这些实施例可用于抑制细胞增殖，抑制肿瘤的生长和/或代谢，治疗或预防癌症，治疗或预防类风湿性关节炎等骨骼退化性疾病，并/或抑制分子如CSF-1R。
• α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation
  作者：Daniel J. St-Cyr、Andrew G. Jamieson、William D. Lubell

  DOI：10.1021/ol1000582

  日期：2010.4.16

  alpha-Amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.
• Homogeneous photodegradation study of 2-mercaptobenzothiazole photocatalysed by sodium decatungstate salts: Kinetics and mechanistic pathways
  作者：A. Allaoui、M.A. Malouki、P. Wong-Wah-Chung

  DOI：10.1016/j.jphotochem.2010.04.010

  日期：2010.5

  The photochemical degradation of a benzothiazole derivative, 2-mercaptobenzothiazole (MBT) has been studied in aqueous solution in the presence of a polyoxometalate (POM): sodium decatungstate salts Na4W10O32 (DTA). In aerated conditions, the photodegradation rate of MBT clearly increased in the presence of DTA by a factor six when compared with the direct photolysis with k(MBT) = 0.25 h(-1) and t(1/2)(MBT)= 2.8 h. For the total comprehension of the degradation mechanism, the oxygen influence has been investigated. Oxygen appeared essential for DTA regeneration, its absence induced a three times inhibition of MBT disappearance and completely stopped the photocatalytic cycle. The main photoproducts were identified with LC-ESI-MS and LC-DAD techniques and using some calculations obtained by B3LYP/6-21G method in Gaussian 4.1 software. All the results allowed to propose a mechanistic pathway. Electron transfer and H atom abstraction processes involving W10O324-center dot excited state species were involved in the degradation. In the primary step of the degradation, the hydroxylation of the aromatic ring leading to four OH-MBT isomers and the formation of disulfide form of MBT were observed. For longer irradiation time, a secondary electron transfer permitted the oxidation of OH-MBT isomers and the formation of sulfoxide derivatives. For prolonged exposure (around 100 h), the complete mineralization was noticed in the presence of sodium decatungstate salts. (C) 2010 Elsevier B.V. All rights reserved.
• CSF-1R INHIBITORS FOR TREATMENT OF CANCER AND BONE DISEASES
  申请人：Novartis AG

  公开号：EP2211862A2

  公开（公告）日：2010-08-04
• [EN] CSF-1R INHIBITORS, COMPOSITIONS, AND METHODS OF USE<br/>[FR] INHIBITEURS CSF-1R, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：NOVARTIS AG

  公开号：WO2009050228A2

  公开（公告）日：2009-04-23

  Disclosed herein are compounds and their oxides, esters, prodrugs, solvates, and pharmaceutically acceptable salts thereof, 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. 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.