1-(4-bromo-2-(methylsulfanyl)-1,3-thiazol-5-yl)ethanone | 1443014-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-bromo-2-(methylsulfanyl)-1,3-thiazol-5-yl)ethanone
• 英文别名: 1-(4-bromo-2-(methylthio)thiazol-5-yl)ethan-1-one；1-(4-Bromo-2-methylsulfanyl-1,3-thiazol-5-yl)ethanone
• CAS: 1443014-85-4
• 化学式: C₆H₆BrNOS₂
• 分子量: 252.156
• InChiKey: KQZDOKYHKXZAIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-bromo-2-(methylsulfanyl)-1,3-thiazol-5-yl)ethanone 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 生成 Ethyl 6-methyl-2-morpholin-4-ylthieno[2,3-d][1,3]thiazole-5-carboxylate
  参考文献：
  名称：

  [EN] ANTI-INFECTIVE COMPOUNDS
  [FR] COMPOSÉS ANTI-INFECTIEUX

  摘要：

  本发明涉及具有通式（I）的小分子化合物，其中A是从式（A）到（K）组成的基团之一，并且其在治疗细菌感染，特别是结核病中的用途。

  公开号：

  WO2015193506A1
• 作为产物：
  描述：

  1-[4-氨基-2-(甲基磺酰基)-1,3-噻唑-5-基]乙酮 在 亚硝酸特丁酯 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 1-(4-bromo-2-(methylsulfanyl)-1,3-thiazol-5-yl)ethanone
  参考文献：
  名称：

  [EN] ANTI-INFECTIVE COMPOUNDS
  [FR] COMPOSÉS ANTI-INFECTIEUX

  摘要：

  本发明涉及具有通式（I）的小分子化合物，其中A是从式（A）到（K）组成的基团之一，并且其在治疗细菌感染，特别是结核病中的用途。

  公开号：

  WO2015193506A1

文献信息

• Copper‐Assisted Synthesis of Novel Pyrazolo[3,4‐ <i>d</i> ]thiazoles
  作者：Nicu‐Cosmin Ostache、Marie‐Aude Hiebel、Adriana‐Luminiţa Fînaru、Gérald Guillaumet、Franck Suzenet

  DOI：10.1002/cctc.201900707

  日期：2019.8.7

  new pyrazolo[3,4‐d]thiazoles for the development of molecules with a high therapeutic potential. The effective and appropriate strategy chosen consists of an intramolecular copper‐catalysed N‐arylation followed by the Liebeskind‐Srogl cross‐coupling reaction. The efficiency of copper and palladium catalysts for the first step of the synthesis was evaluated. These efforts allowed the synthesis of a

  基于吡唑和噻唑骨架的化学和生物学重要性，我们在此报告了一种新型吡唑并[3,4- d ]噻唑的便捷设计，可用于开发具有高治疗潜力的分子。选择的有效和适当的策略包括分子内铜催化的N-芳基化，然后进行Liebeskind-Srogl交叉偶联反应。评价了合成第一步中铜和钯催化剂的效率。这些努力允许合成多种调节的杂环。
• 4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells
  作者：Florence Lefranc、Zhanjie Xu、Patricia Burth、Véronique Mathieu、Germain Revelant、Mauro Velho de Castro Faria、Caroline Noyon、Diogo Gomes Garcia、Damien Dufour、Céline Bruyère、Cassiano Felippe Gonçalves-de-Albuquerque、Pierre Van Antwerpen、Bernard Rogister、Stéphanie Hesse、Gilbert Kirsch、Robert Kiss

  DOI：10.1016/j.ejmech.2013.01.046

  日期：2013.5

  The in vitro growth inhibitory activity of 26 thiazoles (including 4-halogeno-2,5-disubtituted-1,3-thiazoles) and 5 thienothiazoles was assessed on a panel of 6 human cancer cell lines, including glioma cell lines. (4-Chloro-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12a) and (4-bromo-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12b) displayed similar to 10 times greater in vitro growth inhibitory activity than perillyl alcohol (POH), which therapeutically benefits glioma patients through the inhibition of both alpha-1 Na+/K+-ATPase (NAK) and Ras oncogene activity. The in vitro cytostatic activities (as revealed by quantitative videomicroscopy) displayed by 12a and 12b were independent of the intrinsic resistance to pro-apoptotic stimuli associated with cancer cells. Compounds 12a and 12b displayed relatively similar inhibitory activities on purified guinea pig brain preparations that mainly express NAK alpha-2 and alpha-3 subunits, whereas only compound 12b was efficacious against purified guinea pig kidney preparations that mainly express the NAK alpha-1 subunit, which is also expressed in gliomas, melanomas and non-small-cell lung cancers NSCLCs. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Anti-Infective Compounds
  申请人：Institut Pasteur Korea

  公开号：US20170121349A1

  公开（公告）日：2017-05-04

  The present invention relates to small molecule compounds having the general formula (I): wherein A is a moiety selected from the group consisting of formulae (A) to (K) and their use in the treatment of bacterial infections, in particular Tuberculosis.