1-[4-氨基-2-(甲基磺酰基)-1,3-噻唑-5-基]乙酮 | 39736-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-[4-氨基-2-(甲基磺酰基)-1,3-噻唑-5-基]乙酮
• 中文别名: 1-[4-氨基-2-(甲基磺胺)-1,3-噻唑-5-YL]乙酮
• 英文名称: 4-amino-2-methylthio-5-thiazolyl methyl ketone
• 英文别名: 4-amino-5-acetyl-2-(methylthio)thiazole；4-amino-5-acetyl-2-methylthio-thiazole；1-(4-amino-2-methylsulfanyl-thiazol-5-yl)-ethanone；1-[4-amino-2-(methylsulfanyl)-1,3-thiazol-5-yl]ethanone；1-(4-amino-2-methylsulfanyl-1,3-thiazol-5-yl)ethanone
• CAS: 39736-26-0
• 化学式: C₆H₈N₂OS₂
• mdl: MFCD00266087
• 分子量: 188.274
• InChiKey: UGESPDZKMNQVRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  1-[4-氨基-2-(甲基磺酰基)-1,3-噻唑-5-基]乙酮 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 (7-methyl-2-methylthiothiazolo[4,5-d]pyrimidin-5-ylsulfanyl)acetic acid ethyl ester
  参考文献：
  名称：

  New Syntheses of 2-Alkylthio-4-oxo-3,4-dihydroquinazolines, 2 - Alkylthio - quinazolines, as well as Their Hetero Analogues

  摘要：

  N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-yl-sulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-di-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with. amines.

  DOI：

  10.3987/com-00-8954
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 反应 1.0h， 生成 1-[4-氨基-2-(甲基磺酰基)-1,3-噻唑-5-基]乙酮
  参考文献：
  名称：

  4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.01.046

文献信息

• SUBSTITUTED IMIDAZOPYRIMIDINES AND TRIAZOLOPYRIMIDINES
  申请人：Siegel Stephan

  公开号：US20100113441A1

  公开（公告）日：2010-05-06

  The invention relates to substituted imidazopyrimidines and triazolopyrimidines, to methods for the production thereof, and to the use of same for producing medicaments for the treatment and/or prophylaxis of diseases, especially haematological diseases, preferably leucopenia and neutropenia.

  本发明涉及取代的咪唑[嘧啶]和三唑[嘧啶]，及其生产方法，以及用于生产用于治疗和/或预防疾病，特别是血液病，尤其是白血球减少症和粒细胞减少症的药物的应用。
• [EN] ANTI-INFECTIVE COMPOUNDS<br/>[FR] COMPOSÉS ANTI-INFECTIEUX
  申请人：PASTEUR INSTITUT KOREA

  公开号：WO2015193506A1

  公开（公告）日：2015-12-23

  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.

  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。
• Beiträge zum reaktionsverhalten von derivaten der imidodithiokohlensäure—I
  作者：W. Walek、M. Pallas、M. Augustin

  DOI：10.1016/s0040-4020(01)93783-4

  日期：1976.1

  The reaction of potassium-alkyl-cyanoimidodithiocarbonate 1 with α-CH-acid halo compounds to 4-aminothiazoles 3, with monochloramine to 3-amino-1,2,4-thiadiazoles 5, and with α-halocarboxylic acid anilides to 4-thiazolidinones derivatives 12 is described. Characteristics of mass- and IR-spectra of the synthesized compounds are discussed.

  烷基烷基氰基氨基二硫代碳酸钾1与α-CH-酸卤代化合物反应成4-氨基噻唑3，一氯胺反应生成3-氨基-1,2,4-噻二唑5，与α-卤代羧酸酐反应成4-噻唑烷酮描述了导数12。讨论了合成化合物的质谱和红外光谱特征。
• NBS-mediated sequential one-pot synthesis of multifunctionalized thiazoles and thiophenes from 1,3-dicarbonyl compounds and mercaptonitrile salts
  作者：Laichun Luo、Lanlan Meng、Qi Sun、Zemei Ge、Runtao Li

  DOI：10.1016/j.tetlet.2013.11.014

  日期：2014.1

  A NBS-mediated sequential one-pot synthesis of multifunctionalized thiazoles and thiophenes from 1,3-dicarbonyl compounds and mercaptonitrile salts has been developed under mild conditions. This transformation involves sequential bromination/SN2 alkylation/Thorpe–Ziegler cyclization/regio-selective elimination of a –COR group, affording the desired products in moderate to good yields. The sequence

  由NBS介导的从1,3-二羰基化合物和硫醇腈盐开始的多官能噻唑和噻吩的顺序一锅法合成已经在温和的条件下进行。该转化涉及顺序溴化/ S N 2烷基化/索普-齐格勒环化/ -COR基团的区域选择性消除，以中等至良好的收率提供所需的产物。确定了-COR基团离去反应的顺序，并提出了可能的机制。
• IMIDAZO-, PYRAZOLOPYRAZINES AND IMIDAZOTRIAZINES AND THEIR USE
  申请人：Siegel Stephan

  公开号：US20110053929A1

  公开（公告）日：2011-03-03

  The invention relates to substituted imidazo-, pyrazolopyrazines and imidazotriazines and processes for their preparation, and their use for the manufacture of medicaments for the treatment and/or prophylaxis of diseases, in particular of hematological disorders, preferably of leukopenias and neutropenias.

  该发明涉及取代咪唑-、吡唑基咪唑啉和咪唑三嗪，以及其制备方法，以及它们用于制造用于治疗和/或预防疾病的药物，特别是血液疾病，最好是白细胞减少症和中性粒细胞减少症。