4-amino-5-benzoyl-2-(4-morpholinyl)-1,3-thiazole | 72100-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-5-benzoyl-2-(4-morpholinyl)-1,3-thiazole
• 英文别名: 4-amino-5-benzoyl-2-(4-morpholinyl)-thiazole；4-Amino-5-benzoyl-2-morpholinothiazole；(4-Amino-2-morpholin-4-yl-thiazol-5-yl)-phenyl-methanone；(4-amino-2-morpholin-4-yl-1,3-thiazol-5-yl)-phenylmethanone
• CAS: 72100-53-9
• 化学式: C₁₄H₁₅N₃O₂S
• 分子量: 289.358
• InChiKey: PUQLLJCSQZTIAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-5-benzoyl-2-(4-morpholinyl)-1,3-thiazole 在 亚硝酸特丁酯 、 copper dichloride 作用下， 以 乙腈 为溶剂， 以61%的产率得到(4-chloro-2-morpholino-1,3-thiazol-5-yl)(phenyl)methanone
  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
• 作为产物：
  描述：

  氰胺 、 2-Morpholinyl-5-phenyl-1,3-oxathiolium 在 sodium hydroxide 作用下， 以88%的产率得到4-amino-5-benzoyl-2-(4-morpholinyl)-1,3-thiazole
  参考文献：
  名称：

  Heterocyclic cation systems. 14. Synthesis of thieno[3,2-e][1,4]diazepine, thiazolo[4,5-e][1,4]diazepine, and s-triazolo[3,4-c]thiazolo[4,5-e][1,4]diazepine derivatives

  摘要：

  DOI：

  10.1021/jo01290a010

文献信息

• One-pot synthesis of new 2,4,5-trisubstituted 1,3-thiazoles and 1,3-selenazoles
  作者：David Thomae、Enrico Perspicace、Zhanjie Xu、Dorothée Henryon、Serge Schneider、Stéphanie Hesse、Gilbert Kirsch、Pierre Seck

  DOI：10.1016/j.tet.2009.01.104

  日期：2009.4

  In this work, we describe the synthesis of new 2,4,5-trisubstituted-1,3-thiazoles and 1,3-selenazole achieved by an easy one-pot four-step procedure. Expected compounds were obtained in good yield from dimethyl cyanodithioimidocarbonate, which was the common starting material for the preparation of all 1,3-thiazoles and 1,3-selenazoles. Chemical diversity was introduced on thiazole and selenazole rings

  在这项工作中，我们描述了通过简单的一锅四步法实现的新2,4,5-三取代-1,3-噻唑和1,3-硒唑的合成。从氰基二硫代亚氨基碳酸二甲酯中可以以高收率获得预期的化合物，后者是制备所有1,3-噻唑和1,3-硒唑的常用原料。通过改变所用的胺和活化的卤化物，在噻唑和硒唑环上引入了化学多样性。
• Heterocondensed thiophenes and thiazoles by THORPE-ZIEGLER cyclization
  作者：Margit Gruner、Gesine Böttcher、Karl Gewald

  DOI：10.1002/jhet.5570450419

  日期：2008.7

  The syntheses of novel thieno-pyridones, thiazolo-pyridones, thiazolo-pyridines and amino- and diamino-dieno-pyridines were described. Simultaneously, it was demonstrated that in these compounds and in the related 3-aminothiophenes the replacement of the methylthio by the morpholino group is possible. The structures were characterized using 1H-, 13C-NMR, IR and elemental analysis.

  描述了新颖的噻吩并吡啶酮，噻唑并吡啶酮，噻唑并吡啶以及氨基和二氨基二酮基吡啶的合成。同时证明，在这些化合物和相关的3-氨基噻吩中，可以用吗啉代基团代替甲硫基。使用1 H-，13 C-NMR，IR和元素分析对结构进行表征。
• Traceless Solid-Phase Synthesis of 2,4,5-Trisubstituted Thiazoles
  作者：Ill Young Lee、Young-Dae Gong、Jin Young Lee、Hye Jin Lee

  DOI：10.1055/s-2005-872687

  日期：——

  The solid-phase synthesis of trisubstituted thiazoles is described. The synthetic strategy involves the formation of a polymer-bound thiazole by reacting resin-bound cyanodithioimidocarbonic acid and α-bromoketone. The resin-bound thiazole was reacted with acyl chlorides or isocyanates. After oxidation-activation of a thioether linker to a sulfone linker, traceless cleavage was achieved with nucleophiles

  描述了三取代噻唑的固相合成。合成策略涉及通过树脂结合的氰基二硫亚氨基碳酸和α-溴酮反应形成聚合物结合的噻唑。树脂结合的噻唑与酰氯或异氰酸酯反应。硫醚接头氧化活化为砜接头后，用亲核试剂实现无痕切割，得到三取代的噻唑。
• HIRARI K.; SUGIMOTO H.; ISHIBA T., J. ORG. CHEM., 1980, 45, NO 2, 253-260
  作者：HIRARI K.、 SUGIMOTO H.、 ISHIBA T.

  DOI：——

  日期：——
• Heterocyclic cation systems. 14. Synthesis of thieno[3,2-e][1,4]diazepine, thiazolo[4,5-e][1,4]diazepine, and s-triazolo[3,4-c]thiazolo[4,5-e][1,4]diazepine derivatives
  作者：Kentaro Hirai、Hirohiko Sugimoto、Teruyuki Ishiba

  DOI：10.1021/jo01290a010

  日期：1980.1