(S)-2-trifluoroacetamido-1-(4-methylthiophenyl)-1-propanone | 571200-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-trifluoroacetamido-1-(4-methylthiophenyl)-1-propanone
• 英文别名: N-[(S)-4-(Methylthio)-alpha-methylphenacyl]trifluoroacetamide；2,2,2-trifluoro-N-[(2S)-1-(4-methylsulfanylphenyl)-1-oxopropan-2-yl]acetamide
• CAS: 571200-97-0
• 化学式: C₁₂H₁₂F₃NO₂S
• 分子量: 291.294
• InChiKey: NTNKIKYIBPTBLT-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-trifluoroacetamido-1-(4-methylthiophenyl)-1-propanone 在 盐酸 、 异丙醇 作用下， 反应 12.0h， 以42%的产率得到(S)-2-amino-1-(4-methylthiophenyl)-1-propanone hydrochloride
  参考文献：
  名称：

  A two-step method for the preparation of homochiral cathinones

  摘要：

  A simple method for the preparation of homochiral ring-substituted 1-aryl-2-aminopropanones 2 ('cathinones') is described, involving initial Friedel-Crafts acylation of aromatics with (S)- or (R)-N-trifluoroacetylalanyl chloride, followed by acid hydrolysis of the intermediate trifluoroacetamido intermediates 1. for which X-ray diffraction analysis confirmed the structures. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00317-3
• 作为产物：
  描述：

  N-(trifluoroacetyl)-L-alanine 在 吡啶 、 三氯化铝 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (S)-2-trifluoroacetamido-1-(4-methylthiophenyl)-1-propanone
  参考文献：
  名称：

  A two-step method for the preparation of homochiral cathinones

  摘要：

  A simple method for the preparation of homochiral ring-substituted 1-aryl-2-aminopropanones 2 ('cathinones') is described, involving initial Friedel-Crafts acylation of aromatics with (S)- or (R)-N-trifluoroacetylalanyl chloride, followed by acid hydrolysis of the intermediate trifluoroacetamido intermediates 1. for which X-ray diffraction analysis confirmed the structures. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00317-3

文献信息

• Chemical compounds 572
  申请人：Berger Markus

  公开号：US20080214641A1

  公开（公告）日：2008-09-04

  Compounds of formula (I): The present invention relates to novel indazolyl ester or amide derivatives, to pharmaceutical compositions comprising such derivatives, to processes for preparing such novel derivatives and to the use of such derivatives as medicaments

  化合物公式（I）：本发明涉及新型吲唑酯或酰胺衍生物，涉及包含这些衍生物的制药组合物，涉及制备这些新型衍生物的过程，以及将这些衍生物用作药物的用途。
• Chemical Compounds 572
  申请人：Berger Markus

  公开号：US20100197644A1

  公开（公告）日：2010-08-05

  Compounds of formula (I): The present invention relates to novel indazolyl ester or amide derivatives, to pharmaceutical compositions comprising such derivatives, to processes for preparing such novel derivatives and to the use of such derivatives as medicaments

  式(I)的化合物：本发明涉及新型吲哚酰基或酰胺衍生物，以及包含这些衍生物的制药组合物，制备这些新型衍生物的方法以及将这些衍生物用作药物的用途。
• WO2008/76048
  申请人：——

  公开号：——

  公开（公告）日：——
• Human and rat monoamine oxidase-A are differentially inhibited by (S)-4-alkylthioamphetamine derivatives: Insights from molecular modeling studies
  作者：Angélica Fierro、Mauricio Osorio-Olivares、Bruce K. Cassels、Dale E. Edmondson、Silvia Sepúlveda-Boza、Miguel Reyes-Parada

  DOI：10.1016/j.bmc.2007.05.021

  日期：2007.8

  Four enantiomerically pure (S)-4-alkylthioamphetamine derivatives were evaluated as monoamine oxidase (MAO) inhibitors using the human and rat isoforms of the enzyme. Molecular dockings were performed in order to gain insights regarding the binding mode of these inhibitors. All compounds were potent and selective MAO-A inhibitors although different rank orders of potencies were observed against the enzymes from different species. This behavior can be rationalized on the basis of different binding modes to each enzyme, as determined in silico. These findings further support the concept that MAO inhibitory activity of novel compounds, determined with enzymes from diverse mammalian species, should be considered with caution if human MAO is the final target to be addressed. (c) 2007 Elsevier Ltd. All rights reserved.
• INDAZOLYL AMIDE DERIVATIVES FOR THE TREATMENT OF GLUCOCORTICOID RECEPTOR MEDIATED DISORDERS
  申请人：AstraZeneca AB

  公开号：EP2102169B1

  公开（公告）日：2012-06-20