(S)-2-amino-N-phenyl-4-(trifluoromethylthio)butanamide hydrochloride | 943925-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-amino-N-phenyl-4-(trifluoromethylthio)butanamide hydrochloride
• 英文别名: (2S)-2-amino-N-phenyl-4-(trifluoromethylsulfanyl)butanamide;hydrochloride
• CAS: 943925-89-1
• 化学式: C₁₁H₁₃F₃N₂OS*ClH
• 分子量: 314.759
• InChiKey: KATSXFLTJLLSDH-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-phenyl-4-(trifluoromethylthio)butanamide hydrochloride 在 5,5'-二硫双(2-硝基苯甲酸) 、 recombinant Entamoeba histolytica L-methionine γ-lyase 2 、 磷酸吡哆醛 、 水 作用下， 生成 三氟甲硫醇
  参考文献：
  名称：

  Cytotoxic effect of amide derivatives of trifluoromethionine against the enteric protozoan parasite Entamoeba histolytica

  摘要：

  Amoebiasis, caused by infection with the enteric protist Entamoeba histolytica, is one of the major parasitic diseases. Although metronidazole and its derivatives are currently employed in therapy, the paucity of effective drugs and potential clinical resistance necessitate the development of a novel drug. Trifluoromethionine (TFM) is a promising lead compound for antiamoebic drugs. To potentiate the antiamoebic effect of TFM, we synthesised various amide derivatives of TFM and evaluated their cytotoxicity. The amide derivatives of TFM were observed to have a superior cytotoxic effect compared with TFM and metronidazole against E. histolytica in vitro. Although TFM showed cytotoxicity following degradation by methionine gamma-lyase, the derivatives were degraded by the enzyme less efficiently compared with TFM. We further demonstrated that a representative derivative was hydrolysed by the amoebic cell lysate to first yield TFM, followed by degradation similar to TFM. Hydrolysis was partially inhibited by protease inhibitors. A single subcutaneous or oral administration of TFM and its amide derivatives also effectively prevented the formation of amoebic liver abscess in a rodent model. These data demonstrate the improved effectiveness of TFM derivatives against E. histolytica infection and elucidate the mechanisms underlining the mode of action of these compounds. (C) 2009 Elsevier B.V. and the International Society of Chemotherapy. All rights reserved.

  DOI：

  10.1016/j.ijantimicag.2009.08.016
• 作为产物：
  描述：

  Tert-Butyl (S)-1-(phenylcarbamoyl)-3-(trifluoromethylthio)propylcarbamate 在 苯甲醚 、 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以72%的产率得到(S)-2-amino-N-phenyl-4-(trifluoromethylthio)butanamide hydrochloride
  参考文献：
  名称：

  NOVEL TRIHALOMETHIONINE DERIVATIVE AND PHARMACEUTICAL PRODUCT CONTAINING THE SAME

  摘要：

  公式（I）代表的化合物被用作药物的活性成分，用于治疗或预防由原虫或细菌引起的传染病。X代表卤素，Z代表—(CH2)m—，其中m是1-5的整数，R代表以下之一：(i) 氢代表0-5的整数，R1独立代表氢、卤素、具有1-5个碳原子的烷氧基或具有1-5个碳原子的烷基。R2独立代表氢、卤素、具有1-5个碳原子的烷氧基或具有1-5个碳原子的烷基。(iv) 具有1-5个碳原子的烷基，(v) 具有1-5个碳原子的羟基烷基。

  公开号：

  US20100076224A1