S-(N-4-chlorophenyl-N-hydroxycarbamoyl) ethyl sulfoxide | 227466-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-(N-4-chlorophenyl-N-hydroxycarbamoyl) ethyl sulfoxide
• 英文别名: Formamide, N-(4-chlorophenyl)-1-(ethylsulfinyl)-N-hydroxy-；N-(4-chlorophenyl)-1-ethylsulfinyl-N-hydroxyformamide
• CAS: 227466-30-0
• 化学式: C₉H₁₀ClNO₃S
• 分子量: 247.702
• InChiKey: FYNOLGAAOWMZOK-UHFFFAOYSA-N

物化性质

• 沸点：
  442.8±47.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-(N-4-chlorophenyl-N-hydroxycarbamoyl) ethyl sulfoxide 在 巯基乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以86%的产率得到S-(N-4-chlorophenyl-N-hydroxycarbamoyl) thioethylamine
  参考文献：
  名称：

  [EN] MACROMOLECULAR GSH-ACTIVATED GLYOXYLASE I INHIBITORS
  [FR] INHIBITEURS DE GLYOXYLASE I MACROMOLECULAIRES ACTIVES PAR LE GLUTATHION (GSH)

  摘要：

  公开号：

  WO2005115338A3
• 作为产物：
  描述：

  4-氯苯基羟胺 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 S-(N-4-chlorophenyl-N-hydroxycarbamoyl) ethyl sulfoxide
  参考文献：
  名称：

  A New Method for Rapidly Generating Inhibitors of Glyoxalase I inside Tumor Cells Using S-(N-Aryl-N-hydroxycarbamoyl)ethylsulfoxides

  摘要：

  The enediol analogue S-(N-p-chlorophenyl-N-hydroxycarbamoyl)glutathione is a powerful mechanism-based competitive inhibitor of the anticancer target enzyme glyoxalase I. Nevertheless, this compound exhibits limited toxicity toward tumor cells in vitro because it does not readily diffuse across cell membranes. We describe an efficient method for indirectly delivering the enzyme inhibitor into murine leukemia L1210 cells via acyl interchange between intracellular glutathione and the cell-permeable prodrug S-(N-p-chlorophenyl-N-hydroxycarbamoyl)ethylsulfoxide. The second-order rate constant for the acyl-interchange reaction in a cell-free system is 1.84 mM(-1) min(-1) (100 mM potassium phosphate buffer, 5% ethanol, pH 7.5, 25 degrees C). Incubation of L1210 cells with the sulfoxide in vitro results in a rapid increase in the intracellular concentration of the glyoxalase I inhibitor (k(app) = 1.41 +/- 0.03 min(-1) (37 degrees C)) and inhibition of cell growth (GI(50) = 0.5 +/- 0.1 mu M). This represents an improvement in both efficiency and potency over the dialkyl ester prodrug strategy in which the inhibitor is indirectly delivered into tumor cells as the [glycyl,glutamyl] diethyl or dicyclopentyl esters. The fact that pi-glutathione transferase catalyzes the acyl-interchange reaction between GSH and the sulfoxide suggests that the sulfoxide, or related compounds, might exhibit greater selective toxicity toward tumor cells that overexpress the transferase.

  DOI：

  10.1021/jm980712o

文献信息

• COMPETITIVE INHIBITORS OF GLYOXALASE I AND METHOD OF GENERATING SUCH COMPETITIVE INHIBITORS INSIDE TUMOR CELLS
  申请人：University of Maryland at Baltimore County

  公开号：EP1051396A1

  公开（公告）日：2000-11-15
• EP1051396A4
  申请人：——

  公开号：EP1051396A4

  公开（公告）日：2005-01-19
• US5969174A
  申请人：——

  公开号：US5969174A

  公开（公告）日：1999-10-19
• [EN] COMPETITIVE INHIBITORS OF GLYOXALASE I AND METHOD OF GENERATING SUCH COMPETITIVE INHIBITORS INSIDE TUMOR CELLS<br/>[FR] INHIBITEURS COMPETITIFS DE GLYOXALASE I ET METHODES DE GENERATION DE CES INHIBITEURS COMPETITIFS DANS DES CELLULES TUMORALES
  申请人：UNIVERSITY OF MARYLAND AT BALTIMORE COUNTY

  公开号：WO1999035128A1

  公开（公告）日：1999-07-15

  (EN) The present invention provides a compound having structure (I) wherein S* is S=O or O=S=O; and wherein R1 is selected from the group consisting of (C1-C9) alkyl, (C3-C8) cycloalkyl, (C5-C7) cycloalkenyl, and (C6-C20) aryl substituted with halogen or (C1-C18) alkyl; and wherein R2 is selected from the group consisting of alkyl, (C1-C9) alkyl, (C3-C8) cycloalkyl, (C5-C7) cycloalkenyl, and (C6-C20) aryl substituted with hologen or (C1-C18) alkyl. Also provided are various methods of using the compositions of the present invention.(FR) La présente invention concerne un composé présentant la structure (I) dans laquelle S* désigne S=O ou O=S=O; dans laquelle R1 est sélectionné dans le groupe formé par un alkyle en (C1-C9), un cycloalkyle en (C3-C8), un cycloalcényle en (C5-C7) et un aryle en (C6-C20) substitué par un halogène ou un alkyle en (C1-C18); et dans laquelle R2 est sélectionné dans le groupe formé par un alkyle, un alkyle en (C1-C9), un cycloalkyle en (C3-C8), un cycloalcényle en (C5-C7) et un aryle en (C6-C20) substitué par un halogène ou un alkyle en (C1-C18). L'invention concerne également plusieurs méthodes d'utilisation des compositions de la présente invention.
• [EN] MACROMOLECULAR GSH-ACTIVATED GLYOXYLASE I INHIBITORS<br/>[FR] INHIBITEURS DE GLYOXYLASE I MACROMOLECULAIRES ACTIVES PAR LE GLUTATHION (GSH)
  申请人：UNIV MARYLAND

  公开号：WO2005115338A3

  公开（公告）日：2006-02-16