2-(4-Fluoro-benzenesulfonylamino)-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid methyl ester | 900492-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-Fluoro-benzenesulfonylamino)-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid methyl ester
• CAS: 900492-92-4
• 化学式: C₁₈H₁₈FNO₄S
• 分子量: 363.41
• InChiKey: BZADGRBVFLTSQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4-Fluoro-benzenesulfonylamino)-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 生成 2-{[(4-fluorophenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid
  参考文献：
  名称：

  Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

  摘要：

  We have screened molecules for inhibition of MetAP2 as a novel approach toward antiangiogenesis and anticancer therapy using affinity selection/mass spectrometry (ASMS) employing MetAP2 loaded with Mn(2+) as the active site metal. After a series of anthranilic acid sulfonamides with micromolar affinities was identified, chemistry efforts were initiated. The micromolar hits were quickly improved to potent nanomolar inhibitors by chemical modifications guided by insights from X-ray crystallography.

  DOI：

  10.1016/j.bmcl.2006.03.085
• 作为产物：
  描述：

  2-羟基-5,6,7,8-四氢化萘-1-羧酸甲酯 在 吡啶 、 盐酸 、 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 2-(4-Fluoro-benzenesulfonylamino)-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

  摘要：

  We have screened molecules for inhibition of MetAP2 as a novel approach toward antiangiogenesis and anticancer therapy using affinity selection/mass spectrometry (ASMS) employing MetAP2 loaded with Mn(2+) as the active site metal. After a series of anthranilic acid sulfonamides with micromolar affinities was identified, chemistry efforts were initiated. The micromolar hits were quickly improved to potent nanomolar inhibitors by chemical modifications guided by insights from X-ray crystallography.

  DOI：

  10.1016/j.bmcl.2006.03.085