N¹-hydroxy-N⁵-phenethylglutaramide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N¹-hydroxy-N⁵-phenethylglutaramide
• 英文别名: N'-hydroxy-N-(2-phenylethyl)pentanediamide
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: MNMBNWINDLRVJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 4-(phenethylcarbamoyl)butanoate 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以90%的产率得到N¹-hydroxy-N⁵-phenethylglutaramide
  参考文献：
  名称：

  [EN] SANTACRUZAMATE A COMPOSITIONS AND ANALOGS AND METHODS OF USE
  [FR] COMPOSITIONS DE SANTACRUZAMATE A ET ANALOGUES ET PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2014018913A3

文献信息

• Santacruzamate A, a Potent and Selective Histone Deacetylase Inhibitor from the Panamanian Marine Cyanobacterium cf. <i>Symploca</i> sp.
  作者：Christopher M. Pavlik、Christina Y. B. Wong、Sophia Ononye、Dioxelis D. Lopez、Niclas Engene、Kerry L. McPhail、William H. Gerwick、Marcy J. Balunas

  DOI：10.1021/np400198r

  日期：2013.11.22

  A dark brown tuft-forming cyanobacterium, morphologically resembling the genus Symploca, was collected during an expedition to the Coiba National Park, a UNESCO World Heritage Site on the Pacific coast of Panama. Phylogenetic analysis of its 16S rRNA gene sequence indicated that it is 4.5% divergent from the type strain for Symploca and thus is likely a new genus. Fractionation of the crude extract led to the isolation of a new cytotoxin, designated santacruzamate A (1), which has several structural features in common with suberoylanilide hydroxamic acid [(2), SAHA, trade name Vorinostat], a clinically approved histone deacetylase (HDAC) inhibitor used to treat refractory cutaneous T-cell lymphoma. Recognition of the structural similarly of 1 and SAHA led to the characterization of santacruzamate A as a picomolar level selective inhibitor of HDAC2, a Class I HDAC, with relatively little inhibition of HDAC4 or HDAC6, both Class II HDACs. As a result, chemical syntheses of santacruzamate A as well as a structurally intriguing hybrid molecule, which blends aspects of both agents (1 and 2), were achieved and evaluated for their HDAC activity and specificity.
• [EN] SANTACRUZAMATE A COMPOSITIONS AND ANALOGS AND METHODS OF USE<br/>[FR] COMPOSITIONS DE SANTACRUZAMATE A ET ANALOGUES ET PROCÉDÉS D'UTILISATION
  申请人：UNIV CONNECTICUT

  公开号：WO2014018913A3

  公开（公告）日：2014-07-03