6-[3-(naphthalene-2-carbonyl)-ureido]-hexanoic acid hydroxyamide | 1044043-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-[3-(naphthalene-2-carbonyl)-ureido]-hexanoic acid hydroxyamide
• 英文别名: N-[[6-(hydroxyamino)-6-oxohexyl]carbamoyl]naphthalene-2-carboxamide
• CAS: 1044043-10-8
• 化学式: C₁₈H₂₁N₃O₄
• 分子量: 343.382
• InChiKey: HPXNIWNVCNUTRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 6-(3-(2-naphthoyl)ureido)hexanoate 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 6-[3-(naphthalene-2-carbonyl)-ureido]-hexanoic acid hydroxyamide
  参考文献：
  名称：

  Acylurea connected straight chain hydroxamates as novel histone deacetylase inhibitors: Synthesis, SAR, and in vivo antitumor activity

  摘要：

  Thirty-six novel acylurea connected straight chain hydroxamates were designed and synthesized. Structure-activity relationships (SAR) were established for the length of linear chain linker and substitutions on the benzoylurea group. Compounds 5g, 5i, 5n, and 19 showed 10-20-fold enhanced HDAC1 potency compared to SAHA. In general, the cellular potency pIC(50) (COLO205) correlates with enzymatic potency pIC50 ( HDAC1). Compound 5b (SB207), a structurally simple and close analogue to SAHA, is more potent against HDAC1 and HDAC6 compared to the latter. As a representative example of this series, good in vitro enzymatic and cellular potency plus an excellent pharmacokinetic profile has translated into better efficacy than SAHA in both prostate cancer (PC3) and colon cancer (HCT116) xenograft models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.041

文献信息

• Acylurea Connected And Sulfonylurea Connected Hydroxamates
  申请人：Lim Ze-Yi

  公开号：US20080070954A1

  公开（公告）日：2008-03-20

  The present invention relates to hydroxamate compounds which are inhibitors of histone deacetylase. More particularly, the present invention relates to acylurea/sulfonylurea containing compounds and methods for their preparation. These compounds may be useful as medicaments for the treatment of proliferative disorders as well as other diseases involving, relating to or associated with enzymes having histone deacetylase activities.

  本发明涉及羟酰胺化合物，其为组蛋白去乙酰化酶的抑制剂。更具体地说，本发明涉及含有酰基脲/磺酰基脲的化合物及其制备方法。这些化合物可能作为药物用于治疗增殖性疾病以及其他涉及或与具有组蛋白去乙酰化酶活性的酶相关的疾病。