(4-hydroxymethylbenzyl)-carbamic acid 9H-fluoren-9-ylmethyl ester | 475160-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (4-hydroxymethylbenzyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-Fluoren-9-ylmethyl 4-(hydroxymethyl)benzylcarbamate；9H-fluoren-9-ylmethyl N-[[4-(hydroxymethyl)phenyl]methyl]carbamate
• CAS: 475160-89-5
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: UNAKBYNMNKEBDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-hydroxymethylbenzyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 在 对甲苯磺酸 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 生成 (4-dimethoxymethylbenzyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis of 7200 Small Molecules Based on a Substructural Analysis of the Histone Deacetylase Inhibitors Trichostatin and Trapoxin

  摘要：

  [GRAPHICS]Seventy-two hundred potential inhibitors of the histone deacetylase (HDAC) enzyme family, based on a 1,3-dioxane diversity structure, were synthesized on polystyrene macrobeads. The compounds were arrayed for biological assays in a "one bead-one stock solution" format. Metal-chelating functional groups were used to direct the 1,3-dioxanes to HDAC enzymes, which are zinc hydrolases. Representative structures from this library were tested for inhibitory activity and the 1,3-dioxane structure was shown to be compatible with HDAC inhibition.

  DOI：

  10.1021/ol016915f
• 作为产物：
  描述：

  4-氨甲基苯甲酸 在 氯甲酸乙酯 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 15.5h， 生成 (4-hydroxymethylbenzyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis of 7200 Small Molecules Based on a Substructural Analysis of the Histone Deacetylase Inhibitors Trichostatin and Trapoxin

  摘要：

  [GRAPHICS]Seventy-two hundred potential inhibitors of the histone deacetylase (HDAC) enzyme family, based on a 1,3-dioxane diversity structure, were synthesized on polystyrene macrobeads. The compounds were arrayed for biological assays in a "one bead-one stock solution" format. Metal-chelating functional groups were used to direct the 1,3-dioxanes to HDAC enzymes, which are zinc hydrolases. Representative structures from this library were tested for inhibitory activity and the 1,3-dioxane structure was shown to be compatible with HDAC inhibition.

  DOI：

  10.1021/ol016915f

文献信息

• Dioxanes and uses thereof
  申请人：——

  公开号：US20040072849A1

  公开（公告）日：2004-04-15

  In recognition of the need to develop novel therapeutic agents and efficient methods for the synthesis thereof, the present invention provides novel compounds of general formula (I): 1 and pharmaceutically acceptable derivatives thereof, wherein R 1 , R 2 , R 3 , n, X and Y are as defined herein. The present invention also provides pharmaceutical compositions comprising a compound of formula (I) and a pharmaceutically acceptable carrier. The present invention further provides compounds capable of inhibiting histone deacetylatase activity and methods for treating disorders regulated by histone deacetylase activity (e.g., cancer and protozoal infections) comprising administering a therapeutically effective amount of a compound of formula (I) to a subject in need thereof. The present invention additionally provides methods for modulating the glucose-sensitive subset of genes downstream of Ure2p. The present invention also provides methods for preparing compounds of the invention.

  鉴于需要开发新型治疗剂和有效的合成方法，本发明提供了一般式(I)的新化合物： 1 及其药学上可接受的衍生物，其中R 1 ，R 2 ，R 3 ，n，X和Y如本文所定义。本发明还提供了包含一种式(I)化合物和药学上可接受的载体的药物组合物。本发明还提供了能够抑制组蛋白去乙酰化酶活性的化合物以及治疗由组蛋白去乙酰化酶活性调节的疾病的方法（例如，癌症和原虫感染），包括向需要的受体施用一种式(I)化合物的治疗有效量。本发明还提供了调节Ure2p下游葡萄糖敏感基因子集的方法。本发明还提供了制备本发明化合物的方法。
• Pairwise Use of Complexity-Generating Reactions in Diversity-Oriented Organic Synthesis
  作者：Daesung Lee、Jason K. Sello、Stuart L. Schreiber

  DOI：10.1021/ol005574n

  日期：2000.3.1

  [GRAPHICS]Two pairs of complexity-generating reactions with an essential product-substrate relationship along a synthetic pathway are demonstrated, This pathway illustrates a key element in a planning algorithm for diversity-oriented synthesis, This element facilitates the efficient synthesis of structurally complex compounds, and it can be integrated with ones that provide structurally diverse compounds.
• US7244853B2
  申请人：——

  公开号：US7244853B2

  公开（公告）日：2007-07-17
• US8178579B2
  申请人：——

  公开号：US8178579B2

  公开（公告）日：2012-05-15
• [EN] DIOXANES AND USES THEREOF<br/>[FR] DIOXANES ET LEURS UTILISATIONS
  申请人：HARVARD COLLEGE

  公开号：WO2002089782A2

  公开（公告）日：2002-11-14

  In recognition of the need to develop novel therapeutic agents and efficient methods for the synthesis thereof, the present invention provides novel compounds of general formula (I): and pharmaceutically acceptable derivatives thereof, wherein R?1, R2, R3¿, n, X and Y are as defined herein. The present invention also provides pharmaceutical compositions comprising a compound of formula (I) and a pharmaceutically acceptable carrier. The present invention further provides compounds capable of inhibiting histone deacetylatase activity and methods for treating disorders regulated by histone deacetylase activity (e.g., cancer and protozoal infections) comprising administering a therapeutically effective amount of a compound of formula (I) to a subject in need thereof. The present invention additionally provides methods for modulating the glucose-sensitive subset of genes downstream of Ure2p.