ethyl 7-benzyl-2,3-dihydro-5-oxo-5H-thiazolo-[3,2-a]pyrimidine-3-acetate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 7-benzyl-2,3-dihydro-5-oxo-5H-thiazolo-[3,2-a]pyrimidine-3-acetate
• 英文别名: Ethyl 2-(7-benzyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-3-yl)acetate；ethyl 2-(7-benzyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-3-yl)acetate
• 化学式: C₁₇H₁₈N₂O₃S
• 分子量: 330.408
• InChiKey: OFUXIZUHFYXBHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 7-benzyl-2,3-dihydro-5-oxo-5H-thiazolo-[3,2-a]pyrimidine-3-acetate 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以45%的产率得到2-(7-Benzyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-yl)-N-hydroxy-acetamide
  参考文献：
  名称：

  Exploring the connection unit in the HDAC inhibitor pharmacophore model: Novel uracil-based hydroxamates

  摘要：

  Starting from the pharmacophore model for HDAC inhibitor design, a novel series of hydroxamates bearing a uracil moiety as connecting unit (CU) has been prepared and tested. Almost all compounds exhibited HDAC inhibiting activity at low nanomolar concentrations, the N-hydroxy-6-(3,4-dihydro-4-oxo-6-benzyl- and -6-phenyl-2-pyrimidinylthio)hexanamides 1d and 11 being more potent than SAHA in enzymatic assays. Such compounds also caused hyperacetylation in NIH3T3 cell core histones and were endowed with interesting antiproliferative and cytodifferentiating effects in human leukemia (HL-60) cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.081
• 作为产物：
  描述：

  4-溴巴豆酸乙酯 、 6-苄基-2-硫脲嘧啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以77%的产率得到ethyl 7-benzyl-2,3-dihydro-5-oxo-5H-thiazolo-[3,2-a]pyrimidine-3-acetate
  参考文献：
  名称：

  One‐Pot, High‐Yielding Synthesis of Novel Dihydrothiazolo[3,2‐a]pyrimidinones

  摘要：

  DOI：

  10.1080/00397910500384996

文献信息

• Exploring the connection unit in the HDAC inhibitor pharmacophore model: Novel uracil-based hydroxamates
  作者：Antonello Mai、Silvio Massa、Dante Rotili、Riccardo Pezzi、Patrizia Bottoni、Roberto Scatena、Joachim Meraner、Gerald Brosch

  DOI：10.1016/j.bmcl.2005.07.081

  日期：2005.11

  Starting from the pharmacophore model for HDAC inhibitor design, a novel series of hydroxamates bearing a uracil moiety as connecting unit (CU) has been prepared and tested. Almost all compounds exhibited HDAC inhibiting activity at low nanomolar concentrations, the N-hydroxy-6-(3,4-dihydro-4-oxo-6-benzyl- and -6-phenyl-2-pyrimidinylthio)hexanamides 1d and 11 being more potent than SAHA in enzymatic assays. Such compounds also caused hyperacetylation in NIH3T3 cell core histones and were endowed with interesting antiproliferative and cytodifferentiating effects in human leukemia (HL-60) cells. (c) 2005 Elsevier Ltd. All rights reserved.
• One‐Pot, High‐Yielding Synthesis of Novel Dihydrothiazolo[3,2‐<i>a</i>]pyrimidinones
  作者：Dante Rotili、Antonello Mai、Ilaria Ambrogio、Giancarlo Fabrizi

  DOI：10.1080/00397910500384996

  日期：2006.3.1