4-phenethyl-6-(4-(piperazin-1-yl)-1H-pyrazol-3-yl)benzene-1,3-diol | 886843-25-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-phenethyl-6-(4-(piperazin-1-yl)-1H-pyrazol-3-yl)benzene-1,3-diol
• 英文别名: 4-(2-phenylethyl)-6-(4-piperazin-1-yl-1H-pyrazol-5-yl)benzene-1,3-diol
• CAS: 886843-25-0
• 化学式: C₂₁H₂₄N₄O₂
• 分子量: 364.447
• InChiKey: IUWOBILYJWQZQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.4
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-phenethyl-6-(4-(piperazin-1-yl)-1H-pyrazol-3-yl)benzene-1,3-diol 、 对甲砜基氯苄 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-(4-(4-(methylsulfonyl)benzyl)piperazin-1-yl)-1H-pyrazol-3-yl)-6-phenethylbenzene-1,3-diol
  参考文献：
  名称：

  4-Amino derivatives of the Hsp90 inhibitor CCT018159

  摘要：

  Novel piperazinyl, morpholino and piperidyl derivatives of the pyrazole-based Hsp90 inhibitor CCT018159 are described. Structure-activity relationships have been elucidated by X-ray co-crystal analysis of the new Compounds bound to the N-terminal domain of human Hsp90. Key features of the binding mode are essentially identical to the recently reported potent analogue VER-49009. The most potent of the new compounds has a methylsulfonylbenzyl substituent appended to the piperazine nitrogen, possesses an IC50 of less than 600 nM binding against the enzyme and demonstrates low micromolar inhibition of tumour cell proliferation. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.099
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 二氯双(三邻甲苯膦)合钯(II) 、 氢气 、 三氯化硼 、 phenyltrimethylammonium tribromide 、 potassium carbonate 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 正丁醇 为溶剂， 反应 28.08h， 生成 4-phenethyl-6-(4-(piperazin-1-yl)-1H-pyrazol-3-yl)benzene-1,3-diol
  参考文献：
  名称：

  4-Amino derivatives of the Hsp90 inhibitor CCT018159

  摘要：

  Novel piperazinyl, morpholino and piperidyl derivatives of the pyrazole-based Hsp90 inhibitor CCT018159 are described. Structure-activity relationships have been elucidated by X-ray co-crystal analysis of the new Compounds bound to the N-terminal domain of human Hsp90. Key features of the binding mode are essentially identical to the recently reported potent analogue VER-49009. The most potent of the new compounds has a methylsulfonylbenzyl substituent appended to the piperazine nitrogen, possesses an IC50 of less than 600 nM binding against the enzyme and demonstrates low micromolar inhibition of tumour cell proliferation. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.099

文献信息

• 4-Amino derivatives of the Hsp90 inhibitor CCT018159
  作者：Xavier Barril、Mandy C. Beswick、Adam Collier、Martin J. Drysdale、Brian W. Dymock、Alexandra Fink、Kate Grant、Robert Howes、Allan M. Jordan、Andrew Massey、Allan Surgenor、Joanne Wayne、Paul Workman、Lisa Wright

  DOI：10.1016/j.bmcl.2006.01.099

  日期：2006.5

  Novel piperazinyl, morpholino and piperidyl derivatives of the pyrazole-based Hsp90 inhibitor CCT018159 are described. Structure-activity relationships have been elucidated by X-ray co-crystal analysis of the new Compounds bound to the N-terminal domain of human Hsp90. Key features of the binding mode are essentially identical to the recently reported potent analogue VER-49009. The most potent of the new compounds has a methylsulfonylbenzyl substituent appended to the piperazine nitrogen, possesses an IC50 of less than 600 nM binding against the enzyme and demonstrates low micromolar inhibition of tumour cell proliferation. (C) 2006 Elsevier Ltd. All rights reserved.