4-Piperazin-1-ylbenzoyl chloride | 1202570-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-Piperazin-1-ylbenzoyl chloride
• 英文别名: 4-piperazin-1-ylbenzoyl chloride
• CAS: 1202570-10-2
• 化学式: C₁₁H₁₃ClN₂O
• 分子量: 224.69
• InChiKey: POSKJMDABIEGGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-5-[2,4-bis(benzyloxy)-5-isopropylphenyl]isoxazole-3-carboxylic acid ethylamide 、 4-Piperazin-1-ylbenzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 C₄₀H₄₃N₅O₅
  参考文献：
  名称：

  Novel 3,4-Isoxazolediamides as Potent Inhibitors of Chaperone Heat Shock Protein 90

  摘要：

  A structural investigation on the isoxazole scaffold led to the discovery of 3,4-isoxazolediamide compounds endowed with potent Hsp90 inhibitory properties. We have found that compounds possessing a nitrogen atom directly attached to the C-4 heterocycle ring possess in vitro Hsp90 inhibitory properties at least comparable to those of the structurally related 4,S-diarylisoxazole derivatives. A group of compounds from this series of diamides combine potent binding affinity and cell growth inhibitory activity in both series of alkyl- and aryl- or heteroarylarnides, with IC50 in the low nanomolar range. The 3,4-isoxazolediamides were also very effective in causing dramatic depletion of the examined client proteins and, as expected for the Hsp90 inhibitors, always induced a very strong increase in the expression levels of the chaperone Hsp70. In vivo studies against human epidermoid carcinoma A431 showed an antitumor effect of morpholine derivative 73 comparable to that induced by the reference compound 10.

  DOI：

  10.1021/jm201155e

文献信息

• [EN] PYRAZOLO-PYRIDINE DERIVATIVES ACTIVE AS KINASE INHIBITORS<br/>[FR] DÉRIVES DE PYRAZOLO-PYRIDINE ACTIFS EN TANT QU'INHIBITEURS DE LA KINASE
  申请人：PFIZER ITALIA SRL

  公开号：WO2007099166A1

  公开（公告）日：2007-09-07

  [EN] A compound represented by Formula (I): wherein R and R¹ are as defined in the specification, pharmaceutical formulas thereof, and methods of use thereof.
  [FR] La présente invention concerne un composé représenté par la formule (I) : dans laquelle R et R¹ sont tels que définis dans la description, ainsi que des formules pharmaceutiques et des procédés d'utilisation dudit composé.
• Novel 3,4-Isoxazolediamides as Potent Inhibitors of Chaperone Heat Shock Protein 90
  作者：Riccardo Baruchello、Daniele Simoni、Giuseppina Grisolia、Giuseppina Barbato、Paolo Marchetti、Riccardo Rondanin、Stefania Mangiola、Giuseppe Giannini、Tiziana Brunetti、Domenico Alloatti、Grazia Gallo、Andrea Ciacci、Loredana Vesci、Massimo Castorina、Ferdinando M. Milazzo、Maria L. Cervoni、Mario B. Guglielmi、Marcella Barbarino、Rosanna Foderà、Claudio Pisano、Walter Cabri

  DOI：10.1021/jm201155e

  日期：2011.12.22

  A structural investigation on the isoxazole scaffold led to the discovery of 3,4-isoxazolediamide compounds endowed with potent Hsp90 inhibitory properties. We have found that compounds possessing a nitrogen atom directly attached to the C-4 heterocycle ring possess in vitro Hsp90 inhibitory properties at least comparable to those of the structurally related 4,S-diarylisoxazole derivatives. A group of compounds from this series of diamides combine potent binding affinity and cell growth inhibitory activity in both series of alkyl- and aryl- or heteroarylarnides, with IC50 in the low nanomolar range. The 3,4-isoxazolediamides were also very effective in causing dramatic depletion of the examined client proteins and, as expected for the Hsp90 inhibitors, always induced a very strong increase in the expression levels of the chaperone Hsp70. In vivo studies against human epidermoid carcinoma A431 showed an antitumor effect of morpholine derivative 73 comparable to that induced by the reference compound 10.