N-(4-hydroxyphenyl)cyclopropanesulfonamide | 1150100-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-hydroxyphenyl)cyclopropanesulfonamide
• CAS: 1150100-69-8
• 化学式: C₉H₁₁NO₃S
• 分子量: 213.257
• InChiKey: PJYCWLMCJDVJIS-UHFFFAOYSA-N

物化性质

• 沸点：
  399.3±44.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxyphenyl)cyclopropanesulfonamide 在 potassium tert-butylate 、 铁粉 、 potassium carbonate 、 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 N-(3-((4-(cyclopropanesulfonamido)phenoxy)methyl)phenyl)-2-((4,6-dimethylpyrimidin-2-yl)thio)acetamide
  参考文献：
  名称：

  Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)- N -phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors

  摘要：

  Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl) thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42 nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of alpha-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.010
• 作为产物：
  描述：

  对氨基苯酚 、 环丙磺酰氯 以 甲醇 为溶剂， 反应 3.0h， 以84%的产率得到N-(4-hydroxyphenyl)cyclopropanesulfonamide
  参考文献：
  名称：

  [EN] CCR5 ANTAGONISTS AS THERAPEUTIC AGENTS
  [FR] ANTAGONISTES DE CCR5 EN TANT QU'AGENTS THÉRAPEUTIQUES

  摘要：

  本发明涉及在治疗CCR5相关疾病和疾病中有用的化合物，例如，在抑制HIV复制、预防或治疗HIV感染以及治疗由此导致的获得性免疫缺陷综合症（AIDS）方面有用。

  公开号：

  WO2009058919A1

文献信息

• Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)- N -phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors
  作者：Lingling Yang、Xiaobo Ma、Chen Yuan、Yanying He、Ling Li、Sha Fang、Wei Xia、Tao He、Shan Qian、Zhihong Xu、Guobo Li、Zhouyu Wang

  DOI：10.1016/j.ejmech.2017.04.010

  日期：2017.7

  Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl) thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42 nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of alpha-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases. (C) 2017 Elsevier Masson SAS. All rights reserved.
• [EN] CCR5 ANTAGONISTS AS THERAPEUTIC AGENTS<br/>[FR] ANTAGONISTES DE CCR5 EN TANT QU'AGENTS THÉRAPEUTIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009058919A1

  公开（公告）日：2009-05-07

  The present invention relates to compounds useful in the treatment of CCR5-related diseases and disorders, for example, useful in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).

  本发明涉及在治疗CCR5相关疾病和疾病中有用的化合物，例如，在抑制HIV复制、预防或治疗HIV感染以及治疗由此导致的获得性免疫缺陷综合症（AIDS）方面有用。