3-acetyl-N-cyclohexylbenzenesulfonamide | 561011-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-N-cyclohexylbenzenesulfonamide
• CAS: 561011-12-9
• 化学式: C₁₄H₁₉NO₃S
• 分子量: 281.376
• InChiKey: UGLPQHKOWFCYII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetyl-N-cyclohexylbenzenesulfonamide 在 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以23.4%的产率得到3-(2-bromoacetyl)-N-cyclohexylbenzenesulfonamide
  参考文献：
  名称：

  SULPHUR-LINKED COMPOUNDS FOR TREATING OPHTHALMIC DISEASES AND DISORDERS

  摘要：

  提供的是硫连接化合物、其药物组合物以及使用所述化合物和组合物治疗眼科疾病和障碍的方法，例如年龄相关的黄斑变性和斯达加特病。

  公开号：

  US20100093865A1
• 作为产物：
  描述：

  3-乙酰基苯磺酰氯 、 环己胺 以gave crude 3-acetyl-N-cyclohexylbenzenesulfonamide (85) which的产率得到3-acetyl-N-cyclohexylbenzenesulfonamide
  参考文献：
  名称：

  SULPHUR-LINKED COMPOUNDS FOR TREATING OPHTHALMIC DISEASES AND DISORDERS

  摘要：

  提供了硫连接化合物，其制药组合物以及使用所述化合物和组合物治疗眼科疾病和疾病的方法，例如年龄相关性黄斑变性和斯塔加德病。

  公开号：

  US20100093865A1

文献信息

• SULPHUR-LINKED COMPOUNDS FOR TREATING OPHTHALMIC DISEASES AND DISORDERS
  申请人：Scott Ian L.

  公开号：US20100093865A1

  公开（公告）日：2010-04-15

  Provided are sulphur-linked compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.

  提供的是硫连接化合物、其药物组合物以及使用所述化合物和组合物治疗眼科疾病和障碍的方法，例如年龄相关的黄斑变性和斯达加特病。
• SULFUR-LINKED COMPOUNDS FOR TREATING OPTHALMIC DISEASES AND DISORDERS
  申请人：Acucela, Inc.

  公开号：EP2344451A2

  公开（公告）日：2011-07-20
• [EN] SULFUR-LINKED COMPOUNDS FOR TREATING OPTHALMIC DISEASES AND DISORDERS<br/>[FR] COMPOSANTS À LIAISON SOUFRE POUR LE TRAITEMENT DE MALADIES ET DE TROUBLES OPHTALMIQUES
  申请人：ACUCELA INC

  公开号：WO2010028088A2

  公开（公告）日：2010-03-11

  Provided are sulphur-linked compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.
• Fragment-Based Drug Discovery of 2-Thiazolidinones as BRD4 Inhibitors: 2. Structure-Based Optimization
  作者：Lele Zhao、Yingqing Wang、Danyan Cao、Tiantian Chen、Qi Wang、Yanlian Li、Yechun Xu、Naixia Zhang、Xin Wang、Danqi Chen、Lin Chen、Yue-Lei Chen、Guangxin Xia、Zhe Shi、Yu-Chih Liu、Yijyun Lin、Zehong Miao、Jingkang Shen、Bing Xiong

  DOI：10.1021/jm501504k

  日期：2015.2.12

  The signal transduction of acetylated histone can be processed through a recognition module, bromodomain. Several inhibitors targeting BRD4, one of the bromodomain members, are in clinical trials as anticancer drugs. Hereby, we report our efforts on discovery and optimization of a new series of 2-thiazolidinones as BRD4 inhibitors along our previous study. In this work, guided by crystal structure analysis, we reversed the sulfonamide group and identified a new binding mode. A structure-activity relationship study on this new series led to several potent BRD4 inhibitors with IC50 of about 0.05-0.1 mu M in FP binding assay and GI50 of 0.1-0.3 mu M in cell based assays. To complete the lead-like assessment of this series, we further checked its effects on BRD4 downstream protein c-Myc, investigated its selectivity among five different bromodomain proteins, as well as the metabolic stability test, and reinforced the utility of 2-thiazolidinone scaffold as BET bromodomain inhibitors in novel anticancer drug development.