N(4-(2-bromoacetyl)phenyl)benzenesulfonamide | 610258-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N(4-(2-bromoacetyl)phenyl)benzenesulfonamide
• 英文别名: N-[4-(2-bromoacetyl)phenyl]benzenesulfonamide
• CAS: 610258-94-1
• 化学式: C₁₄H₁₂BrNO₃S
• 分子量: 354.224
• InChiKey: PZOOLGZWDJXKCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  N(4-(2-bromoacetyl)phenyl)benzenesulfonamide 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 S-[2-[4-(benzenesulfonamido)phenyl]-2-oxoethyl] ethanethioate
  参考文献：
  名称：

  α-Mercaptoketone based histone deacetylase inhibitors

  摘要：

  In an effort to discover novel non-hydroxamic acid histone deacetylase (HDAC) inhibitors, a novel alpha-mercaptoketone was identified in a high-throughput screen. Lead optimization of the screening hit, led to a number of potent HDAC inhibitors. In particular, alpha-mercaptoketone 19y (KD5150) exhibited nanomolar in vitro activity and inhibition of tumor growth in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.058
• 作为产物：
  描述：

  苯磺酰氯 在 吡啶 、 phenyltrimethylammonium tribromide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 N(4-(2-bromoacetyl)phenyl)benzenesulfonamide
  参考文献：
  名称：

  Discovery and structure-activity relationship of novel 4-hydroxy-thiazolidine-2-thione derivatives as tumor cell specific pyruvate kinase M2 activators

  摘要：

  Pyruvate kinase M2 isoform (PKM2) is a crucial protein responsible for aerobic glycolysis of cancer cells. Activation of PKM2 may alter aberrant metabolism in cancer cells. In this study, we discovered a 4-hydroxy-thiazolidine-2-thione compound 2 as a novel PKM2 activator from a random screening of an in-house compound library. Then a series of novel 4-hydroxy-thiazolidine-2-thione derivatives were designed and synthesized for screening as potent PKM2 activators. Among these, some compounds showed higher PKM2 activation activity than lead compound 2 and also exhibited significant anti proliferative activities on human cancer cell lines at nanomolar concentration. The compound 5w was identified as the most potent antitumor agent, which showed excellent anti-proliferative effects with IC50 values from 0.46 mu M to 0.81 mu M against H1299, HCT116, Hela and PC3 cell lines. 5w also showed less cytotoxicity in non-tumor cell line HELF compared with cancer cells. In addition, Preliminary pharmacological studies revealed that 5w arrests the cell cycle at the G2/M phase in HCT116 cell line. The best PKM2 activation by compound 5t was rationalized through docking studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.023

文献信息

• [EN] HETEROCYCLIC COMPOUNDS USEFUL AS IDO AND/OR TDO MODULATORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILES EN TANT QUE MODULATEURS DE L'IDO ET/OU DE LA TDO
  申请人：EMCURE PHARMACEUTICALS LTD

  公开号：WO2017149469A1

  公开（公告）日：2017-09-08

  Present invention relates to novel heterocyclic compounds as indoleamine 2,3- dioxygenase (IDO) and/or tryptophan 2,3-dioxygenase (TDO) modulators. Compounds of the present invention inhibit tryptophan degradation by modulating IDO and/or TDO. Formula (I) The invention further relates to the process of their preparation, pharmaceutical composition and their use in modulating the activity of indoleamine 2,3-dioxygenase (IDO) and/or tryptophan 2,3- dioxygenase (TDO). The compounds of the invention can be used alone or in combination for the treatment of conditions that benefits from the inhibition of tryptophan degradation.

  本发明涉及新颖的杂环化合物作为吲哚胺2,3-双加氧酶（IDO）和/或色氨酸2,3-双加氧酶（TDO）的调节剂。本发明的化合物通过调节IDO和/or TDO来抑制色氨酸的降解。公式（I）本发明还涉及它们的制备过程、药物组合物及其在调节吲哚胺2,3-双加氧酶（IDO）和/or色氨酸2,3-双加氧酶（TDO）活性方面的应用。本发明的化合物可以单独使用或联合使用，用于治疗从色氨酸降解抑制中受益的条件。
• Discovery and structure-activity relationship of novel 4-hydroxy-thiazolidine-2-thione derivatives as tumor cell specific pyruvate kinase M2 activators
  作者：Ridong Li、Xianling Ning、Shuo Zhou、Zhiqiang Lin、Xingyu Wu、Hong Chen、Xinyu Bai、Xin Wang、Zemei Ge、Runtao Li、Yuxin Yin

  DOI：10.1016/j.ejmech.2017.11.023

  日期：2018.1

  Pyruvate kinase M2 isoform (PKM2) is a crucial protein responsible for aerobic glycolysis of cancer cells. Activation of PKM2 may alter aberrant metabolism in cancer cells. In this study, we discovered a 4-hydroxy-thiazolidine-2-thione compound 2 as a novel PKM2 activator from a random screening of an in-house compound library. Then a series of novel 4-hydroxy-thiazolidine-2-thione derivatives were designed and synthesized for screening as potent PKM2 activators. Among these, some compounds showed higher PKM2 activation activity than lead compound 2 and also exhibited significant anti proliferative activities on human cancer cell lines at nanomolar concentration. The compound 5w was identified as the most potent antitumor agent, which showed excellent anti-proliferative effects with IC50 values from 0.46 mu M to 0.81 mu M against H1299, HCT116, Hela and PC3 cell lines. 5w also showed less cytotoxicity in non-tumor cell line HELF compared with cancer cells. In addition, Preliminary pharmacological studies revealed that 5w arrests the cell cycle at the G2/M phase in HCT116 cell line. The best PKM2 activation by compound 5t was rationalized through docking studies. (C) 2017 Elsevier Masson SAS. All rights reserved.
• α-Mercaptoketone based histone deacetylase inhibitors
  作者：Paul L. Wash、Timothy Z. Hoffman、Brandon M. Wiley、Céline Bonnefous、Nicholas D. Smith、Michael S. Sertic、Charles M. Lawrence、Kent T. Symons、Phan-Manh Nguyen、Kevin D. Lustig、Xin Guo、Tami Annable、Stewart A. Noble、Jeffrey H. Hager、Christian A. Hassig、James W. Malecha

  DOI：10.1016/j.bmcl.2008.10.058

  日期：2008.12

  In an effort to discover novel non-hydroxamic acid histone deacetylase (HDAC) inhibitors, a novel alpha-mercaptoketone was identified in a high-throughput screen. Lead optimization of the screening hit, led to a number of potent HDAC inhibitors. In particular, alpha-mercaptoketone 19y (KD5150) exhibited nanomolar in vitro activity and inhibition of tumor growth in vivo. (C) 2008 Elsevier Ltd. All rights reserved.