4-chloro-3-nitrobenzylsulfonylacetic acid | 872404-53-0

• 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: 4-chloro-3-nitrobenzylsulfonylacetic acid
• 英文别名: 2-(4-Chloro-3-nitrobenzylsulfonyl)acetic acid；2-[(4-chloro-3-nitrophenyl)methylsulfonyl]acetic acid
• CAS: 872404-53-0
• 化学式: C₉H₈ClNO₆S
• 分子量: 293.685
• InChiKey: XYGFLMQHYFGBAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-chloro-3-nitrobenzylsulfonylacetic acid 在 sodium dithionite 、 溶剂黄146 、 苄胺 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 (E)-2',4',6'-trimethoxystyryl-4-chloro-3-aminobenzylsulfone
  参考文献：
  名称：

  Discovery of a Clinical Stage Multi-Kinase Inhibitor Sodium (E)-2-{2-Methoxy-5-[(2′,4′,6′-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na): Synthesis, Structure–Activity Relationship, and Biological Activity

  摘要：

  Cyclin D proteins are elevated in many cancer cells, and targeted deletion of cyclin D1 gene in the mammary tissues protects mice from breast cancer, Accordingly, there is an increasing awareness of this novel nonenzymatic target for cancer therapeutics. We have developed novel, nonalkylating styrylbenzylsulfones that induce cell death in wide variety of cancer cells without affecting the proliferation and survival of normal cells. The development of derivatized styrylbenzylsulfones followed logically from a tumor cell cytotoxicity screen performed in our laboratory that did not have an a priori target profile. Modifications of some of the precursor molecules led to lead optimization with regard to tumor cell cytotoxicity. In this report we describe the synthesis and structure-activity relationships of novel, nonalkylating (E)-styrylbenzylsulfones and the development of the novel anticancer agent sodium (E)-2-{2-methoxy-5-[(2',4',6'-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na), which is in phase III trials for myelodysplastic syndromes (MDS) associated with aberrant expression of cyclin D proteins.

  DOI：

  10.1021/jm200570p
• 作为产物：
  描述：

  4-氯-3-硝基苯甲醇 在 双氧水 、 三溴化磷 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 27.5h， 生成 4-chloro-3-nitrobenzylsulfonylacetic acid
  参考文献：
  名称：

  Discovery of a Clinical Stage Multi-Kinase Inhibitor Sodium (E)-2-{2-Methoxy-5-[(2′,4′,6′-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na): Synthesis, Structure–Activity Relationship, and Biological Activity

  摘要：

  Cyclin D proteins are elevated in many cancer cells, and targeted deletion of cyclin D1 gene in the mammary tissues protects mice from breast cancer, Accordingly, there is an increasing awareness of this novel nonenzymatic target for cancer therapeutics. We have developed novel, nonalkylating styrylbenzylsulfones that induce cell death in wide variety of cancer cells without affecting the proliferation and survival of normal cells. The development of derivatized styrylbenzylsulfones followed logically from a tumor cell cytotoxicity screen performed in our laboratory that did not have an a priori target profile. Modifications of some of the precursor molecules led to lead optimization with regard to tumor cell cytotoxicity. In this report we describe the synthesis and structure-activity relationships of novel, nonalkylating (E)-styrylbenzylsulfones and the development of the novel anticancer agent sodium (E)-2-{2-methoxy-5-[(2',4',6'-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na), which is in phase III trials for myelodysplastic syndromes (MDS) associated with aberrant expression of cyclin D proteins.

  DOI：

  10.1021/jm200570p

文献信息

• Heteroaryl Sulfones and Sulfonamides and Therapeutic Uses Thereof
  申请人：Reddy Premkumar E.

  公开号：US20070232649A1

  公开（公告）日：2007-10-04

  Compounds of Formula I: wherein R 1 , R 2 , M, Q and n are as defined herein, are useful as antiproliferative agents including, for example, as anticancer agents.

  式I的化合物：其中R1、R2、M、Q和n的定义如本文所述，可用作抗增殖剂，包括例如作为抗癌剂。
• Heteroaryl sulfones and sulfonamides and therapeutic uses thereof
  申请人：Temple University-Of The Commonwealth System of Higher Education

  公开号：US08143428B2

  公开（公告）日：2012-03-27

  Compounds of Formula I: wherein R1, R2, M, Q and n are as defined herein, are useful as antiproliferative agents including, for example, as anticancer agents.

  式I的化合物：其中R1、R2、M、Q和n的定义如本文所述，可用作抗增殖剂，例如，作为抗癌剂。
• US8143428B2
  申请人：——

  公开号：US8143428B2

  公开（公告）日：2012-03-27
• Discovery of a Clinical Stage Multi-Kinase Inhibitor Sodium (<i>E</i>)-2-{2-Methoxy-5-[(2′,4′,6′-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na): Synthesis, Structure–Activity Relationship, and Biological Activity
  作者：M. V. Ramana Reddy、Padmavathi Venkatapuram、Muralidhar R. Mallireddigari、Venkat R. Pallela、Stephen C. Cosenza、Kimberly A. Robell、Balaiah Akula、Benjamin S. Hoffman、E. Premkumar Reddy

  DOI：10.1021/jm200570p

  日期：2011.9.22

  Cyclin D proteins are elevated in many cancer cells, and targeted deletion of cyclin D1 gene in the mammary tissues protects mice from breast cancer, Accordingly, there is an increasing awareness of this novel nonenzymatic target for cancer therapeutics. We have developed novel, nonalkylating styrylbenzylsulfones that induce cell death in wide variety of cancer cells without affecting the proliferation and survival of normal cells. The development of derivatized styrylbenzylsulfones followed logically from a tumor cell cytotoxicity screen performed in our laboratory that did not have an a priori target profile. Modifications of some of the precursor molecules led to lead optimization with regard to tumor cell cytotoxicity. In this report we describe the synthesis and structure-activity relationships of novel, nonalkylating (E)-styrylbenzylsulfones and the development of the novel anticancer agent sodium (E)-2-2-methoxy-5-[(2',4',6'-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na), which is in phase III trials for myelodysplastic syndromes (MDS) associated with aberrant expression of cyclin D proteins.