(E)-2',4',6'-trimethoxystyryl-4-bromo-3-aminobenzylsulfone | 851799-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2',4',6'-trimethoxystyryl-4-bromo-3-aminobenzylsulfone
• 英文别名: 5-(((E)-2,4,6-trimethoxystyrylsulfonyl)methyl)-2-bromo-benzenamine；2-bromo-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]aniline
• CAS: 851799-35-4
• 化学式: C₁₈H₂₀BrNO₅S
• 分子量: 442.331
• InChiKey: IWXYIWBKMOJDDJ-VOTSOKGWSA-N

物化性质

• 熔点：
  162-164 °C
• 沸点：
  673.2±55.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  96.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-溴-3-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 sodium dithionite 、 双氧水 、 溶剂黄146 、 苄胺 、 sodium hydroxide 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 水 、 丙酮 为溶剂， 反应 46.0h， 生成 (E)-2',4',6'-trimethoxystyryl-4-bromo-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

文献信息

• [EN] PROTECTION OF TISSUES AND CELLS FROM CYTOTOXIC EFFECTS OF IONIZING RADIATION BY ABL INHIBITORS<br/>[FR] LA PROTECTION DE TISSUS ET DE CELLULES CONTRE LES EFFETS CYTOTOXIQUE D'UN RAYONNEMENT IONISANT PAR DES INHIBITEURS ABL
  申请人：UNIV TEMPLE

  公开号：WO2005065074A2

  公开（公告）日：2005-07-21

  Pre-treatment with one or more compounds of formula (I), as described herein, protects normal cells from the toxic side effects of ionizing radiation. Administration of one or more radioprotective compounds of formula I to a patient prior to anticancer radiotherapy reduces the cytotoxic side effects of the radiation on normal cells. The radioprotective effect of one or more compounds of formula I allows for the safe increase the dosage of anticancer radiation. Amelioration of toxicity following inadvertent radiation exposure may also be mitigated with administration of one or more compounds of formula (I).