(E)-2-methoxy-5-((2,4,6-trimethoxystyrylsulfinyl)methyl)aniline | 852283-21-7

• 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: (E)-2-methoxy-5-((2,4,6-trimethoxystyrylsulfinyl)methyl)aniline
• 英文别名: (E)-2',4',6'-trimethoxystyryl-4-methoxy-3-aminobenzyl sulfoxide；(E)-2,4,6-trimethoxystyryl-3-amino-4-methoxybenzylsulfoxide；2-methoxy-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfinylmethyl]aniline
• CAS: 852283-21-7
• 化学式: C₁₉H₂₃NO₅S
• 分子量: 377.461
• InChiKey: PTLMUODWSDJPNR-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 在 三乙基硼 、 potassium tert-butylate 、 双氧水 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二甲基亚砜 为溶剂， 反应 28.0h， 生成 (E)-2-methoxy-5-((2,4,6-trimethoxystyrylsulfinyl)methyl)aniline
  参考文献：
  名称：

  苄硫醇氢硫醇化为芳基乙炔：应用于 III 期临床抗癌药物 ON 01910·Na (Rigosertib®) 的 (E) 和 (Z) 异构体的合成†

  摘要：

  一种立体选择性且高效的自由基加成方法苄硫醇在 Et 3 B-己烷存在下将芳基乙炔转化为芳基乙炔已被开发用于合成 ( Z ) 和 ( E )-苯乙烯基苄基硫醚，其中碱催化的氢硫醇化已失败。该反应范围被成功扩展，用于合成III期临床抗癌药物( E )-ON 01910·Na及其无活性几何异构体( Z )-ON 01910·Na。有趣的是，与Z异构体相比，所有合成的E异构体都对癌细胞表现出更好的细胞毒性。

  DOI：

  10.1039/c3ob27220f

文献信息

• Unsaturated Sulfides, Sulfones, Sulfoxides and Sulfonamides Synthesis
  申请人：Reddy M.V. Ramana

  公开号：US20090124828A1

  公开（公告）日：2009-05-14

  α,β-Unsaturated sulfides, sulfones, sulfoxides and sulfonamides according to Formula I: wherein Ar 1 , Ar 2 , X, n, * and R are as defined herein, are prepared by dehydration of β-hydroxy sulfides, sulfones, sulfoxides or sulfonamides.

  根据公式I，制备α，β-不饱和硫化物，磺酰酸，亚磺酸和磺酰胺，其中Ar1，Ar2，X，n，*和R的定义如下，通过β-羟基硫化物，磺酰酸，亚磺酸或磺酰胺的脱水反应制备。
• Alpha, beta-unsaturated sulfoxides for treating proliferative disorders
  申请人：Reddy Premkumar E.

  公开号：US20060280746A1

  公开（公告）日：2006-12-14

  αβ-Unsaturated sulfoxides of Formula I: are useful as antiproliferative agents including, for example, anticancer agents, and as radioprotective and chemoprotective agents.

  公式为I的αβ-不饱和亚砜化合物可用作抗增殖剂，包括例如抗癌剂，以及放射保护和化学保护剂。
• 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.
• Synthesis and biological evaluation of benzyl styrylsulfonyl derivatives as potent anticancer mitotic inhibitors
  作者：Osama Chahrour、Ashraf Abdalla、Frankie Lam、Carol Midgley、Shudong Wang

  DOI：10.1016/j.bmcl.2011.03.041

  日期：2011.5

  We herein report the synthesis, biological activity and structure activity relationship of derivatives of benzylstyrylsulfone, benzylstyrylsulfine and benzylsulfonyl-N-phenylacetamide. A lead compound 7 represents a new class of mitotic inhibitors that demonstrates potent anti-proliferative activity and selectively induces cancer cell apoptosis while sparing non-transformed lung fibroblast. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• [EN] ALPHA, BETA-UNSATURATED SULFOXIDES FOR TREATING PROLIFERATIVE DISORDERS<br/>[FR] SULFOXYDES ALPHA,BETA-INSATURES DESTINES A TRAITER DES MALADIES A EVOLUTION CHRONIQUE
  申请人：UNIV TEMPLE

  公开号：WO2005046599A3

  公开（公告）日：2005-10-06