(E)-3,5-dimethylstyryl-4-methoxybenzylsulfone | 409357-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3,5-dimethylstyryl-4-methoxybenzylsulfone
• 英文别名: 1-[(E)-2-[(4-methoxyphenyl)methylsulfonyl]ethenyl]-3,5-dimethylbenzene
• CAS: 409357-77-3
• 化学式: C₁₈H₂₀O₃S
• 分子量: 316.421
• InChiKey: RJYGJPLDSGAFCX-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(4-甲氧基苄基)磺酰基]乙酸 、 3,5-二甲基苯甲醛 在 苄胺 溶剂黄146 作用下， 以58%的产率得到(E)-3,5-dimethylstyryl-4-methoxybenzylsulfone
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of (E)-Styrylbenzylsulfones as Novel Anticancer Agents

  摘要：

  Cell cycle progression is regulated by cyclins and cyclin-dependent kinases, which are formed at specific stages of the cell cycle and regulate the G1/S and G2/M phase transitions, employing a series of "checkpoints" governed by phosphorylation of their substrates. Tumor development is associated with the loss of these checkpoint controls, and this provides an approach for the development of therapeutic agents that can specifically target tumor cells. Here, we describe the synthesis and SAR of a novel group of cytotoxic molecules that selectively induce growth arrest of normal cells in the G1 phase while inducing a mitotic arrest of tumor cells resulting in selective killing of tumor cell populations with little or no effect on normal cell viability. The broad spectrum of antitumor activity in vitro and xenograft models, lack of in vivo toxicity, and drug resistance suggest potential for use of these agents in cancer therapy.

  DOI：

  10.1021/jm701077b

文献信息

• Substituted (e)-styryl benzylsulfones for treating proliferative disorders
  申请人：Reddy Premkumar E.

  公开号：US20050101528A1

  公开（公告）日：2005-05-12

  (E)-Styryl benzylsulfones useful as antiproliferative agents, including, for example, anticancer agents, are provided according to formula I: wherein: R 1 is selected from the group consisting of halogen, C1-C6 alkoxy, nitro, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); and R 2 and R 3 are independently selected from the group consisting of halogen, C1-C6 alkoxy, C1-C6 alkyl, nitro, cyano, hydroxyl, phosphonato, amino, sulfamyl, carboxy, acetoxy, and dimethylamino (C2-C6 alkoxy); provided: R 1 may not be halogen when R 2 and R 3 are both halogen; R 2 may not be 2-halogen when R 3 is 4-halogen; or a pharmaceutically acceptable salt thereof; or formula II: wherein: R 4 is selected from the group consisting of C1-C6 alkoxy, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); R 6 is selected from the group consisting of nitro, hydrogen, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); and R 7 is selected from the group consisting of halogen, C1-C6 alkoxy, C1-C6 alkyl, nitro, cyano, hydroxy, phosphonato, amino, sulfamyl, carboxy, acetoxy, dimethylamino (C2-C6 alkoxy) and trifluoromethyl; provided R 5 and R 6 may not be hydrogen in the same compound; or a pharmaceutically acceptable salt thereof.

  (E)-苯乙烯基苄基砜可用作抗增殖剂，例如包括抗癌剂，其根据式 I 提供： 其中：R 1 选自由卤素、C1-C6 烷氧基、硝基、膦酰基、氨基、氨基磺酰基、羧基、乙酰氧基和二甲基氨基（C2-C6 烷氧基）组成的组；以及 R 2 和 R 3 独立选自由卤素、C1-C6 烷氧基、C1-C6 烷基、硝基、氰基、羟基、膦酰基、氨基、氨基磺酰基、羧基、乙酰氧基和二甲基氨基（C2-C6 烷氧基）组成的组；前提是R 1 不得为卤素，当 R 2 和 R 3 都是卤素时 2 当 R 3 为 4-卤素时，R 2 不得为 2-卤素；或其药学上可接受的盐；或式 II： 其中R 4 选自由 C1-C6 烷氧基、膦酸、氨基、氨基磺酰基、羧基、乙酰氧基和二甲基氨基（C2-C6 烷氧基）组成的组 6 选自由硝基、氢、膦酰基、氨基、氨基磺酰基、羧基、乙酰氧基和二甲基氨基 （C2-C6 烷氧基）组成的组；以及 R 7 选自由卤素、C1-C6 烷氧基、C1-C6 烷基、硝基、氰基、羟基、膦酰基、氨基、氨基磺酰基、羧基、乙酰氧基、二甲基氨基（C2-C6 烷氧基）和三氟甲基组成的组；前提是 R 5 和 R 6 或其药学上可接受的盐。
• [EN] SUBSTITUTED (E)-STYRYL BENZYLSULFONES FOR TREATING PROLIFERATIVE DISORDERS<br/>[FR] (E)-STYRYL BENZYLSULFONES SUBSTITUES DESTINES AU TRAITEMENT DE TROUBLES A EVOLUTION CHRONIQUE
  申请人：UNIV TEMPLE

  公开号：WO2002028828A1

  公开（公告）日：2002-04-11

  (E)-Styryl benzylsulfones useful as antiproliferative agents, including, for example, anticancer agents, are provided according to formula I: wherein: R1 is selected from the group consisting of halogen, C1-C6 alkoxy, nitro, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); and R2 and R3 are independently selected from the group consisting of halogen, C1-C6 alkoxy, C1-C6 alkyl, nitro, cyano, hydroxy, phosphonato, amino, sulfamyl, carboxy, acetoxy, and dimethylamino (C2-C6 alkoxy); provided: R1 may not be halogen when R2 and R3 are both halogen; R2 may not be 2-halogen when R3 is 4-halogen; or a pharmaceutically acceptable salt thereof; or formula II: whrein: R4 is selected from the group consisting of C1-C6 alkoxy, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); R6 is selected from the group consisting of nitro, hydrogen, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); and R7 is selected from the group consisting of halogen, C1-C6 alkoxy, C1-C6 alkyl, nitro, cyano, hydroxy, phosphonato, amino, sulfamyl, carboxy, acetoxy, dimethylamino (C2-C6 alkoxy) and trifluoromethyl; provided R5 and R6 may not be hydrogen in the same compound; or a pharmaceutically acceptable salt thereof.

  提供了一种类Utilizing the following formula: wherein: R1 is selected from the group consisting of halogen, C1-C6 alkoxy, nitro, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); and R2 and R3 are independently selected from the group consisting of halogen, C1-C6 alkoxy, C1-C6 alkyl, nitro, cyano, hydroxy, phosphonato, amino, sulfamyl, carboxy, acetoxy, and dimethylamino (C2-C6 alkoxy); provided: R1 may not be halogen when R2 and R3 are both halogen; R2 may not be 2-halogen when R3 is 4-halogen; or a pharmaceutically acceptable salt thereof; or formula II: wherein: R4 is selected from the group consisting of C1-C6 alkoxy, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); R6 is selected from the group consisting of nitro, hydrogen, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2-C6 alkoxy); and R7 is selected from the group consisting of halogen, C1-C6 alkoxy, C1-C6 alkyl, nitro, cyano, hydroxy, phosphonato, amino, sulfamyl, carboxy, acetoxy, dimethylamino (C2-C6 alkoxy) and trifluoromethyl; provided R5 and R6 may not be hydrogen in the same compound; or a pharmaceutically acceptable salt thereof.
• EP1328511A4
  申请人：——

  公开号：EP1328511A4

  公开（公告）日：2005-11-30
• SUBSTITUTED (E)-STYRYL BENZYLSULFONES FOR TREATING PROLIFERATIVE DISORDERS
  申请人：Temple University - Of The Commonwealth System of Higher Education

  公开号：EP1328511B1

  公开（公告）日：2010-03-24
• US7053123B2
  申请人：——

  公开号：US7053123B2

  公开（公告）日：2006-05-30