(E)-4-fluorostyryl-4-methoxybenzylsulfone | 300699-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-4-fluorostyryl-4-methoxybenzylsulfone
• 英文别名: 1-[[(E)-2-(4-fluorophenyl)ethenyl]sulfonylmethyl]-4-methoxybenzene
• CAS: 300699-94-9
• 化学式: C₁₆H₁₅FO₃S
• 分子量: 306.358
• InChiKey: WVXFQFOSPDKBCO-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (E)-4-fluorostyryl-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

• PROCESSES FOR PREPARING (E)-STYRYLBENZYLSULFONE COMPOUNDS AND USES THEREOF FOR TREATING PROLIFERATIVE DISORDERS
  申请人：SIRIGIREDDY REDDY

  公开号：US20100152491A1

  公开（公告）日：2010-06-17

  Processes for preparing (E)-2,4,6-(Trimethoxystyryl)-3-O-Phosphate Disodium-4-Methoxybenzyl Sulfones and uses thereof as antiproliferative agents, including, for example, anticancer agents, and as radioprotective and chemoprotective agents.

  制备(E)-2,4,6-(三甲氧基苯乙烯基)-3-O-磷酸二钠-4-甲氧基苯甲基磺酮的方法及其作为抗增殖剂的用途，包括作为抗癌剂，以及作为放射保护和化学保护剂的用途。
• Formulations of radioprotective alpha, beta unsaturated aryl sulfones
  申请人：Onconova Therapeutics, Inc.

  公开号：EP2769719A1

  公开（公告）日：2014-08-27

  Solution and suspension formulations are provided for administration prior to or after exposure to ionizing radiation for reducing toxic effects of the radiation in a subject which comprises an effective amount of at least one radioprotective α, β unsaturated aryl sulfone wherein the composition has a pH within the range of about 8 to about 9.

  本发明提供了溶液和悬浮液制剂，用于在电离辐射照射前或照射后给药，以减少辐射对受试者的毒性影响，该制剂包含有效量的至少一种辐射保护性 α、β 不饱和芳基砜，其中组合物的 pH 值在约 8 到约 9 的范围内。
• (E)-styryl sulfone anticancer agents
  申请人：Temple University - Of The Commonwealth System of Higher Education

  公开号：US20040229959A1

  公开（公告）日：2004-11-18

  (E)-styryl benzylsulfones of formula I are useful as anticancer agents: 1 wherein R 1 , R 2 , R 3 , and R 4 are as defined herein.

  (E)-顺式苯甲基乙基硫fonyl 1式的化合物对抗癌药物有潜在应用价值：其中，R1、R2、R3、R4在本文献中定义。
• [EN] (E)-STYRYL SULFONE ANTICANCER AGENTS<br/>[FR] AGENTS ANTICANCER AU (E)-STYRYLSULFONE
  申请人：UNIV TEMPLE

  公开号：WO2000059495A1

  公开（公告）日：2000-10-12

  (E)-styryl benzylsulfones of formula (I) are useful as anticancer agents wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, fluoro, chloro, iodo, bromo, C1-C6 alkyl, C1-C4 alkoxy, nitro, cyano and trifluoromethyl, with the proviso that (a) R1, R2, and R3 not all hydrogen when R4 is 2-chloro or 4-chloro; (b) when R1 and R3 are hydrogen and R2 is 4-bromo or 4-chloro, then R4 may not be 4-chloro, 4-fluoro or 4-bromo; (c) when R1 and R3 are hydrogen and R2 is 4-fluoro, then R4 may not be 4-fluoro or 4-bromo; (d) when R1 is hydrogen, and R4 is 2-fluoro, the R2 and R3 may not be 4-fluoro; and (e) when R1 is hydrogen and R3 is 4-hydrogen, 4-chloro, 4-bromo, 4-methyl or 4-methoxy, and R4 is 2-hydrogen, 2-chloro, or 2-fluoro; then R2 may not be 4-hydrogen, 4-chloro, 4-fluoro, or 4-bromo.

  (E)-styryl Benzylsulfones的化合物式为(I)，它们在化学药物中起抗癌作用。其中，R1、R2、R3和R4基团分别从以下基团中独立选择：氢、氟、卤素（如氯、碘、溴）、有机烷基、有机氧基、硝基、腈基和三氟甲基。以下为条件规定： (a) 当R4基团为2-氯或4-氯时，R1、R2和R3基团不可能全部为氢； (b) 当R1和R3基团为氢，且R2基团为4-溴或4-氯时，R4基团不可能为4-氯、4-氟或4-溴； (c) 当R1和R3基团为氢，且R2基团为4-氟时，R4基团不可能为4-氟或4-溴； (d) 当R1基团为氢，R4基团为2-氟时，R2和R3基团不可能为4-氟； (e) 当R1基团为氢，R3基团为4-氢、4-氯、4-溴、4-甲基或4-甲氧基时，且R4基团为2-氢、2-氯或2-氟时，R2基团不可能为4-氢、4-氯、4-氟或4-溴。
• EP1173160A4
  申请人：——

  公开号：EP1173160A4

  公开（公告）日：2003-02-19