3-(2-Chlorophenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone | 162011-91-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-(2-Chlorophenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone
• 英文别名: 3-(2-Chlorophenyl)-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone；4-(2-chlorophenyl)-3-(4-methylsulfonylphenyl)-2H-furan-5-one
• CAS: 162011-91-8
• 化学式: C₁₇H₁₃ClO₄S
• 分子量: 348.807
• InChiKey: FPGNJXJYBXKRBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-Chlorophenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone 、 1-萘甲醛 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 以92%的产率得到(Z)-3-(2-chlorophenyl)-4-(4-(methylsulfonyl)phenyl)-5-(naphthalen-1-ylmethylene)furan-2(5H)-one
  参考文献：
  名称：

  Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones

  摘要：

  Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 mu M; PD PCDNA cell IC50 = 5 mu M; PD SKP2 cell IC50 = 5 mu M; DU145 cell IC50 = 25 mu M). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.062
• 作为产物：
  描述：

  4-甲砜基苯乙酮 在 氢溴酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.58h， 生成 3-(2-Chlorophenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone
  参考文献：
  名称：

  Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones

  摘要：

  Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 mu M; PD PCDNA cell IC50 = 5 mu M; PD SKP2 cell IC50 = 5 mu M; DU145 cell IC50 = 25 mu M). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.062

文献信息

• Use of carotenoids and/or carotenoid derivatives/analogs for reduction/inhibition of certain negative effects of COX inhibitors
  申请人：Lockwood Samuel F.

  公开号：US20080293679A1

  公开（公告）日：2008-11-27

  Administering carotenoids, and in particular xanthophyll carotenoids, or analogs or derivatives of astaxanthin, lutein, zeaxanthin, lycoxanthin, lycophyll, or lycopene to a subject undergoing treatment with COX-2 inhibitor drugs may reduce at least a portion of the adverse side effects associated with administration of COX-2 selective inhibitor drugs. The carotenoids, or analogs or derivatives thereof may be administered to a subject prior to, at the same time as, or after the commencement of COX-2 selective inhibitor drug therapy. The carotenoids, or analogs or derivatives thereof may be administered to a subject concurrently with COX-2 selective inhibitor drugs therapy. The carotenoids, or analogs or derivatives thereof may be incorporated into pharmaceutical preparation in combination with the COX-2 selective inhibitor drug or may be administered separately. Administration of the analogs or derivatives described herein may reduce peroxidation of LDL and other lipids in the serum and plasma cell membranes of subjects undergoing COX-2 selective inhibitor drug therapy. Administration of the analogs or derivatives described herein may reduce the incidence of deleterious clinical cardiovascular events undergoing COX-2 selective inhibitor drug therapy.

  向正在接受COX-2抑制剂治疗的受试者施用类胡萝卜素，特别是黄质类胡萝卜素，或者是天然类胡萝卜素的类似物或衍生物，如虾青素、叶黄素、玉米黄质、莱科黄素、莱科菲或番茄红素，可能会减少与使用COX-2选择性抑制剂药物相关的不良副作用的至少一部分。这些类胡萝卜素，或者是其类似物或衍生物，可以在受试者开始接受COX-2选择性抑制剂药物治疗之前、同时或之后进行施用。这些类胡萝卜素，或者是其类似物或衍生物，可以与COX-2选择性抑制剂药物治疗同时进行施用。这些类胡萝卜素，或者是其类似物或衍生物，可以与COX-2选择性抑制剂药物组合在一起制成药物制剂，也可以单独施用。施用本文所述的类似物或衍生物可能会减少正在接受COX-2选择性抑制剂药物治疗的受试者血清和血浆细胞膜中低密度脂蛋白和其他脂质的过氧化。施用本文所述的类似物或衍生物可能会减少正在接受COX-2选择性抑制剂药物治疗的受试者发生有害的临床心血管事件的几率。
• [EN] PHENYL HETEROCYCLES AS COX-2 INHIBITORS<br/>[FR] HETEROCYCLES PHENYLIQUES UTILISES COMME INHIBITEURS DE COX-2
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1995018799A1

  公开（公告）日：1995-07-13

  (EN) The invention encompasses the novel compound of Formula (I) useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula (I).(FR) L'invention se rapporte à un nouveau composé de la formule (I), utilisé dans le traitement des maladies induites par cyclooxygénase-2 (COX-2). L'invention se rapporte également à certaines compositions pharmaceutiques destinées au traitement des maladies induites par cyclooxygénase-2 et comprenant les composés de la formule (I).

  该发明涵盖了式（I）的新型化合物，用于治疗环氧合酶-2介导的疾病。该发明还涵盖了某些药物组合物，用于治疗环氧合酶-2介导的疾病，其中包括式（I）的化合物。
• Phenyl heterocycles as cyclooxygenase-2 inhibitors
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0822190A1

  公开（公告）日：1998-02-04

  The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  该发明涵盖了一种新的化合物I式，该化合物对于治疗环氧合酶-2介导的疾病具有用处。该发明还涵盖了某些药物组合物，用于治疗环氧合酶-2介导的疾病，该组合物包括I式化合物。
• Use of inhibitors of cyclooxygenase in the treatment of neurodegenerative diseases
  申请人：Merck Frosst Canada Inc./Merck Frosst Canada & Co.

  公开号：US20010016595A1

  公开（公告）日：2001-08-23

  The present invention provides a method of treating a neurodegenerative disease and in particular Alzheimers disease which comprises administering to a human in need thereof a therapeutically effective amount of a non-steroid COX-II inhibitor. Although a wide range of COX-II inhibitors may be employed but it is preferred to employ compounds of the Formula I: 1

  本发明提供了一种治疗神经退行性疾病，尤其是阿尔茨海默病的方法，该方法包括向需要治疗的人类施用治疗有效量的非甾体COX-II抑制剂。虽然可以使用广泛的COX-II抑制剂，但最好使用I式化合物：1的化合物。
• PHENYL HETEROCYCLES AS COX-2 INHIBITORS
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0739340A1

  公开（公告）日：1996-10-30