4'-Hydroxyrofecoxib | 326604-37-9

• 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: 4'-Hydroxyrofecoxib
• 英文别名: 3-(4-Hydroxy-phenyl)-4-(4-methanesulfonyl-phenyl)-5H-furan-2-one；4-(4-hydroxyphenyl)-3-(4-methylsulfonylphenyl)-2H-furan-5-one
• CAS: 326604-37-9
• 化学式: C₁₇H₁₄O₅S
• 分子量: 330.361
• InChiKey: VHWZIWIGNRZWFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  uridine diphosphoglucuronic acid 、 4'-Hydroxyrofecoxib 在 hepatic enzymes 作用下， 以67%的产率得到(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{4-[4-(4-methanesulfonyl-phenyl)-2-oxo-2,5-dihydro-furan-3-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis, characterization, and activity of metabolites derived from the cyclooxygenase-2 inhibitor rofecoxib (MK-0966, Vioxx™)

  摘要：

  Metabolites of the COX-2 inhibitor rofecoxib (MK-0966, Vioxx(TM)) were prepared by synthetic or biosynthetic methods. Metabolites include products of oxidation, glucuronidation, reduction and hydrolytic ring opening. Based on an in vitro whole blood assay, none of the known human metabolites of rofecoxib inhibits COX-I nor contributes significantly to the inhibition of COX-2. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00538-2
• 作为产物：
  描述：

  4-甲硫基苯乙酮 在 Oxone 、 溴 、 吡啶盐酸盐 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 乙腈 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 21.5h， 生成 4'-Hydroxyrofecoxib
  参考文献：
  名称：

  Isomeric acetoxy analogues of rofecoxib: A novel class of highly potent and selective cyclooxygenase-2 inhibitors

  摘要：

  A group of isomers possessing a 2-, 3-, or 4-acetoxy moiety on the 3-phenyl substituent of rofecoxib were synthesized that exhibit highly potent, and selective, COX-2 inhibitory activity that have the potential to acetylate the COX-2 isozyme.

  DOI：

  10.1016/s0960-894x(02)00537-1

文献信息

• CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING
  申请人：Reiley Pharmaceuticals, Inc.

  公开号：US20150374858A1

  公开（公告）日：2015-12-31

  Conjugates derived from non-steroidal anti-inflammatory drugs (NSAIDs) and methods of use thereof are disclosed, useful for, inter alia, identifying and localizing the site of pathology and/or inflammation responsible for the sensation of pain in a patient; for identifying the sites of primary, secondary, benign, or malignant tumors; and for diagnosing infection or confirming or ruling out suspected infection. The NSAID-based conjugates contain an imaging moiety. The conjugates concentrate at sites of increased cyclooxygenase expression, thus revealing the sites of increased prostaglandin production, which is correlated with pain and inflammation, and correlated with tumor presence and/or location. Identifying areas of increased COX expressing can also aid in screening for infections.

  披露了来自非甾体抗炎药（NSAIDs）的衍生物及其使用方法，这对于识别和定位患者疼痛感觉的病理和/或炎症部位；识别原发、继发、良性或恶性肿瘤的部位；以及诊断感染或确认或排除疑似感染非常有用。基于NSAID的偶联物含有成像基团。这些偶联物在环氧化酶表达增加的部位富集，从而揭示了前列腺素产生增加的部位，这与疼痛和炎症有关，并与肿瘤存在和/或位置有关。识别COX表达增加的区域也有助于筛查感染。
• US9850183B2
  申请人：——

  公开号：US9850183B2

  公开（公告）日：2017-12-26
• [EN] CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING<br/>[FR] CONJUGUES DERIVES DE MEDICAMENTS ANTI-INFLAMMATOIRES NON STEROIDIENS ET PROCEDES D'UTILISATION DE CEUX-CI DANS L'IMAGERIE
  申请人：REILEY PHARMACEUTICALS INC

  公开号：WO2015200187A1

  公开（公告）日：2015-12-30

  Conjugates derived from non-steroidal anti-inflammatory drugs (NSAIDs) and methods of use thereof are disclosed, useful for, inter alia, identifying and localizing the site of pathology and/or inflammation responsible for the sensation of pain in a patient; for identifying the sites of primary, secondary, benign, or malignant tumors; and for diagnosing infection or confirming or ruling out suspected infection. The NSAID-based conjugates contain an imaging moiety. The conjugates concentrate at sites of increased cyclooxygenase expression, thus revealing the sites of increased prostaglandin production, which is correlated with pain and inflammation, and correlated with tumor presence and/or location. Identifying areas of increased COX expressing can also aid in screening for infections.
• Synthesis, characterization, and activity of metabolites derived from the cyclooxygenase-2 inhibitor rofecoxib (MK-0966, Vioxx™)
  作者：Deborah A Nicoll-Griffith、James A Yergey、Laird A Trimble、José M Silva、Chun Li、Nathalie Chauret、Jacques Yves Gauthier、Erich Grimm、Serge Léger、Patrick Roy、Michel Thérien、Zhaoyin Wang、Peppi Prasit、Robert Zamboni、Robert N Young、Christine Brideau、Chi-Chung Chan、Joseph Mancini、Denis Riendeau

  DOI：10.1016/s0960-894x(00)00538-2

  日期：2000.12

  Metabolites of the COX-2 inhibitor rofecoxib (MK-0966, Vioxx(TM)) were prepared by synthetic or biosynthetic methods. Metabolites include products of oxidation, glucuronidation, reduction and hydrolytic ring opening. Based on an in vitro whole blood assay, none of the known human metabolites of rofecoxib inhibits COX-I nor contributes significantly to the inhibition of COX-2. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Isomeric acetoxy analogues of rofecoxib: A novel class of highly potent and selective cyclooxygenase-2 inhibitors
  作者：M Abdur Rahim、P.N Praveen Rao、Edward E Knaus

  DOI：10.1016/s0960-894x(02)00537-1

  日期：2002.10

  A group of isomers possessing a 2-, 3-, or 4-acetoxy moiety on the 3-phenyl substituent of rofecoxib were synthesized that exhibit highly potent, and selective, COX-2 inhibitory activity that have the potential to acetylate the COX-2 isozyme.