3-(4-methoxyphenyl)-4-[4-(methylsulfonyl)phenyl]-2,5-dihydrofuran-2-one | 162011-89-4

• 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-(4-methoxyphenyl)-4-[4-(methylsulfonyl)phenyl]-2,5-dihydrofuran-2-one
• 英文别名: 3-(4-Methoxyphenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone；4-(4-methoxyphenyl)-3-(4-methylsulfonylphenyl)-2H-furan-5-one
• CAS: 162011-89-4
• 化学式: C₁₈H₁₆O₅S
• 分子量: 344.388
• InChiKey: WCNUKLPROMYSTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-4-[4-(methylsulfonyl)phenyl]-2,5-dihydrofuran-2-one 在 吡啶盐酸盐 作用下， 反应 1.0h， 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
• 作为产物：
  描述：

  4-甲硫基苯乙酮 在 Oxone 、 溴 、 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 20.5h， 生成 3-(4-methoxyphenyl)-4-[4-(methylsulfonyl)phenyl]-2,5-dihydrofuran-2-one
  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。
• 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。
• Nontoxic combretafuranone analogues with high in vitro antibacterial activity
  作者：P. Horký、M. Voráčová、K. Konečná、D. Sedlák、P. Bartůněk、J. Vacek、J. Kuneš、M. Pour

  DOI：10.1016/j.ejmech.2017.11.078

  日期：2018.1

  Hydroxymethylation of furanone C5 knocked out cytotoxic effects (up to 40 μM) while maintaining significant activity against Staphylococcus strains in some derivatives. MIC95 of the most promising compound, 3-(4-bromophenyl)-5,5-bis(hydroxymethyl)-4-(4-methylphenyl)-2,5-dihydrofuran-2-one against S. aureus strain ATCC 6538 was 0.98 μM (0.38 μg/mL) and 3.9 μM (1.52 μg/mL) after 24 and 48 h, respectively

  制备了与康布雷他汀A-4和抗真菌5-（酰氧基甲基）-3-（卤代苯基）-2,5-二氢呋喃-2-酮有关的32个3,4-二苯基呋喃酮的文库。评估了对一组癌细胞和正常细胞系的细胞毒性作用以及抗感染活性，并通过对caspase 3和7活化测试的数据对数据进行了补充，例如在某些卤代类似物中观察到了高细胞毒性。3-（3,4-二氯苯基）-4-（4-甲基苯基）-2,5-二氢呋喃-2-酮，IC 50为0.12-0.23μM，但该化合物对非恶性对照细胞也具有高毒性。更重要的是，显着的抗菌活性表明G +在3,4-二芳基呋喃酮类化合物中首次发现了选择性。呋喃酮C5的羟甲基化作用消除了细胞毒性作用（最高40μM），同时在某些衍生物中对葡萄球菌菌株保持了显着的活性。最有前途的化合物对金黄色葡萄球菌ATCC 6538的3-（4-溴苯基）-5,5-双（羟甲基）-4-（4-甲基苯基）-2,5-二氢呋喃-2-酮的MIC 95为24小时和48小时后分别为0
• Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their Solvatochromism, AIE Activity, Mechanochromism, and COX-2-Targeted Bioimaging
  作者：Lijun Xie、Renfu Li、Biyun Zheng、Zuoxu Xie、Xuefen Fang、Yanqi Wang、Gregory D. Cuny、Zhenli Li、Bin Lin、Xueyuan Chen、Ming Hu

  DOI：10.1021/acs.analchem.1c01978

  日期：2021.9.7

  attractive fluorescence properties, such as tunable blue-red emission, solvatochromism, aggression-induced emission behavior, and mechanochromism. Notably, the emission of 2a16 can be switched between green-yellow in the crystalline state and red-orange in the amorphous state by grinding and fuming treatments. Furthermore, the highly fluorescent compound 2a16 (Φf = 0.94 in powder) displayed a much stronger

  Cyclooxygenase-2 (COX-2) 荧光探针是用于癌症早期诊断的有前途的工具。传统上，COX-2 探针的设计是通过一个灵活的接头连接两个部分，一个荧光团和一个 COX-2 结合单元。在此，通过整合方法将结合单元和荧光团合二为一，通过对罗非昔布的一步修饰，开发了一类新的 COX-2 特异性荧光探针。其中，几种新的罗非昔布类似物不仅表现出仍然有效的 COX-2 结合能力，而且还表现出有吸引力的荧光特性，如可调蓝红光发射、溶剂化变色、攻击诱导发射行为和机械致变色。值得注意的是，2a16的排放通过研磨和熏蒸处理，可以在结晶态的绿黄色和非晶态的红橙色之间切换。此外，与COX-2 表达最低的 RAW264.7 正常细胞相比，高荧光化合物2a16（粉末中的Φ f = 0.94）在过度表达 COX-2 的 HeLa 癌细胞中显示出更强的 COX-2 荧光成像。最重要的是，2a16可以通过靶向
• ACQ-to-AIE Transformation by Regioisomerization of Rofecoxib Derivatives for Developing Novel Mechanochromic and Acidochromic Materials
  作者：Wei Liu、Zexin Wang、Renfu Li、Liwei Chen、Xiang Lin、Shitao Sun、Zhenli Li、Jinle Hao、Bin Lin、Xinli Wang、Lijun Xie

  DOI：10.1016/j.molstruc.2022.132728

  日期：2022.7

  Design and syntheses of aggregation-induced emission (AIE) luminescent materials have attracted persistent attention in recent years. Among the various strategies to design novel AIE-active materials, conversion from aggregation-caused quenching (ACQ) to AIE is one of the most efficient because ACQ molecules are capable of being fluorescent in solution already, just not in the aggregated state. In

  近年来，聚集诱导发射（AIE）发光材料的设计和合成一直受到关注。在设计新型 AIE 活性材料的各种策略中，从聚集引起的猝灭 (ACQ) 到 AIE 的转换是最有效的方法之一，因为 ACQ 分子已经能够在溶液中发出荧光，而不是处于聚集状态。在这项研究中，ACQ 到 AIE 的转化是通过两种罗非昔布衍生物p-PDRF和o-PDRF的区域异构化实现的。对于这两种化合物，哌啶基团位于对位的p-PDRF表现出典型的 ACQ 行为，而o-PDRF当哌啶基团重新定位到邻位时，显示出特征性的 AIE 活性。单晶X射线分析表明，不同状态下的相反荧光行为主要是由于区域异构化导致的不同结构构象和不同的分子堆积模式。此外，o-PDRF还表现出明显的溶剂化变色、机械变色和酸变色，具有可逆的多刺激行为。粉末X射线衍射分析表明，扭曲结构的平面化和晶体结构的破坏是调谐固态荧光的原因。总之，数据表明，基于罗非昔布支架的哌啶