4-[3-(4-氟苯基)-5-甲基-1,2-恶唑-4-基]苯磺酰胺 | 181696-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[3-(4-氟苯基)-5-甲基-1,2-恶唑-4-基]苯磺酰胺
• 英文名称: 4-[3-(4-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide
• 英文别名: 4-[3-(4-fluorophenyl)-5-methyl-4-isoxazolyl]benzenesulfonamide；4-(3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)benzenesulfonamide；4-[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide
• CAS: 181696-40-2
• 化学式: C₁₆H₁₃FN₂O₃S
• 分子量: 332.355
• InChiKey: GVLVIZRBGRSLTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氟苯乙酮肟 在 四(三苯基膦)钯 正丁基锂 、 硫酸 、 溴 、 sodium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 正己烷 为溶剂， 反应 50.5h， 生成 4-[3-(4-氟苯基)-5-甲基-1,2-恶唑-4-基]苯磺酰胺
  参考文献：
  名称：

  Convenient Approach to 3,4-Diarylisoxazoles Based on the Suzuki Cross-Coupling Reaction

  摘要：

  DOI：

  10.1002/1615-4169(200212)344:10<1146::aid-adsc1146>3.0.co;2-1

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。
• Substituted isoxazoles for the treatment of inflammation
  申请人：G.D. Searle & Co.

  公开号：EP1223167A3

  公开（公告）日：2002-08-07

  A class of substituted isoxazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula (III) wherein R7 is selected from hydroxyl, lower alkyl, carboxyl, halo, lower carboxylalkyl, lower alkoxycarbonylalkyl, lower alkoxyalkyl, lower carboxyalkoxyalkyl, lower haloalkyl, lower haloalkylsulfonyloxy, lower hydroxyalkyl, lower aryl (hydroxylalkyl), lower carboxyaryloxyalkyl, lower alkoxycarbonylaryloxyalkyl, lower cycloalkyl, lower cycloalkylalkyl, and lower aralkyl; and wherein R8 is one or more radicals independently selected from hydrido, lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, aminosulfonyl, and lower alkylthio; or a pharmaceutically-acceptable salt thereof.

  描述了一类取代的异氧氮杂环化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由公式（III）定义，其中R7从羟基，低烷基，羧基，卤素，低羧基烷基，低烷氧羰基烷基，低烷氧基烷基，低羧氧基烷氧基，低卤代烷基，低卤代烷基磺酰氧基，低羟基烷基，低芳基（羟基烷基），低羧基芳氧基烷基，低烷氧羰基芳氧基烷基，低环烷基，低环烷基烷基和低芳基烷基中选择；R8是一个或多个基团，独立地从氢化物，低烷基亚砜基，低烷基，氰基，羧基，低烷氧羰基，低卤代烷基，羟基，低羟基烷基，低卤代氧基，氨基，低烷基氨基，低芳基氨基，低氨基烷基，硝基，卤素，低烷氧基，氨基磺酰基和低烷硫基中独立选择；或其药学上可接受的盐。
• Novel valdecoxib derivatives by ruthenium(<scp>ii</scp>)-promoted 1,3-dipolar cycloaddition of nitrile oxides with alkynes – synthesis and COX-2 inhibition activity
  作者：Silvia Roscales、Nicole Bechmann、Daniel Holger Weiss、Martin Köckerling、Jens Pietzsch、Torsten Kniess

  DOI：10.1039/c7md00575j

  日期：——

  Novel valdecoxib-based cyclooxygenase-2 inhibitors were synthesized in one step via 1,3-dipolar cycloaddition of nitrile oxides with a series of eleven aryl alkynes, six of them described for the first time. Application of Ru(II)-catalysis leads preferably to the formation of the 3,4-diaryl-substituted isoxazoles, while under thermal heating with base the 3,5-diaryl substitution pattern is favoured

  通过将腈与一系列十一个芳基炔烃进行1,3-偶极环加成反应，一步合成了一种新的基于valdecoxib的环氧合酶-2抑制剂，其中六个首次被描述。Ru（II）催化的应用优选导致3，4-二芳基取代的异恶唑的形成，而在与碱一起热加热下，有利于3，5-二芳基取代的模式。具有小的取代基（H和Me）的新的3,4-二芳基取代的异恶唑显示出高的COX-2抑制亲和力（IC 50= 0.042–0.073μM）和优异的选择性（COX-2 SI> 2000）。相反，3，5-二芳基取代的化合物几乎没有表现出COX活性。4-氟苯基取代基的引入导致保留了较高的COX-2亲和力，使这些化合物与可行的一步反应一起有望成为开发氟18标记的放射性示踪剂的候选物。
• [EN] SUBSTITUTED ISOXAZOLES FOR THE TREATMENT OF INFLAMMATION<br/>[FR] ISOXAZOLES SUBSTITUES UTILISABLES DANS LE TRAITEMENT D'INFLAMMATIONS
  申请人：G.D. SEARLE & CO.

  公开号：WO1996025405A1

  公开（公告）日：1996-08-22

  (EN) A class of substituted isoxazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula (III) whrein R7 is selected from hydroxyl, lower alkyl, carboxyl, halo, lower carboxyalkyl, lower alkoxycarbonylalkyl, lower alkoxyalkyl, lower carboxyalkoxyalkyl, lower haloalkyl, lower haloalkylsulfonyloxy, lower hydroxylalkyl, lower aryl (hydroxylalkyl), lower carboxyaryloxyalkyl, lower alkoxycarbonylaryloxyalkyl, lower cycloalkyl, lower cycloalkylalkyl, and lower aralkyl; and wherein R8 is one or more radicals independently selected from hydrido, lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, aminosulfonyl, and lower alkylthio; or a pharmaceutically-acceptable salt thereof.(FR) Cette invention concerne une classe de composés d'isoxazolyle substitué pouvant être utilisés dans le traitement d'inflammations et de troubles liés à des inflammations. Les composés suscitant un intérêt particulier sont représentés par la formule (III), dans laquelle R7 est choisi parmi hydroxyle, alkyle inférieur, carboxyle, halo, carboxyalkyle inférieur, alcoxycarbonylalkyle inférieur, alcoxyalkyle inférieur, carboxyalcoxyalkyle inférieur, haloalkyle inférieur, haloalkylsulfonyloxy inférieur, hydroxylalkyle inférieur, aryle(hydroxylalkyle) inférieur, carboxyaryloxyalkyle inférieur, alcoxycarbonylaryloxyalkyle inférieur, cycloalkyle inférieur, cycloalkylalkyle inférieur et aralkyle inférieur; et R8 représente un ou plusieurs radicaux choisis indépendamment parmi hydrido, alkylsulfinyle inférieur, alkyle inférieur, cyano, carboxyle, alcoxycarbonyle inférieur, haloalkyle inférieur, hydroxyle, hydroxyalkyle inférieur, haloalcoxy inférieur, amino, alkylamino inférieur, arylamino inférieur, aminoalkyle inférieur, nitro, halo, alcoxy inférieur, aminosulfonyle et alkylthio inférieur. Cette invention concerne également les sels de ces composés acceptables sur le plan pharmaceutique.

  本发明涉及一类取代的异噁唑基化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由公式（III）定义，其中R7选自羟基，较低的烷基，羧基，卤素，较低的羧基烷基，较低的烷氧羰基烷基，较低的烷氧基烷基，较低的羧氧基烷氧基烷基，较低的卤代烷基，较低的卤代烷基磺酰氧基，较低的羟基烷基，较低的芳基（羟基烷基），较低的羧基芳氧基烷基，较低的烷氧羰基芳氧基烷基，较低的环烷基，较低的环烷基烷基和较低的芳基烷基；R8是一个或多个基团，独立选择自氢，较低的烷基亚砜基，较低的烷基，氰基，羧基，较低的烷氧羰基，较低的卤代烷基，羟基，较低的羟基烷基，较低的卤代烷氧基，氨基，较低的烷基氨基，较低的芳基氨基，较低的氨基烷基，硝基，卤素，较低的烷氧基，氨基磺酰基和较低的烷硫基；或其药学上可接受的盐。
• CYCLOOXYGENASE-2 SELECTIVE AGENTS USEFUL AS IMAGING PROBES AND RELATED METHODS
  申请人：Toyokuni Tatsushi

  公开号：US20070286801A1

  公开（公告）日：2007-12-13

  This invention provides novel cyclooxygenase-2 selective agents that are particularly useful as imaging probes in non-invasive imaging techniques, such as PET and SPECT. Preferred cyclooxygenase-2 selective agents inhibit cyclooxygenase-2 activity with greater potency and specificity than conventional cyclooxygenase-2 inhibitors. Other aspects of the invention include pharmaceutical compositions including the cyclooxygenase-2 selective agents as well as methods for detecting and/or inhibiting cyclooxygenase-2. These methods are particularly useful for diagnosing and treating disorders, such as inflammation, which is characterized by elevated cyclooxygenase-2 levels.

  本发明提供了新颖的环氧合酶-2选择性药物，特别适用于非侵入性成像技术，如PET和SPECT的成像探针。优选的环氧合酶-2选择性药物比传统的环氧合酶-2抑制剂具有更强的效力和特异性。本发明的其他方面包括包括环氧合酶-2选择性药物的制药组合物以及检测和/或抑制环氧合酶-2的方法。这些方法特别适用于诊断和治疗疾病，如以升高的环氧合酶-2水平为特征的炎症。