methyl 3-(5-methoxy-2-nitrophenyl)acrylate | 125810-71-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 3-(5-methoxy-2-nitrophenyl)acrylate
• 英文别名: Methyl 3-(5-methoxy-2-nitrophenyl)prop-2-enoate
• CAS: 125810-71-1
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: WWKPRKNINBHMBU-UHFFFAOYSA-N

物化性质

• 沸点：
  402.0±35.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(5-methoxy-2-nitrophenyl)acrylate 在 Wilkinson's catalyst 、 3,5-二乙酰基-1,4-二氢-2,6-二甲基吡啶 、 camphor-10-sulfonic acid 、 [bis(2,2′‐bipyridine)ruthenium(II)](chloride)₂ hexahydrate 、 氢气 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 64.0h， 生成 6-甲氧基-3,4-二氢-2(1H)-喹啉酮
  参考文献：
  名称：

  Reductive Cyclizations of Nitroarenes to Hydroxamic Acids by Visible Light Photoredox Catalysis

  摘要：

  We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated.

  DOI：

  10.1055/s-0033-1338419
• 作为产物：
  描述：

  5-羟基-2-硝基苯甲醛 以 甲苯 为溶剂， 反应 5.0h， 生成 methyl 3-(5-methoxy-2-nitrophenyl)acrylate
  参考文献：
  名称：

  Novel acid-type cyclooxygenase-2 inhibitors: Design, synthesis, and structure–activity relationship for anti-inflammatory drug

  摘要：

  Cyclooxygenase (COX) is a key rate-limiting enzyme for prostaglandin (PG) production cascades in the human body. The mechanisms of both the anti-inflammation effects and the side-effects of traditional COX inhibitors are associated with the existence of two COX isoforms. Thus while COX-1 is predominantly expressed ubiquitously and constitutively, and it serves a housekeeping role in processes such as gastrointestinal (GI) mucosa protection, COX-2 is absent or exhibits a low level of expression in most tissues, and is highly upregulated in response to endotoxin, virus, inflammatory or tissue-injury stimuli/signals, and tumour promoter in the various types of organs, tissues, and cells. Furthermore, COX-2 contribution to PGE(2) and PGI(2) production evokes and sustains systemic or peripheral inflammatory disease, but it is not involved in the COX-1-mediated GI tract events. Also, hypersensitivity of aspirin owing to its inhibitory action against COX-1 is a significant concern clinically. Consequently, highly selective COX-2 inhibitors have been needed for the treatment of inflammatory- and inflammation related-diseases that include pyrexia, inflammation, pain, rheumatoid arthritis, osteoarthritis, and cancers. In this study, a series of novel [2-{[(4-substituted or 4,5-disubstituted)-pyridin-2-yl]carbonyl}-(5- or 6-substituted or 5,6-disubstituted)-1H-indol-3-yl]acetic acid analogues was designed, synthesized, and evaluated to identify potent and selective COX-2 inhibitors as potential agents against inflammatory diseases. As significant findings, the present study clarified unique structure activity relationship of the analogues toward potent and selective COX-2 inhibition in vitro, and identified 2-{6-fluoro-2-[4-methyl-2-pridinyl)carbonyl]-1H-indol-3-yl}acetic acid as a potent and selective COX-2 inhibitor in vitro that demonstrated orally potent anti-inflammation efficacy against carrageenan-induced oedema formation in the foot of SPF/VAF male SD rats as a peripheral inflammation model in vivo. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.053

文献信息

• 2,6-Methano-1,3-benzodiazocines, a process for their preparation and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0335292A2

  公开（公告）日：1989-10-04

  The present invention relates to compounds of the formula I wherein R¹ is hydrogen, loweralkyl, loweralkylcarbonyl, loweralkylaminocarbonyl, cycloalkylaminocarbonyl, loweralkoxycarbonyl, aryloxycarbonyl, or arylaminocarbonyl; R² and R³ are independently hydrogen, loweralkyl, cycloalkylloweralkyl, arylloweralkyl, or loweralkenyl; R⁴ and R⁵ are independently hydrogen or loweralkyl; Y is halogen, loweralkyl, nitro, amino, loweralkylcarbonylamino, arylcarbonylamino, formyl or loweralkylaminocarbonyl; and n is an integer having a value of zero or 1; the geometrical isomers, optical antipodes or pharmaceutically acceptable acid addition salts thereof, and to a process for their preparation. The compound have analgesic acetivities, and can, there­fore, be used as medicaments.

  本发明涉及式 I 的化合物 其中R¹是氢、低级烷基、低级烷基羰基、低级烷基氨基羰基、环烷基氨基羰基、低级烷氧基羰基、芳氧基羰基或芳基氨基羰基；R²和R³独立地是氢、低级烷基、环烷基低级烷基、芳基低级烷基或低级烯基；R⁴和R⁵独立地是氢或低级烷基；Y 是卤素、低级烷基、硝基、氨基、低级烷基羰基氨基、芳基羰基氨基、甲酰基或低级烷基氨基羰基；n 是数值为 0 或 1 的整数；其几何异构体、光学对映异构体或药学上可接受的酸加成盐，以及其制备方法。 这些化合物具有镇痛乙酰活性，因此可用作药物。
• Bicycliccarbonyl indole compounds as anti-inflammatory/analgesic agents and as COX-2 inhibitors
  申请人：PFIZER INC.

  公开号：EP1065204A1

  公开（公告）日：2001-01-03

  This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein A is C 1-6alkylene or -NR1-; Z is C(=L)R2, or SO2R3; U is CH or N; W and Y are independently selected from - CH2-, O, S and -N-R1; m is 1, 2 or 3; q and r are independently 0, 1 or 2; X is independently selected from halogen, C 1-4alkyl, halo-substituted C 1-4 alkyl, hydroxy, C 1-4alkoxy, halo-substituted C 1-4 alkoxy or the like; n is 1 or 2; L is oxygen or sulfur; R1 is hydrogen or C 1-4 alkyl; R2 is hydroxy, C1-6alkyl, halo-substituted C 1-6 alkyl, C 1-6 alkoxy, halo-substitutued C 1-6 alkoxy, C 3-7 cycloalkoxy, C 1-4 alkyl(C 3-7 cycloalkoxy), -NR4R5 or the like; R3 is C 1-6 alkyl or halo-substituted C 1-6 alkyl; and R4 and R5 are independently selected from hydrogen, C 1-6alkyl and halo-substituted C 1-6alkyl. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.

  本发明提供了下式化合物： 或其药学上可接受的盐 其中A为C 1-6烷基或-NR1-；Z为C(＝L)R2或SO2R3；U为CH或N；W和Y独立地选自-CH2-、O、S和-N-R1；m为1、2或3；q和r独立地为0、1或2；X独立地选自卤素、C 1-4烷基、卤代C 1-4烷基、羟基、C 1-4烷氧基、卤代C 1-4烷氧基或类似物；n 是 1 或 2；L 是氧或硫；R1 是氢或 C 1-4 烷基；R2 是羟基、C1-6 烷基、卤代 C 1-6 烷基、C 1-6 烷氧基、卤代 C 1-6 烷氧基、C 3-7 环烷氧基、C 1-4 烷基（C 3-7 环烷氧基）、-NR4R5 或类似物；R3 是 C 1-6 烷基或卤代 C 1-6 烷基；以及 R4 和 R5 独立选自氢、C 1-6 烷基和卤代 C 1-6 烷基。 本发明还提供了一种药物组合物，可用于治疗前列腺素被认为是病原体的病症。
• 2,3-SUBSTITUTED INDOLE COMPOUNDS AS COX-2 INHIBITORS
  申请人：PFIZER INC.

  公开号：EP1045833B1

  公开（公告）日：2005-11-02
• US5010083A
  申请人：——

  公开号：US5010083A

  公开（公告）日：1991-04-23
• US5097033A
  申请人：——

  公开号：US5097033A

  公开（公告）日：1992-03-17