methyl (E)-3-(4′-fluoro-2′-nitrophenyl)acrylate | 231297-56-6

• 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 (E)-3-(4′-fluoro-2′-nitrophenyl)acrylate
• 英文别名: methyl (E)-3-(4-fluoro-2-nitrophenyl)prop-2-enoate；methyl (2E)-3-(4-fluoro-2-nitrophenyl)acrylate；methyl trans-(4-fluoro-2-nitro)cinnamate
• CAS: 231297-56-6
• 化学式: C₁₀H₈FNO₄
• 分子量: 225.176
• InChiKey: OAKIRMGSGSZOKF-HWKANZROSA-N

物化性质

• 沸点：
  341.5±32.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(4′-fluoro-2′-nitrophenyl)acrylate 在 氢气 作用下， 40.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以70%的产率得到7-氟-3,4-二氢-2(1h)-喹啉酮
  参考文献：
  名称：

  通过稳定的芳基重氮盐形成苯胺的多键串联反应：一锅合成3,4-二氢喹啉-2-酮

  摘要：

  开发了一种快速有效的一锅串联方法，该方法可通过稳定的芳基重氮甲苯磺酸盐从易于获得的苯胺生成Heck偶联产物。温和而简单的步骤涉及使用聚合物负载的亚硝酸盐试剂和对羟基苯甲酸酯快速形成芳基重氮盐-甲苯磺酸，然后与丙烯酸酯和苯乙烯进行无碱Heck-Matsuda偶联。使用2-硝基苯胺作为底物，将一锅串联方法扩展到直接合成3,4-二氢喹啉-2-酮。在这种情况下，经过重氮化和Heck-Matsuda偶联生成肉桂酸甲酯，添加氢气并再利用钯催化剂还原硝基和烯烃氢化，可有效形成3,4-二氢喹啉-2-酮。 。一锅四步法的合成效用通过基于喹啉酮的钠离子通道调节剂的五锅法合成得到了证明。

  DOI：

  10.1021/acs.joc.8b01910
• 作为产物：
  描述：

  4-氟-2-硝基苯胺 、 丙烯酸甲酯（MA） 在 palladium diacetate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以78%的产率得到methyl (E)-3-(4′-fluoro-2′-nitrophenyl)acrylate
  参考文献：
  名称：

  通过稳定的芳基重氮盐形成苯胺的多键串联反应：一锅合成3,4-二氢喹啉-2-酮

  摘要：

  开发了一种快速有效的一锅串联方法，该方法可通过稳定的芳基重氮甲苯磺酸盐从易于获得的苯胺生成Heck偶联产物。温和而简单的步骤涉及使用聚合物负载的亚硝酸盐试剂和对羟基苯甲酸酯快速形成芳基重氮盐-甲苯磺酸，然后与丙烯酸酯和苯乙烯进行无碱Heck-Matsuda偶联。使用2-硝基苯胺作为底物，将一锅串联方法扩展到直接合成3,4-二氢喹啉-2-酮。在这种情况下，经过重氮化和Heck-Matsuda偶联生成肉桂酸甲酯，添加氢气并再利用钯催化剂还原硝基和烯烃氢化，可有效形成3,4-二氢喹啉-2-酮。 。一锅四步法的合成效用通过基于喹啉酮的钠离子通道调节剂的五锅法合成得到了证明。

  DOI：

  10.1021/acs.joc.8b01910

文献信息

• [EN] DIACYLGLYCEROL KINASE MODULATING COMPOUNDS<br/>[FR] COMPOSÉS MODULANT LA DIACYLGLYCÉROL KINASE
  申请人：CARNA BIOSCIENCES INC

  公开号：WO2021130638A1

  公开（公告）日：2021-07-01

  The present disclosure provides diacylglycerol kinase modulating compounds, and pharmaceutical compositions thereof, for treating cancer, including solid tumors, and viral infections, such as HIV or hepatitis B virus infection. The compounds can be used alone or in combination with other agents.

  本公开提供了调节二酰基甘油激酶的化合物以及用于治疗癌症（包括实体瘤）和病毒感染（如HIV或乙型肝炎病毒感染）的药物组合物。这些化合物可以单独使用或与其他药物联合使用。
• 2,3-substituted indole compounds as anti-inflammatory and analgesic agents
  申请人：——

  公开号：US06608070B1

  公开（公告）日：2003-08-19

  This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein Z is OH, C1-6 alkoxy, —NR2R3 or heterocycle; Q is selected from the following: (a) an optionally substituted phenyl, (b) an optionally substituted 6-membered monocyclic aromatic group containing one, two, three or four nitrogen atom(s), (c) an optionally substituted 5-membered monocyclic aromatic group containing one heteroatom selected from O, S and N and optionally containing one, two or three nitrogen atom(s) in addition to said heteroatom, (d) an optionally substituted C3-7 cycloalkyl and (e) an optionally substituted benzo-fuzed heterocycle; R1 is hydrogen, C1-4 alkyl or halo; R2 and R3 are independently hydrogen, OH, C1-4 alkoxy, C1-4 alkyl or C1-4 alkyl substituted with halo, OH, C1-4 alkoxy or CN; X is independently selected from H, halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino and CN; and n is 0, 1, 2, 3 and 4. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.

  这项发明提供了以下式的化合物： 或其药学上可接受的盐，其中Z为OH、C1-6烷氧基、—NR2R3或杂环；Q从以下中选择：(a) 可选择取代的苯基，(b) 可选择取代的含有一个、两个、三个或四个氮原子的6-成员单环芳基，(c) 可选择取代的含有O、S和N中选择的一个杂原子的5-成员单环芳基，并且除所述杂原子外还可选择含有一个、两个或三个氮原子，(d) 可选择取代的C3-7环烷基和(e) 可选择取代的苯并噻吩杂环；R1为氢、C1-4烷基或卤素；R2和R3独立地为氢、OH、C1-4烷氧基、C1-4烷基或用卤素、OH、C1-4烷氧基或CN取代的C1-4烷基；X独立地从H、卤素、C1-4烷基、卤素取代的C1-4烷基、OH、C1-4烷氧基、卤素取代的C1-4烷氧基、C1-4烷基硫醚、NO2、NH2、二-(C1-4烷基)氨基和CN中选择；n为0、1、2、3和4。 这项发明还提供了一种用于治疗前列腺素参与的医疗状况的药物组合物。
• [EN] HETEROCYCLIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS UTILISATIONS
  申请人：THE TRUSTEES OF PRINCETON UNIVERISTY

  公开号：WO2021151062A1

  公开（公告）日：2021-07-29

  Provided herein are novel heterocyclic compounds, for example, compounds having Formula I, I-P, II, lI-P, or III. Also provided herein are pharmaceutical compositions comprising the compounds and methods of using the same, for example, in inhibiting aldehyde dehydrogenases and/or for treating various cancers, cancer metastasis, type 2 diabetes, pulmonary arterial hypertension (PAH) or neointimal hyperplasia (NIH).

  本文提供了新颖的杂环化合物，例如具有I、I-P、II、II-P或III式的化合物。本文还提供了包含这些化合物的药物组合物以及使用这些组合物的方法，例如用于抑制醛脱氢酶和/或治疗各种癌症、癌症转移、2型糖尿病、肺动脉高压（PAH）或新生内膜增生（NIH）。
• Novel acid-type cyclooxygenase-2 inhibitors: Design, synthesis, and structure–activity relationship for anti-inflammatory drug
  作者：Shigeo Hayashi、Naomi Ueno、Akio Murase、Yoko Nakagawa、Junji Takada

  DOI：10.1016/j.ejmech.2012.01.053

  日期：2012.4

  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.
• Tetrazolylalkyl indole compounds as anti-inflammatory and analgesic agents
  申请人：PFIZER INC.

  公开号：EP1065206B1

  公开（公告）日：2002-10-09