2-(2-fluoropyridin-4-yl)acetic acid | 1000518-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2-fluoropyridin-4-yl)acetic acid
• CAS: 1000518-05-7
• 化学式: C₇H₆FNO₂
• mdl: MFCD09925241
• 分子量: 155.129
• InChiKey: XSZBBYRBRYUCCG-UHFFFAOYSA-N

物化性质

• 熔点：
  118-123°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-4'-氰基苯乙酮 、 2-(2-fluoropyridin-4-yl)acetic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.66h， 生成 3-(2-fluropyridin-4-yl)-4-(4-cyanophenyl)furan-2(5H)-one
  参考文献：
  名称：

  Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors

  摘要：

  We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structureactivity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC(50)s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.

  DOI：

  10.1021/ml500344j
• 作为产物：
  描述：

  ethyl 2-(2-fluororopyridin-4-yl)acetate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以65.2%的产率得到2-(2-fluoropyridin-4-yl)acetic acid
  参考文献：
  名称：

  [EN] LABELLED COUMARIN DERIVATIVES
  [FR] DÉRIVÉS DE COUMARINE MARQUÉS

  摘要：

  本发明涉及与MAO-A相比具有选择性结合MAO-B的化合物。该发明还提供这些化合物的放射性版本，以及用于合成这些放射性化合物的前体化合物。本发明的放射性化合物可用于体内成像应用。

  公开号：

  WO2016097339A1

文献信息

• 8-Substituted isoquinoline derivative and the use thereof
  申请人：Kaneko Shunsuke

  公开号：US20100261701A1

  公开（公告）日：2010-10-14

  The present invention relates to a compound represented by the following formula (1): wherein D 1 , A 1 , D 2 , R 1 , D 3 , and R 2 each have the same meaning as defined in the present specification or a salt thereof. The compound represented by the formula (1) or a salt thereof has an IKKβ inhibiting activity and the like and is useful for the prevention and/or treatment of IKKβ-associated diseases or symptoms and the like.

  本发明涉及一种由以下式（1）表示的化合物： 其中D1，A1，D2，R1，D3和R2分别具有与本说明书中定义的相同含义或其盐。由式（1）表示的化合物或其盐具有IKKβ抑制活性等，对于预防和/或治疗IKKβ相关疾病或症状等方面是有用的。
• Inhibitors of the acetyltransferase domain of N-acetylglucosamine-1-phosphate-uridylyltransferase/glucosamine-1-phosphate-acetyltransferase (GlmU). Part 2: Optimization of physical properties leading to antibacterial aryl sulfonamides
  作者：Suzanne S. Stokes、Robert Albert、Ed T. Buurman、Beth Andrews、Adam B. Shapiro、Oluyinka M. Green、Andrew R. McKenzie、Ludovic R. Otterbein

  DOI：10.1016/j.bmcl.2012.10.003

  日期：2012.12

  A previously described aryl sulfonamide series, originally found through HTS, targets GlmU, a bifunctional essential enzyme involved in bacterial cell wall synthesis. Using structure-guided design, the potency of enzyme inhibition was increased in multiple isozymes from different bacterial species. Unsuitable physical properties (low Log D and high molecular weight) of those compounds prevented them from entering the cytoplasm of bacteria and inhibiting cell growth. Further modifications described herein led to compounds that possessed antibacterial activity, which was shown to occur through inhibition of GlmU. The left-hand side amide and the right-hand side sulfonamides were modified such that enzyme inhibitory activity was maintained (IC50 <0.1 mu M against GlmU isozymes from Gram-negative organisms), and the lipophilicity was increased giving compounds with Log D -1 to 3. Antibacterial activity in an efflux-pump deficient mutant of Haemophilus influenzae resulted for compounds such as 13. (C) 2012 Elsevier Ltd. All rights reserved.
• US8299055B2
  申请人：——

  公开号：US8299055B2

  公开（公告）日：2012-10-30
• [EN] 8-SUBSTITUTED ISOQUINOLINE DERIVATIVE AND USE THEREOF<br/>[FR] DÉRIVÉ D'ISOQUINOLÉINE SUBSTITUÉ EN POSITION 8 ET SON UTILISATION
  申请人：ASAHI KASEI PHARMA CORP

  公开号：WO2010038465A1

  公开（公告）日：2010-04-08

  　本発明は、下記式（１）： ［式（１）中、Ｄ１、Ａ１、Ｄ２、Ｒ１、Ｄ３及びＲ２は、それぞれ、本明細書中で定義される通りである］で示される化合物又はその塩に関する。式（１）で示される化合物又はその塩は、ＩＫＫβ阻害活性等を有し、ＩＫＫβに関連する疾患又は症状の予防及び／又は治療等に有用である。
• Design of Fluorine-Containing 3,4-Diarylfuran-2(5<i>H</i>)-ones as Selective COX-1 Inhibitors
  作者：Md. Jashim Uddin、Anna V. Elleman、Kebreab Ghebreselasie、Cristina K. Daniel、Brenda C. Crews、Kellie D. Nance、Tamanna Huda、Lawrence J. Marnett

  DOI：10.1021/ml500344j

  日期：2014.11.13

  We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structureactivity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC(50)s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.