2-(5-Formyl-2-methoxyphenoxy)acetamide | 692282-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(5-Formyl-2-methoxyphenoxy)acetamide
• CAS: 692282-22-7
• 化学式: C₁₀H₁₁NO₄
• mdl: MFCD02257680
• 分子量: 209.202
• InChiKey: YEDZZTCCFUMXLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-噻唑烷二酮 、 2-(5-Formyl-2-methoxyphenoxy)acetamide 在 哌啶 作用下， 以 乙醇 为溶剂， 以54%的产率得到2-[5-(2,4-dioxothiazolidin-5-ylidenemethyl)-2-methoxyphenoxy]acetamide
  参考文献：
  名称：

  Structure–activity relationships and molecular modelling of new 5-arylidene-4-thiazolidinone derivatives as aldose reductase inhibitors and potential anti-inflammatory agents

  摘要：

  A series of 5-(carbamoylmethoxy)benzylidene-2-oxo/thioxo-4-thiazolidinone derivatives (6-9) were synthesized as inhibitors of aldose reductase (AR), enzyme which plays a crucial role in the development of diabetes complications as well as in the inflammatory processes associated both to diabetes mellitus and to other pathologies.In vitro inhibitory activity indicated that compounds 6-9a-d were generally good AR inhibitors. Acetic acid derivatives 8a-d and 9a-d were shown to be the best enzyme inhibitors among the tested compounds endowed with significant inhibitory ability levels reaching submicromolar IC50 values.Moreover, some representative AR inhibitors (7a, 7c, 9a, 9c, 9d) were assayed in cultures of human keratinocytes in order to evaluate their capability to reduce NF-kB activation and iNOS expression. Compound 9c proved to be the best derivative endowed with both interesting AR inhibitory effectiveness and ability to reduce NF-kB activation and iNOS expression.Molecular docking and molecular dynamics simulations were undertaken to investigate the binding modes of selected compounds into the active site of AR in order to rationalize the inhibitory effectiveness of these derivatives. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.003
• 作为产物：
  描述：

  异香兰素 、 氯乙酰胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-(5-Formyl-2-methoxyphenoxy)acetamide
  参考文献：
  名称：

  Structure–activity relationships and molecular modelling of new 5-arylidene-4-thiazolidinone derivatives as aldose reductase inhibitors and potential anti-inflammatory agents

  摘要：

  A series of 5-(carbamoylmethoxy)benzylidene-2-oxo/thioxo-4-thiazolidinone derivatives (6-9) were synthesized as inhibitors of aldose reductase (AR), enzyme which plays a crucial role in the development of diabetes complications as well as in the inflammatory processes associated both to diabetes mellitus and to other pathologies.In vitro inhibitory activity indicated that compounds 6-9a-d were generally good AR inhibitors. Acetic acid derivatives 8a-d and 9a-d were shown to be the best enzyme inhibitors among the tested compounds endowed with significant inhibitory ability levels reaching submicromolar IC50 values.Moreover, some representative AR inhibitors (7a, 7c, 9a, 9c, 9d) were assayed in cultures of human keratinocytes in order to evaluate their capability to reduce NF-kB activation and iNOS expression. Compound 9c proved to be the best derivative endowed with both interesting AR inhibitory effectiveness and ability to reduce NF-kB activation and iNOS expression.Molecular docking and molecular dynamics simulations were undertaken to investigate the binding modes of selected compounds into the active site of AR in order to rationalize the inhibitory effectiveness of these derivatives. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.003

文献信息

• An investigation on 4-thiazolidinone derivatives as dual inhibitors of aldose reductase and protein tyrosine phosphatase 1B, in the search for potential agents for the treatment of type 2 diabetes mellitus and its complications
  作者：Rosanna Maccari、Antonella Del Corso、Paolo Paoli、Ilenia Adornato、Giulia Lori、Francesco Balestri、Mario Cappiello、Alexandra Naß、Gerhard Wolber、Rosaria Ottanà

  DOI：10.1016/j.bmcl.2018.10.024

  日期：2018.12

  considered a promising alternative to combinations of drugs, when monotherapy results to be unsatisfactory. In this work, compounds 1–17 were synthesized and in vitro evaluated as DMLs directed to aldose reductase (AR) and protein tyrosine phosphatase 1B (PTP1B), two key enzymes involved in different events which are critical for the onset and progression of type 2 DM and related pathologies. Out of the

  当单药治疗效果不理想时，设计出的多种配体（DMLs）被开发为可同时调节参与多种因素的多种病因，例如糖尿病（DM）的发病机制的选定靶标，被认为是药物组合的一种有前途的替代方法。在这项工作中，化合物1 - 17合成和体外评价涉及醛糖还原酶（AR）和蛋白酪氨酸磷酸酶1B（PTP1B）的DML，参与其是2型的发病和进展的关键不同事件的两个关键酶糖尿病和相关病理。在测试的4-噻唑烷酮衍生物中，化合物12和16表现出强力的AR抑制作用以及对PTP1B的有趣抑制作用，可被认为是进一步优化和平衡双重抑制作用的先导化合物。此外，几个结构部分被确定为可用于通过结合两种靶酶的非催化区域同时抑制人AR和PTP1B的特征。
• Synthesis, biological evaluation, and molecular docking studies of thiazolo[4,5‐ <i>b</i> ]pyridin‐5‐ones as antimicrobial agents
  作者：Victor Kartsev、Athina Geronikaki、Boris Lichitsky、Andrey Komogortsev、Anthi Petrou、Marija Ivanov、Jasmina Glamočlija、Marina Soković

  DOI：10.1002/jhet.4491

  日期：2022.9

  Herein we report the design and synthesis of thiazolo[4,5-b]pyridin-5-ones and evaluation of their antimicrobial activity. The design was based on a molecular hybridization approach. Evaluation of their antibacterial activity revealed that these compounds generally showed moderate antibacterial activity. The best activity was achieved for compound 4p with MIC/MBC in the range of 0.12–0.47 and 0.23–0

  在此，我们报告了噻唑并[4,5 - b ]吡啶-5-酮的设计和合成及其抗菌活性的评估。该设计基于分子杂交方法。对其抗菌活性的评估表明，这些化合物通常显示出中等的抗菌活性。化合物4p的活性最佳，MIC/MBC 分别在 0.12-0.47 和 0.23-0.94 mg mL -1范围内。三种化合物（4g、4n和4p）针对三种耐药菌株进行了测试，即 MRSA、绿脓杆菌和大肠杆菌，显示出比参考药物氨苄青霉素更高的抑制潜力。还测试了这三种化合物抑制生物膜形成的能力，其中两种在 MIC ( 4p ) 浓度和氨苄青霉素浓度（MIC 和 0.5 MIC）中显示出比链霉素更好的活性。就抗真菌活性而言，化合物4i的活性最佳，MIC为0.12-0.47 mg mL -1，MFC为0.23-0.94 mg m -1。根据对接研究，预计对大肠杆菌的抑制作用MurB 酶可能是这些化合物抗菌活性的推定机制，而 14a-
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• BI-FUNCTIONAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Nuevolution A/S

  公开号：EP2558577A1

  公开（公告）日：2013-02-20
• BI-FUNCTINAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Gouliaev Alex Haahr

  公开号：US20130281324A1

  公开（公告）日：2013-10-24

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.