6-甲氧基-4-氧代-4H-苯并吡喃-2-羧酸 | 86277-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6-甲氧基-4-氧代-4H-苯并吡喃-2-羧酸
• 英文名称: 6-methoxy-4-oxo-4H-chromene-2-carboxylic acid
• 英文别名: 6-methoxy-4-oxo-4H-1-benzopyran-2-carboxylic acid；6-methoxy-4-oxochromene-2-carboxylic acid
• CAS: 86277-98-7
• 化学式: C₁₁H₈O₅
• mdl: MFCD01605513
• 分子量: 220.182
• InChiKey: HTRXCGAXFXWJGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  6-甲氧基-4-氧代-4H-苯并吡喃-2-羧酸 在 乙醇 作用下， 生成 3-dimethylaminomethyl-6-methoxy-chromen-4-one
  参考文献：
  名称：

  Chromones in the Mannich Reaction

  摘要：

  DOI：

  10.1021/ja01137a024
• 作为产物：
  描述：

  在 硫酸 、 乙酰氯 作用下， 反应 0.5h， 生成 6-甲氧基-4-氧代-4H-苯并吡喃-2-羧酸
  参考文献：
  名称：

  Neurogenic and neuroprotective donepezil-flavonoid hybrids with sigma-1 affinity and inhibition of key enzymes in Alzheimer's disease

  摘要：

  In this work we describe neurogenic and neuroprotective donepezil-flavonoid hybrids (DFHs), exhibiting nanomolar affinities for the sigma-1 receptor (sigma R-1) and inhibition of key enzymes in Alzheimer's disease (AD), such as acetylcholinesterase (AChE), 5-lipoxygenase (5-LOX), and monoamine oxidases (MAOs). In general, new compounds scavenge free radical species, are predicted to be brain-permeable, and protect neuronal cells against mitochondrial oxidative stress. N-(2-(1-Benzylpiperidin-4-yl)ethyl)-6,7-dimethoxy-4-oxo-4H-chromene-2-carboxamide (18) is highlighted due to its interesting biological profile in sigma R-1, AChE, 5-LOX, MAO-A and MAO-B. In phenotypic assays, it protects a neuronal cell line against mitochondrial oxidative stress and promotes maturation of neural stem cells into a neuronal phenotype, which could contribute to the reparation of neuronal tissues. Molecular modelling studies of 18 in AChE, 5-LOX and sigma R-1 revealed the main interactions with these proteins, which will be further exploited in the optimization of new, more efficient DFHs. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.026

文献信息

• Regiospecific Synthesis of Benzoxepines through Pd-Catalyzed Carbene Migratory Insertion and C–C Bond Cleavage
  作者：Yang Xie、Ping Zhang、Lei Zhou

  DOI：10.1021/acs.joc.5b02413

  日期：2016.3.4

  A new method for the synthesis of benzoxepines via migratory insertion into a Pd carbene followed by C–C bond cleavage was developed. Various benzoxepines were constructed by the regioselective ring expansion concomitant with the introduction of an aryl group at their 5-position.

  开发了一种通过迁移插入Pd卡宾并进行C-C键裂解来合成苯并二氢萘的新方法。通过区域选择性的扩环以及在其5-位上引入芳基来构建各种苯并氧杂松。
• [EN] SUBSTITUTED CYCLOLAKYLS AS MODULATORS OF THE INTEGRATED STRESS PATHWAY<br/>[FR] CYCLOLALKYLES SUBSTITUÉS EN TANT QUE MODULATEURS DE LA VOIE DE STRESS INTÉGRÉE
  申请人：CALICO LIFE SCIENCES LLC

  公开号：WO2020223536A1

  公开（公告）日：2020-11-05

  Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.

  本文提供了用于调节综合应激反应（ISR）并治疗相关疾病、疾病和症状的化合物、组合物和方法。
• Derivatives of 2,2'-iminobisethanol
  申请人：Janssen Pharmaceutica, N.V.

  公开号：US04654362A1

  公开（公告）日：1987-03-31

  Derivatives of 2,2'-iminobisethanol having useful properties in the treatment and/or the prevention of disorders of the coronary-vascular system.

  2,2'-亚氨基二乙醇衍生物，具有治疗和/或预防冠状血管系统疾病的有用特性。
• [EN] ANTI-INFECTIVE AGENTS<br/>[FR] AGENTS ANTI-INFECTIEUX
  申请人：UNIV DUNDEE

  公开号：WO2017221002A1

  公开（公告）日：2017-12-28

  The present invention relates to a novel class of chromene-2-carboxamide compounds inhibitors of general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8 and X are as defined herein, to their use in medicine, and their use as anti-infective agents in particular, to compositions containing them, to processes for their preparation and to intermediates used in such processes.

  本发明涉及一类新型的基于色酮-2-羧酰胺化合物的抑制剂，其通式为(I)，其中R1、R2、R3、R4、R5、R6、R7、R8和X如本文所定义，其在医学上的用途，特别是作为抗感染剂的用途，包括含有它们的组合物，其制备过程以及用于这些过程的中间体。
• Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-Up the Discovery of Chromone-Based Multitarget-Directed Ligands
  作者：Cagide、Oliveira、Reis、Borges

  DOI：10.3390/molecules24234214

  日期：——

  obtained with good yields (54–93%). Only in the case of the nitro substituent (compound 11B), an ester was obtained instead of the desired carboxylic acid. Following this synthetic route chromone carboxylic acids can be attained with a high degree of purity, without the need of the tedious and expensive purification processes through column chromatography. The reaction is safe, cost-effective, fast and robust

  6-溴色酮-2-羧酸 (3) 是通过微波辅助工艺合成的。反应的优化通过不同的参数进行，例如碱类型/试剂当量数、溶剂、温度和反应时间。反应产率提高到87%。新的合成路线是通用的，因为以良好的产率 (54-93%) 获得了几种色酮-2-羧酸（化合物 4B-10B）。仅在硝基取代基（化合物 11B）的情况下，获得酯而不是所需的羧酸。按照这种合成路线，色酮羧酸可以以高纯度获得，而无需通过柱色谱进行繁琐和昂贵的纯化过程。反应安全、经济、快速、稳健，可用于基于chromone scaffold的简洁、面向多样性的文库开发。整个研究可以看作是加快发现基于色酮的多靶标配体的一步。