6-ethoxychromone-3-carbaldehyde | 870811-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-ethoxychromone-3-carbaldehyde
• 英文别名: 6-Ethoxy-4-oxo-4H-chromene-3-carbaldehyde；6-ethoxy-4-oxochromene-3-carbaldehyde
• CAS: 870811-33-9
• 化学式: C₁₂H₁₀O₄
• mdl: MFCD11878822
• 分子量: 218.209
• InChiKey: NOYHUALJWSACLP-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  374.6±42.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-ethoxychromone-3-carbaldehyde 在 sodium chlorite 、 草酰氯 、 氨基磺酸 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 Methyl 6-ethoxy-4-oxochromene-3-carboxylate
  参考文献：
  名称：

  Structure−Activity Relationships of a Novel Class of Endothelin-A Receptor Antagonists and Discovery of Potent and Selective Receptor Antagonist, 2-(Benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4-(4-methoxyphenyl)-2H-chromene-3- carboxylic Acid (S-1255). 1. Study on Structure−Activity Relationships and Basic Structure Crucial for ET_A Antagonism

  摘要：

  A novel series of endothelin-A (ETA) selective receptor antagonists having a 2H-chromene skeleton are described. A lead compound, 2-(benzo[1,3]dioxol-5-yl)-2H-chromene-3-carboxylic acid (3), was found by modifications of our own angiotensin II antagonist. A structure-activity relationship (SAR) study of 3 reveals that the structural requirements essential for potent and selective ETA receptor binding affinity are the m,p-methylenedioxyphenyl, carboxyl, and isopropoxy groups at the 2-, 3-, and 6-positions, respectively, on the (R)-2H-chromene skeleton. The substituent at the 4-position is also important for improving the activity, and various hydrophobic functional groups of 6-9 Angstrom such as liner, branched, and cyclic aliphatic groups, unsubstituted and substituted aryl groups, and even halogen atoms were acceptable. These results suggest that (R)-2-(benzo[1,3]dioxol-5-yl)-6-isopropoxy-2H-chromene-3-carboxylic acid, formula 108, is the crucial basic structure to be recognized by the ETA receptor. The most potent compound is (R)-48 (S-1255), which binds to the ETA receptor with an IC50 value of 0.19 nM and is 630-fold selective for the ETA receptor than for the ETB receptor. This compound has 55% oral bioavailability in rats. On the basis of the SAR, the roles of each substituent in the receptor binding are discussed.

  DOI：

  10.1021/jm010382z
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 potassium carbonate 、 三氯氧磷 作用下， 生成 6-ethoxychromone-3-carbaldehyde
  参考文献：
  名称：

  一种新型色酮衍生物作为双探针，用于比色法在水溶液中通过荧光和铜（II）选择性感测铝（III）

  摘要：

  基于色酮骨架，合成了一个简单新颖的探针，即6-乙氧基色酮-3-甲醛-（呋喃基）（L）。它具有代表性的开启荧光特性，并且比色变化明显，对Al 3+和Cu 2+的选择性高。对于Al 3+，L在EtOH / H 2 O（3/2）水性介质中的其他常见阳离子上方显示绿色荧光。在使用Cu 2+的情况下，L通过肉眼从无色变为黄色而感觉到Cu 2+。而且，L -Al 3+之间的配位比和大号-Cu 2+为1：1，它可以通过作业的情节，来验证1 H NMR和高分辨质谱。因此，L可以用作Al 3+和Cu 2+的固体探针。

  DOI：

  10.1016/j.jphotochem.2019.111955

文献信息

• A novel chromone derivative as dual probe for selective sensing of Al(III) by fluorescent and Cu(II) by colorimetric methods in aqueous solution
  作者：Limei Tian、Jia Xue、Si-liang Li、Zheng-yin Yang

  DOI：10.1016/j.jphotochem.2019.111955

  日期：2019.9

  probe that is 6-ethoxychromone-3-carbaldehyde-(furanyl) hydrazone (L) has been synthesized and completely characterized. It exhibited representative turn-on fluorescent properties and obviously colorimetric changes with high selectivity to Al3+ and Cu2+. For Al3+, L displayed a turn on green fluorescence in EtOH/H2O (3/2) aqueous media over other common cations. With Cu2+, L perceived Cu2+ through

  基于色酮骨架，合成了一个简单新颖的探针，即6-乙氧基色酮-3-甲醛-（呋喃基）（L）。它具有代表性的开启荧光特性，并且比色变化明显，对Al 3+和Cu 2+的选择性高。对于Al 3+，L在EtOH / H 2 O（3/2）水性介质中的其他常见阳离子上方显示绿色荧光。在使用Cu 2+的情况下，L通过肉眼从无色变为黄色而感觉到Cu 2+。而且，L -Al 3+之间的配位比和大号-Cu 2+为1：1，它可以通过作业的情节，来验证1 H NMR和高分辨质谱。因此，L可以用作Al 3+和Cu 2+的固体探针。
• CRTH2 Receptor Ligands For Medicinal Uses
  申请人：Ulven Trond

  公开号：US20090099189A1

  公开（公告）日：2009-04-16

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis, wherein A represents a carboxyl group —COON, or a carboxyl bioisostere; A 1 , is hydrogen or methyl; ring Ar 1 is an optionally substituted phenyl ring 5- or 6-membered monocyclic heteroaryl ring, in which AA 1 CHO— and L2 are linked to adjacent ring atoms; rings Are 2 , Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; t is 0 or 1; L2 and L3 are linker radicals as defined in the description.

  式(I)的化合物可用于治疗对CRTH2受体活性调节敏感的疾病，例如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎，其中A代表羧基—COON或羧基生物同位素；A1为氢或甲基；环Ar1是一个可选取代的苯环5-或6-成员的单环杂环，其中AA1CHO—和L2与相邻的环原子连接；环Are2，Ar3各自独立地表示一个苯环或5-或6-成员的单环杂环，或由一个5-或6-成员的碳环或杂环组成的双环系统，该环或环系统被苯并或与一个5-或6-成员的单环杂环融合，该环或环系统是可选取代的；t为0或1；L2和L3是如描述中所定义的连接基团。
• CRTH2 receptor ligands for medicinal uses
  申请人：Ulven Trond

  公开号：US20110269763A1

  公开（公告）日：2011-11-03

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis: wherein A represents a carboxyl group —COOH, or a carboxyl bioisostere; A 1 is hydrogen or methyl; ring Ar 1 is an optionally substituted phenyl ring or 5- or 6-membered monocyclic heteroaryl ring, in which AA 1 CHO— and L2 are linked to adjacent ring atoms; rings Ar 2 , Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; t is 0 or 1; L2 and L3 are linker radicals as defined in the description.

  式(I)的化合物可用于治疗对CRTH2受体活性调节敏感的疾病，例如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎：其中A代表羧基—COOH或羧基生物同位素；A1为氢或甲基；环Ar1为可选取代的苯环或5-或6-成员的单环杂环，其中AA1CHO—和L2连接到相邻的环原子上；环Ar2、Ar3各自独立地表示苯环或5-或6-成员的单环杂环，或由5-或6-成员的碳环或杂环组成的双环系统，该环或环系统是苯并或与5-或6-成员的单环杂环融合，该环或环系统是可选的取代；t为0或1；L2和L3是如描述中定义的连接基。
• CRTH2 Receptor Ligands for Medical Use
  申请人：7TM Pharma A/S

  公开号：EP2336113A1

  公开（公告）日：2011-06-22

  4-Bromo-2-[1-(2,6-dichlorophenyl)-1H-pyrazole-4-carbonyl]phenoxyl acetic acid is useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis.

  4-溴-2-[1-（2,6-二氯苯基）-1H-吡唑-4-甲酰基]苯氧乙酸可用于治疗对调节 CRTH2 受体活性有反应的疾病，如哮喘、鼻炎、过敏性气道综合征和过敏性鼻支气管炎。
• A new off-on fluorescent sensor for the detection of Al(III) based on a chromone-derived Schiff-base
  作者：Li-mei Liu、Zheng-yin Yang

  DOI：10.1016/j.ica.2017.09.051

  日期：2018.1

  A new Al3+ sensor, 6-ethoxychromone-3-carbaldehyde-(3-hydroxy-2-naphthalene acyl) hydrazone (L), was designed and synthesized. The sensor L could exist steadily and detect Al3+ in the pH range from 5.0 to 8.0 in ethanol and water (3: 1, v/v). This sensor showed good selectivity and high sensitivity towards Al3+ in the presence of most metal ions, and a remarkable enhancement in fluorescence emission intensity at 508 nm (lambda(ex) = 420 nm) was observed with addition of 1equiv Al3+, which was attributed to the inhibition of photoinduced electron-transfer (PET) phenomenon and C=N isomerization process. With the fluorescence titration experiments and the ESI-MS spectrum data, we reached the conclusion that the binding ratio between L and Al3+ was 2: 1. Besides, the binding constant (K-a) between L and Al3+ was calculated to be 9.24 x 103 M-1 and the detection limit of L for Al3+ was as low as 1.82 x 10(-7) M. (C) 2017 Elsevier B.V. All rights reserved.