N-(2-hydroxyethyl)-8-methoxy-2-oxo-2H-chromene-3-carboxamide | 683249-46-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(2-hydroxyethyl)-8-methoxy-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-(2-hydroxyethyl)-8-methoxy-2-oxochromene-3-carboxamide
• CAS: 683249-46-9
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: AMVJXRCZLMEIAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(2-hydroxyethyl)-2-imino-8-methoxychromene-3-carboxamide 在 盐酸 、 水 作用下， 生成 N-(2-hydroxyethyl)-8-methoxy-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships

  摘要：

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.009

文献信息

• Piperidine-Iodine as Efficient Dual Catalyst for the One-Pot, Three-Component Synthesis of Coumarin-3-Carboxamides
  作者：Manuel Velasco、Nancy Romero-Ceronio、Rosalía Torralba、Oswaldo Hernández Abreu、Miguel A. Vilchis-Reyes、Erika Alarcón-Matus、Erika M. Ramos-Rivera、David M. Aparicio、Jacqueline Jiménez、Eric Aguilar García、David Cruz Cruz、Clarisa Villegas Gómez、Cuauhtémoc Alvarado

  DOI：10.3390/molecules27144659

  日期：——

  efficient one-pot, three-component synthetic method for the preparation of coumarin-3-carboxamides was carried out by the reaction of salicylaldehyde, aliphatic primary/secondary amines, and diethylmalonate. The protocol employs piperidine-iodine as a dual system catalyst and ethanol, a green solvent. The main advantages of this approach are that it is a metal-free and clean reaction, has low catalyst loading

  通过水杨醛、脂肪族伯/仲胺和丙二酸二乙酯的反应，进行了一种简单、高效的一锅三组分合成香豆素-3-羧酰胺的制备方法。该协议采用哌啶碘作为双系统催化剂和乙醇，一种绿色溶剂。这种方法的主要优点是它是一种无金属且清洁的反应，催化剂负载量低，并且不需要繁琐的后处理。
• Coumarin-based derivatives targeting<i>Trypanosoma cruzi</i>cruzain and<i>Trypanosoma brucei</i>cathepsin L-like proteases
  作者：Jéssica Alves Nunes、Fabrícia Nunes da Silva、Elany Barbosa da Silva、Clara Andrezza Crisóstomo Bezerra Costa、Johnnatan Duarte de Freitas、Francisco Jaime Bezerra Mendonça-Junior、Miriam Aparecida Giardini、Jair Lage de Siqueira-Neto、James H. McKerrow、Thaiz Rodrigues Teixeira、Louis William Odeesho、Conor R. Caffrey、Sílvia Helena Cardoso、Edeildo Ferreira da Silva-Júnior

  DOI：10.1039/d2nj04946e

  日期：——

  its mechanism of action against the T. cruzi parasite via inhibition of CRZ, although other targets could be involved. In parallel, FN-10, a coumarin-chalcone analog, was active against T. brucei trypomastigotes (EC50: 4.8 μM ± 0.15) but it did not inhibit CRZ or TbrCATL. Accordingly, FN-10 may exhibit its effects via a different macromolecular target(s) in each parasite. For FN-27, molecular dynamics

  原生动物克氏锥虫（恰加斯病的病原体 - 也称为美洲锥虫病）和布氏锥虫（非洲人类锥虫病 - HAT 的病原体）对公共卫生产生负面影响，在多个国家流行，每年导致数千人死亡. 此外，疾病的药物治疗有一些局限性，例如寄生虫耐药性和患者的几种副作用，这会降低治疗的依从性。两种半胱氨酸蛋白酶，来自T. cruzi的 cruzain (CRZ)和来自T. brucei 的组织蛋白酶 L 样酶 ( Tbr CATL), 被认为是这些原生动物的有前途的目标，因为它们负责其生命周期中的许多关键生物过程。香豆素类似物已在多种针对锥虫杀虫剂开发的研究中得到报道，并显示出针对这些寄生虫的不同进化形式的活性。在这项研究中，我们报告了一种基于虚拟片段的药物设计 (vFBDD) 方法来开发能够抑制这些主要半胱氨酸蛋白酶的基于香豆素的类似物。此外，他们的实验验证还涉及酶抑制、基于体外感染细胞的检测和抗锥体鞭毛体检测。一种化
• New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships
  作者：Filipe Areias、Marta Costa、Marián Castro、José Brea、Elisabet Gregori-Puigjané、M. Fernanda Proença、Jordi Mestres、María I. Loza

  DOI：10.1016/j.ejmech.2012.05.009

  日期：2012.8

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.