N-(2-hydroxy-4-methylphenyl)furan-2-carboxamide | 117099-26-0

• 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: N-(2-hydroxy-4-methylphenyl)furan-2-carboxamide
• 英文别名: furan-2-carboxylic acid-(2-hydroxy-4-methyl-anilide)；Furan-2-carbonsaeure-(2-hydroxy-4-methyl-anilid)；N-(2-hydroxy-4-methyl-phenyl)furan-2-carboxamide
• CAS: 117099-26-0
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: OJXFGOLAPIKVGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-4-methylphenyl)furan-2-carboxamide 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 20.5h， 生成 6-(bromomethyl)-2-(furan-2-yl)-1,3-benzoxazole
  参考文献：
  名称：

  Design, synthesis and evaluation of 2-aryl benzoxazoles as promising hit for the A_2Areceptor

  摘要：

  The development of adenosine A_2A receptor antagonists has received much interest in recent years for the treatment of neurodegenerative diseases. Based on docking studies, a new series of 2-arylbenzoxazoles has been identified as potential A_2AR antagonists. Structure-affinity relationship was investigated in position 2, 5 and 6 of the benzoxazole heterocycle leading to compounds with a micromolar affinity towards the A_2A receptor. Compound F1, with an affinity of 1 μm, presented good absorption, distribution, metabolism and excretion properties with an excellent aqueous solubility (184 μm) without being cytotoxic at 100 μm. This compound, along with low-molecular weight compound D1 (K_i = 10 μm), can be easily modulated and thus considered as relevant starting points for further hit-to-lead optimisation.

  DOI：

  10.1080/14756366.2017.1334648
• 作为产物：
  描述：

  糠酸（呋喃甲酸） 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 N-(2-hydroxy-4-methylphenyl)furan-2-carboxamide
  参考文献：
  名称：

  Synthesis and microbiological activity of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of antimicrobial active benzoxazoles

  摘要：

  The synthesis of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of benzoxazoles (II1-15) was performed in order to determine their in vitro antimicrobial activity against three Gram-positive bacteria, two Gram-negative bacteria and the fungus Candida albicans and their activities were compared with several control drugs. The compounds II11, II12, and II13 were found active at a MIC value of 12.5 mug/ml against the Gram-negative microorganism Pseudomonas aeruginosa. Most of the compounds show antibacterial activity at MIC a value of 25 mug/ml against the Gram-positive bacteria Staphylococcus aureus. For the antifungal activity against C. albicans, compound II10 was found more active than the other derivatives. The antimicrobial activity of some of these benzamides, phenylacetamides (II1 and II10) which are the possible metabolites of benzoxazoles, was also compared to their corresponding cyclic analogues III-IV. Compound II10 possesses two dilutions better antifungal activity than its cyclic analogue, benzoxazole IV, against C. albicans. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01226-0

文献信息

• The Mechanism of Dye Formation in Color Photography. VI. The Effect of a Non-ionic Surfactant on the Rate of Coupling
  作者：L. K. J. Tong、M. Carolyn Glesmann

  DOI：10.1021/ja01573a018

  日期：1957.8
• Synthesis and microbiological activity of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of antimicrobial active benzoxazoles
  作者：Esin Akı-Şener、Kamuran K. Bingöl、Özlem Temiz-Arpacı、İsmail Yalçın、Nurten Altanlar

  DOI：10.1016/s0014-827x(02)01226-0

  日期：2002.5

  The synthesis of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of benzoxazoles (II1-15) was performed in order to determine their in vitro antimicrobial activity against three Gram-positive bacteria, two Gram-negative bacteria and the fungus Candida albicans and their activities were compared with several control drugs. The compounds II11, II12, and II13 were found active at a MIC value of 12.5 mug/ml against the Gram-negative microorganism Pseudomonas aeruginosa. Most of the compounds show antibacterial activity at MIC a value of 25 mug/ml against the Gram-positive bacteria Staphylococcus aureus. For the antifungal activity against C. albicans, compound II10 was found more active than the other derivatives. The antimicrobial activity of some of these benzamides, phenylacetamides (II1 and II10) which are the possible metabolites of benzoxazoles, was also compared to their corresponding cyclic analogues III-IV. Compound II10 possesses two dilutions better antifungal activity than its cyclic analogue, benzoxazole IV, against C. albicans. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Design, synthesis and evaluation of 2-aryl benzoxazoles as promising hit for the A_2Areceptor
  作者：Romain Duroux、Nicolas Renault、Joana Esteves Cuelho、Laurence Agouridas、David Blum、Luisa V. Lopes、Patricia Melnyk、Saïd Yous

  DOI：10.1080/14756366.2017.1334648

  日期：2017.1.1

  The development of adenosine A_2A receptor antagonists has received much interest in recent years for the treatment of neurodegenerative diseases. Based on docking studies, a new series of 2-arylbenzoxazoles has been identified as potential A_2AR antagonists. Structure-affinity relationship was investigated in position 2, 5 and 6 of the benzoxazole heterocycle leading to compounds with a micromolar affinity towards the A_2A receptor. Compound F1, with an affinity of 1 μm, presented good absorption, distribution, metabolism and excretion properties with an excellent aqueous solubility (184 μm) without being cytotoxic at 100 μm. This compound, along with low-molecular weight compound D1 (K_i = 10 μm), can be easily modulated and thus considered as relevant starting points for further hit-to-lead optimisation.