7-methoxy-3-methyl-4-oxo-4H-chromene-2-carboxylic acid | 1298119-93-3

• 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: 7-methoxy-3-methyl-4-oxo-4H-chromene-2-carboxylic acid
• 英文别名: 7-Methoxy-3-methyl-4-oxochromene-2-carboxylic acid
• CAS: 1298119-93-3
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: TWSBAAGKQHCSJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-methyl-4-oxo-4H-chromene-2-carboxylic acid 在 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-7-methoxy-N-(4-(4-methoxyphenethylamino)-3,4-dioxo-1-phenylbutan-2-yl)-3-methyl-4-oxo-4H-chromene-2-carboxamide
  参考文献：
  名称：

  Synthesis of chromone carboxamide derivatives with antioxidative and calpain inhibitory properties

  摘要：

  The overactivation of mu-calpain can cause serious cell damage in several diseases. Furthermore, cell death in a number of neurodegenerative disorders is linked to the overproduction of reactive oxygen species. Therefore, antioxidants and mu-calpain inhibitors could have the therapeutic potentials to treat cell death related diseases. New chromone carboxamide derivatives 3 were synthesized to provide alternative mu-calpain inhibitors to compound 2, a conformationally constrained structural variant of MDL 28,170. Compounds 3h and 3l exhibited the most potent p-calpain inhibitory activities (IC50 = 0.09-0.10 mu M), and were comparable to 2 in this respect (IC50 = 0.07 mu M). Compound 31 showed both potent p-calpain inhibitory activity (IC50 = 0.28 mu M) and antioxidant activities in DPPH scavenging and lipid peroxidation inhibition assays. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.025
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲酸乙酯 在 吡啶 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 13.0h， 生成 7-methoxy-3-methyl-4-oxo-4H-chromene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of chromone carboxamide derivatives with antioxidative and calpain inhibitory properties

  摘要：

  The overactivation of mu-calpain can cause serious cell damage in several diseases. Furthermore, cell death in a number of neurodegenerative disorders is linked to the overproduction of reactive oxygen species. Therefore, antioxidants and mu-calpain inhibitors could have the therapeutic potentials to treat cell death related diseases. New chromone carboxamide derivatives 3 were synthesized to provide alternative mu-calpain inhibitors to compound 2, a conformationally constrained structural variant of MDL 28,170. Compounds 3h and 3l exhibited the most potent p-calpain inhibitory activities (IC50 = 0.09-0.10 mu M), and were comparable to 2 in this respect (IC50 = 0.07 mu M). Compound 31 showed both potent p-calpain inhibitory activity (IC50 = 0.28 mu M) and antioxidant activities in DPPH scavenging and lipid peroxidation inhibition assays. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.025

文献信息

• Rational repurposing, synthesis, <i>in vitro</i> and <i>in silico</i> studies of chromone-peptidyl hybrids as potential agents against <i>Leishmania donovani</i>
  作者：Ahmed H. E. Hassan、Waleed A. Bayoumi、Selwan M. El-Sayed、Trong-Nhat Phan、Yeon Ju Kim、Chae Hyeon Lee、Soo Bin Cho、Taegeun Oh、Gyeongpyo Ham、Kazem Mahmoud、Joo Hwan No、Yong Sup Lee

  DOI：10.1080/14756366.2023.2229071

  日期：2023.12.31

  Abstract A chromone-peptidyl hybrids series was synthesised and rationally repurposed towards identification of potential antileishmanial hits against visceral leishmaniasis. Three hybrids 7c, 7n, and 7h showed potential IC50 values (9.8, 10, and 12 µM, respectively) which were comparable to erufosine IC50 (9.8 µM) but lower potency than miltefosine IC50 (3.5 µM). Preliminary assessment of cytotoxicity

  摘要 合成了色酮-肽基杂合体系列，并合理地重新调整用途，以鉴定针对内脏利什曼病的潜在抗利什曼病。三种杂交体7c、7n和7h显示出潜在的 IC 50值（分别为 9.8、10 和 12 µM），与埃卢福辛 IC 50 (9.8 µM)相当，但效力低于米替福辛 IC 50 (3.5 µM)。使用人 THP-1 细胞对细胞毒性进行初步评估，发现色酮-肽杂合体7c和7n在高达 100 µM 时无细胞毒性，而埃吕福辛和米替福辛的 CC 50分别为 19.4 µM 和 >40 µM。计算机模拟研究指出，肽基部分的N - p-甲氧基苯乙基取代基以及色酮部分苯环的氧基取代功能是与Ld CALP 结合的关键因素。总之，这些发现表明色酮-肽基杂合体7c和7n作为潜在的和预期的非细胞毒性抗利什曼病命中化合物，可用于开发潜在的抗内脏利什曼病抗利什曼病药物。
• Synthesis of chromone carboxamide derivatives with antioxidative and calpain inhibitory properties
  作者：Sang Hoon Kim、Young Hoon Lee、Seo Yun Jung、Hyoung Ja Kim、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.ejmech.2011.02.025

  日期：2011.5

  The overactivation of mu-calpain can cause serious cell damage in several diseases. Furthermore, cell death in a number of neurodegenerative disorders is linked to the overproduction of reactive oxygen species. Therefore, antioxidants and mu-calpain inhibitors could have the therapeutic potentials to treat cell death related diseases. New chromone carboxamide derivatives 3 were synthesized to provide alternative mu-calpain inhibitors to compound 2, a conformationally constrained structural variant of MDL 28,170. Compounds 3h and 3l exhibited the most potent p-calpain inhibitory activities (IC50 = 0.09-0.10 mu M), and were comparable to 2 in this respect (IC50 = 0.07 mu M). Compound 31 showed both potent p-calpain inhibitory activity (IC50 = 0.28 mu M) and antioxidant activities in DPPH scavenging and lipid peroxidation inhibition assays. (C) 2011 Elsevier Masson SAS. All rights reserved.