4-(2-hydroxy-3-morpholinopropoxy)-2H-chromen-2-one | 1202866-03-2

• 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: 4-(2-hydroxy-3-morpholinopropoxy)-2H-chromen-2-one
• 英文别名: 4-(2-hydroxy-3-morpholin-4-ylpropoxy)chromen-2-one；4-(2-Hydroxy-3-morpholin-4-ylpropoxy)chromen-2-one
• CAS: 1202866-03-2
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: ARHAGSCPEROKGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxy-3-morpholinopropoxy)-2H-chromen-2-one 、 苯甲酰氯 在 氨 作用下， 以 甲苯 、 苯 为溶剂， 以3.37 g的产率得到2-morpholino-1-[(2-oxo-2H-chromen-4-yloxy)methyl]ethyl benzoate
  参考文献：
  名称：

  New syntheses on the basis of 4-hydroxy-2H-chromen-2-ones

  摘要：

  Alkylation of 4-hydroxy-2H-chromen-2-ones with 2-chloromethyloxirane in acetone in the presence of potassium carbonate gave 4-(2,3-epoxypropoxy)-2H-chromen-2-ones which were treated with various amines to obtain the corresponding 4-(3-amino-2-hydroxypropoxy)-2H-chromen-2-ones, and the latter were acylated at the hydroxy group with benzoyl chloride.

  DOI：

  10.1134/s1070428009070161
• 作为产物：
  描述：

  4-羟基香豆素 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 4-(2-hydroxy-3-morpholinopropoxy)-2H-chromen-2-one
  参考文献：
  名称：

  Biotransformation of newly synthesized coumarin derivatives by Candida albicans as potential antibacterial, antioxidant and cytotoxic agents

  摘要：

  In this study, one bioactive coumarin analog was obtained as a result of biotransformation of three inactive coumarin derivatives by free cells of Candida albicans. The bioactive analog was purified by Column chromatography and HPLC. The presence of coumarin moiety in the biotrasformed product was confirmed by lambda(max) at 350-400 nm and FT-IR spectrum. The structure of the purified compound established by LC-MS and H-1 NMR suggests the chances of biotransformation of 7-(3-(Cyclopropylamino)-2-hydroxypropoxy)-4-methyl-2H-chromen-2-one (MW 289 Da) into 7-(3-Cyclopropylamino-2-hydroxy-propoxy)-4-methoxymethyl-chromen-2-one or 7-(3-Cyclopropylamino-2-methoxy-propoxy)-4-hydroxymethyl-chromen-2-one as a main product (MW 318 Da). The extra peak of 332 Da in LC-MS further confirms the presence of small proportion of 7-(3-Cyclopropylamino-2-methoxy-propoxy)-4-methoxymethyl-chromen-2-one apart from the main product. Oxidation followed by methylation reaction might be responsible for this conversion. The biotransformed product showed antimicrobial activity against Bacillus pumilus, Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae and Salmonella typhi followed by decent antioxidant activity (6.756 mu g IC50). The efficacy of coumarin-analog on cellular proliferation was found at 40 mu M concentration against human breast cancer MDA-MB-231 cells in MTT assay, which is insignificant against normal breast tissue MCF-10A cells at the same concentration. These findings suggest the potential use of C. albicans for achieving pharmacologically active coumarin analogs showing antibacterial, antioxidant and cytotoxic activity.

  DOI：

  10.1016/j.procbio.2019.08.024

文献信息

• Synthesis and biological evaluation of 4-oxycoumarin derivatives as a new class of antifilarial agents
  作者：Sweta Misra、Lav Kumar Singh、Priyanka、Jyoti Gupta、Shailja Misra-Bhattacharya、Diksha Katiyar

  DOI：10.1016/j.ejmech.2015.02.043

  日期：2015.4

  A series of 4-oxycoumarin derivatives was synthesized, characterized and evaluated in vitro and in vivo for antifilarial activity against the human lymphatic filarial parasite, Brugia malayi. A majority of the compounds studied showed potent in vitro activity with low IC50 values in the micro molar (mu M) range (0.014-1.73 and 0.0056-0.43) against adult worms and microfilariae, respectively. Compounds 8 and 9 were identified to be the most promising antifilarial candidate molecules exhibiting activity in the nanomolar (nM) range. The IC50 values for compound 8 were 14 nM and 5.6 nM while for compound 9 were 94 nM and 13 nM, respectively, for adult worm and microfilaria. These two compounds also displayed promising adulticidal activity (74.9 +/- 4.8% and 69.4 +/- 2.8%, respectively) in the primary rodent (jird) screen. This study also serves as a starting point for investigating structure-activity relationship with different amino substituents. (C) 2015 Elsevier Masson SAS. All rights reserved.
• New syntheses on the basis of 4-hydroxy-2H-chromen-2-ones
  作者：A. A. Avetisyan、A. G. Alvandzhyan、K. S. Avetisyan

  DOI：10.1134/s1070428009070161

  日期：2009.7

  Alkylation of 4-hydroxy-2H-chromen-2-ones with 2-chloromethyloxirane in acetone in the presence of potassium carbonate gave 4-(2,3-epoxypropoxy)-2H-chromen-2-ones which were treated with various amines to obtain the corresponding 4-(3-amino-2-hydroxypropoxy)-2H-chromen-2-ones, and the latter were acylated at the hydroxy group with benzoyl chloride.
• Biotransformation of newly synthesized coumarin derivatives by Candida albicans as potential antibacterial, antioxidant and cytotoxic agents
  作者：Ambreen、Shafiul Haque、Vineeta Singh、Diksha Katiyar、Mohd Tariq Ali Khan、Vikash Tripathi、Hesham El Enshasy、Mukesh Pasupuleti、Bhartendu Nath Mishra

  DOI：10.1016/j.procbio.2019.08.024

  日期：2019.12

  In this study, one bioactive coumarin analog was obtained as a result of biotransformation of three inactive coumarin derivatives by free cells of Candida albicans. The bioactive analog was purified by Column chromatography and HPLC. The presence of coumarin moiety in the biotrasformed product was confirmed by lambda(max) at 350-400 nm and FT-IR spectrum. The structure of the purified compound established by LC-MS and H-1 NMR suggests the chances of biotransformation of 7-(3-(Cyclopropylamino)-2-hydroxypropoxy)-4-methyl-2H-chromen-2-one (MW 289 Da) into 7-(3-Cyclopropylamino-2-hydroxy-propoxy)-4-methoxymethyl-chromen-2-one or 7-(3-Cyclopropylamino-2-methoxy-propoxy)-4-hydroxymethyl-chromen-2-one as a main product (MW 318 Da). The extra peak of 332 Da in LC-MS further confirms the presence of small proportion of 7-(3-Cyclopropylamino-2-methoxy-propoxy)-4-methoxymethyl-chromen-2-one apart from the main product. Oxidation followed by methylation reaction might be responsible for this conversion. The biotransformed product showed antimicrobial activity against Bacillus pumilus, Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae and Salmonella typhi followed by decent antioxidant activity (6.756 mu g IC50). The efficacy of coumarin-analog on cellular proliferation was found at 40 mu M concentration against human breast cancer MDA-MB-231 cells in MTT assay, which is insignificant against normal breast tissue MCF-10A cells at the same concentration. These findings suggest the potential use of C. albicans for achieving pharmacologically active coumarin analogs showing antibacterial, antioxidant and cytotoxic activity.