methyl 2-oxo-2,6,7,8-tetrahydrocyclopenta[g]chromene-4-carboxylate | 1204665-85-9

• 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: methyl 2-oxo-2,6,7,8-tetrahydrocyclopenta[g]chromene-4-carboxylate
• 英文别名: methyl 2-oxo-7,8-dihydro-6H-cyclopenta[g]chromene-4-carboxylate
• CAS: 1204665-85-9
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: OPTGLNHHKQRBLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-茚醇 、 丁炔二酸二甲酯 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以43%的产率得到methyl 2-oxo-2,6,7,8-tetrahydrocyclopenta[g]chromene-4-carboxylate
  参考文献：
  名称：

  Synthesis and anti-inflammatory evaluation of novel angularly or linearly fused coumarins

  摘要：

  Angular [7,8]-fused coumarins were obtained from the reaction of [2,3]-fused phenols with DMAD and PPh3, while linear [6,7]-fused coumarins were formed from the analogous reaction of [3,4]-fused phenols with DMAD and PPh3. These compounds were tested in vitro for antioxidant activity and they found to present significant scavenging activity. In parallel, these new compounds were evaluated in vivo for anti-inflammatory activity and they found to inhibit the carrageenin-induced paw edema (34-65%). Although their interaction with the free stable radical DPPH was low, the methyl 2,2-dimethyl-8-oxo-3,8-dihydro-2H-furo[2,3-h]chromene-6-carboxylate was the most potent (65%) in the in vivo experiment. The later seems to be a potent soybean Lipoxygenase inhibitor and does not acquire gastrointestinal toxicity. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.004

文献信息

• Synthesis and anti-inflammatory evaluation of novel angularly or linearly fused coumarins
  作者：Theodoros Symeonidis、Konstantina C. Fylaktakidou、Dimitra J. Hadjipavlou-Litina、Konstantinos E. Litinas

  DOI：10.1016/j.ejmech.2009.09.004

  日期：2009.12

  Angular [7,8]-fused coumarins were obtained from the reaction of [2,3]-fused phenols with DMAD and PPh3, while linear [6,7]-fused coumarins were formed from the analogous reaction of [3,4]-fused phenols with DMAD and PPh3. These compounds were tested in vitro for antioxidant activity and they found to present significant scavenging activity. In parallel, these new compounds were evaluated in vivo for anti-inflammatory activity and they found to inhibit the carrageenin-induced paw edema (34-65%). Although their interaction with the free stable radical DPPH was low, the methyl 2,2-dimethyl-8-oxo-3,8-dihydro-2H-furo[2,3-h]chromene-6-carboxylate was the most potent (65%) in the in vivo experiment. The later seems to be a potent soybean Lipoxygenase inhibitor and does not acquire gastrointestinal toxicity. (C) 2009 Elsevier Masson SAS. All rights reserved.