5,7-dihydroxy-3,3-dimethyl-4a-(2-hydroxyethyl)-7-(3-methylbutanoyl)-2,3,4,4a,9a,9b-hexahydro-2,4-methano-1H-xanthene-5-carboxaldehyde | 1017239-28-9

• 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: 5,7-dihydroxy-3,3-dimethyl-4a-(2-hydroxyethyl)-7-(3-methylbutanoyl)-2,3,4,4a,9a,9b-hexahydro-2,4-methano-1H-xanthene-5-carboxaldehyde
• 英文别名: (1R,2S,11R,13S)-6,8-dihydroxy-2-(2-hydroxyethyl)-14,14-dimethyl-7-(3-methylbutanoyl)-3-oxatetracyclo[11.1.1.02,11.04,9]pentadeca-4,6,8-triene-5-carbaldehyde
• CAS: 1017239-28-9
• 化学式: C₂₄H₃₂O₆
• 分子量: 416.514
• InChiKey: PVGZSQXEQPJJOZ-ATWPWFFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(3-methylbutan-1-one) 、 (1R)6,6-二甲基联环(3.1.1)庚烷-2-烯-2-乙醇 在 sodium acetate 、 溶剂黄146 作用下， 反应 0.07h， 以32%的产率得到5,7-dihydroxy-3,3-dimethyl-4a-(2-hydroxyethyl)-7-(3-methylbutanoyl)-2,3,4,4a,9a,9b-hexahydro-2,4-methano-1H-xanthene-5-carboxaldehyde
  参考文献：
  名称：

  S-Euglobals: Biomimetic synthesis, antileishmanial, antimalarial, and antimicrobial activities☆

  摘要：

  Several new euglobal analogues (named as S-euglobals) were synthesized from phloroglucinol via a biomimetic three-component reaction involving Knoevenagel condensation followed by [4+2]-Diels-Alder cycloaddition with monoterpene. Newly synthesized euglobal analogues involve monoterpenes that have not yet been encountered in natural euglobals. S-Euglobals along with previously synthesized robustadial A and B were evaluated for in vitro antileishmanial, antimalarial, antimicrobial, and cytotoxic activities. Out of 16, nine analogues were found to exhibit antileishmanial activity against Leishmania donovani promastigotes. Analogue 7 was the most potent with IC50 of 2.4 mu g/mL and IC90 of 8 mu g/mL, followed by analogues 8 and 11 (IC50 5.5 and 9.5 mu g/mL). Antilelshmanial activity of robustadial A (5) and B (6) was moderate with IC50 of 20 and 16 mu g/mL, respectively. Robustadial A and B and S-euglobal 8 exhibited weak antimalarial activity against Plasmodium falciparum (IC50 of 2.7-4.76 mu g/mL). Few of the eualobal analogues showed antibacterial activity against methicillin-resistant Staphylococcus aureus. Amongst these, analogue I I was the most potent with IC50 of 1.0 mu g/mL and MIC of 5.0 mu g/mL. Most of the compounds were not cytotoxic up to 25 mu g/mL in a panel of cell lines consisting of both cancer (SK-MEL, KB, BT-549, and SK-OV-3) as well as non-cancer kidney (Vero and LLC-PK11) cells. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.055

文献信息

• S-Euglobals: Biomimetic synthesis, antileishmanial, antimalarial, and antimicrobial activities☆
  作者：Sandip B. Bharate、Shabana I. Khan、Babu L. Tekwani、Melissa Jacob、Ikhlas A. Khan、Inder Pal Singh

  DOI：10.1016/j.bmc.2007.10.055

  日期：2008.2.1

  Several new euglobal analogues (named as S-euglobals) were synthesized from phloroglucinol via a biomimetic three-component reaction involving Knoevenagel condensation followed by [4+2]-Diels-Alder cycloaddition with monoterpene. Newly synthesized euglobal analogues involve monoterpenes that have not yet been encountered in natural euglobals. S-Euglobals along with previously synthesized robustadial A and B were evaluated for in vitro antileishmanial, antimalarial, antimicrobial, and cytotoxic activities. Out of 16, nine analogues were found to exhibit antileishmanial activity against Leishmania donovani promastigotes. Analogue 7 was the most potent with IC50 of 2.4 mu g/mL and IC90 of 8 mu g/mL, followed by analogues 8 and 11 (IC50 5.5 and 9.5 mu g/mL). Antilelshmanial activity of robustadial A (5) and B (6) was moderate with IC50 of 20 and 16 mu g/mL, respectively. Robustadial A and B and S-euglobal 8 exhibited weak antimalarial activity against Plasmodium falciparum (IC50 of 2.7-4.76 mu g/mL). Few of the eualobal analogues showed antibacterial activity against methicillin-resistant Staphylococcus aureus. Amongst these, analogue I I was the most potent with IC50 of 1.0 mu g/mL and MIC of 5.0 mu g/mL. Most of the compounds were not cytotoxic up to 25 mu g/mL in a panel of cell lines consisting of both cancer (SK-MEL, KB, BT-549, and SK-OV-3) as well as non-cancer kidney (Vero and LLC-PK11) cells. (C) 2007 Elsevier Ltd. All rights reserved.