3,4-dihydro-5,7-dihydroxy-3',3'-dimethyl-6,8-bis(3-methylbutanoyl)-spiro-2H-benzopyran-2,2'-bicyclo[2.1.1]heptane | 1017239-50-7

• 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: 3,4-dihydro-5,7-dihydroxy-3',3'-dimethyl-6,8-bis(3-methylbutanoyl)-spiro-2H-benzopyran-2,2'-bicyclo[2.1.1]heptane
• 英文别名: 1-[(1'S,2R,4'R)-5,7-dihydroxy-2',2'-dimethyl-8-(3-methylbutanoyl)spiro[3,4-dihydrochromene-2,3'-bicyclo[2.2.1]heptane]-6-yl]-3-methylbutan-1-one
• CAS: 1017239-50-7
• 化学式: C₂₇H₃₈O₅
• 分子量: 442.596
• InChiKey: QTNQHDPCTDYNED-ANAQZDLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 dl-camphene 、 1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(3-methylbutan-1-one) 在 sodium acetate 、 溶剂黄146 作用下， 反应 0.07h， 以65%的产率得到3,4-dihydro-5,7-dihydroxy-3',3'-dimethyl-6,8-bis(3-methylbutanoyl)-spiro-2H-benzopyran-2,2'-bicyclo[2.1.1]heptane
  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.