8-acetyl-3,4-dihydro-5,7-dihydroxy-3',3'-dimethyl-spiro-[2H-1-benzopyran-2,2'-bicyclo[2.2.1]heptane]-6-carbaldehyde

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 8-acetyl-3,4-dihydro-5,7-dihydroxy-3',3'-dimethyl-spiro-[2H-1-benzopyran-2,2'-bicyclo[2.2.1]heptane]-6-carbaldehyde
• 英文别名: (1'S,2R,4'R)-8-acetyl-5,7-dihydroxy-2',2'-dimethylspiro[3,4-dihydrochromene-2,3'-bicyclo[2.2.1]heptane]-6-carbaldehyde
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: IPTOUBBZPOBHBO-XXRNEEKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  formyl acetyl phloroglucinol 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 4.0h， 生成 8-acetyl-3,4-dihydro-5,7-dihydroxy-3',3'-dimethyl-spiro-[2H-1-benzopyran-2,2'-bicyclo[2.2.1]heptane]-6-carbaldehyde
  参考文献：
  名称：

  Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues

  摘要：

  In the present communication, naturally occurring phloroglucinol-monoterpene adducts, euglobals G1-G4 (3b/a and 4a/b) and 16 new analogues (13a/b-18a/b and 19-22) were synthesized by biomimetic approach. These synthetic compounds differ from natural euglobals in the nature of monoterpene and acyl functionality. All of these compounds were evaluated for their antibacterial, antifungal, antileishmanial and antimalarial activities. Analogue 17b possessed good antibacterial activity against methicillin-resistant Staphylococcus aureus, while analogues 19-22 possessed potent antifungal activity against Candida glabrata with IC(50)s ranging from 1.5 to 2.5 mu g/mL. Euglobals along with all synthesized analogues exhibited antileishmanial activity. Amongst these, euglobal G2 (3a), G3 (4a) and analogues 13a and 14a showed potent antileishmanial activity with IC50s ranging from 2.8 to 3.9 mu g/mL. Analogue 16a possessed antimalarial activity against chloroquine sensitive D6 clone of Plasmodium falciparum. None of the compounds showed toxicity against mammalian kidney fibroblasts (vero cells) upto the concentration of 4.76 mu g/ml. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.027

文献信息

• Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues
  作者：Sandip B. Bharate、Kamlesh K. Bhutani、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Ikhlas A. Khan、Inder Pal Singh

  DOI：10.1016/j.bmc.2005.10.027

  日期：2006.3

  In the present communication, naturally occurring phloroglucinol-monoterpene adducts, euglobals G1-G4 (3b/a and 4a/b) and 16 new analogues (13a/b-18a/b and 19-22) were synthesized by biomimetic approach. These synthetic compounds differ from natural euglobals in the nature of monoterpene and acyl functionality. All of these compounds were evaluated for their antibacterial, antifungal, antileishmanial and antimalarial activities. Analogue 17b possessed good antibacterial activity against methicillin-resistant Staphylococcus aureus, while analogues 19-22 possessed potent antifungal activity against Candida glabrata with IC(50)s ranging from 1.5 to 2.5 mu g/mL. Euglobals along with all synthesized analogues exhibited antileishmanial activity. Amongst these, euglobal G2 (3a), G3 (4a) and analogues 13a and 14a showed potent antileishmanial activity with IC50s ranging from 2.8 to 3.9 mu g/mL. Analogue 16a possessed antimalarial activity against chloroquine sensitive D6 clone of Plasmodium falciparum. None of the compounds showed toxicity against mammalian kidney fibroblasts (vero cells) upto the concentration of 4.76 mu g/ml. (c) 2005 Elsevier Ltd. All rights reserved.