5-[(3E)-4,8-dimethylnona-3,7-dienyl]-2H-tetrazole | 1018832-11-5

• 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: 5-[(3E)-4,8-dimethylnona-3,7-dienyl]-2H-tetrazole
• CAS: 1018832-11-5
• 化学式: C₁₂H₂₀N₄
• 分子量: 220.318
• InChiKey: DXEOUWVXWPKRRO-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-5,9-dimethyldeca-4,8-dienenitrile 在 sodium azide 、 三乙胺盐酸盐 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以93%的产率得到5-[(3E)-4,8-dimethylnona-3,7-dienyl]-2H-tetrazole
  参考文献：
  名称：

  Influence of heterocyclic and oxime-containing farnesol analogs on quorum sensing and pathogenicity in Candida albicans

  摘要：

  A series of synthetic molecules combining a geranyl backbone with a heterocyclic or oxime head group are quorum-sensing molecules that block the yeast to mycelium transition in the dimorphic fungus Candida albicans. A number of the analogs have an IC50 <= 10 mu M, a level of potency essentially identical to the natural quorum sensing signal, the sesquiterpene farnesol. Two of the most potent analogs, neither toxic toward healthy mice, display remarkably different effects when co-administered with C. albicans. While neither offers protection from candidiasis, one analog mimics farnesol in acting as a virulence factor, whereas the other has no effect. The results offer the first example of highly potent synthetic fungal quorum-sensing molecules, and provide the first evidence for the ability to decouple quorum sensing and virulence. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.011

文献信息

• Influence of heterocyclic and oxime-containing farnesol analogs on quorum sensing and pathogenicity in Candida albicans
  作者：Roman Shchepin、Dhammika H.M.L.P. Navarathna、Raluca Dumitru、Shane Lippold、Kenneth W. Nickerson、Patrick H. Dussault

  DOI：10.1016/j.bmc.2007.11.011

  日期：2008.2.15

  A series of synthetic molecules combining a geranyl backbone with a heterocyclic or oxime head group are quorum-sensing molecules that block the yeast to mycelium transition in the dimorphic fungus Candida albicans. A number of the analogs have an IC50 <= 10 mu M, a level of potency essentially identical to the natural quorum sensing signal, the sesquiterpene farnesol. Two of the most potent analogs, neither toxic toward healthy mice, display remarkably different effects when co-administered with C. albicans. While neither offers protection from candidiasis, one analog mimics farnesol in acting as a virulence factor, whereas the other has no effect. The results offer the first example of highly potent synthetic fungal quorum-sensing molecules, and provide the first evidence for the ability to decouple quorum sensing and virulence. (C) 2007 Elsevier Ltd. All rights reserved.