3,3,5-trimethylcyclohexa-1,5-diene-1-yl acetate | 31608-30-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,3,5-trimethylcyclohexa-1,5-diene-1-yl acetate
• 英文别名: acetic acid-(3,3,5-trimethyl-cyclohexa-1,5-dienyl ester)；Essigsaeure-(3,3,5-trimethyl-cyclohexa-1,5-dienylester)；(3,3,5-Trimethylcyclohexa-1,5-dien-1-yl) acetate
• CAS: 31608-30-7
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: LESKSFAATUIABK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3,5-trimethylcyclohexa-1,5-diene-1-yl acetate 在 水 作用下， 生成 (1S,2S,4R)-2-Chloro-1,5,5-trimethyl-8-oxo-bicyclo[2.2.2]octane-2-carbonitrile
  参考文献：
  名称：

  Damiano-Gal,J. et al., Bulletin de la Societe Chimique de France, 1977, p. 345 - 350

  摘要：

  DOI：
• 作为产物：
  描述：

  异佛尔酮 、 乙酸酐 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到3,3,5-trimethylcyclohexa-1,5-diene-1-yl acetate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Water‐Soluble Esterase‐Activated CO‐Releasing Molecules Targeting Mitochondria

  摘要：

  AbstractDue to the beneficial effects of carbon monoxide as a cell‐protective and anti‐inflammatory agent, CO‐releasing molecules (CORMs) offer some promising potential applications in medicine. In this context, we synthesized a set of acyloxy‐cyclohexadiene‐Fe(CO)3 complexes, all displaying a N‐methyl‐pyridinium triflate moiety in the ester side chain, as mitochondria‐targeting esterase‐triggered CORM prodrugs. Whereas the compounds in which the acyloxy substituent is attached to the 2‐position of the diene‐Fe(CO)3 unit (A series) spontaneously release CO upon dissolution in phosphate buffer, which remarkably is partly suppressed in the presence of porcine liver esterase (PLE), the 1‐substituted isomers (B series) show the expected PLE‐induced release of CO (up to 3 equiv.). The biological activity of Mito‐CORMs 2/3‐B and their isophorone‐derived analogs 2/3‐A’, which also displayed PLE‐induced CO release, was assessed by using human umbilical vein endothelial cells (HUVEC). Whereas Mito‐CORMs 2/3‐B were not cytotoxic up to 500 μM (MTT assay), Mito‐CORMs 2/3‐A’ caused significant toxicity at concentrations above 50 μM. The anti‐inflammatory potential of both Mito‐CORM variants was demonstrated by concentration‐dependent down‐regulation of the pro‐inflammatory markers VCAM‐1, ICAM‐1 and CXCL1 as well as induction of HO‐1 in TNFα‐stimulated human umbilical vein endothelial cells (HUVECs; western blotting and qPCR). Energy phenotyping by seahorse real‐time cell metabolic analysis, revealed opposing shifts of metabolic potentials in cells treated either with Mito‐CORMs 2/3‐B (increased mitochondrial respiration and glycolytic activity) or Mito‐CORMs 2/3‐A’ (suppressed mitochondrial respiration and increased glycolytic activity). Thus, the Mito‐CORMs represent valuable tools for the safe and targeted delivery of CO to mitochondria as a subcellular compartment to induce positive anti‐inflammatory effects with only minor shifts in cellular energy metabolism. Also, due to their water solubility, these compounds provide a promising starting point for further pharmacological studies.

  DOI：

  10.1002/chem.202201670

文献信息

• Contreras, Fernando Gomes; Lora-Tamayo, Manuel; Sanz, Ana M, Heterocycles, 1989, vol. 28, # 2, p. 791 - 803
  作者：Contreras, Fernando Gomes、Lora-Tamayo, Manuel、Sanz, Ana M

  DOI：——

  日期：——
• The Aromatization and Rearrangement of Cyclic Ketones. III. 2,3,5- and 3,4,5- Trimethylphenol from Isophorone¹
  作者：F. Marshall Beringer、Emil J. Geering

  DOI：10.1021/ja01107a023

  日期：1953.6
• US3975153A
  申请人：——

  公开号：US3975153A

  公开（公告）日：1976-08-17