tricyclo[3.3.1.1^3,7]decane-1-carboxylic acid 4-formyl-2-methoxyphenyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: tricyclo[3.3.1.1^3,7]decane-1-carboxylic acid 4-formyl-2-methoxyphenyl ester
• 英文别名: 3-methoxy-4-(1-adamantylcarbonyloxy)benzaldehyde；4-formyl-2-methoxyphenyl adamantane-1-carboxylate；adamantane-1-carboxylic acid vanillin ester；4-Formyl-2-methoxyphenyl tricyclo[3.3.1.1~3,7~]decane-1-carboxylate；(4-formyl-2-methoxyphenyl) adamantane-1-carboxylate
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: WXYHWHMISRNSTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氨基苯甲酸丁酯 、 tricyclo[3.3.1.1^3,7]decane-1-carboxylic acid 4-formyl-2-methoxyphenyl ester 以 甲醇 为溶剂， 以91%的产率得到butyl 4-{(E)-[4-(adamantan-1-ylcarbonyloxy)-3-methoxyphenyl]methylideneamino}benzoate
  参考文献：
  名称：

  Synthesis and properties of (E)-4-[alkyl(aryl)iminomethyl]-2-methoxy(ethoxy)phenyl adamantane-1-carboxylates

  摘要：

  Condensation of 4-formyl-2-methoxy(ethoxy)phenyl adamantane-1-carboxylates with aliphatic, cycloaliphatic, and aromatic amines gave the corresponding adamantane-containing Schiff bases as E isomers with respect to the CH=N azomethine bond. The reaction of 2-methoxy-4-(naphthalen-2-yliminomethyl)phenyl adamantane-1-carboxylate with cyclohexane-1,3-dione and dimedone led to the formation of 2-methoxy-4-(11-oxo-7,8,9,10,11,12-hexahydrobenzo[a]acridin-12-yl)phenyl adamantane-1-carboxylates. Quantum-chemical calculations of the energies of formation of E and Z isomers of some of the synthesized Schiff bases were performed.

  DOI：

  10.1134/s107042801004010x
• 作为产物：
  描述：

  金刚烷酰氯 、 香草醛 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tricyclo[3.3.1.1^3,7]decane-1-carboxylic acid 4-formyl-2-methoxyphenyl ester
  参考文献：
  名称：

  姜黄素-BF2 /姜黄素对的模块化合成及其在人癌细胞系中比较抗增殖活性的灵活策略。

  摘要：

  描述了一种实现CUR-BF2和CUR化合物合成相互转化的简便协议，该协议显着拓宽了姜黄素的制备范围，提供了更大的化合物库，从而能够对癌细胞中更大的合成类似物库进行比较抗增殖和凋亡研究线。

  DOI：

  10.1002/cmdc.201900640

文献信息

• Synthesis of aromatic azomethines by condensation of substituted benzaldehydes with 4-aminophenylene-N-imide of maleopimaric acid
  作者：E. A. Dikusar、M. P. Bei、A. P. Yuvchenko、V. I. Potkin

  DOI：10.1134/s1070363210070170

  日期：2010.7

  Preparative method of synthesis of aromatic azomethines by condensation of substituted benzaldehydes of vanillin series with 4-aminophenylene-N-imide of maleopimaric acid was developed.

  研制了香兰素系列取代苯甲醛与马来酸4-氨基亚苯基-N-酰亚胺缩合合成芳族甲亚胺的制备方法。
• Synthesis of azomethines by condensation of substituted benzaldehydes with 3-aminophenylen-N-imide of maleopimaric acid
  作者：M. P. Bey、A. P. Yuvchenko、E. A. Dikusar、V. I. Potkin

  DOI：10.1134/s1070363211030200

  日期：2011.3

  New method for the synthesis of azomethines by condensation of substituted benzaldehydes of the vanillin series with 3-aminophenylen-N-imide of maleopimaric acid is developed.

  提出了将香兰素系列取代苯甲醛与马来酸3-氨基苯甲基-N-酰亚胺缩合合成偶氮甲碱的新方法。
• [EN] NOVEL CURCUMIN ANALOGS WITH ANTICANCER ACTIVITY<br/>[FR] NOUVEAUX ANALOGUES DE LA CURCUMINE AYANT UNE ACTIVITÉ ANTICANCÉREUSE
  申请人：FAWZY ITEN MAMDOUH

  公开号：WO2015067282A1

  公开（公告）日：2015-05-14

  Novel Curcumin analogs were designed, synthesized with 1, 5-diaryl-3-oxo-1,4-pentadienyl pharmacophore and evaluated for their antitumor activities in 5 different cell lines; [ovarian cancer (A2780), renal adenocarcinoma (ACHN), prostate cancer (PC-3), colorectal cancer (Hct-116) and a leukemic monocyte lymphoma (U937-GTB)]. Compounds VII and IV exhibited highly potent cytotoxic activity with IC50 values in 1-2.5 μΜ and 11.4-23.2 μM ranges respectively. Also in silico molecular docking study was carried out using Podophyllotoxin-tubulin complex as template to predict the binding affinity of the target compounds to the receptor. On the other hand, in vitro tubulin polymerization assay was performed to both analogs to test their effect on tubulin and results showed that both analogs IV and VII stabilize microtubules with 79.8 % and 60.6 % respectively causing cancer cell apoptosis with the same mechanism as Paclitaxel which it was compared to during the assay.

  设计并合成了新型的姜黄素类似物，具有1,5-二芳基-3-酮基-1,4-戊二烯基药效团，并在5种不同的细胞系中评估其抗肿瘤活性; [卵巢癌（A2780），肾腺癌（ACHN），前列腺癌（PC-3），结直肠癌（Hct-116）和一种白血病单核细胞淋巴瘤（U937-GTB）]。化合物VII和IV表现出高度有效的细胞毒性活性，其IC50值分别在1-2.5μΜ和11.4-23.2μM范围内。此外，使用Podophyllotoxin-tubulin复合物作为模板进行了体外分子对接研究，以预测目标化合物与受体的结合亲和力。另一方面，进行了体外微管聚合实验，以测试两种类似物对微管的影响，结果显示，两种类似物IV和VII稳定微管，分别导致79.8％和60.6％的癌细胞凋亡，其机制与紫杉醇相同，该药物在实验中进行了比较。
• ——
  作者：E. A. Dikusar、N. G. Kozlov、V. I. Potkin、N. V. Kovganko

  DOI：10.1023/a:1025474619550

  日期：——

  Esters 1b-15b were prepared from cetyl alcohol 1a, terpenols 2a-6a, sterols 7a-10a, plant phenols 11a-13a, and alcohols 14a-15a by reaction with 1-adamantanecarboxylic acid chloride in the presence of pyridine.
• Synthesis of chiral azomethines starting from L-valine methyl ester hydrochloride and substituted benzaldehydes of vanillin series
  作者：E. A. Dikusar、V. I. Potkin、N. A. Zhukovskaya

  DOI：10.1134/s1070428010050076

  日期：2010.5

  A preparative method of synthesis of chiral azomethines was developed consisting in the reaction of L-valine methyl ester hydrochloride reaction with substituted benzaldehydes of vanillin series.