(2E,6E,10E)-3,7-dimethyl-11-((tetrahydro-2H-pyran-2-yloxy)methyl)dodeca-2,6,10-trienyl acetate | 135896-09-2

• 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: (2E,6E,10E)-3,7-dimethyl-11-((tetrahydro-2H-pyran-2-yloxy)methyl)dodeca-2,6,10-trienyl acetate
• 英文别名: [(2E,6E,10E)-3,7,11-trimethyl-12-(oxan-2-yloxy)dodeca-2,6,10-trienyl] acetate
• CAS: 135896-09-2
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: ARPOISKKZFCKLH-ZSLRMYRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E,6E,10E)-3,7-dimethyl-11-((tetrahydro-2H-pyran-2-yloxy)methyl)dodeca-2,6,10-trienyl acetate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 溴 、 叔丁基锂 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Clark, J. Stephen; Myatt, James; Wilson, Claire, Chemical Communications, 2003, # 13, p. 1546 - 1547

  摘要：

  DOI：
• 作为产物：
  描述：

  反,反-西基乙酸 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 对甲苯磺酸 、 水杨酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2E,6E,10E)-3,7-dimethyl-11-((tetrahydro-2H-pyran-2-yloxy)methyl)dodeca-2,6,10-trienyl acetate
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of ω-oxygenated analogues of vitamin K2: Study of modification and structure–activity relationship of vitamin K2 metabolites

  摘要：

  Novel omega-oxygenated vitamin K-2 analogues, which are candidates for metabolites of vitamin K-2 homologues, were efficiently synthesized and their apoptosis-inducing activity was evaluated. We revealed that some of those analogues were biologically active and the side-chain part played an important role in apoptosis-inducing activity. Our results can provide useful information to develop the structure-activity relationship of vitamin K-2 analogues for new drugs based on vitamin K. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.082

文献信息

• Design and synthesis of biologically active analogues of vitamin K2: Evaluation of their biological activities with cultured human cell lines
  作者：Yoshitomo Suhara、Yoshihisa Hirota、Kimie Nakagawa、Maya Kamao、Naoko Tsugawa、Toshio Okano

  DOI：10.1016/j.bmc.2007.12.025

  日期：2008.3.15

  Novel omega-oxygenated vitamin K(2) analogues were efficiently synthesized and their biological activities were evaluated. Some were biologically active and the side-chain played an important role in gamma-carboxylation and apoptosis-inducing activity. The results provide useful information on the structure-activity relationship of vitamin K(2) analogues for the development of new drugs.

  新型的ω-氧化的维生素K（2）类似物被有效地合成，并对其生物学活性进行了评估。一些具有生物活性，并且侧链在γ-羧化和诱导细胞凋亡的活性中起重要作用。结果提供了有关维生素K（2）类似物的结构-活性关系的新药开发有用的信息。
• Synthesis of Novel Vitamin K₂ Analogues with Modification at the ω-Terminal Position and Their Biological Evaluation as Potent Steroid and Xenobiotic Receptor (SXR) Agonists
  作者：Yoshitomo Suhara、Masato Watanabe、Kimie Nakagawa、Akimori Wada、Yoichi Ito、Kazuyoshi Takeda、Kazuhiko Takahashi、Toshio Okano

  DOI：10.1021/jm200025f

  日期：2011.6.23

  Vitamin K-2 is a ligand for a nuclear receptor, steroid and xenobiotic receptor (SXR), that induces the gene expressions of CYP3A4. We synthesized vitamin K-2 analogues with hydroxyl or phenyl groups at the omega-terminal of the side chain. The up-regulation of SXR-mediated transcription of the target gene by the analogues was dependent on the length of the side chain and the hydrophobicity of the omega-terminal residues. Phenyl analogue menaquinone-3 was as active as the known SXR ligand rifampicin.