1-(4-methylnaphtalen-1-yl)but-3-en 1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-methylnaphtalen-1-yl)but-3-en 1-ol
• 英文别名: (S)-1-(4-methylnaphthalen-1-yl)-but-3-en-1-ol；(1S)-1-(4-methylnaphthalen-1-yl)but-3-en-1-ol
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: GAHWQFSKSDFGAI-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基-1-萘醛 、 烯丙基三丁基锡 在 bismuth(lll) trifluoromethanesulfonate 、 2,6-bis((2S-(Ph₂(HO)C)pyrrolidino)methyl)-4-methylphenol 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 69.0h， 以79%的产率得到1-(4-methylnaphtalen-1-yl)but-3-en 1-ol
  参考文献：
  名称：

  三氟甲基磺酸铋催化芳香醛的不对称烯丙基化

  摘要：

  适合BiL 2：使用Bi（OTf）3和Trost（R，R）-ProPhenol配体（见方案）开发了一种高度对映体选择性催化芳族醛烯丙基化的方法。对于各种芳族醛，均获得了良好的收率和高对映选择性。所公开的方法是使用手性Bi III配合物进行醛的对映选择性烯丙基化反应的第一个实例。还报道了Bi III预催化剂的初步表征。

  DOI：

  10.1002/chem.201103646

文献信息

• 6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties
  作者：Pınar Kasaplar、Özgür Yılmazer、Ali Çağır

  DOI：10.1016/j.bmc.2008.10.069

  日期：2009.1

  (R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines. (C) 2008 Elsevier Ltd. All rights reserved.
• Antiproliferative activity of (R)-4′-methylklavuzon on hepatocellular carcinoma cells and EpCAM+/CD133+ cancer stem cells via SIRT1 and Exportin-1 (CRM1) inhibition
  作者：Murat Delman、Sanem Tercan Avcı、İsmail Akçok、Tuğçe Kanbur、Esra Erdal、Ali Çağır

  DOI：10.1016/j.ejmech.2019.07.024

  日期：2019.10

  Cytotoxic effects of (R)-4'-methylklavuzon were investigated on hepatocellular carcinoma cells (HuH-7 and HepG2) and HuH-7 EpCAM(+)/CD133(+) cancer stem cells. IC50 of (R)-4'-methylklavuzon was found as 1.25 mu M for HuH-7 parental cells while it was found as 2.50 mu M for HuH-7 EpCAM(+)/CD133(+) cancer stem cells. (R)-4'-methylklavuzon tended to show more efficient in vitro cytotoxicity with its lower IC50 values on hepatocellular carcinoma cell lines compared to its lead molecule, goniothalamin and FDA-approved drugs, sorafenib and regorafenib. Cell-based Sirtuin/HDAC enzyme activity measurements revealed that endogenous Sirtuin/HDAC enzymes were reduced by 40% compared to control. SIRT1 protein levels were upregulated indicating triggered DNA repair mechanism. p53 was overexpressed in HepG2 cells. (R)-4'methylklavuzon inhibited CRM1 protein providing increased retention of p53 and RIOK2 protein in the nucleus. HuH-7 parental and EpCAM(+)/CD133(+) cancer stem cell spheroids lost intact morphology. 3D HepG2 spheroid viabilities were decreased in a correlation with upregulation in p53 protein levels. (C) 2019 Elsevier Masson SAS. All rights reserved.