lapachol laurate

• 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: lapachol laurate
• 英文别名: [3-(3-Methylbut-2-enyl)-1,4-dioxo-2-naphthyl] dodecanoate；[3-(3-methylbut-2-enyl)-1,4-dioxonaphthalen-2-yl] dodecanoate
• 化学式: C₂₇H₃₆O₄
• 分子量: 424.58
• InChiKey: VADRSGILUPVRJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  月桂酰氯 、 黄钟花醌 在 lutidine 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到lapachol laurate
  参考文献：
  名称：

  在人早幼粒细胞白血病HL-60细胞系中具有细胞毒活性的萘醌衍生物的合成和药效基团建模。

  摘要：

  催化剂/ HypoGen药效团建模方法和三维定量结构-活性关系（3D-QSAR）/比较分子相似性指数分析（CoMSIA）方法已成功用于解释一组测试的51种天然和合成萘醌衍生物的细胞毒活性在人早幼粒细胞白血病HL-60细胞系中。计算模型促进了对抗肿瘤特性至关重要的配体结构元素的鉴定。高活性β-环-吡喃-1,2-萘醌[0.1 microM

  DOI：

  10.1021/jm060849b

文献信息

• Synthesis and Pharmacophore Modeling of Naphthoquinone Derivatives with Cytotoxic Activity in Human Promyelocytic Leukemia HL-60 Cell Line
  作者：Elisa Pérez-Sacau、Raquel G. Díaz-Peñate、Ana Estévez-Braun、Angel G. Ravelo、Jose M. García-Castellano、Leonardo Pardo、Mercedes Campillo

  DOI：10.1021/jm060849b

  日期：2007.2.1

  quantitative structure-activity relationship (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to explain the cytotoxic activity of a set of 51 natural and synthesized naphthoquinone derivatives tested in human promyelocytic leukemia HL-60 cell line. The computational models have facilitated the identification of structural elements of the ligands

  催化剂/ HypoGen药效团建模方法和三维定量结构-活性关系（3D-QSAR）/比较分子相似性指数分析（CoMSIA）方法已成功用于解释一组测试的51种天然和合成萘醌衍生物的细胞毒活性在人早幼粒细胞白血病HL-60细胞系中。计算模型促进了对抗肿瘤特性至关重要的配体结构元素的鉴定。高活性β-环-吡喃-1,2-萘醌[0.1 microM
• Inhibitory effects of lapachol derivatives on epstein-barr virus activation
  作者：Elisa Pérez Sacau、Ana Estévez-Braun、Ángel G Ravelo、Esteban A Ferro、Harunkuni Tokuda、Teruo Mukainaka、Hoyoku Nishino

  DOI：10.1016/s0968-0896(02)00542-4

  日期：2003.2

  Sixteen derivatives (2-17) synthesized from the naphthoquinone lapachol (1), were tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA), as a test for potential cancer chemopreventive agents. They exhibited a variety of inhibitory activities from very high to moderate, which allow us to suggest structure-activity relationships. Ten of these derivatives are reported for the first time, their structures being thoroughly determined by spectroscopic methods. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Growth inhibitory activity for cancer cell lines of lapachol and its natural and semi-synthetic derivatives
  作者：Serena Fiorito、Francesco Epifano、Céline Bruyère、Véronique Mathieu、Robert Kiss、Salvatore Genovese

  DOI：10.1016/j.bmcl.2013.12.049

  日期：2014.1

  A series of 17 selected natural and semisynthetic 1,4-naphthoquinones were synthesized, and their growth inhibitory activity was evaluated in vitro. The compounds were tested on six human cancer cell lines using the MTT colorimetric assay. The data revealed that of the chemicals under study only lapachol, its acetate and 3-geranyllawsone displayed the highest activity, recording mean IC50 values ranging from 15 to 22 mu M. (C) 2013 Elsevier Ltd. All rights reserved.