Isolapachol | 126809-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Isolapachol
• 英文别名: (E)-2-hydroxy-3-(3-methylbut-1-en-1-yl)naphthalene-1,4-dione
• CAS: 126809-81-2
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: FHECNCZIYPTBRB-BQYQJAHWSA-N

物化性质

• 沸点：
  397.7±42.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Isolapachol 在 苯基氯化硒 、 silica gel 作用下， 生成 2-isopropylnaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  硒试剂在萘并[2,3 - b ]呋喃-4,9-二酮的合成中

  摘要：

  苯硒醚化用于从2-羟基萘醌合成萘并[2,3 - b ]呋喃-4,9-二酮和萘并[2,3-b]吡喃-5,10-二酮。

  DOI：

  10.1016/s0040-4039(00)97194-6
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 以75%的产率得到
  参考文献：
  名称：

  SUGANUMA, XIROYUKI;FUDZIMURA, XIROSI

  摘要：

  DOI：

文献信息

• Molecular mechanism of action of new 1,4-naphthoquinones tethered to 1,2,3-1H-triazoles with cytotoxic and selective effect against oral squamous cell carcinoma
  作者：Ingrid Cavalcanti Chipoline、Anna Carolina Carvalho da Fonseca、Gabriella Ribeiro Machado da Costa、Michele Pereira de Souza、Vitor Won-Held Rabelo、Lucas N. de Queiroz、Theo Luiz Ferraz de Souza、Elan Cardozo Paes de Almeida、Paula Alvarez Abreu、Bruno Pontes、Vitor Francisco Ferreira、Fernando de Carvalho da Silva、Bruno K. Robbs

  DOI：10.1016/j.bioorg.2020.103984

  日期：2020.8

  compounds with cytotoxic effect demonstrated on different cancer types. In the present study, thirty-five 1,4-naphthoquinones tethered to 1,2,3-1H-triazoles were synthesized and the antitumor activity and molecular mechanisms were evaluated in several assays including in vitro and in vivo models of OSCC and normal oral human cells. Compounds 16a, 16b and 16 g were able to induce cytotoxicity in three different

  尽管诊断和治疗取得了进步，但是口腔鳞状细胞癌（OSCC）由于其高发病率和低存活率而成为公共卫生问题。此外，最常见的OSCC化疗药物，如卡铂和顺铂，产生重要的副作用，证明开发新药的紧迫性。萘醌是一类重要的天然产物或合成化合物，对不同类型的癌症均显示出细胞毒作用。在本研究中，合成了35个与1,2,3-1 H-三唑拴在一起的1,4-萘醌，并在包括OSCC和正常人的体内和体外模型在内的多种测定中评估了其抗肿瘤活性和分子机制。口腔人类细胞。化合物16a，16b和16g能够在人OSCC的三种不同肿瘤细胞系（SCC4，SCC9和SCC25）中诱导细胞毒性，并且比经典和化学相似的对照对肿瘤细胞更具毒性和选择性（选择性指数，SI> 2） （卡铂和Lapachol）。化合物16g显示出较高的SI值。此外，化合物16A，16B和16克SCC9细胞显著减少集落形成在测试浓度。使用高浓度化合物16a，16b和16g
• Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase
  作者：Felipe A. Calil、Juliana S. David、Estela R.C. Chiappetta、Fernando Fumagalli、Rodrigo B. Mello、Franco H.A. Leite、Marcelo S. Castilho、Flavio S. Emery、M.Cristina Nonato

  DOI：10.1016/j.ejmech.2019.02.018

  日期：2019.4

  Schistosomiasis ranks second only to malaria as the most common parasitic disease worldwide. 700 million people are at risk and 240 million are already infected. Praziquantel is the anthelmintic of choice but decreasing efficacy has already been documented. In this work, we exploited the inhibition of Schistosoma mansoni dihydroorotate dehydrogenase (SmDHODH) as a strategy to develop new therapeutics to fight schistosomiasis. A series of quinones (atovaquone derivatives and precursors) was evaluated regarding potency and selectivity against both SmDHODH and human DHODH. The best compound identified is 17 (2-hydroxy-3-isopentylnaphthalene-1,4-dione) with IC50 = 23 +/- 4 nM and selectivity index of 30.83. Some of the new compounds are useful pharmacological tools and represent new lead structures for further optimization. (C) 2019 Elsevier Masson SAS. All rights reserved.
• DE, OLIVEIRA ALAIDE BRAGA;RASLAN, DELIO SOARES;KHUONG-HUU, FRANCOISE, TETRAHEDRON LETT., 31,(1990) N7, C. 6873-6876
  作者：DE, OLIVEIRA ALAIDE BRAGA、RASLAN, DELIO SOARES、KHUONG-HUU, FRANCOISE

  DOI：——

  日期：——
• BOCK, K.;JACOBSEN, N.;TEREM, B., J. CHEM. SOC. PERKIN TRANS., 1986, N 4, 659-664
  作者：BOCK, K.、JACOBSEN, N.、TEREM, B.

  DOI：——

  日期：——
• 2-(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinone, process for its production and processes for producing 2-(1-alkenyl)-3-hydroxy-1,4-naphthoquinone and 2-alkyl-3-acyloxy-1,4-naphthoquinone by using it
  申请人：KAWASAKI KASEI CHEMICALS LTD.

  公开号：EP0330186B1

  公开（公告）日：1993-05-19