7-methoxy-1,4-dioxo-3-(phenyliodonio)-1,4-dihydronaphthalen-2-olate | 908128-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-methoxy-1,4-dioxo-3-(phenyliodonio)-1,4-dihydronaphthalen-2-olate
• CAS: 908128-22-3；1040247-66-2
• 化学式: C₁₇H₁₁IO₄
• 分子量: 406.176
• InChiKey: MGFBQDHFULKCSB-UHFFFAOYSA-N

物化性质

• 熔点：
  204-209 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.43
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-methoxy-1,4-dioxo-3-(phenyliodonio)-1,4-dihydronaphthalen-2-olate 在 盐酸 、 三甲基氯硅烷 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以93%的产率得到3-chloro-2-hydroxy-7-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone

  摘要：

  Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.04.034
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 potassium tert-butylate 、 氧气 作用下， 以 氯仿 、 叔丁醇 为溶剂， 反应 6.0h， 生成 7-methoxy-1,4-dioxo-3-(phenyliodonio)-1,4-dihydronaphthalen-2-olate
  参考文献：
  名称：

  Synthesis and Cytotoxicity on Human Leukemia Cells of Furonaphthoquinones Isolated from <i>Tabebuia</i> Plants

  摘要：

  呋喃萘醌类化合物是抗癌药物分子很有前途的骨架。特别是甲氧基化的呋喃萘醌类化合物是 Tabebuia 植物的特征成分。在这项研究中，我们在钯和亚铜催化剂存在下，通过 Sonogashira 偶联和分子内环化反应，以 3-苯基碘-1,2,4-三氧代-1,2,3,4-四氢萘化物和 3-丁炔-2-醇为原料，进行了有效的一锅级联反应，合成了呋喃萘醌类化合物。此外，我们还证明了合成的呋喃萘醌类化合物对人类白血病 U937 和 HL-60 细胞具有适度的细胞毒性。我们的工作凸显了呋喃并萘醌类化合物作为抗白血病药物的重要性。

  DOI：

  10.1248/cpb.c13-00011

文献信息

• Synthetic methods for the preparation of ARQ 501 (β-Lapachone) human blood metabolites
  作者：Rui-Yang Yang、Darin Kizer、Hui Wu、Erika Volckova、Xiu-Sheng Miao、Syed M. Ali、Manish Tandon、Ronald E. Savage、Thomas C.K. Chan、Mark A. Ashwell

  DOI：10.1016/j.bmc.2008.03.073

  日期：2008.5

  ARQ 501 (3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione), a synthetic version of beta-Lapachone, is a promising anti-cancer agent currently in multiple Phase II clinical trials. Promising anti-cancer activity was observed in Phase I and Phase II trials. Metabolism by red blood cells of drugs is an understudied area of research and the metabolites arising from oxidative ring opening (M2 and M3), decarbonylation/ ring contraction (M5), and decarbonylation/ oxidation (M4 and M6) of ARQ 501 offer a unique opportunity to provide insight into these metabolic processes. Since these metabolites were not detected in in vitro incubations of ARQ 501 with liver microsomes and were structurally diverse, confirmation by chemical synthesis was considered essential. In this report, we disclose the synthetic routes employed and the characterization of the reference standards for these blood metabolites as well as additional postulated structures, which were not confirmed as metabolites. (C) 2008 Elsevier Ltd. All rights reserved.