8-(3,4,5-trimethoxyphenyl)-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-one | 1240483-57-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 8-(3,4,5-trimethoxyphenyl)-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-one
• 英文别名: 8-(3,4,5-trimethoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one；3,4-dihydro-6,7-methylenedioxy-4-(3,4,5-trimethoxyphenyl)coumarin；8-(3,4,5-trimethoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromen-6-one；8-(3,4,5-trimethoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]chromen-6-one
• CAS: 1240483-57-1
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: YKHKEGYKVZMNNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,3-benzodioxol-5-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate 在 potassium tert-butylate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以64%的产率得到8-(3,4,5-trimethoxyphenyl)-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-one
  参考文献：
  名称：

  N-杂环卡宾/钾离子协同催化α，β-不饱和酰基偶氮的苯甲酰化反应

  摘要：

  开发了α，β-不饱和酰基的催化苯基化反应。N-杂环卡宾和钾离子的结合可协同催化α，β-不饱和酰基zo与酚盐的环化，酚盐直接由α，β-不饱和酚盐产生。机理研究表明，钾离子在该反应中起着至关重要的作用。

  DOI：

  10.1002/ejoc.201600838

文献信息

• Design and Synthesis of C-Ring Lactone- and Lactam-Based Podophyllotoxin Analogues as Anticancer Agents
  作者：Pragya Singh、Uzma Faridi、Suchita Srivastava、Jonnala Kotesh Kumar、Mahender Pandurang Darokar、Suaib Luqman、Karuna Shanker、Chandan Singh Chanotiya、Atul Gupta、Madan Mohan Gupta、Arvind Singh Negi

  DOI：10.1248/cpb.58.242

  日期：——

  A series of novel podophyllotoxin (PDT) analogues was synthesized in which the lactone moiety was shifted to C ring. Some of the derivatives were also synthesized with modified A ring. Analogues 23 and 25 exhibited potent in vitro cytotoxicity against colon cancer (CaCO2) cell line. p-Demethylated E-ring analogues exhibited better potency than the corresponding methylated analogues. These analogues showed toxicity comparable to PDT against human erythrocytes albeit at much higher concentrations (100 μg/ml) than their cytotoxicity values.

  合成了一系列新的蒽醌类（PDT）类似物，其中内酯部分被移至C环。一些衍生物的A环也进行了改造。类似物23和25在体外对结肠癌（CaCO2）细胞系表现出强的细胞毒性。去甲基化的E环类似物的效力优于相应的甲基化类似物。这些类似物对人红细胞的毒性与PDT相当，尽管浓度要高得多（100 μg/ml），才显示出其细胞毒性值。
• Neoflavonoids as Inhibitors of HIV-1 Replication by Targeting the Tat and NF-κB Pathways
  作者：Dionisio Olmedo、José López-Pérez、Esther del Olmo、Luis Bedoya、Rocío Sancho、José Alcamí、Eduardo Muñoz、Arturo Feliciano、Mahabir Gupta

  DOI：10.3390/molecules22020321

  日期：——

  Twenty-eight neoflavonoids have been prepared and evaluated in vitro against HIV-1. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase reporter gene. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Seven 4-phenylchromen-2-one derivatives showed HIV transcriptional inhibitory activity but only the phenylchrome-2-one 10 inhibited NF-κB and displayed anti-Tat activity simultaneously. Compounds 10, 14, and 25, inhibited HIV replication in both targets at concentrations <25 μM. The assays of these synthetic 4-phenylchromen-2-ones may aid in the investigation of some aspects of the anti-HIV activity of such compounds and could serve as a scaffold for designing better anti-HIV compounds, which may lead to a potential anti-HIV therapeutic drug.

  已经制备并在体外评估了28种新黄酮类化合物对HIV-1的活性。抗病毒活性是在感染了带有荧光素酶报告基因的病毒克隆的MT-2细胞上进行评估的。HIV转录和Tat功能的抑制在稳定转染了HIV-LTR和Tat蛋白的细胞上进行测试。七种4-苯基色烯-2-酮衍生物显示出HIV转录抑制活性，但只有苯基色烯-2-酮10同时抑制了NF-κB并显示出抗Tat活性。化合物10、14和25在<25 μM的浓度下抑制了两种靶标中的HIV复制。这些合成的4-苯基色烯-2-酮的测定可能有助于研究此类化合物的抗HIV活性的某些方面，并可能作为设计更好抗HIV化合物的框架，从而导致潜在的抗HIV治疗药物的出现。
• N-Heterocyclic Carbene/Potassium Ion Cooperatively Catalyzed Phenylation Reactions of α,β-Unsaturated Acylazoliums
  作者：Jinhua Zheng、Kejie Zhu、Yaofeng Yuan、Jiajia Cheng

  DOI：10.1002/ejoc.201600838

  日期：2016.9

  catalytic phenylation reaction of α,β‐unsaturated acylazoliums was developed. A combination of N‐heterocyclic carbene and potassium ion cooperatively catalyzed the cyclization of α,β‐unsaturated acylazoliums with phenolates, which are directly generated from α,β‐unsaturated phenolic esters. Mechanistic studies demonstrated that the potassium ion plays a vital role in this reaction.

  开发了α，β-不饱和酰基的催化苯基化反应。N-杂环卡宾和钾离子的结合可协同催化α，β-不饱和酰基zo与酚盐的环化，酚盐直接由α，β-不饱和酚盐产生。机理研究表明，钾离子在该反应中起着至关重要的作用。