7-(2-azidoethoxy)-4-methyl-2H-chromen-2-one | 1430852-57-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(2-azidoethoxy)-4-methyl-2H-chromen-2-one
• 英文别名: 7-(2-Azidoethoxy)-4-methylchromen-2-one；7-(2-azidoethoxy)-4-methylchromen-2-one
• CAS: 1430852-57-5
• 化学式: C₁₂H₁₁N₃O₃
• 分子量: 245.238
• InChiKey: NHNVLZMXXRYXPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  7-(2-溴乙氧基)-4-甲基-2H-色烯-2-酮	7-(2-bromoethoxy)-4-methyl-2H-chromen-2-one	7471-76-3	C12H11BrO3	283.122
  羟甲香豆素	7-hydroxy-4-methyl-chromen-2-one	90-33-5	C10H8O3	176.172

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Tert-butyl 4-[[1-[2-(4-methyl-2-oxochromen-7-yl)oxyethyl]triazol-4-yl]methylsulfanylcarbothioyl]piperazine-1-carboxylate	1430852-58-6	C25H31N5O5S2	545.684

反应信息

• 作为反应物：
  描述：

  4-戊炔-1-醇 、 7-(2-azidoethoxy)-4-methyl-2H-chromen-2-one 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以86%的产率得到7-(2-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)ethoxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  探索在富勒烯支架上显示的多聚香豆素对碳酸酐酶的抑制作用†

  摘要：

  碳酸酐酶（CA）是无处不在的Zn金属-酶催化CO的可逆水合/脱水2 / HCO 3 - 。CA参与许多关键的生物学过程，因此它们的抑制已成为有吸引力的研究领域。已经报道了不同的​​CA抑制剂（CAI）家族，其中大多数与Zn（II）相互作用。）在活动站点上。一些化合物（如香豆素）在结合活性位点腔的入口之前先被水解，因此起“自杀”抑制剂的作用。这项研究报告了多聚体自杀抑制剂的首次合成，旨在解决CA多价抑制的选择性和效力。借助CuAAC反应，将十二个香豆素单元移植到中央富勒烯支架上，并针对4个相关CA对最终的十二聚体进行了分析。多聚体总是比单体物种更强的抑制剂，但是没有发现强的“多价效应”。但是，我们的研究表明，香豆素在C 60周围的多聚体呈递确实影响了所测定的4种CA之间相对抑制的选择性。

  DOI：

  10.1039/c5ob01005e
• 作为产物：
  描述：

  羟甲香豆素 在 sodium azide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.0h， 生成 7-(2-azidoethoxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Design, Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry

  摘要：

  为开发新型化疗药物，我们采用杂化策略设计了4类新型化合物。本研究通过点击化学合成了20种双氢青蒿素-香豆素杂化物（10a-e，11a-e，12a-e，13a-e），并通过高分辨质谱（HRMS）和核磁共振（NMR）对其结构进行了表征。我们在常氧或缺氧条件下，使用MTT法分别对3种癌细胞系（HCT-116、MDA-MB-231和HT-29）进行了细胞毒性活性测试。目标化合物表现出中等活性，IC50值在0.05至125.40微摩尔范围内，其中大部分化合物在缺氧条件下对HT-29细胞显示出更好的活性。大多数化合物在缺氧条件下的活性比常氧条件下高出1至10倍。化合物10a-e对HT-29细胞的选择性优于其他两种细胞系。这些结果表明，我们设计的CA IX抑制剂与其作用模式在一定程度上相符，值得进一步研究。

  DOI：

  10.3390/molecules21060758

文献信息

• <i>Retracted:</i> Synthesis, Molecular Properties, and Biological Evaluation of Hybrid 1,2,3‐Triazolylpolyaza Heterocyclic Compounds
  作者：Srinivasa Rao Dasari、Subbaiah Tondepu、Lakshmana Rao Vadali、Mutyala Naidu Ganivada、Nareshvarma Seelam

  DOI：10.1002/jhet.3395

  日期：2019.1

  this research article, a highly efficient, cost‐effective synthesis of various hybrid molecules possessing 1,2,3‐triazolyltetrazoles and evaluation of their biological activity have been addressed. The structure elucidation of these new library hybrid molecules has been carried out by IR, 1H NMR, 13C NMR, and mass spectral analysis. The compounds have been screened for their anticancer activity against

  在这篇研究文章中，已经解决了具有1,2,3-三唑基四唑的各种杂合分子的高效，经济高效的合成及其生物活性的评价。这些新文库杂合分子的结构阐明已通过IR，1 H NMR，13 C NMR和质谱分析进行。筛选了这些化合物对人结肠癌细胞系Colo-205和人肺癌细胞HOP-205的抗癌活性，结果证明大多数化合物显示出非常好的治疗性质。特别是化合物3d，3j，6a和6e与阿霉素相比，它们对所有测试的人类癌细胞系的细胞毒性更高，分别增长68％，101.8％，94％和104.5％。在本研究中，对3a – j和6a – h系列进行了分子特性预测，Molinspiration进行了药物相似性评估以及Molsoft软件程序进行了毒性风险分析。所有18种类似物均基于Lipinski的“ 5条规则”进行合成，筛选其抗菌和抗癌药物为口服生物可利用药物/铅。
• Synthesis and use of “clickable” bay-region tetrasubstituted perylene tetracarboxylic tetraesters and a perylene monoimide diester as energy acceptors
  作者：Edanur Aydin、Bilal Nisanci、Murat Acar、Arif Dastan、Özgür Altan Bozdemir

  DOI：10.1039/c4nj01565g

  日期：——

  Novel perylene derivatives are ready to be used as functional energy acceptors in light-harvesting systems.

  新型的苝衍生物已经可以用作光合系统中的功能性能量受体。
• Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents
  作者：Haonan Yu、Zhuang Hou、Ye Tian、Yanhua Mou、Chun Guo

  DOI：10.1016/j.ejmech.2018.04.005

  日期：2018.5

  To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G(0)/G(1) phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Design and synthesis of novel 1,2,3-triazole-dithiocarbamate hybrids as potential anticancer agents
  作者：Ying-Chao Duan、Yong-Cheng Ma、En Zhang、Xiao-Jing Shi、Meng-Meng Wang、Xian-Wei Ye、Hong-Min Liu

  DOI：10.1016/j.ejmech.2012.12.046

  日期：2013.4

  A series of novel 1,2,3-triazole-dithiocarbamate hybrids were designed, synthesized and evaluated for anticancer activity against four selected human tumor cell lines (MGC-803, MCF-7, PC-3, EC-109). Majority of the synthesized compounds exhibited moderate to potent activity against MGC-803 and MCF-7. Among them, compounds 3a and 3c showed excellent broad spectrum anticancer activity with IC50 values ranging from 0.73 to 11.61 mu M and 0.49-12.45 mu M, respectively. Particularly, compound 3a was more potent than 5-fluorouracil against all tested human cancer cell lines. Flow cytometry analysis demonstrated that treatment of MGC-803 with 3c led to cell cycle arrest at G2/M phase accompanied by an increase in apoptotic cell death after 12 h. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design, Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry
  作者：Ye Tian、Zhen Liang、Hang Xu、Yanhua Mou、Chun Guo

  DOI：10.3390/molecules21060758

  日期：——

  In order to develop novel chemotherapeutic agents with potent anticancer activities, we designed four series of novel compounds employing hybridization strategy. Twenty novel dihydroartemisinin-coumarin hybrids, 10a–e, 11a–e, 12a–e, 13a–e, were synthesized via click chemistry in this study and their structures were characterized by HRMS and NMR. The cytotoxic activities were measured by MTT assay against three cancer cell lines (HCT-116, MDA-MB-231, and HT-29) under normoxic or anoxic conditions, respectively. The target compounds exhibited moderate activity with IC50 values in the 0.05–125.40 μM range, and these compounds exhibited better activity against HT-29 cell line under anoxic condition. The cytotoxic activities of most compounds under anoxic condition displayed one- to 10-fold greater activity than under normoxic condition. Compounds 10a–e showed better selectivity against the HT-29 cell line than the other two cell lines. These results indicated that our design of CA IX inhibitors does correspond with its action mode to some degree and deserves further investigation.

  为开发新型化疗药物，我们采用杂化策略设计了4类新型化合物。本研究通过点击化学合成了20种双氢青蒿素-香豆素杂化物（10a-e，11a-e，12a-e，13a-e），并通过高分辨质谱（HRMS）和核磁共振（NMR）对其结构进行了表征。我们在常氧或缺氧条件下，使用MTT法分别对3种癌细胞系（HCT-116、MDA-MB-231和HT-29）进行了细胞毒性活性测试。目标化合物表现出中等活性，IC50值在0.05至125.40微摩尔范围内，其中大部分化合物在缺氧条件下对HT-29细胞显示出更好的活性。大多数化合物在缺氧条件下的活性比常氧条件下高出1至10倍。化合物10a-e对HT-29细胞的选择性优于其他两种细胞系。这些结果表明，我们设计的CA IX抑制剂与其作用模式在一定程度上相符，值得进一步研究。