5-hydroxy-4,8,8-trimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one | 106726-13-0

• 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: 5-hydroxy-4,8,8-trimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one
• 英文别名: 5-hydroxy-5',5a',9-trimethylpyrano[2',3'-f]-(8H)-chromen-2-one；5-hydroxy-4,8,8-trimethyl-8H-pyrano[2,3-f]chromen-2-one；5-hydroxy-4,8,8-trimethylpyrano[2,3-h]chromen-2-one
• CAS: 106726-13-0
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: HBQUYQAZVHOJSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4,8,8-trimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 、 N,N-二乙基氯乙胺 在 potassium carbonate 、 盐酸 作用下， 以 丙酮 、 甲醇 为溶剂， 以70%的产率得到5-(2-(diethylamino)ethoxy)-5',5a',9-trimethylpyrano[2',3'-f]-(8H)-chromen-2-one hydrochloride
  参考文献：
  名称：

  Anticancer effects of O-aminoalkyl derivatives of alloxanthoxyletin and seselin

  摘要：

  Seselin and alloxanthoxyletin, naturally occurring pyranocoumarins, were recently isolated from a number of plant sources, such as family of Rutaceae. It was previously reported that their natural and synthetic derivatives show cytotoxic and antitumor activity. In the present study new series of O-aminoalkyl substituted alloxanthoxyletins and seselins were synthesized and evaluated for their anticancer toxicity. Microwave assisted synthesis was used, and the structures of the compounds were confirmed by H-1 NMR, C-13 NMR and MS spectroscopic data. The molecular and crystal structure of 3a was analyzed by single crystal X-ray diffraction. Alloxanthoxyletin derivatives 2a, 2b, and 2d showed the highest cytotoxic potential against HTB-140 cells with IC50 of 2.48, 2.80 and 2.98 mu M, respectively. In vitro drug sensitivity testing in HaCaT, A549 and HTB-140 cells were also performed. Tumor cells showed a higher sensitivity to tested compounds than normal cells. Compounds 2a, 2b and 2d inhibited cell migration and exerted stronger effect on A549 and HTB-140 cells than on HaCaT cells. In order to explain the basic mechanism of cell death induction we have investigated the effect of derivatives 2a, 2b and 2d on early and late apoptosis using annexin V-FITC/7-AAD flow cytometry analysis. Derivatives 2a and 2b were much more potent inducers of early apoptosis in HTB-140 cells compared to HaCaT and A549 cells.

  DOI：

  10.1016/j.biopha.2017.09.050
• 作为产物：
  描述：

  5,7-二羟基-4-甲基香豆素 、 4,4-二甲氧基-2-甲基-2-丁醇 、 吡啶 生成 5-hydroxy-4,8,8-trimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one
  参考文献：
  名称：

  ZAWADOWSKI, TEODOR;MAZUR, ANDRZEJ;RUMP, SLAWOMIR;BORKOWSKA, GRAZYNA, ACTA POL. PHARM., 44,(1987) N 3-4, 276-280

  摘要：

  DOI：

文献信息

• Anticancer effects of alloxanthoxyletin and fatty acids esters – In vitro study on cancer HTB-140 and A549 cells
  作者：Michał Jóźwiak、Marta Struga、Piotr Roszkowski、Agnieszka Filipek、Grażyna Nowicka、Wioletta Olejarz

  DOI：10.1016/j.biopha.2018.12.005

  日期：2019.2

  such as family of Rutaceae, and its synthetic derivatives show cytotoxic and antitumor activities. In the present study new eleven esters of alloxanthoxyletin and fatty acids were synthesized and evaluated for their anticancer toxicity. The structures of the compounds were confirmed by Proton Nuclear Magnetic Resonance (H NMR), Carbon-13 Nuclear Magnetic Resonance (C NMR) and High Resolution Mass Spectrometry

  别氧烷氧基letin是一种天然的吡喃香​​豆素，它是从芸苔科等多种植物中分离得到的，其合成衍生物具有细胞毒性和抗肿瘤活性。在本研究中，合成了新的十一种四氧杂环丁烷酯和脂肪酸酯，并评估了它们的抗癌毒性。化合物的结构通过质子核磁共振（1 H NMR），碳13核磁共振（13 C NMR）和高分辨率质谱（HRMS）分析确认。对于所有化合物，使用3-（4,5-二甲基噻唑基-2）-2,5-二苯基四唑溴化物（MTT）分析法测定对人黑素瘤细胞（HTB-140），人上皮性肺癌细胞（A549）的细胞毒性作用和人类角质形成细胞系（HaCaT）。对于活性最高的化合物（8-11），进行了乳酸脱氢酶（LDH）分析，以评估细胞损伤的水平以及迁移抑制分析。为了解释细胞死亡诱导的基本机理，在膜联蛋白V-FITC / 7-AAD流式细胞仪分析中研究了衍生物8-11对早期和晚期凋亡的影响。结果表明，与人角质形成细胞（HaCaT
• Zawadowski, Teodor; Mazur, Andrzej; Kleps, Jerzy, Polish Journal of Chemistry, 1985, vol. 59, # 5-6, p. 547 - 552
  作者：Zawadowski, Teodor、Mazur, Andrzej、Kleps, Jerzy

  DOI：——

  日期：——
• Anticancer effects of O-aminoalkyl derivatives of alloxanthoxyletin and seselin
  作者：Kinga Ostrowska、Wioletta Olejarz、Małgorzata Wrzosek、Alicja Głuszko、Grażyna Nowicka、Mirosław Szczepański、Ilona B. Materek、Anna E. Kozioł、Marta Struga

  DOI：10.1016/j.biopha.2017.09.050

  日期：2017.11

  Seselin and alloxanthoxyletin, naturally occurring pyranocoumarins, were recently isolated from a number of plant sources, such as family of Rutaceae. It was previously reported that their natural and synthetic derivatives show cytotoxic and antitumor activity. In the present study new series of O-aminoalkyl substituted alloxanthoxyletins and seselins were synthesized and evaluated for their anticancer toxicity. Microwave assisted synthesis was used, and the structures of the compounds were confirmed by H-1 NMR, C-13 NMR and MS spectroscopic data. The molecular and crystal structure of 3a was analyzed by single crystal X-ray diffraction. Alloxanthoxyletin derivatives 2a, 2b, and 2d showed the highest cytotoxic potential against HTB-140 cells with IC50 of 2.48, 2.80 and 2.98 mu M, respectively. In vitro drug sensitivity testing in HaCaT, A549 and HTB-140 cells were also performed. Tumor cells showed a higher sensitivity to tested compounds than normal cells. Compounds 2a, 2b and 2d inhibited cell migration and exerted stronger effect on A549 and HTB-140 cells than on HaCaT cells. In order to explain the basic mechanism of cell death induction we have investigated the effect of derivatives 2a, 2b and 2d on early and late apoptosis using annexin V-FITC/7-AAD flow cytometry analysis. Derivatives 2a and 2b were much more potent inducers of early apoptosis in HTB-140 cells compared to HaCaT and A549 cells.
• ZAWADOWSKI, TEODOR;MAZUR, ANDRZEJ;RUMP, SLAWOMIR;BORKOWSKA, GRAZYNA, ACTA POL. PHARM., 44,(1987) N 3-4, 276-280
  作者：ZAWADOWSKI, TEODOR、MAZUR, ANDRZEJ、RUMP, SLAWOMIR、BORKOWSKA, GRAZYNA

  DOI：——

  日期：——