5-(hydroxymethyl)-7H-furo[3,2-g]chromen-7-one | 1256267-27-2

• 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-(hydroxymethyl)-7H-furo[3,2-g]chromen-7-one
• 英文别名: 5-hydroxymethyl-7H-furo[3,2-g]benzopyran-7-one；5-(Hydroxymethyl)furo[3,2-g]chromen-7-one
• CAS: 1256267-27-2
• 化学式: C₁₂H₈O₄
• 分子量: 216.193
• InChiKey: NZGZWRPXPMIHRW-UHFFFAOYSA-N

物化性质

• 熔点：
  206-208 °C
• 沸点：
  449.6±35.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(hydroxymethyl)-7H-furo[3,2-g]chromen-7-one 在 三溴化硼 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到5-(bromomethyl)-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure–activity relationship study

  摘要：

  Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of la were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 mu g/mL) than 1a (MIC = 6.25 mu g/mL), and is even potent than the positive control metronidazole (MIC = 0.50 mu g/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of la have also led to an outline of structure-activity relationship. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.045
• 作为产物：
  描述：

  乙醛,[(4-甲基-2-羰基-2H-1-苯并吡喃-7-基)氧代]- 在 selenium(IV) oxide 、 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 5,5-dimethyl-1,3-cyclohexadiene 、 水 为溶剂， 反应 18.5h， 生成 5-(hydroxymethyl)-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Novel Furocoumarin Derivatives Stimulate Melanogenesis in B16 Melanoma Cells by Up-Regulation of MITF and TYR Family via Akt/GSK3β/β-Catenin Signaling Pathways

  摘要：

  白玉盘提取物和补骨脂素是小叶白蜡树的传统维吾尔药材,用于治疗白癜风,其活性成分呋喃香豆素被发现是目前对该皮肤病最有效的药物。因此,根据我们以前的研究,设计并合成了一系列新的呋喃香豆素衍生物(8a-8p)以改善这种活性。合成的衍生物在鼠B16细胞中对黑色素合成的生物学评价和SAR(结构-活性关系)进行了总结。八种衍生物比阳性对照(8-MOP,8-甲氧基补骨脂素)更有效,特别是化合物8n(200%)和8o(197%),其效力几乎是8-MOP(136%)的1.5倍。此外,8n激活黑色素生物合成的信号途径被确定。我们的结果表明,它不仅提高了黑色素含量,而且刺激了酪氨酸酶的活性,呈浓度依赖性。通过Westernblot分析观察到磷酸化Akt(也称为PKB,蛋白激酶B)和非激活GSK3β(糖原合酶激酶3β)的增加,抑制了β-catenin的降解。β-catenin的积累可能导致MITF(小眼相关转录因子)和TYR(酪氨酸酶)家族的转录激活,以及随后诱导黑色素合成。

  DOI：

  10.3390/ijms19030746

文献信息

• 一种补骨脂素酯类衍生物及用途
  申请人：中国科学院新疆理化技术研究所

  公开号：CN106565734B

  公开（公告）日：2018-07-03

  本发明涉及一种补骨脂素酯类衍生物及用途，该类化合物为4‑甲基‑7‑羟基香豆素（中间体1）；4‑甲基‑7‑羟乙氧基香豆素（中间体2）；4‑甲基‑7‑甲酰甲氧基香豆素（中间体3）；5‑甲基‑7H‑呋喃[3,2‑g]苯并吡喃‑7‑酮(化合物4)；7‑氧代‑7H‑呋喃[3,2‑g]苯并吡喃‑5‑甲醛（化合物5）；5‑羟甲基‑7H‑呋喃[3,2‑g]苯并吡喃‑7‑酮（化合物6）；(7‑氧代‑7H‑呋喃[3,2‑g]苯并吡喃‑5‑基)甲基乙酸酯（化合物7）和化合物8a‑8p。并考察这20个补骨脂素酯类衍生物对小鼠B16细胞中黑素生成的影响和对白色念珠菌、大肠杆菌、金黄色葡萄球菌的抑制作用。其结果化合物4‑7，化合物8a‑8d和化合物8k‑8o用于制备治疗白癜风的药物。所获得的补骨脂素席夫碱类衍生物用于制备治疗白色念珠菌感染的药物，且化合物5和化合物7还用于制备治疗金黄色葡萄球菌感染的药物。
• Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure–activity relationship study
  作者：Bang-Le Zhang、Cheng-Qi Fan、Lei Dong、Fang-Dao Wang、Jian-Min Yue

  DOI：10.1016/j.ejmech.2010.08.045

  日期：2010.11

  Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of la were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 mu g/mL) than 1a (MIC = 6.25 mu g/mL), and is even potent than the positive control metronidazole (MIC = 0.50 mu g/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of la have also led to an outline of structure-activity relationship. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Novel Furocoumarin Derivatives Stimulate Melanogenesis in B16 Melanoma Cells by Up-Regulation of MITF and TYR Family via Akt/GSK3β/β-Catenin Signaling Pathways
  作者：Chao Niu、Li Yin、Haji Aisa

  DOI：10.3390/ijms19030746

  日期：——

  The extracts of Ficuscarica L. and Psoralen corylifolia L. are traditional Uygur medicines for the treatment of vitiligo, and its active ingredients furocoumarins, were are found to be the most effective agents against this skin disorder nowadays. Therefore, a series of novel easter derivatives (8a–8p) of furocoumarin were designed and synthesized based on our previous research to improve this activity in the present study. The synthesized derivatives were biologically evaluated for melanin synthesis in murine B16 cells and the SAR (structure-activity relationship) was summarized. Eight derivatives were more potent than positive control (8-MOP, 8-methoxypsoralan), especially compounds 8n (200%) and 8o (197%), which were nearly 1.5-fold potency when compared with 8-MOP (136%). Furthermore, the signaling pathway by which 8n activates the melanin biosynthesis was defined. Our results showed that it not only elevated the melanin content, but also stimulated the activity of tyrosinasein a concentration-dependent manner. Increasing of phosphorylation of Akt (also named PKB, protein kinase B) and non-activated GSK3β (glycogen synthase kinase 3 beta), which inhibited the degradation of β-catenin were observed through Western blot analysis. The accumulation of β-catenin probably led to the activation of transcription of MITF (microphthalmia-associated transcription factor) and TYR (tyrosinase) family, as well as the subsequent induction of melanin synthesis.

  白玉盘提取物和补骨脂素是小叶白蜡树的传统维吾尔药材,用于治疗白癜风,其活性成分呋喃香豆素被发现是目前对该皮肤病最有效的药物。因此,根据我们以前的研究,设计并合成了一系列新的呋喃香豆素衍生物(8a-8p)以改善这种活性。合成的衍生物在鼠B16细胞中对黑色素合成的生物学评价和SAR(结构-活性关系)进行了总结。八种衍生物比阳性对照(8-MOP,8-甲氧基补骨脂素)更有效,特别是化合物8n(200%)和8o(197%),其效力几乎是8-MOP(136%)的1.5倍。此外,8n激活黑色素生物合成的信号途径被确定。我们的结果表明,它不仅提高了黑色素含量,而且刺激了酪氨酸酶的活性,呈浓度依赖性。通过Westernblot分析观察到磷酸化Akt(也称为PKB,蛋白激酶B)和非激活GSK3β(糖原合酶激酶3β)的增加,抑制了β-catenin的降解。β-catenin的积累可能导致MITF(小眼相关转录因子)和TYR(酪氨酸酶)家族的转录激活,以及随后诱导黑色素合成。