7-香叶草氧基-6-甲氧基香豆素 | 28587-43-1

• 物质功能分类: 天然产物 - 香豆素
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 7-香叶草氧基-6-甲氧基香豆素
• 英文名称: 6-methoxy-7-geranyloxycoumarin
• 英文别名: 7-geranyloxy-6-methoxycoumarin；O-geranylscopoletin；7-[(2E)-3,7-dimethylocta-2,6-dienoxy]-6-methoxychromen-2-one
• CAS: 28587-43-1
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: NLNMITFNBJXRRP-XNTDXEJSSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  487.1±45.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090
• 储存条件：
  2-8℃，干燥保存，密封存放。

制备方法与用途

生物活性化合物7-O-甲基桂皮芸香苷（7-O-Geranylscopoletin）源自Atalantia monophylla的根部。Atalantia monophylla 的各部位均表现出生物学活性，可用于治疗慢性风湿病、麻痹、解痉和活化及偏瘫的相关研究。

反应信息

• 作为反应物：
  描述：

  7-香叶草氧基-6-甲氧基香豆素 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 silica gel 作用下， 反应 0.17h， 以78%的产率得到artekeiskeanin A
  参考文献：
  名称：

  Maes, Dominick; Van Syngel, Kris; De Kimpe, Norbert, Heterocycles, 2008, vol. 75, # 4, p. 1020 - 1021

  摘要：

  DOI：
• 作为产物：
  描述：

  香叶基溴 、 东莨菪内酯 生成 7-香叶草氧基-6-甲氧基香豆素
  参考文献：
  名称：

  Natural oxyprenylated coumarins are modulators of melanogenesis

  摘要：

  Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor 13 and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.04.051

文献信息

• [EN] INHIBITORS OF ANTIBIOTIC RESISTANCE MEDIATED BY ARN T<br/>[FR] INHIBITEURS DE RÉSISTANCE AUX ANTIBIOTIQUES MÉDIÉE PAR L'ARN T
  申请人：UNIV DEGLI STUDI ROMA LA SAPIENZA

  公开号：WO2021014422A1

  公开（公告）日：2021-01-28

  The present invention relates to diterpene compounds of general formula (I) capable of contrasting the antibiotic-resistance mediated by the ArnT enzyme, to their use as a medicament, in particular for use as an adjuvant of an antibiotic therapy in the treatment of antibiotic-resistant bacterial infections. The invention relates also to associations of one or more of the compounds of formula (I) with at least another active ingredient, in particular an antibacterial agent and/or an antibiotic, and compositions comprising one or more compounds of formula (I) or the association according to the present invention and at least one pharmaceutically acceptable excipient and/or carrier as well as to products, in particular medical devices, comprising at least a compound, an association or a composition according to the present invention. Moreover, the invention relates to the use of compounds of formula (I) to sensitize a bacterium to an antibacterial agent or an antibiotic, for example, colistin (polymyxin E) or polymyxin B and to an in vivo or in vitro method for sensitizing a bacterium to an antibacterial agent or an antibiotic comprising the exposure of said bacterium to one or more compounds of formula (I) together with colistin.

  本发明涉及通式（I）的二萜化合物，其能够对抗由ArnT酶介导的抗生素耐药性，以及它们作为药物的用途，特别是作为抗生素治疗中的辅助剂，用于治疗抗生素耐药性细菌感染。本发明还涉及将通式（I）的一个或多个化合物与至少另一种活性成分，特别是抗菌剂和/或抗生素，结合在一起的组合物，以及包含一个或多个通式（I）化合物或根据本发明的组合物和至少一种药用可接受的载体和/或载体的组合物，以及包含至少一种化合物、组合物或组合物的产品，特别是医疗器械。此外，本发明涉及使用通式（I）的化合物使细菌对抗菌剂或抗生素敏感化的用途，例如，科利斯汀（多粘菌素E）或多粘菌素B，以及一种体内或体外的方法，用于使细菌对抗菌剂或抗生素敏感化，包括将该细菌暴露于与科利斯汀一起使用的一个或多个通式（I）化合物。
• INHIBITORS OF ANTIBIOTIC RESISTANCE MEDIATED BY ARNT
  申请人：UNIVERSITÀ DEGLI STUDI DI ROMA "LA SAPIENZA"

  公开号：US20220259249A1

  公开（公告）日：2022-08-18

  The present invention relates to diterpene compounds of general formula (I) capable of contrasting the antibiotic-resistance mediated by the ArnT enzyme, to their use as a medicament, in particular for use as an adjuvant of an antibiotic therapy in the treatment of antibiotic-resistant bacterial infections. The invention relates also to associations of one or more of the compounds of formula (I) with at least another active ingredient, in particular an antibacterial agent and/or an antibiotic, and compositions comprising one or more compounds of formula (I) or the association according to the present invention and at least one pharmaceutically acceptable excipient and/or carrier as well as to products, in particular medical devices, comprising at least a compound, an association or a composition according to the present invention. Moreover, the invention relates to the use of compounds of formula (I) to sensitize a bacterium to an antibacterial agent or an antibiotic, for example, colistin (polymyxin E) or polymyxin B and to an in vivo or in vitro method for sensitizing a bacterium to an antibacterial agent or an antibiotic comprising the exposure of said bacterium to one or more compounds of formula (I) together with colistin.
• Maes, Dominick; Van Syngel, Kris; De Kimpe, Norbert, Heterocycles, 2008, vol. 75, # 4, p. 1020 - 1021
  作者：Maes, Dominick、Van Syngel, Kris、De Kimpe, Norbert

  DOI：——

  日期：——
• Natural oxyprenylated coumarins are modulators of melanogenesis
  作者：Serena Fiorito、Francesco Epifano、Francesca Preziuso、Ivana Cacciatore、Antonio di Stefano、Vito Alessandro Taddeo、Philippe de Medina、Salvatore Genovese

  DOI：10.1016/j.ejmech.2018.04.051

  日期：2018.5

  Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor 13 and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses. (C) 2018 Elsevier Masson SAS. All rights reserved.