4,8-二甲基-7-羟基-6-硝基香豆素 | 10080-43-0

• 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
• 中文名称: 4,8-二甲基-7-羟基-6-硝基香豆素
• 英文名称: 6-Nitro-7-hydroxy-4,8-dimethyl-cumarin
• 英文别名: 7-hydroxy-4,8-dimethyl-6-nitro-2H-chromen-2-one；7-hydroxy-4,8-dimethyl-6-nitrochromen-2-one
• CAS: 10080-43-0
• 化学式: C₁₁H₉NO₅
• mdl: MFCD01334879
• 分子量: 235.196
• InChiKey: FMANVVQEVGBGGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,8-二甲基-7-羟基-6-硝基香豆素 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 6-amino-7-hydroxy-4,8-dimethylcoumarin
  参考文献：
  名称：

  新型香豆素-吡咯杂化物的设计，合成和抗真菌评估

  摘要：

  设计，制备了一系列带有吡咯骨架的香豆素衍生物，并评估了它们对六种植物病原真菌的体外抗真菌活性。抗真菌活性筛选结果表明，一些合成的杂种对被测真菌表现出潜在的杀真菌活性。特别是，化合物6j，6k，6o，6p和6r表现出了对茄状根瘤菌的显着抗真菌作用，并具有EC 50值分别为3.94、7.75、6.38、6.25和7.67μg/ mL。上述活性比商品化杀菌剂Boscalid（11.52μg/ mL）和Osthole（9.79μg/ mL）更有效。这些结果为进一步合理设计基于香豆素的杀菌剂提供了重要参考。

  DOI：

  10.1002/jhet.4180
• 作为产物：
  描述：

  7-羟基-4,8-二甲基香豆素 在 硫酸 、 potassium nitrate 作用下， 生成 4,8-二甲基-7-羟基-6-硝基香豆素
  参考文献：
  名称：

  新型香豆素-吡咯杂化物的设计，合成和抗真菌评估

  摘要：

  设计，制备了一系列带有吡咯骨架的香豆素衍生物，并评估了它们对六种植物病原真菌的体外抗真菌活性。抗真菌活性筛选结果表明，一些合成的杂种对被测真菌表现出潜在的杀真菌活性。特别是，化合物6j，6k，6o，6p和6r表现出了对茄状根瘤菌的显着抗真菌作用，并具有EC 50值分别为3.94、7.75、6.38、6.25和7.67μg/ mL。上述活性比商品化杀菌剂Boscalid（11.52μg/ mL）和Osthole（9.79μg/ mL）更有效。这些结果为进一步合理设计基于香豆素的杀菌剂提供了重要参考。

  DOI：

  10.1002/jhet.4180

文献信息

• 4′-Substituted-4′,5′-dihydropsoralens and therapeutical uses thereof
  申请人：——

  公开号：US06177424B1

  公开（公告）日：2001-01-23

  The invention relates to 4′-substituted-4′,5′-dihydropsoralen compounds of formula(V): In the formula R is hydrogen, a halogen, CN or an acyl group; T is a halogen, CN, a carboalkoxy group NR1R2, or (N+R1R2R3)X−, R1 and R2 are independently a C1-C6 alkyl, or R1 and R2 together with the nitrogen form a 5-8 member heterocyclic ring, or when T is (N+R1R2R3)X−, R1 and R2 together with the nitrogen form a 5-8 member heterocyclic ring or heterocyclic aromatic ring; R3 is hydrogen, a C1-C12 alkyl, or, when R1 and R2 together with the nitrogen form a heterocyclic aromatic ring, R3 is a double bond within the heterocyclic aromatic ring; X− is a halide. In another embodiment, the invention relates to processes for preparing 4′-substituted-4′,5′-dihydropsoralen compounds described above. The compounds of the invention have beneficial pharmaceutical properties and can be used alone or in pharmaceutical compositions used to treat a proliferative skin disorder and to treat microbial infections in a mammal by administering to the mammal an effective amount of a compound of the invention and then irradiating the mammal with ultraviolet light.

  本发明涉及公式（V）的4'-取代-4'，5'-二氢基香豆素化合物：在公式中，R为氢，卤素，CN或酰基基团；T为卤素，CN，羧基烷氧基基团NR1R2或（N+R1R2R3）X−，R1和R2分别为C1-C6烷基，或者R1和R2与氮一起形成5-8成员杂环环，或者当T为（N+R1R2R3）X−时，R1和R2与氮一起形成5-8成员杂环环或杂环芳香环；R3为氢，C1-C12烷基，或者当R1和R2与氮一起形成杂环芳香环时，R3为杂环芳香环内的双键；X−为卤化物。在另一实施例中，本发明涉及制备上述4'-取代-4'，5'-二氢基香豆素化合物的过程。本发明的化合物具有有益的药理学性质，可以单独使用或与药物组合物一起使用，用于治疗增生性皮肤疾病，并通过给哺乳动物施加有效量的本发明化合物，然后照射哺乳动物的紫外线来治疗微生物感染。
• Phototoxicity of 7-oxycoumarins with keratinocytes in culture
  作者：Christophe Guillon、Yi-Hua Jan、Diane E. Heck、Thomas M. Mariano、Robert D. Rapp、Michele Jetter、Keith Kardos、Marilyn Whittemore、Eric Akyea、Ivan Jabin、Jeffrey D. Laskin、Ned D. Heindel

  DOI：10.1016/j.bioorg.2019.103014

  日期：2019.8

  Seventy-one 7-oxycoumarins, 66 synthesized and 5 commercially sourced, were tested for their ability to inhibit growth in murine PAM212 keratinocytes. Forty-nine compounds from the library demonstrated light-induced lethality. None was toxic in the absence of UVA light. Structure-activity correlations indicate that the ability of the compounds to inhibit cell growth was dependent not only on their physiochemical characteristics, but also on their ability to absorb UVA light. Relative lipophilicity was an important factor as was electron density in the pyrone ring. Coumarins with electron withdrawing moieties - cyan and fluoro at C-3 - were considerably less active while those with bromines or iodine at that location displayed enhanced activity. Coumarins that were found to inhibit keratinocyte growth were also tested for photo-induced DNA plasmid nicking. A concentration-dependent alteration in migration on neutral gels caused by nicking was observed.
• Kanodia, Saraswati; Thapliyal, Prakash Chander, Journal of the Indian Chemical Society, 2011, vol. 88, # 2, p. 241 - 244
  作者：Kanodia, Saraswati、Thapliyal, Prakash Chander

  DOI：——

  日期：——
• Synthetic Approaches to 4,8-Dimethyl-4’-(N-pyridinium-methyl)-4’,5’-dihydropsoralens and Their Activity against PAM 212 Keratinocytes
  作者：Marilyn Whittemore、Ned Heindel、Christophe Guillon、Thomas McNeel、Robert Rapp、Thomas Mariano、Diane Heck、Jeffrey Laskin

  DOI：10.3987/com-01-9197

  日期：——

  Synthetic approaches to novel 4,8-dimethyl-4'-halomethyl-4',5'-dihydropsoralens as synthetic precursors to 4,8-dimethyl-4'-(N-pyridiniummethyl)-4',5'-dihydropsoralens are described. The compounds are potential therapeutic agents for improved psoralen ultraviolet radiation therapy with reduced mutagenicity.
• 4'-SUBSTITUTED-4',5'-DIHYDROPSORALENS AND THERAPEUTICAL USES THEREOF
  申请人：BUCKMAN LABORATORIES INTERNATIONAL, INC.

  公开号：EP1144417A1

  公开（公告）日：2001-10-17