7-hydroxy-8-(piperidinomethyl)coumarin | 92646-99-6

• 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-hydroxy-8-(piperidinomethyl)coumarin
• 英文别名: 8-Piperidinomethyl-7-hydroxycoumarin；7-hydroxy-8-(piperidin-1-ylmethyl)chromen-2-one
• CAS: 92646-99-6
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: HCOQDCSXZLTSRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-8-(piperidinomethyl)coumarin 、 2-(1-pirrolidinil)-7-metossicromone 在 乙酸酐 作用下， 反应 1.5h， 以64.5%的产率得到3-[(7-Hydroxy-2-oxochromen-8-yl)methyl]-7-methoxy-2-pyrrolidin-1-ylchromen-4-one
  参考文献：
  名称：

  苯并吡喃的不对称亚甲基衍生物对嗜中性白细胞O（2）（-）的抑制作用：用作潜在的消炎药。

  摘要：

  合成并测试了苯并吡喃9的一些不对称衍生物，以验证其对PKC的抑制活性。为此，在乙酸存在下，用2-（二烷基氨基）苯并吡喃-4-酮或3-（二烷基氨基）萘并[2,1-b]吡喃-1-酮8处理7-羟基香豆素6的曼尼希碱。用丙酸酐或丙酸酐产生化合物9。用PMA和f-MLF刺激的人类嗜中性粒细胞用作细胞模型。化合物9的效率建立在其减少活化的人类嗜中性粒细胞产生O（2）（-）的能力上。在色酮部分的7位带有乙酰氧基的化合物9d和9f似乎有效地抵消了中性粒细胞的活化。

  DOI：

  10.1016/s0223-5234(01)01279-x
• 作为产物：
  描述：

  哌啶 、 聚合甲醛 、 7-羟基香豆素 以 乙醇 为溶剂， 反应 6.0h， 以56.4%的产率得到7-hydroxy-8-(piperidinomethyl)coumarin
  参考文献：
  名称：

  苯并吡喃的不对称亚甲基衍生物对嗜中性白细胞O（2）（-）的抑制作用：用作潜在的消炎药。

  摘要：

  合成并测试了苯并吡喃9的一些不对称衍生物，以验证其对PKC的抑制活性。为此，在乙酸存在下，用2-（二烷基氨基）苯并吡喃-4-酮或3-（二烷基氨基）萘并[2,1-b]吡喃-1-酮8处理7-羟基香豆素6的曼尼希碱。用丙酸酐或丙酸酐产生化合物9。用PMA和f-MLF刺激的人类嗜中性粒细胞用作细胞模型。化合物9的效率建立在其减少活化的人类嗜中性粒细胞产生O（2）（-）的能力上。在色酮部分的7位带有乙酰氧基的化合物9d和9f似乎有效地抵消了中性粒细胞的活化。

  DOI：

  10.1016/s0223-5234(01)01279-x

文献信息

• Synthesis and Antiinflammatory Activity of Coumarin Derivatives^,
  作者：Christos A. Kontogiorgis、Dimitra J. Hadjipavlou-Litina

  DOI：10.1021/jm0580149

  日期：2005.10.1

  The synthesis of several coumarin Mannich bases is described. The structures of the synthesized compounds were confirmed by spectral and elemental analysis. Their lipophilicity was determined experimentally by RPTLC method. All compounds were evaluated for their antiinflammatory and antioxidant activity and for their ability to inhibit in vitro lipoxygenase. The derivatives were found to present antioxidant

  描述了几种香豆素曼尼希碱的合成。通过光谱和元素分析证实了合成化合物的结构。它们的亲脂性通过RPTLC方法实验确定。评价所有化合物的抗炎和抗氧化活性，以及​​它们抑制体外脂氧合酶的能力。发现该衍生物具有抗氧化和抗炎活性。测试的衍生物抑制角叉菜胶诱导的后爪水肿。它们还显着抑制了弗氏佐剂诱导的关节炎。已发现体内活性最高的化合物10对大鼠的佐剂诱导的关节炎具有保护作用。体外生物学活性是浓度依赖性的。亲水性，游离7-OH的存在，就SAR而言，对8位取代基的空间和空间需求是最重要的因素。试图使分子的几种物理化学性质与其体内/体外活性相关。
• Unsymmetrical methylene derivatives of indoles as antiproliferative agents
  作者：M Mazzei

  DOI：10.1016/s0223-5234(01)01286-7

  日期：2001.12.1

  Indole-3-carbinol is a natural product which has been shown to reduce the incidence of spontaneous and carcinogen-induced mammary tumours in animals, Eighteen unsymmetrical methylene derivatives of indoles were prepared by reaction of Mannich bases of 7-hydroxycoumarins with substituted indoles in acetic or propionic anhydride. The synthesised molecules were tested in vitro against the MCF7 and MDA-MB-231 breast cancer cell lines by MTT and cell count assays. Results from 16 tested compounds showed that 60% of them exerted some effects against the MDA-MB-231 compared to about 30% towards the MCF7. Among all, the 3-(7'-acetoxy-4-methylcoumarin-8'-yl)methyl-2-methylindole resulted the most effective in both cell lines, compared to indole-3-carbinol, In conclusion, these preliminary results report that some of these compounds might be promising potential antiproliferative agents. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae
  作者：Mauro Mazzei、Erika Nieddu、Mariangela Miele、Alessandro Balbi、Marco Ferrone、Maurizio Fermeglia、Marco T. Mazzei、Sabrina Pricl、Paolo La Colla、Fabio Marongiu、Cristina Ibba、Roberta Loddo

  DOI：10.1016/j.bmc.2007.11.045

  日期：2008.3

  Some Mannich bases of 7-hydroxycoumarin (2) and their simple derivatives (3 and 4) were prepared and tested against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). This study was directed toward Flaviviridae and, in particular, HCV surrogate viruses (BVDV, YFV). The 7-hydroxy derivatives 2 were generally devoid of activity, but when position 7 was propylated, the resulting 7-propyloxy derivatives 3 were in some cases endowed with an interesting activity against BVDV. The formation of 7-benzoyl derivatives 4 gave compounds generally lacking in activity against Flaviviridae, whereas the appearance of activity against RSV has been observed. Also some unsymmetrical methylene derivatives 5-7 (namely coumarins bridged to chromones or indoles) were found moderately active in antiviral tests. Derivatives 3 were submitted to a molecular modeling study using DNA polymerase of HCV as a target. The good correlation between calculated molecular modeling IC50 and experimental EC50 indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses. (C) 2007 Elsevier Ltd. All rights reserved.
• Inhibition of neutrophil O2− production by unsymmetrical methylene derivatives of benzopyrans: their use as potential antiinflammatory agents
  作者：Mauro Mazzei、Ramona Dondero、Enzo Sottofattori、Edon Melloni、Roberto Minafra

  DOI：10.1016/s0223-5234(01)01279-x

  日期：2001.12

  Some unsymmetrical derivatives of benzopyrans 9 were synthesized and tested to verify their PKC inhibitory activity. For this purpose, the Mannich bases of 7-hydroxycoumarins 6 were treated with 2-(dialkylamino)benzopyran-4-ones or 3-(dialkylamino)naphtho[2,1-b]pyran-1-ones 8 in the presence of acetic or propionic anhydride, yielding compounds 9. Human neutrophils stimulated with either PMA and f-MLF

  合成并测试了苯并吡喃9的一些不对称衍生物，以验证其对PKC的抑制活性。为此，在乙酸存在下，用2-（二烷基氨基）苯并吡喃-4-酮或3-（二烷基氨基）萘并[2,1-b]吡喃-1-酮8处理7-羟基香豆素6的曼尼希碱。用丙酸酐或丙酸酐产生化合物9。用PMA和f-MLF刺激的人类嗜中性粒细胞用作细胞模型。化合物9的效率建立在其减少活化的人类嗜中性粒细胞产生O（2）（-）的能力上。在色酮部分的7位带有乙酰氧基的化合物9d和9f似乎有效地抵消了中性粒细胞的活化。