2-[Bis(2-methoxyethyl)amino]-7-methoxychromen-4-one | 247147-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-[Bis(2-methoxyethyl)amino]-7-methoxychromen-4-one
• CAS: 247147-92-8
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: LNCIZXZAYYNQEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[Bis(2-methoxyethyl)amino]-7-methoxychromen-4-one 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 24.12h， 生成 [2-[3-[Bis(2-methoxyethyl)amino]-1,2-oxazol-5-yl]-5-methoxyphenyl] 4-nitrobenzoate
  参考文献：
  名称：

  N,N-Dialkylaminosubstituted chromones and isoxazoles as potential anti-inflammatory agents

  摘要：

  The ability of some N,N-dialkylaminosubstituted chromones and isoxazoles to inhibit the protein kinase C (PKC) dependent signal transduction pathway was tested. As a cellular model, human neutrophils stimulated with either phorbol myristate acetate (PMA) or formylmethionine-leucine-phenylalanine (f-MLF) were used. The efficiency of the compounds was established by their capacity to reduce the O-2(-) production by activated human neutrophils. Compounds carrying a 3-bis(2-methoxyethyl)amino group, a substituent found active in previously tested tricyclic compounds, do not show significant anti-PKC activity in this study. On the other hand, substitution with a 1-piperidinyl group leads all tested compounds to a high biological activity against stimulated neutrophils. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00051-8
• 作为产物：
  描述：

  3-甲氧基苯酚 、 3-[双(2-甲氧基乙基)氨基]-3-氧代丙酸乙酯 在 三氯氧磷 、 水 、 sodium acetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 以34%的产率得到2-[Bis(2-methoxyethyl)amino]-7-methoxychromen-4-one
  参考文献：
  名称：

  N,N-Dialkylaminosubstituted chromones and isoxazoles as potential anti-inflammatory agents

  摘要：

  The ability of some N,N-dialkylaminosubstituted chromones and isoxazoles to inhibit the protein kinase C (PKC) dependent signal transduction pathway was tested. As a cellular model, human neutrophils stimulated with either phorbol myristate acetate (PMA) or formylmethionine-leucine-phenylalanine (f-MLF) were used. The efficiency of the compounds was established by their capacity to reduce the O-2(-) production by activated human neutrophils. Compounds carrying a 3-bis(2-methoxyethyl)amino group, a substituent found active in previously tested tricyclic compounds, do not show significant anti-PKC activity in this study. On the other hand, substitution with a 1-piperidinyl group leads all tested compounds to a high biological activity against stimulated neutrophils. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00051-8

文献信息

• 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。