7-diethylaminocoumarin-3-isocyanate | 940281-88-9

• 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-diethylaminocoumarin-3-isocyanate
• 英文别名: 7-(Diethylamino)-3-isocyanatochromen-2-one；7-(diethylamino)-3-isocyanatochromen-2-one
• CAS: 940281-88-9
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: WYCVTMFSYSDNEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.1±45.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-diethylaminocoumarin-3-isocyanate 、 5-amino-3-phenyl-1,2,3-oxadiazol-3-ium chloride 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以68%的产率得到((7-(diethylamino)-2-oxo-2H-chromen-3-yl)carbamoyl)(3-phenyl-1,2,3-oxadiazol-3-ium-5-yl)amide
  参考文献：
  名称：

  Fluorogenic iminosydnones: bioorthogonal tools for double turn-on click-and-release reactions

  摘要：

  Iminosydnones能够在连接到它们的核心结构时熄灭两种荧光团。生物正交点击和释放反应与环辛炔诱导两种产物的显著荧光增强，从而允许在细胞中追踪它们。

  DOI：

  10.1039/d0cc03067h
• 作为产物：
  描述：

  7-(二乙基氨基)香豆素-3-羰基叠氮化物 以 苯 为溶剂， 反应 5.0h， 生成 7-diethylaminocoumarin-3-isocyanate
  参考文献：
  名称：

  Synthesis of carbamate derivatives of iejimalides. Retention of normal antiproliferative activity and localization of binding in cancer cells

  摘要：

  The syntheses of six iejimalide carbamate derivatives are described. Their biological activity and those of the unmodified iejimalides A and B against breast and prostate cancer cell lines were determined. These results show that the serine hydroxyl group of iejimalides A and B is a permissive site that can be functionalized to form carbamate derivatives without significant loss of normal biological activity. This method of derivatization will be valuable for cellular target identification, mechanism of action studies, and drug development efforts. A fluorescent derivative does not exhibit binding to the cytoskeletal features of cancer cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.046

文献信息

• Synthesis of carbamate derivatives of iejimalides. Retention of normal antiproliferative activity and localization of binding in cancer cells
  作者：Dirk Schweitzer、Junyi Zhu、Gotam Jarori、Junichi Tanaka、Tatsuo Higa、V. Jo Davisson、Paul Helquist

  DOI：10.1016/j.bmc.2007.02.046

  日期：2007.5

  The syntheses of six iejimalide carbamate derivatives are described. Their biological activity and those of the unmodified iejimalides A and B against breast and prostate cancer cell lines were determined. These results show that the serine hydroxyl group of iejimalides A and B is a permissive site that can be functionalized to form carbamate derivatives without significant loss of normal biological activity. This method of derivatization will be valuable for cellular target identification, mechanism of action studies, and drug development efforts. A fluorescent derivative does not exhibit binding to the cytoskeletal features of cancer cells. (c) 2007 Elsevier Ltd. All rights reserved.
• Fluorogenic iminosydnones: bioorthogonal tools for double turn-on click-and-release reactions
  作者：Margaux Riomet、Karine Porte、Anne Wijkhuisen、Davide Audisio、Frédéric Taran

  DOI：10.1039/d0cc03067h

  日期：——

  Iminosydnones are able to quench two fluorophores when connected to their core structure. Bioorthogonal click and release reaction with cyclooctynes provokes significant fluorescence enhancement of the two products, allowing their tracking in cells.

  Iminosydnones能够在连接到它们的核心结构时熄灭两种荧光团。生物正交点击和释放反应与环辛炔诱导两种产物的显著荧光增强，从而允许在细胞中追踪它们。
• Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation
  作者：Kouji Kuramochi、Shunsuke Yukizawa、Seiki Ikeda、Takashi Sunoki、Satoshi Arai、Rie Matsui、Akinori Morita、Yoshiyuki Mizushina、Kengo Sakaguchi、Fumio Sugawara、Masahiko Ikekita、Susumu Kobayashi

  DOI：10.1016/j.bmc.2008.03.029

  日期：2008.5

  Epolactaene, isolated from cultured Penicillium sp. BM 1689-P mycelium, induces neurite outgrowth and arrests the cell cycle of the human neuroblastoma cell line, SH-SY5Y, at the G1 phase. We have found that epolactaene and its derivatives induce apoptosis in the human leukemia B-cell line, BALL-1. In this study, we prepared fluorescent and biotinylated epolactaene derivatives. We characterized the cellular location and the identification of BALL-1 proteins that reacted with these compounds. The results obtained from the reaction of epolactaene or its derivative with N-acetylcysteine methyl ester indicate that these compounds induce the disulfide formation and the alpha-position of the epoxylactam core is the reactive site. (c) 2008 Elsevier Ltd. All rights reserved.