N-(5-(dimethylamino)naphth-1-yl)sulfonyloleamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(5-(dimethylamino)naphth-1-yl)sulfonyloleamide
• 英文别名: dansyl oleamide；(Z)-N-[5-(dimethylamino)naphthalen-1-yl]sulfonyloctadec-9-enamide
• 化学式: C₃₀H₄₆N₂O₃S
• 分子量: 514.773
• InChiKey: YVAOQVMYWDBXCE-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  36
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  油酸酰胺 、 丹酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以18%的产率得到N-(5-(dimethylamino)naphth-1-yl)sulfonyloleamide
  参考文献：
  名称：

  Synthesis of N-functionalized oleamide derivatives

  摘要：

  Oleamide is an interesting compound, which shows various pharmacological activities including the inhibitory effect of gap junction formation. Recently, the studies of the gap junction have been some of the hot topics in biology and its inhibitors have become more useful tools [Cravatt, B. F.; Garcia, 0. P.; Siuzdak, G.; Gilula, N. B.; Henriksen, S. J.; Boger, D. L.; Lerner, R. A. Science 1995, 268, 1506-1509; Cravatt, B. F.; Lerner, R. A.; Boger, D. L. J. Am. Chem. Soc. 1996,118,580-590; Guan, X; Cravatt, B. F.; Ehring, G. R.; Hall, J. E.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. J. Cell Biol. 1997,139,1785-1792; Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. E; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998,95,4810-4815; Ito, A.; Morita, N.; Miura, D.; Koma, Y; Kataoka, T. R.; Yamasaki, H.; Kitamura, Y.; Kita, Y; Nojima, H. Carcinogenesis 2004, 25, 2015-2022]. However, many reports suggest that the functionalizations of oleamide to retain its biological activity were difficult [Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. E; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4810-4815; Ito, A.; Morita, N.; Miura, D.; Koma, Y.; Kataoka, T. R.; Yamasaki, H.; Kitamura, Y.; Kita, Y; Nojima, H. Carcinogenesis 2004, 25, 2015-2022]. The synthesis of the functionalized oleamide derivatives, whose biological activity is not blocked, has become attractive in both the biological and chemical fields.Herein, by linking the fluorophore to the oleamide by alkyl chains, we synthesized the fluorescently tagged oleamide whose biological feature is similar to that of oleamide. Moreover, we also synthesized other bioactive derivatives tagged by other groups such as the sugars and biotin via alkyl chain linkers. (C) 2007 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2007.02.074

文献信息

• Synthesis of N-functionalized oleamide derivatives
  作者：Yusuke Ohba、Yukiko Kanao、Mayuko Takatsuji、Motoki Ito、Norikazu Yabuta、Hiroshi Nojima、Yasuyuki Kita

  DOI：10.1016/j.tet.2007.02.074

  日期：2007.4

  Oleamide is an interesting compound, which shows various pharmacological activities including the inhibitory effect of gap junction formation. Recently, the studies of the gap junction have been some of the hot topics in biology and its inhibitors have become more useful tools [Cravatt, B. F.; Garcia, 0. P.; Siuzdak, G.; Gilula, N. B.; Henriksen, S. J.; Boger, D. L.; Lerner, R. A. Science 1995, 268, 1506-1509; Cravatt, B. F.; Lerner, R. A.; Boger, D. L. J. Am. Chem. Soc. 1996,118,580-590; Guan, X; Cravatt, B. F.; Ehring, G. R.; Hall, J. E.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. J. Cell Biol. 1997,139,1785-1792; Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. E; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998,95,4810-4815; Ito, A.; Morita, N.; Miura, D.; Koma, Y; Kataoka, T. R.; Yamasaki, H.; Kitamura, Y.; Kita, Y; Nojima, H. Carcinogenesis 2004, 25, 2015-2022]. However, many reports suggest that the functionalizations of oleamide to retain its biological activity were difficult [Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. E; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4810-4815; Ito, A.; Morita, N.; Miura, D.; Koma, Y.; Kataoka, T. R.; Yamasaki, H.; Kitamura, Y.; Kita, Y; Nojima, H. Carcinogenesis 2004, 25, 2015-2022]. The synthesis of the functionalized oleamide derivatives, whose biological activity is not blocked, has become attractive in both the biological and chemical fields.Herein, by linking the fluorophore to the oleamide by alkyl chains, we synthesized the fluorescently tagged oleamide whose biological feature is similar to that of oleamide. Moreover, we also synthesized other bioactive derivatives tagged by other groups such as the sugars and biotin via alkyl chain linkers. (C) 2007 Elsevier Ltd. All rights reserved,