N-(10-aminodecyl)-5-(dimethylamino)naphthalen-1-sulfonamide | 73603-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(10-aminodecyl)-5-(dimethylamino)naphthalen-1-sulfonamide
• 英文别名: N-dansyl-1,10-diaminodecane；N-(10-aminodecyl)-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 73603-41-5
• 化学式: C₂₂H₃₅N₃O₂S
• 分子量: 405.605
• InChiKey: IHQJPWZYQORAHE-UHFFFAOYSA-N

物化性质

• 沸点：
  552.1±48.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(10-aminodecyl)-5-(dimethylamino)naphthalen-1-sulfonamide 在 sodium hydroxide 、 苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 48.25h， 生成 5-methyl-4-N-<10-N-dansylaminodecyl> cytidine
  参考文献：
  名称：

  Synthesis of flurocent or biotinylated nucleoside compounds

  摘要：

  DOI：

  10.1016/s0040-4020(01)81640-9
• 作为产物：
  描述：

  2-(10-溴癸基)-1H-异吲哚-1,3(2H)-二酮 在 一水合肼 、 lithium hexamethyldisilazane 作用下， 以 乙醇 为溶剂， 反应 52.5h， 生成 N-(10-aminodecyl)-5-(dimethylamino)naphthalen-1-sulfonamide
  参考文献：
  名称：

  腺苷受体的荧光探针：N6-丹磺酰基氨基烷基取代的NECA衍生物的合成与生物学。

  摘要：

  描述了用于腺苷受体的新的荧光配体。这些化合物是通过在NECA（一种强力的腺苷激动剂）的N6位插入带有增加碳链长度（3至12）的烷基间隔基的丹磺氨基烷基部分而获得的。其中，具有C6烷基间隔基的化合物被证明是最令人感兴趣的化合物，显示出对A1受体亚型的显着选择性。此外，在荧光显微镜检测中，它被证明能够在小脑皮层的分子层水平上观察和定位该受体亚型。

  DOI：

  10.1016/s0960-894x(98)00582-4

文献信息

• Fluorescence Anisotropy and Mobility of Dansyl Fluorophore in Labelled Homologous Alkanes
  作者：Drahomír Výprachtický、Veronika Pokorná、Jan Pecka、František Mikeš

  DOI：10.1135/cccc19991369

  日期：——

  Using the steady-state and time-resolved fluorescence anisotropy, the mobility of 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl) fluorophore in homologous 1-[2-acetamido-3-(1H-indol-3-yl)propanamido]-n-[5-(dimethylamino)naphthalene-1-sulfonamido]alkanes 1 was studied in binary solvents glycerol-water. Steady-state fluorescence data were evaluated by the generalized Perrin equation and the micro-Brownian motion of dansyl fluorophore was described by means of average characteristics (rotational relaxation times) of the rotational relaxation spectrum. The rotational relaxation time of "fast" motions caused by torsional vibrations of single bonds within the rotational-isomeric states decreases with increasing number of methylene groups in homologous compounds. The rotational relaxation time of "slow" motions due to conformational changes of the chain between the tryptophane and dansyl fluorophore remains at first approximately constant with increasing number of methylene groups but increases considerably for long aliphatic chains. The observed decrease in the rate of conformational changes of a long aliphatic chain is probably due to intramolecular interaction of parts of the methylene chain in a medium with high water content. The values of activation enthalpy ∆H^≠ and activation entropy ∆S^≠ calculated from experimental data corroborate such interpretation. Time-resolved anisotropy of dansyl fluorophore at a particular binary solvent composition confirmed the shape of rotational relaxation spectrum and the measured rotational correlation times have been discussed. The time-dependent decays of anisotropy supported our previous interpretation in terms of intramolecular association of the long aliphatic chain in polar medium.

  使用稳态和时间分辨荧光各向异性，研究了5-(二甲氨基)萘磺酰（丹磺）荧光物质在同系列1-[2-乙酰胺基-3-(1H-吲哚-3-基)丙酰胺基]-n-[5-(二甲氨基)萘磺酰胺基]烷烃1中在二元溶剂甘油-水中的运动性。稳态荧光数据通过广义Perrin方程进行评估，丹磺荧光物质的微布朗运动通过旋转弛豫谱的平均特性（旋转弛豫时间）描述。由于同系列化合物中甲基烷基数目增加而引起的由单键扭转振动引起的“快速”运动的旋转弛豫时间随之减少。由于色氨酸和丹磺荧光物质之间链条的构象变化引起的“慢速”运动的旋转弛豫时间，起初随着甲基烷基数目的增加大致保持恒定，但对于长链脂肪烃来说会显著增加。观察到长链脂肪烃构象变化速率的减少可能是由于在水含量较高的介质中甲基链部分之间的分子内相互作用所致。从实验数据计算得到的活化焓ΔH≠和活化熵ΔS≠的值支持这种解释。在特定二元溶剂组成下，丹磺荧光物质的时间分辨各向异性证实了旋转弛豫谱的形状，并讨论了测得的旋转相关时间。各向异性的时间依赖衰减支持了我们先前在极性介质中关于长链脂肪烃分子内缔合的解释。
• Solvatochromic characteristics of dansyl molecular probes bearing alkyl diamine chains
  作者：Sorin Mocanu、Gabriela Ionita、Iulia Matei

  DOI：10.1016/j.saa.2020.118413

  日期：2020.8

  n-diamine chains of different length (DA1.n, n = 2-8, 10, 12) was characterized in terms of the absorptive and emissive features in solvents of different polarity and hydrogen bond donor/hydrogen bond acceptor character. The probes show solvent-dependent absorption, a feature that is uncommon among dansyl derivatives. The dual emission of DA1.n probes is strong in non-aqueous solvents and is influenced by the

  一系列带有不同长度的线性烷基-1，n-二胺链（DA1.n，n = 2-8，10，12）的基于丹磺酰基的荧光探针的特征在于在不同溶剂中的吸收和发射特征极性和氢键供体/氢键受体特性。探针显示出溶剂依赖性吸收，这在丹磺酰基衍生物中并不常见。DA1.n探针的双重发射在非水溶剂中很强，并且受链长和与溶剂的相互作用的影响。在Kamlet-Taft和Catalán溶剂变色模型的基础上，合理化了溶剂对光谱参数的影响，以量化极性驱动和氢键相互作用的程度。对两个模型预测的结果进行了比较讨论。在基态下，DA1。n个探针充当氢键受体。在激发态下，氢键作用较弱，溶质与溶剂的相互作用受溶剂极性增加的控制，该极性导致发射的大红移。与先前报道的相应的双丹磺酰荧光探针系列（2DA1.n）的光谱特征进行了比较。
• 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,
• Synthesis of novel dansyl-labeled Celecoxib derivatives
  作者：Andreas Lill、Klaus Scholich、Holger Stark

  DOI：10.1016/j.tetlet.2013.09.025

  日期：2013.12

  Four novel dansyl-labeled derivatives of Celecoxib, a cyclooxygenase-2 (COX-2) selective inhibitor, were designed and synthesized. To realize the fluorophore-linker-approach divergent and convergent synthetic strategies were applied. Therefore Celecoxib p-benzoic acid, 8, was synthesized in a new and convenient way. The yield and the synthetic route to Celecoxib, 1, its pyrazolylic acid, 7, and its pyrazolylic methyl ester, 6, were improved. Through a convenient synthesis 1,11-diamino-3,6,9-trioxundecane, 19, was obtained in high yield and purity and used as a linker for the dansyl moiety. (C) 2013 Elsevier Ltd. All rights reserved.
• SARFATI, S. R.;POCHET, S.;GUERREIRO, C.;NAMANE, A.;HUYNH-DINH, T.;IGOLEN,+, TETRAHEDRON, 43,(1987) N 15, 3491-3497
  作者：SARFATI, S. R.、POCHET, S.、GUERREIRO, C.、NAMANE, A.、HUYNH-DINH, T.、IGOLEN,+

  DOI：——

  日期：——