N-4-(1-芘)丁酰基-L-苯基丙氨酸乙酯 | 1331912-17-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-4-(1-芘)丁酰基-L-苯基丙氨酸乙酯
• 中文别名: N-4-（1-P）丁酰基-L-苯丙氨酸，乙基酯
• 英文名称: N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanine ethyl ester
• 英文别名: N-4-(1-Pyrene)butyroyl-L-phenylalanine Ethyl Ester；ethyl (2S)-3-phenyl-2-(4-pyren-1-ylbutanoylamino)propanoate
• CAS: 1331912-17-4
• 化学式: C₃₁H₂₉NO₃
• 分子量: 463.576
• InChiKey: OTXWSIGCMVMENA-MHZLTWQESA-N

物化性质

• 沸点：
  692.2±50.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-4-(1-芘)丁酰基-L-苯基丙氨酸乙酯 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 四丁基氟化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyuridine
  参考文献：
  名称：

  Delivery of Floxuridine Derivatives to Cancer Cells by Water-Soluble Organometallic Cages

  摘要：

  The self-assembly of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (tpt) triangular panels with p-cymene (pPr(i)C(6)H(4)Me) ruthenium building blocks and 2,5-dioxydo-1,4-benzoquinonato (dobq) or 5,8-dioxydo-1,4-naphthoquinonato (donq) bridges, in the presence of a pyrenyl-nucleoside derivatives (pyreneR),. affords the triangular prismatic host guest compounds [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(dobq)(3)](6+) ([(pyrene-R)C1](6+)) and [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(donq)(3)](6+) ([(pyrene-R)C2](6+)), respectively. The inclusion of six monosubstituted pyrenyl-nucleosides (pyrene-R1 = 5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R2 = 5-fluoro-5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R3 = 5'-{N-[1-oxo-4-(1-pyrenyl)butyl]glycyl}-2'-deoxyuridine, pyrene-R4 = 5-fluoro-5'-{N[1-oxo-4-(1-pyrenyl)butyl]-glycyl}2'-deoxyuridine, pyrene-R5 = 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyvuridine, pyrene-R6 = 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyuridine) has been accomplished. The carceplex nature of [(pyrene-R)C1](6+) with the pyrenyl moiety firmly encapsulated in the hydrophobic cavity of the cage with the nucleoside groups pointing outward was confirmed by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), while the host-guest nature of [(pyrene-R)C2](6+) was studied in solution by NMR techniques. In contrast to the floxuridine compounds used in the clinic, the host-guest complexes are highly water-soluble. Consequently, the cytotoxicities of these water-soluble compounds have been established using human ovarian A2780 and A2780cisR cancer cells. All the host guest systems are more cytotoxic than the empty cages alone [1][CF3SO3](6) (IC50 = 23 mu M) and [2][CF3SO3](6) (IC50 = 10 mu M), the most active compound [pyrene-R4C1][CF3SO3](6) being 2 orders of magnitude more cytotoxic (IC50 = 0.3 mu M) on these human ovarian cancer cell lines (A2780 and A2780cisR).

  DOI：

  10.1021/bc200472n
• 作为产物：
  描述：

  1-芘丁酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 N-4-(1-芘)丁酰基-L-苯基丙氨酸乙酯
  参考文献：
  名称：

  折叠的短氮杂肽用于基于构象转换的荧光传感

  摘要：

  本文中，我们报告了一种基于构象转换的荧光传感方案，该方案使用了包含折叠的β-turn结构的基于二肽的酰胺基硫脲（氮杂肽）。酰胺基硫脲在其两个末端配备了一个电子受体和一个电子供体或两个荧光团，因此由于两个末端紧密靠近的转弯结构，它显示出增强的激基复合物或受激准分子发射；另一方面，由于阴离子结合复合物的最终扩展构象，它在阴离子与硫脲部分结合时显示出显着的比例荧光响应。

  DOI：

  10.1039/c7cc06915d

文献信息

• Site-Specific Photocleavage of Proteins
  作者：Challa V. Kumar、Apinya Buranaprapuk

  DOI：10.1002/anie.199720851

  日期：1997.10.17
• Delivery of Floxuridine Derivatives to Cancer Cells by Water-Soluble Organometallic Cages
  作者：Jeong Wu Yi、Nicolas P. E. Barry、Mona A. Furrer、Olivier Zava、Paul J. Dyson、Bruno Therrien、Byeang Hyean Kim

  DOI：10.1021/bc200472n

  日期：2012.3.21

  The self-assembly of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (tpt) triangular panels with p-cymene (pPr(i)C(6)H(4)Me) ruthenium building blocks and 2,5-dioxydo-1,4-benzoquinonato (dobq) or 5,8-dioxydo-1,4-naphthoquinonato (donq) bridges, in the presence of a pyrenyl-nucleoside derivatives (pyreneR),. affords the triangular prismatic host guest compounds [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(dobq)(3)](6+) ([(pyrene-R)C1](6+)) and [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(donq)(3)](6+) ([(pyrene-R)C2](6+)), respectively. The inclusion of six monosubstituted pyrenyl-nucleosides (pyrene-R1 = 5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R2 = 5-fluoro-5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R3 = 5'-N-[1-oxo-4-(1-pyrenyl)butyl]glycyl}-2'-deoxyuridine, pyrene-R4 = 5-fluoro-5'-N[1-oxo-4-(1-pyrenyl)butyl]-glycyl}2'-deoxyuridine, pyrene-R5 = 5-fluoro-5'-N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyvuridine, pyrene-R6 = 5-fluoro-5'-N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyuridine) has been accomplished. The carceplex nature of [(pyrene-R)C1](6+) with the pyrenyl moiety firmly encapsulated in the hydrophobic cavity of the cage with the nucleoside groups pointing outward was confirmed by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), while the host-guest nature of [(pyrene-R)C2](6+) was studied in solution by NMR techniques. In contrast to the floxuridine compounds used in the clinic, the host-guest complexes are highly water-soluble. Consequently, the cytotoxicities of these water-soluble compounds have been established using human ovarian A2780 and A2780cisR cancer cells. All the host guest systems are more cytotoxic than the empty cages alone [1][CF3SO3](6) (IC50 = 23 mu M) and [2][CF3SO3](6) (IC50 = 10 mu M), the most active compound [pyrene-R4C1][CF3SO3](6) being 2 orders of magnitude more cytotoxic (IC50 = 0.3 mu M) on these human ovarian cancer cell lines (A2780 and A2780cisR).
• Folded short azapeptide for conformation switching-based fluorescence sensing
  作者：Yuan Yuan、Xiao-Sheng Yan、Xiao-Rui Li、Jin-Lian Cao、Zhao Li、Yun-Bao Jiang

  DOI：10.1039/c7cc06915d

  日期：——

  Herein, we report a conformation switching-based fluorescence sensing scheme using dipeptide-based amidothioureas (azapeptides) that contain a folded β-turn structure. Amidothiourea is equipped at its two termini with an electron acceptor and an electron donor or two fluorophores, such that it exhibits enhanced exciplex or excimer emission because of the turn structure in which the two termini are

  本文中，我们报告了一种基于构象转换的荧光传感方案，该方案使用了包含折叠的β-turn结构的基于二肽的酰胺基硫脲（氮杂肽）。酰胺基硫脲在其两个末端配备了一个电子受体和一个电子供体或两个荧光团，因此由于两个末端紧密靠近的转弯结构，它显示出增强的激基复合物或受激准分子发射；另一方面，由于阴离子结合复合物的最终扩展构象，它在阴离子与硫脲部分结合时显示出显着的比例荧光响应。