N-[4-(1-芘基)丁酰基]甘氨酸 | 228414-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: N-[4-(1-芘基)丁酰基]甘氨酸
• 中文别名: 苯基乙酸-三乙基铅烷基(1:1)
• 英文名称: N-4-(1-Pyrene)butyroylglycine
• 英文别名: 2-(4-pyren-1-ylbutanoylamino)acetic acid
• CAS: 228414-55-9
• 化学式: C₃₈H₃₃N₂O₄PolS
• 分子量: 345.4
• InChiKey: ZYPJIZQPSJBSOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[4-(1-芘基)丁酰基]甘氨酸 在 4-二甲氨基吡啶 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 5'-{n-[1-oxo-4-(1-pyrenyl)butyl]-glycyl}-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 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 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 3.0h， 生成 N-[4-(1-芘基)丁酰基]甘氨酸
  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

文献信息

• Nucleic Acid Templated Reactions: Consequences of Probe Reactivity and Readout Strategy for Amplified Signaling and Sequence Selectivity
  作者：Tom N. Grossmann、Oliver Seitz

  DOI：10.1002/chem.200900025

  日期：2009.7.6

  Making the right signals: Reactions in which the DNA target acts as a catalyst allow amplified signaling in the detection of DNA. The reactivity of the peptide nucleic acid (PNA) probes determines whether a given probe set provides high sensitivity or high selectivity. The careful adjustment of reactivity, probe affinity, and the use of a product‐selective readout method allows improvements in the

  发出正确的信号：以DNA靶为催化剂的反应可以在DNA检测中放大信号。肽核酸（PNA）探针的反应性决定了给定的探针组是提供高灵敏度还是高选择性。仔细调整反应性，探针亲和力，并使用产物选择性读出方法，可以改善对DNA单碱基突变的灵敏分析，而几乎没有背景干扰。
• Discovery of thioether-bridged cyclic pentapeptides binding to Grb2-SH2 domain with high affinity
  作者：Sheng Jiang、Chenzhong Liao、Lakshman Bindu、Biaolin Yin、Karen W. Worthy、Robert J. Fisher、Terrence R. Burke、Marc C. Nicklaus、Peter P. Roller

  DOI：10.1016/j.bmcl.2009.03.134

  日期：2009.5

  Blocking the interaction between phosphotyrosine (pTyr)-containing activated receptors and the Src homology 2 (SH2) domain of the growth factor receptor-bound protein 2 (Grb 2) is considered to be an effective and non-cytotoxic strategy to develop new anti-proliferate agents due to its potential to shut down the Ras activation pathway. In this study, a series of phosphotyrosine containing cyclic pentapeptides were designed and synthesized based upon the phage library derived cyclopeptide, G1TE. A comprehensive SAR study was also carried out to develop potent Grb2-SH2 domain antagonists based upon this novel template. With both the peptidomimetic optimization of the amino acid side-chains and the constraint of the backbone conformation guided by molecular modeling, we developed several potent antagonists with low micromolar range binding affinity, such as cyclic peptide 15 with an K(d) = 0.359 mu M, which is providing a novel template for the development of Grb2-SH2 domain antagonists as potential therapeutics for certain cancers. (C) 2009 Elsevier Ltd. All rights reserved.
• 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).