3-{4-[2-(pyrimidin-2-ylamino)ethyloxy]benzoylamino}-2(S)-benzenesulfonylaminopropionic acid | 174665-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-{4-[2-(pyrimidin-2-ylamino)ethyloxy]benzoylamino}-2(S)-benzenesulfonylaminopropionic acid
• 英文别名: (2S)-2-(benzenesulfonamido)-3-[[4-[2-(pyrimidin-2-ylamino)ethoxy]benzoyl]amino]propanoic acid
• CAS: 174665-30-6
• 化学式: C₂₂H₂₃N₅O₆S
• 分子量: 485.521
• InChiKey: VSXNWBIIJRVNPN-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-{4-[2-(pyrimidin-2-ylamino)ethyloxy]benzoylamino}-2(S)-benzenesulfonylaminopropionic acid 在 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 作用下， 反应 2.0h， 以75%的产率得到2-Benzenesulfonylamino-3-{4-[2-(1,4,5,6-tetrahydro-pyrimidin-2-ylamino)-ethoxy]-benzoylamino}-propionic acid
  参考文献：
  名称：

  Nonpeptide α_vβ₃ Antagonists. 1. Transformation of a Potent, Integrin-Selective α_IIbβ₃ Antagonist into a Potent α_vβ₃ Antagonist

  摘要：

  Modification of the potent fibrinogen receptor (alpha(IIb)beta(3)) antagonist 1 generated compounds with high affinity for the vitronectin receptor alpha(v)beta(3). Sequential modification of the basic N-terminus of 1 led to the identification of the 5,6,7,8-tetrahydro[1,8]naphthyridine moiety (THN) as a lipophilic, moderately basic N-terminus that provides molecules with excellent potency and selectivity for the integrin receptor alpha(v)beta(3). The THN-containing analogue 5 is a potent inhibitor of bone resorption in vitro and in vivo. In addition, the identification of a novel, nonpeptide radioligand with high affinity to alpha(v)beta(3) is also reported.

  DOI：

  10.1021/jm000133v
• 作为产物：
  描述：

  4-(2-氨基乙氧基)苯甲酸甲酯 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 苯甲醚 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 108.0h， 生成 3-{4-[2-(pyrimidin-2-ylamino)ethyloxy]benzoylamino}-2(S)-benzenesulfonylaminopropionic acid
  参考文献：
  名称：

  Nonpeptide α_vβ₃ Antagonists. 1. Transformation of a Potent, Integrin-Selective α_IIbβ₃ Antagonist into a Potent α_vβ₃ Antagonist

  摘要：

  Modification of the potent fibrinogen receptor (alpha(IIb)beta(3)) antagonist 1 generated compounds with high affinity for the vitronectin receptor alpha(v)beta(3). Sequential modification of the basic N-terminus of 1 led to the identification of the 5,6,7,8-tetrahydro[1,8]naphthyridine moiety (THN) as a lipophilic, moderately basic N-terminus that provides molecules with excellent potency and selectivity for the integrin receptor alpha(v)beta(3). The THN-containing analogue 5 is a potent inhibitor of bone resorption in vitro and in vivo. In addition, the identification of a novel, nonpeptide radioligand with high affinity to alpha(v)beta(3) is also reported.

  DOI：

  10.1021/jm000133v

文献信息

• Nonpeptide α_vβ₃ Antagonists. 1. Transformation of a Potent, Integrin-Selective α_IIbβ₃ Antagonist into a Potent α_vβ₃ Antagonist
  作者：Mark E. Duggan、Le T. Duong、John E. Fisher、Terence G. Hamill、William F. Hoffman、Joel R. Huff、Nathan C. Ihle、Chih-Tai Leu、Rose M. Nagy、James J. Perkins、Sevgi B. Rodan、Gregg Wesolowski、David B. Whitman、Amy E. Zartman、Gideon A. Rodan、George D. Hartman

  DOI：10.1021/jm000133v

  日期：2000.10.1

  Modification of the potent fibrinogen receptor (alpha(IIb)beta(3)) antagonist 1 generated compounds with high affinity for the vitronectin receptor alpha(v)beta(3). Sequential modification of the basic N-terminus of 1 led to the identification of the 5,6,7,8-tetrahydro[1,8]naphthyridine moiety (THN) as a lipophilic, moderately basic N-terminus that provides molecules with excellent potency and selectivity for the integrin receptor alpha(v)beta(3). The THN-containing analogue 5 is a potent inhibitor of bone resorption in vitro and in vivo. In addition, the identification of a novel, nonpeptide radioligand with high affinity to alpha(v)beta(3) is also reported.