N^α-t-butyloxycarbonyl-O-(2-bromobenzyl)-L-tyrosine | 60242-82-2

• 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
• 英文名称: N^α-t-butyloxycarbonyl-O-(2-bromobenzyl)-L-tyrosine
• 英文别名: (S)-3-(4-((2-bromobenzyl)oxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid；(2S)-3-[4-[(2-bromophenyl)methoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 60242-82-2
• 化学式: C₂₁H₂₄BrNO₅
• 分子量: 450.329
• InChiKey: CIZMMWKZAPLNKY-SFHVURJKSA-N

物化性质

• 沸点：
  589.9±50.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^α-t-butyloxycarbonyl-O-(2-bromobenzyl)-L-tyrosine 、 二环己胺 以 乙醚 、 Petroleum ether 为溶剂， 生成 N^α-t-butyloxycarbonyl-O-(2-bromobenzyl)-L-tyrosine dicyclohexyammonium salt
  参考文献：
  名称：

  Salem, Ezzeldin M.; Schou, O., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 1, p. 62 - 64

  摘要：

  DOI：
• 作为产物：
  描述：

  L-酪氨酸 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 N^α-t-butyloxycarbonyl-O-(2-bromobenzyl)-L-tyrosine
  参考文献：
  名称：

  Salem, Ezzeldin M.; Schou, O., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 1, p. 62 - 64

  摘要：

  DOI：

文献信息

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  作者：Chen Chen、Yiming Nie、Guangsen Xu、Xinying Yang、Hao Fang、Xuben Hou

  DOI：10.1016/j.bmc.2019.05.003

  日期：2019.7

  Bcl-2 family proteins, which divides into pro-apoptosis proteins and anti-apoptosis proteins, are involved in cell apoptosis progression. As numerous studies illustrated, targeting Bcl-2 family proteins is more and more attractive and practicable to cancer treatment. In this work, we designed and synthesized a series of indomethacin derivatives as new inhibitors for Bcl-2 family proteins. Our results

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• Ring Size in Octreotide Amide Modulates Differently Agonist versus Antagonist Binding Affinity and Selectivity
  作者：Christy Rani R. Grace、Judit Erchegyi、Manoj Samant、Renzo Cescato、Veronique Piccand、Roland Riek、Jean Claude Reubi、Jean E. Rivier

  DOI：10.1021/jm701445q

  日期：2008.5.1

  H-DPhe(2)-c[Cys(3) -Phe(7) -DTrp(8)-Lys(9)-Thr(10)-Cys(14)] -Thr(15) -NH(2) (1) (a somatostatin agonist, SRIF numbering) and H-Cpa(2) -c[DCys(3) -Tyr(7) -DTrp(8)-Lys(9)-Thr(10)-Cys(14)] -Nal(15)-NH(2) (4) (a somatostatin antagonist) are based on the structure of octreotide that binds to three somatostatin receptor subtypes (SSt(2/3/5)) with significant binding affinity. Analogues of 1 and 4 were synthesized with norcysteine (Ncy), homocysteine (Hcy), or D-homocysteine (DHcy) at positions 3 and/or 14. Introducing Ncy at positions 3 and 14 constrained the backbone flexibility, resulting in loss of binding affinity at all sst(s) The introduction of Hey at positions 3 and 14 improved selectivity for sst(2) as a result of significant loss of binding affinity at the other ssts. Substitution by DHcy at position 3 in the antagonist scaffold (5), on the other hand, resulted in a significant loss of binding affinity at sst(2) and sst(3) as compared to the different affinities of the parent compound (4). The 3D NMR structures of the analogues in dimethylsulfoxide are consistent with the observed binding affinities.