tert-butyl N-[(2S)-1-[4-[(2-methylpropan-2-yl)oxy]phenyl]but-3-yn-2-yl]carbamate | 1454659-66-5

• 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: tert-butyl N-[(2S)-1-[4-[(2-methylpropan-2-yl)oxy]phenyl]but-3-yn-2-yl]carbamate
• CAS: 1454659-66-5
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: JRGUGZWSIOLKCO-OAHLLOKOSA-N

物化性质

• 沸点：
  437.9±40.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  疊氮乙酸 、 tert-butyl N-[(2S)-1-[4-[(2-methylpropan-2-yl)oxy]phenyl]but-3-yn-2-yl]carbamate 在 2,6-二甲基吡啶 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以93%的产率得到2-[4-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[4-[(2-methylpropan-2-yl)oxy]phenyl]ethyl]triazol-1-yl]acetic acid
  参考文献：
  名称：

  Systematic replacement of amides by 1,4-disubstituted[1,2,3]triazoles in Leu-enkephalin and the impact on the delta opioid receptor activity

  摘要：

  Using Cu(I)-catalyzed azide-alkyne cycloaddition in a mixed classical organic phase and solid phase peptide synthesis approach, we synthesized four analogs of Leu-enkephalin to systematically replace amides by 1,4-disubstituted[1,2,3] triazoles. The peptidomimetics obtained were characterized by competitive binding, contractility assays and ERK1/2 phosphorylation. The present study reveals that the analog bearing a triazole between Phe and Leu retains some potency, more than all the others, suggesting that the hydrogen bond acceptor capacity of the last amide of Leu-enkephalin is essential for the biological activity of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.020
• 作为产物：
  描述：

  Boc-O-叔丁基-L-酪氨酸 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以80%的产率得到tert-butyl N-[(2S)-1-[4-[(2-methylpropan-2-yl)oxy]phenyl]but-3-yn-2-yl]carbamate
  参考文献：
  名称：

  Systematic replacement of amides by 1,4-disubstituted[1,2,3]triazoles in Leu-enkephalin and the impact on the delta opioid receptor activity

  摘要：

  Using Cu(I)-catalyzed azide-alkyne cycloaddition in a mixed classical organic phase and solid phase peptide synthesis approach, we synthesized four analogs of Leu-enkephalin to systematically replace amides by 1,4-disubstituted[1,2,3] triazoles. The peptidomimetics obtained were characterized by competitive binding, contractility assays and ERK1/2 phosphorylation. The present study reveals that the analog bearing a triazole between Phe and Leu retains some potency, more than all the others, suggesting that the hydrogen bond acceptor capacity of the last amide of Leu-enkephalin is essential for the biological activity of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.020

文献信息

• Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates
  作者：Jens Engel-Andreasen、Isabelle Wellhöfer、Kathrine Wich、Christian A. Olsen

  DOI：10.1021/acs.joc.7b01744

  日期：2017.11.3

  incorporated as a peptide bond bioisostere to provide protease resistance in peptidomimetics. Herein, we report the synthesis of peptidomimetic building blocks containing backbone-fluorinated 1,4-disubstituted 1,2,3-triazole moieties. Synthetic protocols for the preparation of various Xaa-Gly dipeptide surrogates in the form of Xaa-ψ[triazole]-F2Gly building blocks were established, and selected examples were

  可以将1,2,3-三唑部分作为肽键生物等排体掺入以在拟肽中提供蛋白酶抗性。在这里，我们报道了含有骨架氟化的1，4-二取代的1,2,3-三唑部分的拟肽结构单元的合成。建立了用于制备Xaa-ψ[triazole] -F 2 Gly结构单元形式的各种Xaa-Gly二肽替代物的合成方案，并将选定的实例引入作为模型化合物的内源性阿片受体阿片受体配体亮脑啡肽。
• A zwitterionic near-infrared dye linked TrkC targeting agent for imaging metastatic breast cancer
  作者：Zhen Yang、Syed Muhammad Usama、Feng Li、Kevin Burgess、Zheng Li

  DOI：10.1039/c8md00190a

  日期：——

  devoted to targeting agents for imaging and chemotherapy of tumors in cancer research, but there remain significant unmet needs in that area. We have reported a series of preclinical TrkC targeting agents for diagnoses and treatment of metastatic breast cancer; however, with respect to optical imaging, there are limitations to the agents already disclosed. In this work, a TrkC targeting fragment was

  在癌症研究中，已经投入了大量精力用于肿瘤成像和化学治疗的靶向剂，但是在该领域仍然存在大量未满足的需求。我们已经报道了一系列临床前TrkC靶向药物，用于诊断和治疗转移性乳腺癌。然而，关于光学成像，已经公开的试剂有局限性。在这项工作中，TrkC靶向片段配备了两性离子花青染料，以提供用于体内成像转移性乳腺肿瘤的近红外探针，其激发和发射波长分别为760和780 nm，并有助于水的溶解。最终设计。令我们高兴的是，新开发的探针保持了针对TrkC +的特定目标4T1转移性乳腺肿瘤细胞以及TrkC +转移性乳腺肿瘤组织。注射到带有4T1肿瘤的小鼠体内后，可通过探针的荧光信号在体内和离体观察肿瘤。这些数据似乎鼓励进一步研究，以开发用于诊断转移性乳腺肿瘤的TrkC靶向剂。