(R)-3-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | 500213-40-1

• 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: (R)-3-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
• CAS: 500213-40-1
• 化学式: C₂₅H₃₀N₂O₅
• 分子量: 438.524
• InChiKey: BZJRJMCTLDIZHU-LEWJYISDSA-N

物化性质

• 沸点：
  615.3±55.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-3-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(S)-3-Phenyl-2-[((R)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl)-amino]-propionic acid methyl ester
  参考文献：
  名称：

  B类协同霉素的逐步合成策略

  摘要：

  描述了作为B类协同霉素核心结构的四个大环肽的合成，以及最终的B类衍生物的合成。我们对这些协同霉素衍生物的合成途径允许在大环的所有点上引入氨基酸取代，从而导致结构上多样化的B类类似物。

  DOI：

  10.1016/j.tetlet.2004.01.048
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 、 BOC-D-1,2,3,4-四氢异喹啉-3-羧酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 生成 (R)-3-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  B类协同霉素的逐步合成策略

  摘要：

  描述了作为B类协同霉素核心结构的四个大环肽的合成，以及最终的B类衍生物的合成。我们对这些协同霉素衍生物的合成途径允许在大环的所有点上引入氨基酸取代，从而导致结构上多样化的B类类似物。

  DOI：

  10.1016/j.tetlet.2004.01.048

文献信息

• Synthesis of Highly Substituted Imidazolidine-2,4-dione (Hydantoin) through Tf₂O-Mediated Dual Activation of Boc-Protected Dipeptidyl Compounds
  作者：Hui Liu、Zhimin Yang、Zhengying Pan

  DOI：10.1021/ol502900j

  日期：2014.11.21

  Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products

  高取代度的手性乙内酰脲很容易在温和的条件下一步一步由简单的二肽合成。该反应通过Tf 2 O-吡啶双重活化酰胺和叔丁氧羰基（Boc）保护基而进行。该方法已成功地用于制备多种生物活性化合物，包括药物类似物和天然产物。
• Novel antibiotics: C-2 symmetrical macrocycles inhibiting Holliday junction DNA binding by E. coli RuvC
  作者：Po-Shen Pan、Fiona A. Curtis、Chris L. Carroll、Irene Medina、Lisa A. Liotta、Gary J. Sharples、Shelli R. McAlpine

  DOI：10.1016/j.bmc.2006.03.028

  日期：2006.7.15

  Holliday junctions (HJs) are formed as transient DNA intermediates during site-specific and homologous recombination. Both of these genetic exchange pathways are critical for normal DNA metabolism and repair. Trapping HJs leads to bacterial cell death by preventing proper segregation of the resulting interlinked chromosomes. Macrocyclic peptides designed to target this intermediate were synthesized with the goal of identifying compounds with specificity for this unique molecular target. We discovered ten macrocycles, both hexameric and octameric peptides, capable of trapping HJs in vitro. Those macrocycles containing tyrosine residues proved most effective. These data demonstrate that C-2 symmetrical macrocycles offer excellent synthetic targets for the development of novel antibiotic agents. Furthermore, the active compounds identified provide valuable tools for probing different pathways of recombinational exchange. (c) 2006 Elsevier Ltd. All rights reserved.
• Novel antibiotics: second generation macrocyclic peptides designed to trap Holliday junctions
  作者：Lisa A. Liotta、Irene Medina、Jennifer L. Robinson、Chris L. Carroll、Po-Shen Pan、Ricardo Corral、Jennifer V.C. Johnston、Kristina M. Cook、Fiona A. Curtis、Gary J. Sharples、Shelli R. McAlpine

  DOI：10.1016/j.tetlet.2004.09.084

  日期：2004.11

  Described are the syntheses of 15 macrocyclic peptides designed to trap Holliday junctions (HJs) in bacteria during site-specific and homologous recombination. This leads to inhibiting bacterial growth. These second generation macrocycles were based on the C-2 symmetrical HJ. They were synthesized using a strategy that permits elucidation of the amino acid role in binding HJs. The syntheses of these macrocycles are an important step in the development of a new class of antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.
• Novel Antibiotics:  Macrocyclic Peptides Designed to Trap Holliday Junctions
  作者：Megan L. Bolla、Enrique V. Azevedo、Jason M. Smith、Rachel E. Taylor、Dev K. Ranjit、Anca M. Segall、Shelli R. McAlpine

  DOI：10.1021/ol020204f

  日期：2003.1.1

  Described are the syntheses of eight macrocyclic peptides designed to trap Holliday junctions in bacteria, thereby inhibiting bacterial growth. These macrocycles were designed from linear dimerized hexapeptides that bind to the C-2 symmetrical Holliday junction. They were synthesized from three monomers using a combinatorial-like strategy that permits elucidation of the monomer role in accumulation of Holliday junctions and antibiotic activity. These macrocycles are an important step in designing and synthesizing a new class of antibiotics.