Z-L-Lys(Z)-Bt | 1228183-54-7

• 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: Z-L-Lys(Z)-Bt
• 英文别名: benzyl N-[(2S)-1-(benzotriazol-1-yl)-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamate
• CAS: 1228183-54-7
• 化学式: C₂₈H₂₉N₅O₅
• 分子量: 515.569
• InChiKey: MQIZPUOECIAASY-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Z-L-Lys(Z)-Bt 、 5-氨基水杨酸 以 水 为溶剂， 反应 2.0h， 以77%的产率得到(S)-5-(2,6-bis{[(benzyloxy)carbonyl]amino}hexanamido)-2-hydroxybenzoic acid
  参考文献：
  名称：

  Green, Catalyst-Free Synthesis of Mesalazine Conjugates

  摘要：

  A greener protocol for the synthesis of mesalazine conjugates is reported. Mesalazine conjugates are prepared in high yields by a one-pot reaction of mesalazine and aminoacyl/peptidoylbenzotriazoles in water under microwave irradiation.

  DOI：

  10.1055/s-0033-1338532
• 作为产物：
  描述：

  T406石油添加剂 、 N,N’-双苄氧羰基-L-赖氨酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Z-L-Lys(Z)-Bt
  参考文献：
  名称：

  奎宁-肽结合物的合成及抗疟生物测定

  摘要：

  使用苯并三唑方法，使用微波辐射以52–95％的产率合成奎宁的氨基酸和肽共轭物。这些结合物中的大多数保留体外抗疟活性，IC 50值低于100 n m，类似于奎宁。

  DOI：

  10.1111/cbdd.12134

文献信息

• Syntheses of Hydrazino Peptides and Conjugates
  作者：Siva S. Panda、Claudia El-Nachef、Kiran Bajaj、Alan R. Katritzky

  DOI：10.1002/ejoc.201201731

  日期：2013.7

  (α-Benzyloxycarbonyl-aminoacyl)benzotriazolides (Cbz = benzyloxycarbonyl) underwent a coupling reaction with α-hydrazino acids under microwave irradiation to form hybrid hydrazino dipeptides (42–71 %). Chiral acylations of β-N-Cbz-α-hydrazino acylbenzotriazolides were successfully carried out with N-, S-, O-, and C-nucleophiles in yields of 49–88 %.

  （α-苄氧羰基-氨基酰基）苯并三唑化物（Cbz = 苄氧羰基）在微波辐射下与 α-肼酸发生偶联反应，形成杂合肼二肽（42-71%）。β-N-Cbz-α-肼基酰基苯并三唑化物的手性酰化成功地用 N-、S-、O-和 C-亲核试剂进行，产率为 49-88%。
• Synthesis and antibacterial evaluation of amino acid–antibiotic conjugates
  作者：Mohamed A. Ibrahim、Siva S. Panda、Antoinette S. Birs、Juan C. Serrano、Claudio F. Gonzalez、Khalid A. Alamry、Alan R. Katritzky

  DOI：10.1016/j.bmcl.2014.01.065

  日期：2014.4

  Amino acid conjugates of quinolone, metronidazole and sulfadiazine antibiotics were synthesized in good yields using benzotriazole methodology. All the conjugates were screened for their antibacterial activity using methods adapted from the Clinical and Laboratory Standards Institute. Antibiotic conjugates were tested for activity in four medically relevant organisms; Staphylococcus aureus (RN4220), Escherichia coli (DH5a), Pseudomonas aeruginosa (PAO1), and Bacillus subtilis (168). Several antibiotic conjugates show promising results against several of the strains screened. (c) 2014 Published by Elsevier Ltd.
• Chemical modification of oximes with N-protected amino acids
  作者：Nana N. Barbakadze、Rachel A. Jones、Nicole Rivera Rosario、Nanuli Sh Nadaraia、Meri L. Kakhabrishvili、C. Dennis Hall、Alan R. Katritzky

  DOI：10.1016/j.tet.2014.07.040

  日期：2014.10

  The modification of oximes, including 5 alpha-steroids, with N-protected amino acids, in solution phase, using benzotriazole methodology is reported. (C) 2014 Elsevier Ltd. All rights reserved.
• Amino Acyl Conjugates of Nitrogen Heterocycles as Potential Pharmacophores
  作者：Alan R. Katritzky、Kiran Bajaj、Mael Charpentier、Ebrahim Ghazvini Zadeh

  DOI：10.1021/jo100625y

  日期：2010.6.4

  2-Methyl- and 4-methylpyridine and 2-methylquinoline are converted by benzotriazole-activated (Cbz)-protected amino acids into chiral potential novel pharmacophore aminoacyl conjugates (33-53%).
• Synthesis and Antimalarial Bioassay of Quinine - Peptide Conjugates
  作者：Siva S. Panda、Mohamed A. Ibrahim、Hasan Küçükbay、Marvin J. Meyers、Francis M. Sverdrup、Said A. El-Feky、Alan R. Katritzky

  DOI：10.1111/cbdd.12134

  日期：2013.10

  Amino acid and peptide conjugates of quinine were synthesized using microwave irradiation in 52–95% yields using benzotriazole methodology. The majority of these conjugates retain in vitro antimalarial activity with IC50 values below 100 nm, similar to quinine.

  使用苯并三唑方法，使用微波辐射以52–95％的产率合成奎宁的氨基酸和肽共轭物。这些结合物中的大多数保留体外抗疟活性，IC 50值低于100 n m，类似于奎宁。