(S)-benzyl (1-((2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate | 1286678-64-5

• 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: (S)-benzyl (1-((2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• 英文别名: Cbz-Phe-Gly-Bt；benzyl N-[(2S)-1-[[2-(benzotriazol-1-yl)-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 1286678-64-5
• 化学式: C₂₅H₂₃N₅O₄
• 分子量: 457.489
• InChiKey: XSMCDVIMBLNQCO-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-benzyl (1-((2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 在 potassium hydrogencarbonate 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 S-[(benzyloxy)carbonyl]-L-alanyl-L-phenylalanyl-N-[(benzyloxy)carbonyl]-L-phenylalanylglycyl-L-cysteine
  参考文献：
  名称：

  手性N-，O-和S-酰基异肽的溶液相合成

  摘要：

  摘要 据报道，在溶液相中，使用苯并三唑可以方便地从含有色氨酸，酪氨酸和半胱氨酸单元的二肽和三肽合成手性N-，O-和S-酰基单异肽和二异肽。 据报道，在溶液相中，使用苯并三唑可以方便地从含有色氨酸，酪氨酸和半胱氨酸单元的二肽和三肽合成手性N-，O-和S-酰基单异肽和二异肽。

  DOI：

  10.1055/s-0033-1340089
• 作为产物：
  描述：

  (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.25h， 生成 (S)-benzyl (1-((2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis, molecular docking and anticancer studies of peptides and iso-peptides

  摘要：

  Chiral peptides and iso-peptides were synthesized in excellent yield by using benzotriazole mediated solution phase synthesis. Benzotriazole acted both as activating and leaving group, eliminating frequent use of protection and subsequent deprotection. The procedure was based on the hypothesis that epimerization should be suppressed in solution due to a faster coupling rate than SPPS. All the synthesized peptides complied with Lipinski's Ro5 except for the rotatable bonds. Inhibition of cell proliferation of cancer cell lines is one of the most commonly used methods to study the effectiveness of any anticancer agents. Synthesized peptides and iso-peptides were tested against three cancer cell lines (MCF-7, MDA-MB 231) to determine their anti-proliferative potential. NF kappa B was also determined. Molecular docking studies were also carried out to complement the experimental results. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.020

文献信息

• Synthesis of novel dipeptide sulfonamide conjugates with effective carbonic anhydrase I, II, IX, and XII inhibitory properties
  作者：Nesrin Buğday、F. Zehra Küçükbay、Hasan Küçükbay、Silvia Bua、Gianluca Bartolucci、Janis Leitans、Andris Kazaks、Kaspars Tars、Claudiu T. Supuran

  DOI：10.1016/j.bioorg.2018.08.032

  日期：2018.12

  derivatives incorporating dipeptide tails were synthesized by facile acylation reactions of homosulfanilamide through benzotriazole or dicyclohexyl carbodiimide (DCC) mediated coupling reactions. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA IX and hCA XII. Most of the synthesized compounds showed good

  通过高硫磺酰胺通过苯并三唑或二环己基碳二亚胺（DCC）介导的偶联反应的轻松酰化反应，合成了包含二肽尾巴的二十四种新型磺酰胺衍生物。评估了新化合物的碳酸酐酶（CA，EC 4.2.1.1）对四种人（h）异构体hCA I，hCA II，hCA IX和hCA XII的抑制活性。大多数合成的化合物显示出良好的体外碳酸酐酶抑制特性，其抑制常数在低纳摩尔范围内。特别地，在二肽序列中结合了Ala，Phe和Met的新的二肽-磺酰胺缀合物显示出对CA IX和XII的最有效的抑制活性。
• Catalyst-free facile synthesis of 2-substituted benzothiazoles
  作者：Siva S. Panda、Mohamed A. Ibrahim、Alexander A. Oliferenko、Abdullah M. Asiri、Alan R. Katritzky

  DOI：10.1039/c3gc41255e

  日期：——

  2-Substituted benzothiazoles were synthesized in excellent yields by a benzotriazole methodology, with the conditions being efficient, green, economical, and suitable for broad applications in medicinal chemistry and the synthesis of specialty chemicals.

  2个替代 苯并噻唑 合成了高产率的 苯并三唑 方法学，条件是有效，绿色，经济并且适合在药物化学和特种化学合成中广泛应用。
• Synthesis and carbonic anhydrase inhibitory properties of novel 4-(2-aminoethyl)benzenesulfonamide-dipeptide conjugates
  作者：Hasan Küçükbay、Nesrin Buğday、F. Zehra Küçükbay、Emanuela Berrino、Gianluca Bartolucci、Sonia Del Prete、Clemente Capasso、Claudiu T. Supuran

  DOI：10.1016/j.bioorg.2018.11.003

  日期：2019.3

  incorporating dipeptide were synthesized by facile acylation through benzotriazole mediated reactions and their structures were identified by 1H NMR, 13C NMR, MS and FT-IR spectroscopic techniques and elemental analysis. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA IV and hCA XII. Most of the synthesized

  通过苯并三唑介导的反应进行酰化反应，合成了三十种新的二肽磺酰胺衍生物，并通过1 H NMR，13 C NMR，MS和FT-IR光谱技术及元素分析鉴定了其结构。评估了新化合物的碳酸酐酶（CA，EC 4.2.1.1）对四种人（h）同工型hCA I，hCA II，hCA IV和hCA XII的抑制活性。大多数合成的化合物在体外均表现出优异的性能碳酸酐酶的抑制特性可与临床使用的药物乙酰唑酰胺（AAZ）媲美。新的未保护的二肽-磺酰胺结合物显示出非常有效的抑制活性，在针对II和XII的低纳摩尔范围内，作为hCA I和IV抑制剂的效果较差。与AAZ相比，三十种化合物中的四种还显示出对hCA XII的强抑制活性。
• Synthesis of Taurine-Containing Peptides, Sulfonopeptides, and <i>N</i>- and <i>O</i>-Conjugates
  作者：Peter Vertesaljai、Suvendu Biswas、Iryna Lebedyeva、Evan Broggi、Abdullah M. Asiri、Alan R. Katritzky

  DOI：10.1021/jo500181g

  日期：2014.3.21

  Taurine-containing water-soluble peptidomimetics were designed and synthesized. N-terminal taurine acylations allowed synthesis of a number of taurine-containing peptides. N-protection of taurine with Cbz and SO2-activation with benzotriazole followed by coupling with various amino esters, dipeptides and nucleophiles provided taurine N- and O-conjugates and sulfonopeptides.
• Peptidoyl Benzotriazolide-Mediated Acylation of Nitrile-Activated Methylene Groups
  作者：Alan Katritzky、Sandhyamayee Sahu、Iryna Lebedyeva、Siva Panda

  DOI：10.1055/s-0033-1338473

  日期：——

  Peptidoyl benzotriazoles permit the acylation of active methylene groups of nitriles to provide CH-acylated nitrile enols from alpha-amino acids or from di- or tripeptides with no loss of chirality.