(S)-2-(2-azidoacetamido)-3-phenylpropanoic acid | 904789-99-7

• 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)-2-(2-azidoacetamido)-3-phenylpropanoic acid
• 英文别名: (2S)-2-[(2-azidoacetyl)amino]-3-phenylpropanoic acid
• CAS: 904789-99-7
• 化学式: C₁₁H₁₂N₄O₃
• 分子量: 248.241
• InChiKey: OGPGBAPYNRZPKS-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-azidoacetamido)-3-phenylpropanoic acid 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (S)-S-phenyl 2-(2-azidoacetamido)-3-phenylpropanethioate
  参考文献：
  名称：

  Efficient Synthesis of 2,5-Diketopiperazines by Staudinger-Mediated Cyclization

  摘要：

  Solution- and solid-phase Staudinger-mediated cyclizations were assessed to efficiently prepare hetero-2,5-diketopiperazines from their protected azido dipeptide thioesters under microwave irradiation. Short reaction time, good yields and ease of purification are the main assets of this methodology.

  DOI：

  10.1055/s-0031-1290446
• 作为产物：
  描述：

  N-(氯乙酰基)-L-苯丙氨酸 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以78%的产率得到(S)-2-(2-azidoacetamido)-3-phenylpropanoic acid
  参考文献：
  名称：

  Efficient Synthesis of 2,5-Diketopiperazines by Staudinger-Mediated Cyclization

  摘要：

  Solution- and solid-phase Staudinger-mediated cyclizations were assessed to efficiently prepare hetero-2,5-diketopiperazines from their protected azido dipeptide thioesters under microwave irradiation. Short reaction time, good yields and ease of purification are the main assets of this methodology.

  DOI：

  10.1055/s-0031-1290446

文献信息

• Metal-Free, Regioselective Triazole Ligations that Deliver Locked<i>cis</i>Peptide Mimetics
  作者：Ahsanullah、Peter Schmieder、Ronald Kühne、Jörg Rademann

  DOI：10.1002/anie.200806390

  日期：2009.6.22

  Metal‐free triazole turns: 1,5‐Disubstituted peptidyl triazoles are obtained regioselectively from the 1,3‐dipolar cycloaddition of peptidyl phosphoranes and azides. Peptide turns are thus formed that contain a conformationally locked cis peptide bond. Being regioselective and free of heavy metals, this reaction may find broad application in chemical biology and medicinal chemistry.

  不含金属的三唑类化合物：从1,3-偶极环加成的肽基膦烷和叠氮化物区域选择性地获得1,5-二取代的肽基三唑。因此形成包含构象锁定的顺式 肽键的肽匝。该反应具有区域选择性并且不含重金属，可以在化学生物学和药物化学中找到广泛的应用。
• Synthesis, antimalarial properties and 2D-QSAR studies of novel triazole-quinine conjugates
  作者：Hassan M. Faidallah、Siva S. Panda、Juan C. Serrano、Adel S. Girgis、Khalid A. Khan、Khalid A. Alamry、Tanya Therathanakorn、Marvin J. Meyers、Francis M. Sverdrup、Christopher S. Eickhoff、Stephen G. Getchell、Alan R. Katritzky

  DOI：10.1016/j.bmc.2016.05.060

  日期：2016.8

  2,3-triazole-quinine conjugates 8a–g, 10a–o, 11a–h and 13 utilizing benzotriazole-mediated synthetic approach with excellent yields. Some of the synthesized analogs (11a, 11d–h) exhibited antimalarial properties against Plasmodium falciparum strain 3D7 with potency higher than that of quinine (standard reference used) through in vitro standard procedure bio-assay. Statistically significant BMLR-QSAR

  点击化学技术利用苯并三唑介导的合成方法，以优异的收率得到了新颖的1,2,3-三唑-奎宁偶联物8a – g，10a – o，11a – h和13。一些合成的类似物（11a，11d – h）对恶性疟原虫具有抗疟疾特性。通过体外标准程序生物测定，菌株3D7的效力高于奎宁（使用的标准参照物）。具有统计意义的BMLR-QSAR模型描述了生物特性，验证了观察到的生物学观察结果，并确定了控制生物活性的最重要参数。
• Synthesis, antibacterial properties and 2D-QSAR studies of quinolone-triazole conjugates
  作者：Hassan M. Faidallah、Adel S. Girgis、Anand D. Tiwari、Hitesh H. Honkanadavar、Sean J. Thomas、Ahmed Samir、Atef Kalmouch、Khalid A. Alamry、Khalid A. Khan、Tarek S. Ibrahim、Amany M.M. AL-Mahmoudy、Abdullah M. Asiri、Siva S. Panda

  DOI：10.1016/j.ejmech.2017.10.042

  日期：2018.1

  via microwave assisted click chemistry technique. Some of the aryl-substituted conjugates 17–19 show promising antibacterial properties against the tested Gram-positive (S. aureus and S. pyogenes) and Gram-negative bacteria (S. typhi) with potency higher than that of the parent antibiotics 1–3. 2D-QSAR modeling supports the observed biological properties.

  通过微波辅助点击化学技术合成了一组结合1,2,3-三唑的喹诺酮类抗生素共轭物10-15、17-19。一些被芳基取代的结合物17-19对被测革兰氏阳性菌（金黄色葡萄球菌和化脓性链球菌）和革兰氏阴性菌（鼠伤寒沙门氏菌）显示出有希望的抗菌性能，其效力要高于母体抗生素1–19。 3。2D-QSAR建模支持观察到的生物学特性。
• &lt;i&gt;In Situ&lt;/i&gt; Click Chemistry for the Identification of a Potent D-Amino Acid Oxidase Inhibitor
  作者：Shohei Toguchi、Tomoyasu Hirose、Kazuko Yorita、Kiyoshi Fukui、K. Barry Sharpless、Satoshi Ōmura、Toshiaki Sunazuka

  DOI：10.1248/cpb.c15-00867

  日期：——

  In situ click chemistry is a target-guided synthesis approach for discovering novel lead compounds by assembling organic azides and alkynes into triazoles inside the affinity site of target biogenic molecules such as proteins. We report in situ click chemistry screening with human D-amino acid oxidase (hDAO), which led to the identification of a more potent hDAO inhibitor. The hDAO inhibitors have

  原位点击化学是一种目标指导的合成方法，用于通过在目标生物基因分子（例如蛋白质）的亲和位点内将有机叠氮化物和炔烃组装成三唑来发现新型先导化合物。我们报告了人类D-氨基酸氧化酶（hDAO）的原位点击化学筛选，这导致了更有效的hDAO抑制剂的鉴定。hDAO抑制剂具有作为抗精神病药的化学治疗潜力。与原位点击化学的锚定分子相比，新的抑制剂显示出对hDAO的竞争性抑制作用，并且对hDAO的抑制活性显着提高。
• Macrocyclic Peptide, Method for Producing Same, and Screening Method Using Macrocyclic Peptide Library
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20160209421A1

  公开（公告）日：2016-07-21

  An object of the present invention is to provide a peptide excellent in resistance against metabolism, having a stable structure in vivo, and capable of penetrating a cell membrane and reaching in cells. The present invention provides a macrocyclic peptide having a macrocyclic structure comprised of four or more amino acids. At least two amino acids not adjacent to each other have a hydrophobic side chain and the hydrophobic side chains interact with each other inside the ring of the macrocyclic peptide in a hydrophilic environment.

  本发明的目的是提供一种具有抗代谢能力、在体内具有稳定结构、能够穿透细胞膜并进入细胞的肽。本发明提供一种具有四个或更多氨基酸构成的大环肽，其具有大环结构。至少有两个不相邻的氨基酸具有疏水侧链，并且这些疏水侧链在大环肽的环内在亲水环境中相互作用。