3-(methylsulfonyl)-4-phenyl-4H-1,2,4-triazole | 3588-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(methylsulfonyl)-4-phenyl-4H-1,2,4-triazole
• 英文别名: 4-Phenyl-1,2,4-triazolil-methylsulfon-(3)；3-methanesulfonyl-4-phenyl-4H-[1,2,4]triazole；3-methylsulfonyl-4-phenyl-1,2,4-triazole
• CAS: 3588-96-3
• 化学式: C₉H₉N₃O₂S
• 分子量: 223.255
• InChiKey: CXEIPEUGEOAESW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(methylthio)-4-phenyl-4H-1,2,4-triazole 在 hexaammonium heptamolybdate tetrahydrate 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以77%的产率得到3-(methylsulfonyl)-4-phenyl-4H-1,2,4-triazole
  参考文献：
  名称：

  使用 Julia-Kocieński 样试剂快速、稳定、化学选择性标记硫醇：一种血清稳定的马来酰亚胺基蛋白质缀合替代品

  摘要：

  已发现在各种缓冲条件下甲基磺酰基苯基恶二唑化合物对半胱氨酸具有精确的化学选择性。此外，所得到的蛋白质偶联物比人血浆中的半胱氨酸-马来酰亚胺偶联物（HSA=人血清白蛋白，MBP-C-HA=麦芽糖结合蛋白）具有更好的稳定性。这种新的硫醇点击反应为生成稳定的蛋白质偶联物和聚乙二醇化蛋白质提供了一种新方法。

  DOI：

  10.1002/anie.201306241

文献信息

• METHOD FOR NON-ENZYMATIC COMBINATION OF NUCLEIC ACID CHAINS
  申请人：Japan Science and Technology Agency

  公开号：EP3187584A1

  公开（公告）日：2017-07-05

  Provided, as a technique for binding a nucleic acid chain and a nucleic acid chain by a natural structure or an analogous structure thereto, is a non-enzymatic nucleic acid chain binding method, which is a method for binding a nucleic acid chain and a nucleic acid chain not via an enzymatic reaction, including a step of reacting a nucleic acid chain having a phosphorothioate group and a nucleic acid chain having a hydroxyl group or amino group in the presence of an electrophile.

  作为一种通过天然结构或类似结构结合核酸链和核酸链的技术，提供了一种非酶结合核酸链的方法，它是一种不通过酶反应结合核酸链和核酸链的方法，包括在亲电子体存在的情况下，使具有硫代磷酸基的核酸链和具有羟基或氨基的核酸链发生反应的步骤。
• Method for non-enzymatic combination of nucleic acid chains
  申请人：JAPAN SCIENCE AND TECHNOLOGY AGENCY

  公开号：US10570385B2

  公开（公告）日：2020-02-25

  A non-enzymatic method is provided for binding a first nucleic acid chain to a second nucleic acid chain without introducing a sulfur atom into the combined nucleic acid chain, the method comprising reacting a first nucleic acid chain having a phosphorothioate group at the 3′ or 5′ terminus with a second nucleic acid chain having a hydroxyl group or an amino group at the 3′ or 5′ terminus in the presence of an electrophile that has a leaving group and is configured to leave the leaving group and bind to a sulfur atom of the phosphorothioate group of the first nucleic acid chain at the site to which the leaving group had been bound, and remove the sulfur atom from the phosphorothioate group of the first nucleic acid chain and a hydrogen atom from the hydroxyl group or from the amino group of the second nucleic acid chain via a nucleophilic substitution with an oxygen atom of the hydroxyl group or a nitrogen atom of the amino group of the second nucleic acid chain, and thereby form a bond between a phosphorus atom of the phosphate group of the first nucleic acid chain and the oxygen atom or the nitrogen atom of the second nucleic acid chain. Examples of structures produced by the binding method are shown below.

  本发明提供了一种非酶促方法，用于将第一核酸链与第二核酸链结合而不在结合的核酸链中引入硫原子、该方法包括使第一核酸链与第二核酸链反应，第一核酸链的 3′或 5′末端具有硫代磷酸酯基团，第二核酸链的 3′或 5′末端具有羟基或氨基。具有离去基团的亲电子体，该亲电子体配置成离开离去基团，并在离去基团结合的部位与第一核酸链的硫代磷酸酯基团的硫原子结合、并通过与第二核酸链的羟基的氧原子或氨基的氮原子的亲核取代作用，从第一核酸链的硫代磷酸酯基团中除去硫原子，并从第二核酸链的羟基或氨基中除去氢原子，从而在第一核酸链的磷酸基团的磷原子与第二核酸链的氧原子或氮原子之间形成键。下面举例说明该结合方法产生的结构。
• Rapid, Stable, Chemoselective Labeling of Thiols with Julia-Kocieński-like Reagents: A Serum-Stable Alternative to Maleimide-Based Protein Conjugation
  作者：Narihiro Toda、Shigehiro Asano、Carlos F. Barbas

  DOI：10.1002/anie.201306241

  日期：2013.11.25

  Exquisite chemoselectivity for cysteine has been found for methylsulfonylphenyloxadiazole compounds under various buffer conditions. Furthermore, the resulting protein conjugates have superior stability to cysteine–maleimide conjugates in human plasma (HSA=human serum albumin, MBP‐C‐HA=maltose‐binding protein). This new thiol‐click reaction offers a new approach to generate stable protein conjugates

  已发现在各种缓冲条件下甲基磺酰基苯基恶二唑化合物对半胱氨酸具有精确的化学选择性。此外，所得到的蛋白质偶联物比人血浆中的半胱氨酸-马来酰亚胺偶联物（HSA=人血清白蛋白，MBP-C-HA=麦芽糖结合蛋白）具有更好的稳定性。这种新的硫醇点击反应为生成稳定的蛋白质偶联物和聚乙二醇化蛋白质提供了一种新方法。