N'-(3-thioxo-3H-1,2,4-dithiazol-5-yl)-morpholinomethanimidamide | 1198320-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N'-(3-thioxo-3H-1,2,4-dithiazol-5-yl)-morpholinomethanimidamide
• CAS: 1198320-78-3
• 化学式: C₇H₉N₃OS₃
• 分子量: 247.366
• InChiKey: NRYBXIBEPARVTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.72
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3-氨基-1,2,4-二噻唑-5-硫酮 、 4-(二甲氧基甲基)吗啉 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N'-(3-thioxo-3H-1,2,4-dithiazol-5-yl)-morpholinomethanimidamide
  参考文献：
  名称：

  Reactivity of 3H-1,2,4-dithiazole-3-thiones and 3H-1,2-dithiole-3-thiones as sulfurizing agents for oligonucleotide synthesis

  摘要：

  The reactivity of 5-amino-3H-1,2,4-dithiazole-3-thiones substituted at their amino group and 5-amino-3H-1,2-dithiole-3-thiones substituted at their amino group and C4 toward compounds containing P(III) atoms has been studied. N,N-Disubstituted-N'-(3-thioxo-3H-1,2,4-dithiazol-5-yl)methanimidamides were selected as novel efficient sulfur transfer reagents suitable for DNA and RNA synthesis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.086

文献信息

• SULFUR TRANSFER REAGENTS FOR OLIGONUCLEOTIDE SYNTHESIS
  申请人：Guzaev Andrei P.

  公开号：US20090306358A1

  公开（公告）日：2009-12-10

  The use of N-formamidino-5-amino-3H-1,2,4-dithiazole-3-thiones as novel, efficient sulfur-transfer reagents is disclosed. The sulfur transfer from these reagents to compounds containing P(III) atom, triphenylphosphine, 5′-O-DMT-thymidine 2-cyanoethyl-(N,N-diisopropyl)phosphoramidite, and 5′-O-DMT-3′-O-levulinyl dithymidilyl 2-cyanoethyl phosphite, was studied in solution by 31 P NMR and HPLC. The sulfur transfer from title compounds was also studied in the solid-phase synthesis of oligonucleotide phosphorothioates by phosphoramidite methods. In this application, the efficiency of the sulfur transfer reaction for 2′-deoxyoligonucleotides was better than 99.5%. The novel sulfurizing agents are synthesized, at low cost, using simple chemical methods. As opposed to many sulfur transfer reagents known in the prior art such as 1,2-benzodithiol-3-one-1,1-dioxide (Beaucage reagent) and 5-ethoxy-3H-1,2,4-dithiazole-2-one (EDIT), the sulfurizing agents disclosed herein are highly stable in solution, which increases their practical and commercial value.

  本发明公开了N-甲酰基-5-氨基-3H-1,2,4-二噻唑-3-硫酮作为新型高效硫转移试剂的使用。通过31P NMR和HPLC研究了这些试剂向含有P（III）原子、三苯基膦、5'-O-DMT-胸腺嘧啶-2-氰基乙基（N,N-二异丙基）磷酰胺和5'-O-DMT-3'-O-左旋糖酰基二胸腺嘧啶基2-氰基乙基亚磷酸酯化合物中的硫转移。此外，还通过磷酰胺法研究了这些化合物在寡核苷酸磷酸硫酯的固相合成中的硫转移。在该应用中，2'-脱氧寡核苷酸的硫转移反应效率高达99.5%以上。这些新型硫化试剂可以使用简单的化学方法低成本合成。与许多已知的硫转移试剂（如1,2-苯并二噻唑-3-酮-1,1-二氧化物（Beaucage试剂）和5-乙氧基-3H-1,2,4-二噻唑-2-酮（EDIT））相比，本发明公开的硫化试剂在溶液中高度稳定，从而增加了它们的实用和商业价值。
• ³⁴S: A New Opportunity for the Efficient Synthesis of Stable Isotope Labeled Compounds
  作者：Sumei Ren、Patrick S. Fier、Hong Ren、Andrew J. Hoover、David Hesk、Rosemary Marques、Ingrid Mergelsberg

  DOI：10.1002/chem.201801494

  日期：2018.5.17

  The synthesis of stable isotope labeled (SIL) complex drug molecules with a ≥3 mass unit increase from the parent compound is essential for drug discovery and development. Typical approaches that rely on 2H, 13C, and 15N isotopes can be very challenging or even intractable, and can delay the drug development process. This work introduces a new concept for the synthesis of labeled compounds that relies

  稳定的同位素标记（SIL）复杂药物分子的合成要比母体化合物增加≥3质量单位，这对于药物发现和开发至关重要。依赖于2 H，13 C和15 N同位素的典型方法可能非常具有挑战性，甚至难以解决，并且可能会延迟药物开发过程。这项工作引入了对标记的化合物，它依赖于使用的合成的新概念34 S.的合成实用程序34 S为与[的有效合成证明34 S]硫代磷酸酯[ 34 š 2 ] -PS-核苷酸-TTT和[ 13 C，15 N，34S]-头孢唑烷。此外，开发了一种在不稀释同位素的情况下使用元素34 S将亚磷酸酯直接氧化为[ 34 S]硫代磷酸酯的方法。