1-methyl-2-thiocytosine | 33399-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-methyl-2-thiocytosine
• 英文别名: 4-amino-1-methyl-1H-pyrimidine-2-thione；4-amino-1-methyl-2-pyrimidinethione；4-amino-1-methylpyrimidin-2-thione；1-Methyl-2-thio-cytosin, 1-Methyl-2-thioxo-cytosin；4-Amino-1-methylpyrimidin-2(1H)-thion；1-Methyl-2-thio-cytosin；2(1H)-Pyrimidinethione, 4-amino-1-methyl-；4-amino-1-methylpyrimidine-2-thione
• CAS: 33399-91-6
• 化学式: C₅H₇N₃S
• mdl: MFCD18811407
• 分子量: 141.197
• InChiKey: UCTBMIHEDBGELA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-2-thiocytosine 在 苯甲醚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  新型3-[（氨基嘧啶基）硫代]甲基头孢菌素的合成及抑菌活性。

  摘要：

  合成了一系列具有3-[（氨基嘧啶基）硫基]甲基取代基的新型头孢菌素化合物。它们对包括铜绿假单胞菌在内的各种细菌显示出很高的抗菌活性。还研究了与各种硫代嘧啶，硫代嘧啶，双环硫代三唑并嘧啶鎓和双环硫代咪唑并嘧啶鎓作为3'-取代基的结构活性关系；具有季铵化嘧啶鎓部分的头孢菌素比中性嘧啶头孢菌素具有更好的抗菌活性，并且使嘧啶鎓部分上的正电荷稳定对于更好的活性至关重要。根据半经验的PM3计算，嘧啶鎓环上的氨基和烷硫基取代基在电荷稳定和离域中起主要作用。

  DOI：

  10.1021/jm00048a018
• 作为产物：
  描述：

  3-乙氧基丙烯腈 、 N-甲硫脲 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 1-methyl-2-thiocytosine
  参考文献：
  名称：

  Novel cephalosporin compounds and processes for the preparation thereof

  摘要：

  本发明涉及新型头孢菌素化合物，药学上可接受的无毒盐、生理可水解的酯、水合物和溶剂合物及其异构体，具有强大和广泛的抗菌活性。本发明的化合物在头孢菌素核的3位具有(1,5,6-取代-4-氨基嘧啶-2-基)硫甲基基团，具体由以下式(I)表示：

  公开号：

  EP0584797A3

文献信息

• Structural and Computational Studies of 1-Methyl-2-thiocytosine and its Coordination Mode in a Dinuclear Platinum(IV) Complex [(PtMe₃)₂(μ-1-MeSCy-1κN³,1:2κ²S)₂][BF₄]₂
  作者：Cornelia Vetter、Christoph Wagner、Ralph Kluge、Dirk Steinborn

  DOI：10.1515/znb-2010-0507

  日期：2010.5.1

  X-Ray diffraction analysis of 1-methyl-2-thiocytosine (1-MeSCy, 1) revealed that its crystals contain two structurally very similar independent molecules (A, B). These molecules are connected through a complex network of hydrogen bonds. Centrosymmetric di- and tetrameric units AAʹ and BAAʹBʹ, respectively, are formed through N-H...N hydrogen bonds (N4a...N3aʹ 3.019(4) Å , AAʹ; N4a...N3b 2.988(4) Å, BAAʹBʹ), and the tetrameric units are connected through N-H...S hydrogen bonds. The arrangement of A and B molecules found in crystals of 1 was confirmed by DFT calculations up to tetrameric BAAʹBʹ units, yielding similar equilibrium structures, and the energies of the N-H...N hydrogen bonds between A and Aʹ and A and B were calculated to be about 10 kcal mol⁻¹. Reaction of 1-MeSCy (1) with [PtMe₃(Me₂CO)₃][BF₄] (2) led to the formation of the ionic dinuclear complex [(PtMe₃)₂(μ-1-MeSCy-1κN³,1:2κ²S)₂][BF₄]₂ (3) which was fully characterized by NMR (¹H, ¹³C, ¹⁹⁵Pt) and IR spectroscopy, ESI mass spectrometry and microanalysis. A singlecrystal X-ray diffraction analysis of 3 confirmed the dinuclear structure of the complex. The complex cation consists of a central [Pt₂(μ-S)₂] core having bound the 1-methyl-2-thiocytosine ligands in a 1κN³,1:2κ²S coordination mode in a face-to-face arrangement, the thionucleobase ligands being present as the amino-thione tautomer.

  1-甲基-2-硫代胞嘧啶（1-MeSCy，1）的X射线衍射分析表明其晶体包含两个结构非常相似的独立分子（A，B）。这些分子通过复杂的氢键网络连接在一起。通过N-H...N氢键（N4a...N3aʹ 3.019(4) Å，AAʹ；N4a...N3b 2.988(4) Å，BAAʹBʹ），形成中心对称的二聚体和四聚体单元AAʹ和BAAʹBʹ，四聚体单元通过N-H...S氢键连接。通过DFT计算，证实了晶体中A和B分子的排列方式，直到四聚体BAAʹBʹ单元，得到了类似的平衡结构，并计算出A和Aʹ以及A和B之间的N-H...N氢键的能量约为10 kcal mol⁻¹。将1-MeSCy（1）与[PtMe₃(Me₂CO)₃][BF₄]（2）反应，形成了离子二核配合物[(PtMe₃)₂(μ-1-MeSCy-1κN³,1:2κ²S)₂][BF₄]₂（3），并通过NMR（¹H，¹³C，¹⁹⁵Pt）和IR光谱、ESI质谱和微量分析进行了完全表征。3的单晶X射线衍射分析确认了该配合物的二核结构。该配合物阳离子由一个中心的[Pt₂(μ-S)₂]核心组成，以面对面的方式以1κN³,1:2κ²S配位模式结合1-甲基-2-硫代胞嘧啶配体，硫代嘌呤碱基配体以氨基硫醇互变异构体的形式存在。
• Synthesis, characterization, and cytotoxicity of trimethylplatinum(IV) complexes with 2-thiocytosine and 1-methyl-2-thiocytosine ligands
  作者：Cornelia Vetter、Christoph Wagner、Goran N. Kaluđerović、Reinhard Paschke、Dirk Steinborn

  DOI：10.1016/j.ica.2008.03.085

  日期：2009.1

  The reaction of [PtMe3(MeOH)(bpy)][BF4] (1) with the thionucleobases 2-thiocytosine (SCy, 2) and 1-methyl-2-thiocytosine (1-MeSCy, 3) resulted in the formation of the complexes [PtMe3(bpy)(SCy-kS)][BF4] (4) and [PtMe3(bpy)(1-MeSCy-kS)] [BF4] (5), respectively. The complexes were characterized by H-1 and C-13 NMR spectroscopy as well as by single-crystal X-ray analyses of 4 center dot MeOH and 5. In 4 center dot MeOH two strong hydrogen bonds (N4-H center dot center dot center dot N3': N4 center dot center dot center dot N3' 2.976(7)angstrom) between the thiocytosine ligands give rise to base pairing thus forming dinuclear cations [PtMe3(bpy)(SCy-kS)}(2)](2+). In both complexes the platinum atom is octahedrally coordinated [PtC3N2S] by three methyl ligands, the 2,2'-bipyridine ligand and the kS coordinated nucleobase (configuration index: OC-6-33). The structural investigations gave evidence that the sulfur atoms of the nucleobase ligands in 4 center dot MeOH and 5 have to be regarded as sp(3) and sp(2) hybridized, respectively. Thus, the ligand in 4 center dot MeOH has to be considered as the deprotonated thiol-amino form of thiocytosine being reprotonated at N1. In complex 5 the 1-MeSCy is coordinated in its thione-amino form. DFT-calculations of the base-paired dinuclear cation in 4 as well as of 4 itself gave proof of the strength of the hydrogen bond (8.5 kcal/mol) and exhibited that cation-anion interactions influence the conformation of the complex. In vitro cytotoxicity studies of 4 and 5 using nine different human tumor cell lines revealed moderate cytotoxic activity. (c) 2008 Elsevier B.V. All rights reserved.
• Synthesis and Antimicrobial Activity of Novel [(3-Aminopyrimidiniumyl)thio]methyl Cephalosporins
  作者：Yong-Zu Kim、Jong-Chan Lim、Jae-Hong Yeo、Chan-Sik Bang、Won-Sup Kim、Sam-Sik Kim、Yong-Min Woo、Duck-Ho Yang、Hunseung Oh、Keepyung Nahm

  DOI：10.1021/jm00048a018

  日期：1994.10

  A series of novel cephalosporin compounds which have 3-[(aminopyrimidiniumyl)thio]methyl substituents was synthesized. They show high antimicrobial activity against various bacterial species including Pseudomonas aeruginosa. Structure-activity relationships with various thiopyrimidines, thiopyrimidiniums, bicyclic thiotriazolopyrimidiniums, and bicyclic thioimidazolopyrimidiniums as 3'-substituents

  合成了一系列具有3-[（氨基嘧啶基）硫基]甲基取代基的新型头孢菌素化合物。它们对包括铜绿假单胞菌在内的各种细菌显示出很高的抗菌活性。还研究了与各种硫代嘧啶，硫代嘧啶，双环硫代三唑并嘧啶鎓和双环硫代咪唑并嘧啶鎓作为3'-取代基的结构活性关系；具有季铵化嘧啶鎓部分的头孢菌素比中性嘧啶头孢菌素具有更好的抗菌活性，并且使嘧啶鎓部分上的正电荷稳定对于更好的活性至关重要。根据半经验的PM3计算，嘧啶鎓环上的氨基和烷硫基取代基在电荷稳定和离域中起主要作用。
• Novel cephalosporin compounds and processes for the preparation thereof
  申请人：LUCKY LTD.

  公开号：EP0584797A3

  公开（公告）日：1994-06-08

  The present invention relates to novel cephalosporin compounds, pharmaceutically acceptable non-toxic salts, physiologically hydrolyzable esters, hydrates and solvates and isomers thereof which possess potent and broad antibacterial activities. The compounds of the present invention have a (1,5,6-substituted-4-aminopyrimidinium-2-yl)thiomethyl group in 3-position of the cephem nucleus and is specifically represented by the following formula(I):

  本发明涉及新型头孢菌素化合物，药学上可接受的无毒盐、生理可水解的酯、水合物和溶剂合物及其异构体，具有强大和广泛的抗菌活性。本发明的化合物在头孢菌素核的3位具有(1,5,6-取代-4-氨基嘧啶-2-基)硫甲基基团，具体由以下式(I)表示：