6-甲基-1H,3H-嘧啶-2,4-二硫酮 | 6308-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-甲基-1H,3H-嘧啶-2,4-二硫酮
• 英文名称: 2,4-dithio-6-methyluracil
• 英文别名: 6-methyl-1H-pyrimidine-2,4-dithione；6-Methyl-1H-pyrimidin-2,4-dithion；6-methyl-1H,3H-pyrimidine-2,4-dithione；6-methyl-2,4-dithio-uracil；6-Methyl-2,4-dithiouracil；6-methyl-1H-pyrimidine-2,4-dithione
• CAS: 6308-38-9
• 化学式: C₅H₆N₂S₂
• mdl: MFCD00196752
• 分子量: 158.248
• InChiKey: CQOAJLIZQSKDFC-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C (decomp)
• 沸点：
  236.0±23.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：
  88.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  6-甲基-1H,3H-嘧啶-2,4-二硫酮 在 氨 、 水 作用下， 生成 2-疏基-4-氨基-6-甲基嘧啶
  参考文献：
  名称：

  A Synthesis of 4-Amino-2-thiopyrimidines

  摘要：

  DOI：

  10.1021/ja01175a001
• 作为产物：
  描述：

  2,4-二氯-6-甲基嘧啶 在 乙醇 、 potassium hydrosulfide 作用下， 生成 6-甲基-1H,3H-嘧啶-2,4-二硫酮
  参考文献：
  名称：

  Gabriel; Colman, Chemische Berichte, 1899, vol. 32, p. 2934

  摘要：

  DOI：

文献信息

• Synthesis and study of the radioprotective properties of the pyrimidine analogs of isothiouronium
  作者：B. V. Golomolzin、E. A. Tarakhtii、I. P. Tregubenko、N. M. Perova

  DOI：10.1007/bf00773821

  日期：1984.9

  class [8]. Heterocyciic analogs of AET, i.e., compounds containing an amidine grouping in the heterocyclic ring, have been little studied. It is here possible to mention aminothiol derivatives of purine [2, 3], imidazoline [4, 9], benzimidazole [5], and quinazoline [i, 6] showing in several cases marked radioprotective activity. In continuation of the work on the search for new, more effective radioprotectors

  B-氨基乙基硫脲 (AET) 的高辐射防护特性促使研究人员研究大量此类衍生物 [8]。AET的杂环类似物，即在杂环中含有脒基的化合物，很少被研究。此处可以提及嘌呤 [2, 3]、咪唑啉 [4, 9]、苯并咪唑 [5] 和喹唑啉 [i, 6] 的氨基硫醇衍生物，在几种情况下显示出显着的辐射防护活性。在继续寻找新的、更有效的辐射防护剂的工作中，研究含有嘧啶环的氨基硫醇衍生物似乎很有趣，嘧啶环是核苷酸碱基的主要生物结构之一。
• A Rapid and Efficient Synthesis of Sulfur Analogues of Pyrimidine Bases
  作者：Andrzej R. Łapucha

  DOI：10.1055/s-1987-27906

  日期：——

  An improved procedure for thionation of some natural pyrimidine bases with tetraphosphorus decasulfide/sodium hydrogen carbonate is reported. Some substituted uracils and 2-thiouracils were converted into a series of analogues in which the oxygen at position 4 was replaced by sulfur atom. The advantage of this method of thionation over the older procedures is based on the tetraphosphorus decasulfide/sodium hydrogen carbonate mixture giving rise to excellent yields and simplified isolation of the desired pure products.

  报告了一种改进的硫化天然嘧啶碱基的程序，使用了十磷化十硫化物/氢碳酸钠。某些取代的尿嘧啶和2-硫尿嘧啶被转化为一系列类似物，其中4位的氧被硫原子替代。这种硫化方法相较于旧有程序的优势在于，十磷化十硫化物/氢碳酸钠的混合物能够产生优异的产率，并简化了所需纯产品的分离。
• Synthesis and Antiviral Evaluation of Novel 2,3-Dihydroxypropyl Nucleosides from 2- and 4-Thiouracils
  作者：Adel A.-H. Abdel-Rahman、Abd-Allah SH. El-Etrawy、Ahmed E.-S. Abdel-Megied、Ibrahim F. Zeid、El Sayed H. El Ashry

  DOI：10.1080/15257770802086898

  日期：2008.11.13

  chloride (2) afforded 2-[[(2,2-Dimethyl-1,3-dioxolan-4-yl) methyl]thio]pyrimidin-4(1H)-ones 3a-c and 4-[[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]thio] pyrimidin-2(1H)-ones 8a,b, respectively. Further alkylation with 2 and/or 2,3-O-isopropylidine-1-O-(4-toluenesulfonyl)-glycerol (4) gave the acyclo N-nucleosides 5a-c and 9a,b whose deprotection afforded 6a-c and 10a,b. 2-(Methylthio)pyrimidin-4(1H)-ones 11a-c

  用2，3-O-异亚丙基-2，3-二羟丙基氯（2）对2-硫尿嘧啶1a-c和4-硫尿嘧啶7a，b进行区域选择性烷基化，得到2-[[（（2，2-二甲基-1,3-）二氧戊环-4-基）甲基]硫基]嘧啶-4（1H）-基3a-c和4-[[（（2,2-二甲基-1,3-二氧戊环-4-基）甲基]硫基]嘧啶-2 （1H）-分别为8a，b。用2和/或2,3-O-异丙基-1--1-O-（4-甲苯磺酰基）-甘油（4）进一步烷基化得到无环N-核苷5a-c和9a，b，它们的脱保护得到6a-c和10a ，b。将2-（甲硫基）嘧啶-4（1H）-酮11a-c和4-（甲硫基）嘧啶-2（1H）-酮14a，b用2和/或4处理得到12a-c和15a，b将它们去保护得到13a-c和16a，b。用两个当量的2处理嘧啶-2,4（1H，3H）-二硫酮17a-c，得到2,4-双[[（（2,2-二甲基-1,3-二氧杂戊-4-基）甲基]] [硫代]
• Cephalosporin derivatives
  申请人：Mochida Pharmaceutical Co., Ltd.

  公开号：US04888332A1

  公开（公告）日：1989-12-19

  The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof. The novel cephalosporin derivatives according to the present invention contain condensed heterocyclic groups, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring as substituents at the 3-position of the cephem skeleton, and a hydroxyimino, an alkyloxyimino or an acyloxyimino moiety as substituents at the 7-position of the cephem skeleton. The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against gram-negative bacteria and also against gram-positive bacteria including methicillin-resistant Staphylococcus aureus. These compounds are extremely useful for the treatment of infectious diseases.

  本发明涉及新型头孢菌素衍生物、其制备方法、以新型头孢菌素衍生物作为活性成分的预防和/或治疗传染病的组合物，以及头孢菌素衍生物合成中的中间体化合物和其制备方法。本发明的新型头孢菌素衍生物包含紧缩杂环基团，特别是三唑嘧啶环或噻唑嘧啶环作为头孢菌素骨架的3位取代基，并且在头孢菌素骨架的7位取代基是羟肟基、烷氧基肟基或酰氧基肟基。本发明中含有上述取代基的化合物对革兰氏阴性菌和包括甲氧西林耐药金黄色葡萄球菌在内的革兰氏阳性菌具有强大的抗菌活性。这些化合物对于治疗传染病非常有用。
• Study of the protonation (methylation) position and tautomeric structure of thiopyrimidine derivatives by 2D 1H—15H NMR HSQC/HMBC. Experimental approach and theoretical modeling
  作者：A. V. Kozlov、V. E. Semenov、A. S. Mikhailov、A. V. Il’yasov、V. S. Reznik、Sh. K. Latypov

  DOI：10.1007/s11172-009-0008-4

  日期：2009.1

  Two-dimensional 1H—15N NMR HSQC/HMBC experiments enable the unambiguous determination of the protonation (methylation) position and tautomeric structure of nitrogen-containing heterocycles. In investigated thiopyrimidines protonation (or methylation) occurs at the N(1) atom of the pyrimidine ring. The tautomeric structures of these compounds were established based on the analysis of 1H—15N NMR spectra. Ab initio calculations of chemical shifts (GIAO B3LYP/6-31G(d)//HF/6-31G) are in full agreement with experimental values. The stability of various protonated (methylated) and tautomeric species is explained in terms of a thermodynamic approach.

  二维 1H-15N NMR HSQC/HMBC 实验能够明确确定含氮杂环的质子化（甲基化）位置和同分异构体结构。在所研究的噻吩嘧啶中，质子化（或甲基化）发生在嘧啶环的 N（1）原子上。根据 1H-15N NMR 光谱分析，确定了这些化合物的同分异构体结构。化学位移的 Ab initio 计算（GIAO B3LYP/6-31G(d)//HF/6-31G）与实验值完全一致。热力学方法解释了各种质子化（甲基化）和同分异构体的稳定性。