2-<<2''-(dimethylamino)ethyl>thio>pyrimidine | 108772-84-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-<<2''-(dimethylamino)ethyl>thio>pyrimidine
• 英文别名: N,N-dimethyl-2-(pyrimidin-2'-ylthio)ethylamine；N,N-dimethyl-2-(pyrimidin-2-ylthio)ethanamine；N,N-dimethyl-2-pyrimidin-2-ylsulfanylethanamine
• CAS: 108772-84-5
• 化学式: C₈H₁₃N₃S
• 分子量: 183.277
• InChiKey: ZQKKNAQCHCJXDH-UHFFFAOYSA-N

物化性质

• 沸点：
  273.3±23.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<<2''-(dimethylamino)ethyl>thio>pyrimidine 生成 2-<<2''-(dimethylamino)ethyl>thio>-4,6-bis<3'-<<2'''-(dimethylamino)ethyl>thio>phenyl>pyrimidine
  参考文献：
  名称：

  Quantitative structure-activity relationship analysis of cation-substituted polyaromatic compounds as potentiators (amplifiers) of bleomycin-mediated degradation of DNA

  摘要：

  A set of 21 polyheteroaromatic compounds substituted with flexible cationic groups and of similar molecular size has been analyzed for binding with DNA and for effects on the bleomycin-mediated degradation of the DNA double helix. Increases in apparent rates of the DNA digestion were observed in all cases under the experimental conditions of noncompetitive binding of these compounds and bleomycin to DNA. Surprisingly, the quantitative structure-activity relationship analysis revealed two distinct correlations despite close structural similarities for the set of bleomycin amplifiers. These unusual results are explained in terms of the formation of two stereochemically different ternary complexes of activated bleomycin-DNA-amplifier. The relevance of this finding for the design of new bleomycin amplifiers is discussed.

  DOI：

  10.1021/jm00106a017
• 作为产物：
  描述：

  2-氯嘧啶 、 2-甲胺乙硫醇盐酸盐 在 sodium ethanolate 作用下， 生成 2-<<2''-(dimethylamino)ethyl>thio>pyrimidine
  参考文献：
  名称：

  博来霉素介导的DNA降解的扩增。

  摘要：

  引入了三个简单且独立的测试来研究DNA嵌入化合物对博来霉素介导的DNA体外消化的影响。这些方法基于DNA溶液的增色变化，DNA溶液粘度的变化以及从消化的DNA中释放出的四种碱基的HPLC定量分析。这三个测试均给出了可比的结果。但是，从技术上讲，粘度法是最简单的，同时也是最灵敏的。通过三个未融合的杂多芳族嵌入剂分子（即N- [2''-（（二甲氨基）乙基] -4-噻吩-2'-嘧啶-2-胺（1N），N，N）扩增博来霉素介导的DNA降解-二甲基-2-[（（4'-thien-2''-ylpyrimidin-2'-yl）thio]乙胺（1S）和新合成的2,5-bis [2'-[[2'' -（二甲氨基）乙基]硫代]嘧啶-4'基]噻吩（2）与这些化合物的相应DNA结合常数相关性很好，并且是浓度依赖性的。这些化合物的扩增活性随浓度增加而增加。迄今发现，具有强结合力的化合物2是博莱霉素在体外的最佳扩增剂。融合

  DOI：

  10.1021/jm00391a025

文献信息

• Decyanative Cross-Coupling of Cyanopyrimidines with O-, S-, and N-Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines
  作者：Xiangyang Wei、Caiyang Zhang、Yifei Wang、Qi Zhan、Guiying Qiu、Ling Fan、Guodong Yin

  DOI：10.1002/ejoc.201901364

  日期：2019.11.14

  A cross‐coupling reaction of cyanopyrimidines with aliphatic alcohols, thiols (or S‐alkylisothiourea salts) or amines gives the corresponding alkoxylpyrimidines, aminopyrimidines or alkylthiopyrimidines. The wide substrate scope with excellent yields makes cyanopyrimidines a promising alternative substrate class to the frequently used pyrimidines halides for the formation of C–O, C–S, and C–N bonds

  氰基嘧啶与脂族醇，硫醇（或S-烷基异硫脲盐）或胺的交叉偶联反应可得到相应的烷氧基嘧啶，氨基嘧啶或烷基硫嘧啶。宽范围的底物范围和优异的收率使氰基嘧啶成为用于形成C–O，C–S和C–N键的常用嘧啶卤化物的有前途的替代底物类别。
• Cesium carbonate-promoted synthesis of aryl methyl sulfides using <i>S</i>-methylisothiourea sulfate under transition-metal-free conditions
  作者：Caiyang Zhang、You Zhou、Jintao Huang、Canhui Tu、Xiaoai Zhou、Guodong Yin

  DOI：10.1039/c8ob01758a

  日期：——

  cyclopropylmethylthio groups can be easily introduced into the aromatic rings from the corresponding S-[2-(dimethylamino)ethyl]isothiourea dihydrochloride and S-cyclopropylmethylisothiourea hydrobromide. The possible reaction mechanism is proposed. It is believed that this route to aryl alkyl sulfides is well competitive with currently known methods due to its wide substrate scope, excellent yields, easy

  在碳酸铯的存在下，开发了通过芳基卤化物与可商购的S-甲基异硫脲硫酸盐反应的有效合成芳基甲基硫醚的方法。这种无味且高度结晶的固体可用作恶臭甲硫醇的替代品。在不使用柱色谱分离的情况下，克级反应也可以顺利进行。类似地，2-（二甲基氨基）乙硫基和环丙基甲硫基可容易地从相应的S- [2-（二甲氨基）乙基]异硫脲二盐酸盐和S中引入芳环。-环丙基甲基异硫脲氢溴酸盐。提出了可能的反应机理。据信，由于其广泛的底物范围，优异的收率，易于操作和无过渡金属的条件，该制备芳基烷基硫化物的方法与目前已知的方法具有很好的竞争性。
• Molecular basis for bleomycin amplification: conformational and stereoelectronic effects in unfused amplifiers
  作者：Lucjan Strekowski、Jerzy L. Mokrosz、Farial A. Tanious、Rebecca A. Watson、Donald Harden、Maria Mokrosz、W. Daniel Edwards、W. David Wilson

  DOI：10.1021/jm00401a027

  日期：1988.6

  biphenyl compounds substituted with an amino side chain (protonated in water) have been tested for (i) binding with DNA and (ii) their effect on the digestion of the DNA double helix by a bleomycin-iron complex. Only the DNA intercalating molecules amplify the digestion of DNA. One 2,2'-bipyridine derivative tested is an inhibitor of the bleomycin reaction because it removes ferrous ion from the bleomycin

  已经测试了16个未融合的杂双芳香族化合物和联苯化合物（被水质子化）的氨基侧链（i）与DNA结合，以及（ii）它们对博来霉素-铁络合物对DNA双螺旋的消化作用。只有DNA插入分子才能扩增DNA的消化。测试的一种2,2'-联吡啶衍生物是博来霉素反应的抑制剂，因为它从博来霉素复合物中去除了亚铁离子。插入的未融合双芳烃系统的极性对于分子与天然DNA的有效结合以及同时对其扩增活性至关重要。具有双芳族系统的分子在侧阳离子链的方向上广泛极化，因此插入位点构成偶极子的正部分，显示出与DNA的强结合力和良好的扩增活性 对于决定扩增活性的强插入力，重要的是分子的两个杂芳族子系统的偶极子的正端都远离侧链。这项工作为合成新型高效博来霉素放大器提供了一般指导。
• New approach to conformational analysis of heterobiaryls in solution
  作者：Lucjan Strekowski、Farial A Tanious、Subramanian Chandrasekaran、Rebecca A Watson、W.David Wilson

  DOI：10.1016/s0040-4039(00)85394-0

  日期：1986.1

  Native DNA is used in conformational studies of heterobiaryls. Evidence is presented that the 4-(2′-furyl)pyrimidine and 4-(2′-thienyl)-pyrimidine systems exist in solution in an essentially planar and conformation, respectively. The 5-methy1-4-(2′-thieny1)pyrimidine system is also

  天然DNA用于杂二芳基的构象研究。证据表明4-（2'-呋喃基）嘧啶和4-（2'-噻吩基）-嘧啶体系分别以基本上平面和构象的形式存在于溶液中。5-methy1-4-（2'-thieny1）嘧啶系统也是
• STREKOWSKI, L.;STREKOWSKA, A.;WATSON, R. A.;TANIOUS, F. A.;NGUYEN, L. T.;+, J. MED. CHEM., 30,(1987) N 8, 1415-1420
  作者：STREKOWSKI, L.、STREKOWSKA, A.、WATSON, R. A.、TANIOUS, F. A.、NGUYEN, L. T.、+

  DOI：——

  日期：——