2,3'-bis<<2''-(dimethylamino)ethyl>thio>-4-phenylpyrimidine | 129224-78-8

• 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: 2,3'-bis<<2''-(dimethylamino)ethyl>thio>-4-phenylpyrimidine
• 英文别名: Ethanamine, 2-((4-(3-((2-(dimethylamino)ethyl)thio)phenyl)-2-pyrimidinyl)thio)-N,N-dimethyl-；2-[3-[2-[2-(dimethylamino)ethylsulfanyl]pyrimidin-4-yl]phenyl]sulfanyl-N,N-dimethylethanamine
• CAS: 129224-78-8
• 化学式: C₁₈H₂₆N₄S₂
• 分子量: 362.563
• InChiKey: CPMOHYYYNYDKDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  82.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3'-bis<<2''-(dimethylamino)ethyl>thio>-4-phenylpyrimidine 生成 2-[3-[2-[2-(dimethylamino)ethylsulfanyl]pyrimidin-4-yl]phenyl]sulfanyl-N,N-dimethylethanamine;dihydrobromide
  参考文献：
  名称：

  STREKOWSKI, LUCJAN;WILSON, W. DAVID;MOKROSZ, JERZY L.;MOKROSZ, MARIA J.;H+, J. MEC. CHEM., 34,(1991) N, C. 580-588

  摘要：

  DOI：
• 作为产物：
  描述：

  3-<<2'-(dimethylamino)ethyl>thio>phenyllithium 、 2-<<2''-(dimethylamino)ethyl>thio>pyrimidine 生成 2,3'-bis<<2''-(dimethylamino)ethyl>thio>-4-phenylpyrimidine
  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

文献信息

• STREKOWSKI, LUCJAN;WILSON, W. DAVID;MOKROSZ, JERZY L.;MOKROSZ, MARIA J.;H+, J. MEC. CHEM., 34,(1991) N, C. 580-588
  作者：STREKOWSKI, LUCJAN、WILSON, W. DAVID、MOKROSZ, JERZY L.、MOKROSZ, MARIA J.、H+

  DOI：——

  日期：——
• [EN] NUCLEIC ACID INTERACTING UNFUSED HETEROPOLYCYCLIC COMPOUNDS
  申请人：GEORGIA STATE UNIVERSITY FOUNDATION, INC.

  公开号：WO1989011279A1

  公开（公告）日：1989-11-30

  (EN) The compounds of the present invention are derivatized unfused heteropolycyclic compounds, primarily heterotricyclic compounds, formed by replacing the halogen atoms adjacent to diazine ring nitrogens or the benzylic halogenin 2,6-bis[4-(bromomethyl)phenyl]pyridine with one of a variety of common nucleophiles such as the hydroxide ion, alkoxides, mercaptides, and amines. These compounds interact with nucleic acids, thereby inhibiting translation and interfering with viral replication processes, such as the replication of HIV, the virus believed to cause AIDS. The preferred compounds at this time are 2,6-bis[4'-[(dimethylamino)methyl]phenyl]pyridine (DH-23); 4,6-bis[4'-[[2''-(dimethylamino)ethyl]thio]phenyl]-5-methylpyrimidine (LS-22); N-[2''-(dimethylamino)ethyl]-4-(benzo[b]thiophen-2'-yl)quinazolin-2-amine (M-116); N,N-bis(2''''-hydroxyethyl)-2-[[4'-(benzo[b]thiopen-2''-yl)-6'-(thien-2'''-yl)pyrimidin-2'-yl]oxy]ethylamine (DH-42); bis-4,6-[4'-[[2''-(dimethylamino)ethyl]thio]phenyl]pyrimidine (LS-20); 1-methyl-4-[2'-[[4''-(naphth-2'''-yl) quinazolin-2''-yl]thio]ethyl]piperazine (M-69); N,N-bis-(2'-hydroxyethyl)-4,6-bis(thien-2''-yl)pyrimidin-2-amine (M-103); N,N-bis(2'-hydroxyethyl)-2-[[4'',6''-bis(thien-2'''-yl)pyrimidine-2''yl]oxy]ethylamine (M-105); and 4-[3'-[[2''-(dimethylamino)ethyl]thio]phenyl]-2-[[2'''-(dimethylamino)ethyl]thio] pyrimidine (DH-19). Advantages of these compounds include low cost and ease of manufacture.(FR) Les composés de la présente invention sont des composés hétéropolycycliques non fusionnés dérivés, essentiellement des composés hétérotricycliques, formés en remplaçant les atomes d'halogène adjacents aux atomes d'azote de l'anneau diazine ou l'halogénine benzylique 2,6-bis[4-(bromométhyle)phényle]pyridine avec un nucléophile d'une variété de nucléophiles communs tels que l'ion hydroxyde, des alcoxydes, des mercaptides et des amines. Ces composés ont une interaction avec des acides nucléiques, inhibant ainsi la translation et interférant avec des procédés de réplication virale, tels que la réplication de HIV, le virus provoquant le SIDA. Les composés préférés sont 2,6-bis[4'-[diméthylamino]méthyle]phényle]pyridine (DH-23); 4,6-bis[4'-[[2''-(diméthylamino)éthyle]thio]phényle]-5-méthylpyrimidine (LS-22); N-[2''-(diméthylamino)éthyle]-4-(benzo[b]thiophène-2'-yle)quinazoline-2-amine (M-116); N,N-bis(2''''-hydroxyéthyle)-2-[[4'-(benzo[b]thiophène-2''-yle)-6'-(thiène-2'''-yl)pyrimidine-2'-yle]oxy]éthylamine (DH-42); bis-4,6-[4'-[[2''-(diméthylamino)éthyle]thio]phényle]pyrimidine (LS-20); 1-méthyle-4-[2'-[[4''-(naphth-2'''-yle) quinazoline-2''-yle]thio]éthyle]pipérazine (M-69); N,N-bis-(2'-hydroxyéthyle)-4,6-bis(thiène-2''-yle)pyrimidine-2-amine (M-103); N,N-bis(2'-hydroxyéthyle)-2-[[4'',6''-bis(thiène-2'''-yle)pyrimidine-2''yle]oxy]éthylamine (M-105); et 4-[3'-[[2''-(diméthylamino)éthyle]thio]phényle]-2-[[2'''-(diméthylamino)éthyle]thio] pyrimidine (DH-19). Ces composés sont avantageux car ils sont peu coûteux et faciles à produire.
• Quantitative structure-activity relationship analysis of cation-substituted polyaromatic compounds as potentiators (amplifiers) of bleomycin-mediated degradation of DNA
  作者：Lucjan Strekowski、W. David Wilson、Jerzy L. Mokrosz、Maria J. Mokrosz、Donald B. Harden、Farial A. Tanious、Roman L. Wydra、Sidney A. Crow

  DOI：10.1021/jm00106a017

  日期：1991.2

  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.