2-(methylthio)perimidinium iodide | 89473-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类 - 二氮杂萘
• 英文名称: 2-(methylthio)perimidinium iodide
• 英文别名: 2-methylsulfanyl-1H-perimidin-1-ium;iodide
• CAS: 89473-00-7
• 化学式: C₁₂H₁₀N₂S*HI
• 分子量: 342.203
• InChiKey: YGUVGXIWQUIDPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(methylthio)perimidinium iodide 在 一水合肼 作用下， 反应 0.5h， 以72%的产率得到2-hydrazino-1H-perimidine
  参考文献：
  名称：

  Burkhardt, U.; Johne, S., Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 2, p. 237 - 244

  摘要：

  DOI：
• 作为产物：
  描述：

  1,8-二氨基萘 在 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 10.0h， 生成 2-(methylthio)perimidinium iodide
  参考文献：
  名称：

  Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR

  摘要：

  Basic molecular building blocks such as benzene rings, amidines, guanidines, and amino groups have been combined in a systematic way to generate ligand candidates for HIV-1 TAR RNA. Ranking of the resulting compounds was achieved in a fluorimetric Tat-TAR competition assay. Although simple molecules such as phenylguanidine are inactive, few iteration steps led to a set of ligands with IC50 values ranging from 40 to 150 mu M. 1,7-Diaminoisoquinoline 17 and 2,4,6-triaminoquinazoline 22 have been further characterized by NMR titrations with TAR RNA. Compound 22 is bound to TAR at two high affinity sites and shows slow exchange between the free ligand and the RNA complex. These results encourage investigations of dimeric ligands built from two copies of compound 22 or related heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.004

文献信息

• 13C and1H NMR studies of structure and tautomerism in some perimidines
  作者：P. D. Woodgate、J. M. Herbert、W. A. Denny

  DOI：10.1002/mrc.1260260304

  日期：1988.3

  The 13C NMR spectra of some 1- and 2-substituted perimidines and perimidinium salts are discussed and assigned. Although the spectra of most of the 2-substituted perimidines are comparatively simple, several examples display 13C and 1H spectral characteristics indicative of inhibition of prototropic tautomerism.

  讨论并归属了一些1-和2-取代嘧啶及其嘧啶盐的13C NMR谱。虽然大部分2-取代嘧啶的谱图相对简单，但有多个例子显示出13C和1H谱特征，表明质子互变异构受到抑制。
• Potential antitumor agents. 53. Synthesis, DNA binding properties, and biological activity of perimidines designed as minimal DNA-intercalating agents
  作者：John M. Herbert、Paul D. Woodgate、William A. Denny

  DOI：10.1021/jm00394a025

  日期：1987.11

  A series of compounds based on perimidine have been synthesized and evaluated for their DNA-binding properties and antitumor activity. The fused tricyclic permidine chromophore appears to be the minimal structural requirement for intercalative binding to DNA since the mode of binding could be dictated by the position of attachment of the side chain. The intercalating compounds have DNA association constants (log K = 5.8-6.5) and cytotoxic potencies (IC50 = 500-1500 nM) comparable to those shown by other classes of linear, tricyclic DNA-intercalating antitumor agents (acridinecarboxamides, phenazinecarboxamides), but none of the compounds showed in vivo activity.
• Liu, Kang-Chien; Chen, Hsiu-Ho, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 911 - 912
  作者：Liu, Kang-Chien、Chen, Hsiu-Ho

  DOI：——

  日期：——
• LIU, KANG-CHIEN;CHEN, HSIU-HO, J. HETEROCYCL. CHEM., 1984, 21, N 3, 911-912
  作者：LIU, KANG-CHIEN、CHEN, HSIU-HO

  DOI：——

  日期：——
• BURKHARDT U.; JOHNE S., J. PRAKT. CHEM., 328,(1986) N 2, 237-244
  作者：BURKHARDT U.、 JOHNE S.

  DOI：——

  日期：——