methyl N-(3-methylphenyl)imidothiocarbamate hydroiodide | 65069-77-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl N-(3-methylphenyl)imidothiocarbamate hydroiodide
• 英文别名: methyl N'-(3-methylphenyl)carbamimidothioate;hydroiodide
• CAS: 65069-77-4
• 化学式: C₉H₁₂N₂S*HI
• 分子量: 308.186
• InChiKey: RTOQIJGSWRUUAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl N-(3-methylphenyl)imidothiocarbamate hydroiodide 在 肼 作用下， 生成
  参考文献：
  名称：

  Kramer, C.-R.; Schelenz, Th.; Stein, J., Zeitschrift fur Physikalische Chemie (Leipzig), 1984, vol. 265, # 5, p. 849 - 864

  摘要：

  DOI：
• 作为产物：
  描述：

  间甲苯基-2-硫脲 、 碘甲烷 以 丙酮 为溶剂， 反应 2.0h， 以85%的产率得到methyl N-(3-methylphenyl)imidothiocarbamate hydroiodide
  参考文献：
  名称：

  A Versatile Synthesis of NovelN,N,N″-Trisubstituted Guanidines

  摘要：

  N,N,N″-三取代胍（大部分是N″-芳基-N-氮杂环烷羧基亚胺）通常以良好的产率通过以下步骤制备：将单取代硫脲与甲基碘在甲醇或丙酮中进行S-甲基化反应，然后将所得的甲基氨基甲亚胺硫醇氢碘酸盐与二级胺在沸腾的叔丁醇或丙酮腈中反应。

  DOI：

  10.1055/s-1988-27606

文献信息

• SAR studies of 4-pyridyl heterocyclic anilines that selectively induce autophagic cell death in von Hippel-Lindau-deficient renal cell carcinoma cells
  作者：Muriel Bonnet、Jack U. Flanagan、Denise A. Chan、Edwin W. Lai、Phuong Nguyen、Amato J. Giaccia、Michael P. Hay

  DOI：10.1016/j.bmc.2011.04.042

  日期：2011.6

  We recently identified a class of pyridyl aniline thiazoles (PAT) that displayed selective cytotoxicity for von Hippel-Lindau (VHL) deficient renal cell carcinoma (RCC) cells in vitro and in vivo. Structure-activity relationship (SAR) studies were used to develop a comparative molecular field analysis (CoMFA) model that related VHL-selective potency to the three-dimensional arrangement of chemical features of the chemotype. We now report the further molecular alignment-guided exploration of the chemotype to discover potent and selective PAT analogues. The contribution of the central thiazole ring was explored using a series of five-and six-membered ring heterocyclic replacements to vary the electronic and steric interactions in the central unit. We also explored a positive steric CoMFA contour adjacent to the pyridyl ring using Pd-catalysed cross-coupling Suzuki-Miyaura, Sonogashira and nucleophilic displacement reactions to prepare of a series of aryl-, alkynyl-, alkoxy- and alkylamino-substituted pyridines, respectively. In vitro potency and selectivity were determined using paired RCC cell lines: the VHL-null cell line RCC4 and the VHL-positive cell line RCC4-VHL. Active analogues selectively induced autophagy in RCC4 cells. We have used the new SAR data to further develop the CoMFA model, and compared this to a 2D-QSAR method. Our progress towards realising the therapeutic potential of this chemotype as a targeted cytotoxic therapy for the treatment of RCC by exploiting the absence of the VHL tumour suppressor gene is reported. (C) 2011 Elsevier Ltd. All rights reserved.
• A Versatile Synthesis of Novel<i>N</i>,<i>N</i>,<i>N</i>″-Trisubstituted Guanidines
  作者：C. R. Rasmussen、F. J. Villani, Jr.、B. E. Reynolds、J. N. Plampin、A. R. Hood、L. R. Hecker、S. O. Nortey、A. Hanslin、M. J. Costanzo、R. M. Howse, Jr.、A. J. Molinari

  DOI：10.1055/s-1988-27606

  日期：——

  N,N,N″-Trisubstituted guanidines (most of them N″-aryl-N-azacycloalkanecarboximidamides) are prepared in generally good yields by S-methylation of monosubstituted thioureas with methyl iodide in methanol or acetone and reaction of the resultant methyl carbamimidothioate hydroiodides with secondary amines in boiling tert-butyl alcohol or acetonitrile.

  N,N,N″-三取代胍（大部分是N″-芳基-N-氮杂环烷羧基亚胺）通常以良好的产率通过以下步骤制备：将单取代硫脲与甲基碘在甲醇或丙酮中进行S-甲基化反应，然后将所得的甲基氨基甲亚胺硫醇氢碘酸盐与二级胺在沸腾的叔丁醇或丙酮腈中反应。
• Kramer, C.-R.; Schelenz, Th.; Stein, J., Zeitschrift fur Physikalische Chemie (Leipzig), 1984, vol. 265, # 5, p. 849 - 864
  作者：Kramer, C.-R.、Schelenz, Th.、Stein, J.

  DOI：——

  日期：——