6,8-dimethyl-2-thioxo-2,3-dihydroimidazo[1,5-a]-1,3,5-triazin-4(1H)-one | 70187-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6,8-dimethyl-2-thioxo-2,3-dihydroimidazo[1,5-a]-1,3,5-triazin-4(1H)-one
• 英文别名: 6,8-dimethyl-2-thioxo-2,3-dihydro-1H-imidazo[1,5-a][1,3,5]triazin-4-one；6,8-DiMe-4-O-2-S-IMT；2-Mercapto-6,8-dimethyl-3h-imidazo[1,5-a][1,3,5]triazin-4-one；6,8-dimethyl-2-sulfanylidene-1H-imidazo[1,5-a][1,3,5]triazin-4-one
• CAS: 70187-81-4
• 化学式: C₇H₈N₄OS
• 分子量: 196.233
• InChiKey: FXZJIHLOQQDJDE-UHFFFAOYSA-N

物化性质

• 熔点：
  241-242 °C (decomp)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-dimethyl-2-thioxo-2,3-dihydroimidazo[1,5-a]-1,3,5-triazin-4(1H)-one 在 水 作用下， 反应 14.0h， 以82%的产率得到(9CI)-(2,5-二甲基-1H-咪唑-4-基)-硫脲
  参考文献：
  名称：

  An Efficient Route to Novel 4,5‐Di‐ and 2,4,5‐Tri Substituted Imidazoles from Imidazo[1,5‐a]‐1,3,5‐triazine (5,8‐Diaza‐7,9‐dideazapurine) Derivatives

  摘要：

  Two new types of imidazole derivatives: N-(2-R-1-5-R-2-1H-imidazol-4-yl) thioureas 7a-g and N-(2-R-1-5-R-2-1H-imidazol-4-yl) formamides 8b,c,g were obtained in high yields by the hydrolytic degradation of 6-R-1-8-R-2-2-thioxo-2,3-dihydroimidazo[1,5-a]-1,3,5-triazin-4(1H)-ones 5a-g and 6-R-1-8-R-2-imidazo[l,5-a]-1,3,5-triazin-4(3H)-ones 6b,c,d, respectively. The tautomeric preferences of the new imidazoles were determined.

  DOI：

  10.1081/ncn-120027822
• 作为产物：
  描述：

  2-N-乙酰氨基-2-氰基丙酸乙酯 、 硫脲 、 sodium ethanolate 以6%的产率得到
  参考文献：
  名称：

  HOLTWICK J. B.; GOLANKIEWICZ B.; HOLMES B. N.; LEONARD N. J., J. ORG. CHEM., 1979, 44, NO 22, 3835-3839

  摘要：

  DOI：

文献信息

• Synthesis and antiviral activity of benzyl-substituted imidazo[1,5-a]-1,3,5-triazine (5,8-diaza-7,9-dideazapurine) derivatives
  作者：Bozenna Golankiewicz、Piot Januszczyk、Satoru Ikeda、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00018a015

  日期：1995.9

  8-(4-methylbenzyl)-2-[(4-methylbenzyl) thio]imidazo[1,5-a]-1,3,5-triazin-4-one (13) and 8-[5-(benzyloxy)pentyl]-2-[(4-methylbenzyl)thio]imidazo [1,5-a]-1,3,5-triazin-4-one (15) inhibited influenza A virus at a concentration of 4.1 and 5.3 microM, and 2-(benzylthio)-6, 8-dimethylimidazo[1,5-a]-1,3,5-triazin-4-one (16) and 6, 8-dimethyl-2-[(4-methylbenzyl)thio]imidazo[1,5-a]1,3, 5-triazin-4-one (17) inhibited respiratory

  合成了各种带有C-，O-和S-苄基和/或4-甲基苄基的咪唑并[1,5-a] -1,3,5-三嗪衍生物，并研究了它们对复制的抑制作用。正粘病毒和副粘病毒。通过氯代三甲基硅烷/ HMDS-合成了关键化合物8-R-2-thioxo-2,3-dihydroimidazo [1,5-a] -1,3,5-triazin-4（1H）-ones 3a，b，d。的环化反应-相应的6-氨基-5-（甲酰氨基）-5-R-2-巯基嘧啶-4（5H）-2a，b，d的重排（R =苄基，4-甲基苄基和5-（苄氧基） ）戊基）。将化合物3a，b进一步转化为4-硫酮5a，b和4-二甲基氨基衍生物7a，b。S-甲基，S-苄基和S-（4-甲基苄基）衍生物12-19的制备是通过处理thioxo化合物3b，d，5b，和8b在醇/碳酸钾体系中与甲基碘或适当的芳烷基溴化物一起使用。发现苄基和硫代结构单元的同时存在对于任何选择性的生物活性都
• Golankiwicz, Bozenna; Januszczyk, Piotr; Zeidler, Joanna, Journal of Chemical Research, Miniprint, 1994, # 3, p. 644 - 671
  作者：Golankiwicz, Bozenna、Januszczyk, Piotr、Zeidler, Joanna、Popenda, Mariusz、Bartoszak, Elzbieta、Kosturkiewicz, Zofia

  DOI：——

  日期：——
• GOLANKIEWICZ B.; HOLTWICK J. B.; HOLMES B. N.; DUESLER E. N.; LEONARD N. +, J. ORG. CHEM., 1979, 44, NO 10, 1740-1742
  作者：GOLANKIEWICZ B.、 HOLTWICK J. B.、 HOLMES B. N.、 DUESLER E. N.、 LEONARD N. +

  DOI：——

  日期：——
• Synthesis, spectroscopical characterization and the biological activity in vitro of new platinum(II) complexes with imidazo[1,5-a]-1,3,5-triazine derivatives and dimethylsulfoxide
  作者：Iwona Łakomska、Bożenna Golankiewicz、Joanna Wietrzyk、Marzena Pełczyńska、Anna Nasulewicz、Adam Opolski、Jerzy Sitkowski、Lech Kozerski、Edward Szłyk

  DOI：10.1016/j.ica.2004.12.033

  日期：2005.3

  A series of platinum(II) complexes with 6,8-dimethylimidazo[1,5-a]-1,3,5-triazin-4(3H)-one (6,8-DiMe-4-O-IMT) (I) and 6,8-dimethyl-2-thioxo-2,3-dihydroimidazo[1,5-a]-1,3,5-triazin-4(1H)-one (6,8-DiMe-4-O-2-S-IMT) (II) of formula trans-[PtCl2-(dmso)(6,8-DiMe-4-O-IMT)] (1a) and trans-[PtCl2(dmso)(6,8-DiMe-4-O-2-S-IMT)] (2a) have been prepared and characterized with H-1, C-13, N-15, Pt-195 NMR and IR. Significant 15N NMR upfield coordination shifts (81-96 ppm) of N(7) atom indicate this nitrogen atom as a coordination site. The multinuclear NMR and IR spectra indicate the square planar geometry with N(7) bonded heterocycles, S-bonded dimethylsulfoxide and two trans chloride anions. The platinum(II) complexes were tested for their antiproliferative activity in vitro against the cells of four human cell lines: SW707 rectal adenocarcinoma, A549 non-small cell lung carcinoma, T47D breast cancer and HCV29T bladder cancer. The activity of (1a, 2a) was lower than that of cisplatin. (c) 2005 Elsevier B.V. All rights reserved.