N-[imino(pyrrolidin-1-yl)methyl]guanidine hydrochloride | 10162-76-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[imino(pyrrolidin-1-yl)methyl]guanidine hydrochloride
• 英文别名: pyrrolidinylbiguanide hydrochloride；N1-pyrrolidine biguanide hydrochloride；(pyrrolidine-1-carboximidoyl)-guanidine; hydrochloride；(Pyrrolidin-1-carbimidoyl)-guanidin; Hydrochlorid；N-(diaminomethylidene)pyrrolidine-1-carboximidamide;hydron;chloride
• CAS: 10162-76-2
• 化学式: C₆H₁₃N₅*ClH
• 分子量: 191.664
• InChiKey: KUJPSSUYOPFZNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.5
• 氢给体数：
  4
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-[imino(pyrrolidin-1-yl)methyl]guanidine hydrochloride 在 sodium ethanolate 、 sodium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-amino-N-phenyl-6-(pyrrolidin-1-yl)-1,3,5-triazine-2-carboxamide
  参考文献：
  名称：

  Synthesis, structure and anticancer activity of novel 2,4-diamino-1,3,5-triazine derivatives

  摘要：

  A series of 2-(4,6-diamino-1,3,5-triazin-2-yl)-2-{[4-(dimethylamino)-phenyl]imino}acetonitriles 19-27 have been synthesized by the reaction of 2-(4-amino-6-alkylamino-1,3,5-triazin-2-yl)acetonitriles 10-15 with p-nitrosodimethylaniline. Unexpectedly, a similar reaction of acetonitriles 10, 14, 15, 17 and 18 with nitrosobenzene led to the formation of 4,6-diamino-N-phenyl-1,3,5-triazine-2-carboxamides 28-32. The in vitro antitumor activity of the compounds obtained has been tested and 2-[4-Amino-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-yl]-2{[4-(dimethylamino)phenyl]imino}acetonitrile (19) having remarkable activity against melanoma MALME-3 M cell line (GI(50) = 3.3 x 10(-8) M, TGI = 1.1 x 10(-6) M) is a leading candidate for further development. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.013

文献信息

• 三取代均三嗪类化合物及其制备方法
  申请人：浙江大学

  公开号：CN105384702B

  公开（公告）日：2018-04-10

  本发明提供一种三取代均三嗪类化合物，将双胍类化合物的盐酸盐与1,1‑二溴乙烯类化合物混合加入有机溶剂中，在金属铜的催化下，在配体和碱的存在下，在60～130℃温度下搅拌反应2～25小时，经处理制得目标化合物。本发明的开发了结构新颖的三取代均三嗪类化合物的制备方法，该工艺反应条件温和，操作方便，成本低，有着广泛的工业应用前景。本发明所提供的三取代均三嗪类化合物显示一定的抗乳腺癌活性，为新药筛选及开发奠定了基础，具有较好的实用价值。结构通式如下。
• Ruthenium-catalyzed synthesis of tri-substituted 1,3,5-triazines from alcohols and biguanides
  作者：Ming Zeng、Tao Wang、Dong-Mei Cui、Chen Zhang

  DOI：10.1039/c6nj01620k

  日期：——

  An efficient ruthenium-catalyzed synthesis of tri-substituted 1,3,5-triazines from alcohols and biguanides under mild conditions has been developed. The reaction occurred in moderate to good yields and tolerated benzyl alcohol containing functionalities such as halogens. Monosubstituted to tetrasubstituted biguanidines also afforded the desired products.

  已经开发了在温和条件下由醇和双胍有效钌催化合成三取代1,3,5-三嗪的方法。该反应以中等至良好的收率和容许的含苄醇的官能团如卤素发生。单取代至四取代的双胍也提供了所需的产物。
• Synthesis, structure and anticancer activity of novel 2,4-diamino-1,3,5-triazine derivatives
  作者：F. Sączewski、A. Bułakowska、P. Bednarski、R. Grunert

  DOI：10.1016/j.ejmech.2005.10.013

  日期：2006.2

  A series of 2-(4,6-diamino-1,3,5-triazin-2-yl)-2-[4-(dimethylamino)-phenyl]imino}acetonitriles 19-27 have been synthesized by the reaction of 2-(4-amino-6-alkylamino-1,3,5-triazin-2-yl)acetonitriles 10-15 with p-nitrosodimethylaniline. Unexpectedly, a similar reaction of acetonitriles 10, 14, 15, 17 and 18 with nitrosobenzene led to the formation of 4,6-diamino-N-phenyl-1,3,5-triazine-2-carboxamides 28-32. The in vitro antitumor activity of the compounds obtained has been tested and 2-[4-Amino-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-yl]-2[4-(dimethylamino)phenyl]imino}acetonitrile (19) having remarkable activity against melanoma MALME-3 M cell line (GI(50) = 3.3 x 10(-8) M, TGI = 1.1 x 10(-6) M) is a leading candidate for further development. (c) 2005 Elsevier SAS. All rights reserved.