2-[4-amino-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazol-1-yl)-1,3,5-triazin-2-yl]acetonitrile | 501331-91-5

• 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: 2-[4-amino-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazol-1-yl)-1,3,5-triazin-2-yl]acetonitrile
• 英文别名: 2-[4-amino-6-(3,5,5-trimethyl-4H-pyrazol-1-yl)-1,3,5-triazin-2-yl]acetonitrile
• CAS: 501331-91-5
• 化学式: C₁₁H₁₅N₇
• 分子量: 245.287
• InChiKey: DKIGVDDXYMFRIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  236-237 °C(Solv: 1-butanol (71-36-3))
• 沸点：
  497.0±47.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[4-amino-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazol-1-yl)-1,3,5-triazin-2-yl]acetonitrile 在 氢氧化钾 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以67%的产率得到2-[4-amino-6-(3,5,5-trimethyl-4,5-dihydro-pyrazol-1-yl)-[1,3,5]triazin-2-yl]-N-hydroxy-acetamidine
  参考文献：
  名称：

  Synthesis and antitumor activity of novel 2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazine derivatives

  摘要：

  The syntheses and antitumor activities of novel 2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazine derivatives 4-38 are described. All the compounds prepared were screened at the National Cancer Institute (NCI) for their activities against a panel of 60 tumor cell lines and relationships between structure and antitumor activity in vitro are discussed. The triazines 11, 16, 20, 23, 23 and 34-38 exhibited modest or fairly high activity against one or more human tumor cell lines. Prominent compound with remarkable activity (log G150, < - 8.00- -5.00) to all investigated cell lines and highly potent (log G150. < - 8.00- -7.64) against some cell lines of Leukemia (CCRF-CEM, K-562, RPMI-8226, SR), CNS Cancer (SF-539) and Breast Cancer (T-47D) was 2-[2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazin-6-yl]-3-(5-nitro-2-thienyl)acrylonitrile (25). (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01379-x
• 作为产物：
  描述：

  3,5,5-trimethyl-4,5-dihydro-1H-pyrazole; hydrochloride 在 sodium ethanolate 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 10.0h， 生成 2-[4-amino-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazol-1-yl)-1,3,5-triazin-2-yl]acetonitrile
  参考文献：
  名称：

  Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties

  摘要：

  一系列2-亚氨基-2H-香豆-3-基-1,3,5-三嗪化合物5–12被合成，这些化合物是2,4-二氨基-1,3,5-三嗪和2-亚氨基香豆素的杂合物。合成方法是将2-(4,6-二氨基-1,3,5-三嗪-2-基)乙腈1–4与2-羟基苯甲醛反应。随后，在水相DMF中加热，化合物2-亚氨基-2H-香豆-3-基-1,3,5-三嗪10和12转化为相应的2H-香豆-3-基-1,3,5-三嗪13和14，这基本上是2,4-二氨基-1,3,5-三嗪和香豆素的杂合物。新合成化合物的体外抗癌活性在五种人类癌细胞系（DAN-G，A-427，LCLC-103H，SISO和RT-4）中进行了评估。显示出最大细胞毒性活性的化合物为4-[7-(二乙氨基)-2-亚氨基-2H-香豆-3-基]-6-(4-苯基哌嗪-1-基)-1,3,5-三嗪-2-胺（11，IC50范围为1.51–2.60 μM）。

  DOI：

  10.3390/molecules23071616

文献信息

• 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.
• Methods for the Identification and Use of Compounds Suitable for the Treatment of Drug Resistant Cancer Cells
  申请人：Szakacs Gergely

  公开号：US20080214606A1

  公开（公告）日：2008-09-04

  The present invention relates to novel methods for the identification of compounds useful for the treatment of drug resistance, and to novel treatment methods using the identified compounds.
• Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties
  作者：Anna Makowska、Franciszek Sączewski、Patrick Bednarski、Jarosław Sączewski、Łukasz Balewski

  DOI：10.3390/molecules23071616

  日期：——

  A series of 2-imino-2H-chromen-3-yl-1,3,5-triazine compounds 5–12, which are namely hybrids of 2,4-diamino-1,3,5-triazines and 2-imino-coumarins, was synthesized by reacting 2-(4,6-diamine-1,3,5-triazin-2-yl)acetonitriles 1–4 with 2-hydroxybenzaldehydes. After this, upon heating in aqueous DMF, 2-imino-2H-chromen-3-yl-1,3,5-triazines 10 and 12 were converted into the corresponding 2H-chromen-3-yl-1,3,5-triazines 13 and 14, which are essentially hybrids of 2,4-diamino-1,3,5-triazines and coumarins. The in vitro anticancer activity of the newly prepared compounds was evaluated against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO and RT-4. The greatest cytotoxic activity displayed 4-[7-(diethylamino)-2-imino-2H-chromen-3-yl]-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-amine (11, IC50 in the range of 1.51–2.60 μM).

  一系列2-亚氨基-2H-香豆-3-基-1,3,5-三嗪化合物5–12被合成，这些化合物是2,4-二氨基-1,3,5-三嗪和2-亚氨基香豆素的杂合物。合成方法是将2-(4,6-二氨基-1,3,5-三嗪-2-基)乙腈1–4与2-羟基苯甲醛反应。随后，在水相DMF中加热，化合物2-亚氨基-2H-香豆-3-基-1,3,5-三嗪10和12转化为相应的2H-香豆-3-基-1,3,5-三嗪13和14，这基本上是2,4-二氨基-1,3,5-三嗪和香豆素的杂合物。新合成化合物的体外抗癌活性在五种人类癌细胞系（DAN-G，A-427，LCLC-103H，SISO和RT-4）中进行了评估。显示出最大细胞毒性活性的化合物为4-[7-(二乙氨基)-2-亚氨基-2H-香豆-3-基]-6-(4-苯基哌嗪-1-基)-1,3,5-三嗪-2-胺（11，IC50范围为1.51–2.60 μM）。
• Synthesis and antitumor activity of novel 2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazine derivatives
  作者：Z Brzozowski、F Sączewski

  DOI：10.1016/s0223-5234(02)01379-x

  日期：2002.9

  The syntheses and antitumor activities of novel 2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazine derivatives 4-38 are described. All the compounds prepared were screened at the National Cancer Institute (NCI) for their activities against a panel of 60 tumor cell lines and relationships between structure and antitumor activity in vitro are discussed. The triazines 11, 16, 20, 23, 23 and 34-38 exhibited modest or fairly high activity against one or more human tumor cell lines. Prominent compound with remarkable activity (log G150, < - 8.00- -5.00) to all investigated cell lines and highly potent (log G150. < - 8.00- -7.64) against some cell lines of Leukemia (CCRF-CEM, K-562, RPMI-8226, SR), CNS Cancer (SF-539) and Breast Cancer (T-47D) was 2-[2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazin-6-yl]-3-(5-nitro-2-thienyl)acrylonitrile (25). (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.