6-(氯甲基)-N,N-二甲基-1,3,5-三嗪-2,4-二胺 | 21320-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 中文名称: 6-(氯甲基)-N,N-二甲基-1,3,5-三嗪-2,4-二胺
• 中文别名: [4-氨基-6-(氯甲基)-S-三嗪-2-基]-二甲基-胺
• 英文名称: 2-amino-4-dimethylamino-6-chloromethyl-1,3,5-triazine
• 英文别名: 4-amino-6-dimethylamino-2-chloromethyl[1,3,5]triazine；2-Amino-4-dimethylamino-6-chlormethyl-symm.-triazin；2-Amino-6-chlormethyl-4-dimethylamino-s-triazin；6-chloromethyl-N,N-dimethyl-[1,3,5]triazine-2,4-diamine；6-(chloromethyl)-N,N-dimethyl-1,3,5-triazine-2,4-diamine；6-(chloromethyl)-2-N,2-N-dimethyl-1,3,5-triazine-2,4-diamine
• CAS: 21320-37-6
• 化学式: C₆H₁₀ClN₅
• mdl: MFCD00463462
• 分子量: 187.632
• InChiKey: WMWUQLMRNQGYEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933699090

反应信息

• 作为反应物：
  描述：

  1-[1-diethylamino-1-phenylmeth-(Z)-ylidene]-3-(furan-2-carbonyl)thiourea 、 6-(氯甲基)-N,N-二甲基-1,3,5-三嗪-2,4-二胺 以 甲醇 为溶剂， 反应 24.0h， 以54%的产率得到N-(5-(4-amino-6-(dimethylamino)-1,3,5-triazin-2-yl)-4-phenylthiazol-2-yl)furan-2-carboxamide
  参考文献：
  名称：

  New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides

  摘要：

  A series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamide and furamide analogues were investigated in radioligand binding studies at adenosine receptor subtypes with an aim to obtain potent and selective adenosine receptor ligands. Benzamide and furamide linked to thiazole was found to be crucial for high adenosine receptor affinity. The most potent compound indentified in this study was 5d with low nanomolar affinity for all four adenosine receptor subtypes. Compounds 5a and 5g showed moderate selectivity for A(2A) adenosine receptors. Molecular docking versus all four human adenosine receptors combined with membrane molecular dynamics studies were performed to rationalise the peculiar selectivity profile of 5d antagonist. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.020
• 作为产物：
  描述：

  盐酸二甲双胍 、 氯乙酸甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 33.0h， 以60%的产率得到6-(氯甲基)-N,N-二甲基-1,3,5-三嗪-2,4-二胺
  参考文献：
  名称：

  新型2,4-二氨基-1,3,5-三嗪衍生物的合成，结构表征和抗肿瘤活性。

  摘要：

  描述了合成，基于NMR的结构解析和8的X射线分析以及新型2,4-二氨基-1,3,5-三嗪衍生物5和7-22的抗肿瘤活性。在NCI上进行的筛选显示，大多数衍生物在0.148-56.2 microM浓度的各种肿瘤细胞系上具有中等至强的生长抑制活性。2-Amino-6-bromomethyl-4-（3,5,5-trimethyl-2-pyrazoline）-1,3,5-triazine 11显示出最有效的抗肿瘤活性，其平均中点值为log（10）GI50，所有测试的log（10）TGI50和log（10）LC50分别等于-5.26，-4.81和-4.37，因此，可以将其视为抗癌剂进一步开发的先导结构。

  DOI：

  10.1016/s0223-5234(00)01194-6

文献信息

• An efficient one-pot synthesis of functionally diverse 2-aminothiazoles from isothiocyanates, amidines/guanidines and halomethylenes
  作者：Hitesh B. Jalani、Amit N. Pandya、Dhaivat H. Pandya、Jayesh A. Sharma、V. Sudarsanam、Kamala K. Vasu

  DOI：10.1016/j.tetlet.2013.07.122

  日期：2013.9

  efficient one-pot method for the synthesis of 2-aminothiazoles using simple starting materials like isothiocyanates, amidines/guanidines and various halomethylenes is reported. The synthesis of 2-aminothiazoles involves reactions such as nucleophilic addition, S-alkylation and intramolecular nucleophilic substitution in which amines departs as the leaving group.

  报道了一种有效的一锅法，该方法使用诸如异硫氰酸酯，am /胍和各种卤代亚甲基之类的简单原料来合成2-氨基噻唑。2-氨基噻唑的合成涉及诸如亲核加成，S-烷基化和分子内亲核取代的反应，其中胺作为离去基团离开。
• Carbonic anhydrase inhibitors. Regioselective synthesis of novel series 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2012.08.006

  日期：2012.10

  A series of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides 4-6, 9-17 and 21-31 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and cancer-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed K(I)s in the range of 224-4830 nM, whereas toward hCA II, K(I)s = 318-873 nM. Isozyme hCA IX was inhibited with K(I)s = 11.8-93.4 nM, and hCA XII with 23.5 -82.3 nM. Compounds 12-14, 27 and 29-31 have an activity against hCA I (K(I)s = 224-889 nM) which is comparable to the clinically used sulfonamide DCP (K(I)s = 1200 nM). Several of new compounds, including 9, 10, 21, 24, 26-28 and 30 have an activity against hCA IX (K(I)s = 11.8-38.6 nM) which is comparable or more effective than the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). Compounds 9, 10, 13, 21-23, 26 and 27 were also very effective hCA XII inhibitors, with inhibition constants ranged from 23.5 to 47.2 nM comparable or more effective than sulfonamides EZA (K(I)s = 22 nM) or DCP (K(I)s = 50 nM), respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• ——
  作者：V. I. Kelarev、M. A. Silin、O. A. Borisova

  DOI：10.1023/a:1025102300933

  日期：——
• Synthetic antibacterials. I. Nitrofurylvinyl-s-triazine derivatives
  作者：Sadao Nishigaki、Fumio Yoneda、Hideko Matsumoto、Keiko Morinaga

  DOI：10.1021/jm00301a010

  日期：1969.1
• Synthesis, structural characterization and antitumor activity of novel 2,4-diamino-1,3,5-triazine derivatives
  作者：Z. Brzozowski、F. Sączewski、M. Gdaniec

  DOI：10.1016/s0223-5234(00)01194-6

  日期：2000.12

  The syntheses, structural elucidation based on NMR spectroscopy and X-ray analysis of 8 as well as antitumor activities of novel 2,4-diamino-1,3,5-triazine derivatives 5 and 7-22 are described. Screenings performed at NCI showed that most derivatives possessed a moderate to strong growth inhibition activity on various tumor panel cell lines between 0.148 and 56.2 microM concentrations. 2-Amino-6-bromomethyl-4-(3

  描述了合成，基于NMR的结构解析和8的X射线分析以及新型2,4-二氨基-1,3,5-三嗪衍生物5和7-22的抗肿瘤活性。在NCI上进行的筛选显示，大多数衍生物在0.148-56.2 microM浓度的各种肿瘤细胞系上具有中等至强的生长抑制活性。2-Amino-6-bromomethyl-4-（3,5,5-trimethyl-2-pyrazoline）-1,3,5-triazine 11显示出最有效的抗肿瘤活性，其平均中点值为log（10）GI50，所有测试的log（10）TGI50和log（10）LC50分别等于-5.26，-4.81和-4.37，因此，可以将其视为抗癌剂进一步开发的先导结构。