6-chloro-2,4-bis-(3',4'-methylenedioxybenzylamino)-1,3,5-triazine | 1338346-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-chloro-2,4-bis-(3',4'-methylenedioxybenzylamino)-1,3,5-triazine
• 英文别名: 6-chloro-N2,N4-bis(benzo[d][1,3]dioxol-5-ylmethyl)-1,3,5-triazine-2,4-diamine
• CAS: 1338346-99-8
• 化学式: C₁₉H₁₆ClN₅O₄
• 分子量: 413.82
• InChiKey: NJUZOORUNMTACX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.65
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苄胺 、 6-chloro-2,4-bis-(3',4'-methylenedioxybenzylamino)-1,3,5-triazine 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以80%的产率得到N²,N⁴-bis(benzo[d][1,3]dioxol-5-ylmethyl)-N⁶-(3,4,5-trimethoxybenzyl)-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  Preparation of Some Novel Trisubstituted 1,3,5-Triazines and Hybrid Linker Mode 1,3,5-Triazine Derivatives and Their Biological Evaluation

  摘要：

  We report a new route to the preparation of C-3-symmetrical multivalent hybrid-type molecules having a tris-aminoethylamine (TAEA) linker group and 1,3,5-triazine recognition moieties in the molecule and we also report the results of biological evaluation of their anti-herpes simplex virus type 1 (anti-HSV-1) activity and cytotoxic activity against Vero cells. Among the tested compounds, a new mid-size C-2-symmetrical multivalent hybrid-type molecule (10aq) showed a high level of anti-HSV-1 activity (EC50 = 19.7 mu M) with low cytotoxicity (CC50 > 200 mu M) against Vero cells. A new C-S-symmetrical multivalent derivative (4ab) also showed high anti-HSV-1 activity (EC50 = 1.77 mu M) with low cytotoxicity (CC50 > 200 mu M). The hybrid-type C-2-symmetrical multivalent mid-size molecule (10aq) seems to be an interesting new lead in the search for new hybrid-type symmetrical multivalent antiviral compounds.

  DOI：

  10.3987/com-19-14052
• 作为产物：
  描述：

  三聚氯氰 、 3,4-亚甲二氧基苄胺 以 四氢呋喃 为溶剂， 反应 0.5h， 以96%的产率得到6-chloro-2,4-bis-(3',4'-methylenedioxybenzylamino)-1,3,5-triazine
  参考文献：
  名称：

  一些具有苄胺取代基的新型C3和CS对称的三取代三嗪三嗪衍生物的制备和抗病毒活性。

  摘要：

  我们报告在三嗪（TAZ）模板上构建的新的C3和CS对称分子的制备。评估了1型抗单纯疱疹病毒（抗HSV-1）和合成的TAZ衍生物对Vero细胞的细胞毒活性。结果表明，TAZ模板上苄胺基团中苯环上存在一个供电子基团，是表达这些C3型高水平抗HSV-1活性和低细胞毒性的重要结构因素TAZ衍生物。在测试的TAZ衍生物中，化合物4f和7h表现出最高的抗HSV-1活性（分别为EC50 = 0.98和1.23 µM）和对Vero细胞的低细胞毒性活性（50％细胞毒性浓度（CC50）= 292.2和> 200 µM，分别）。

  DOI：

  10.1248/cpb.c18-00274

文献信息

• Some Hybrid Linker Mode C2-Symmetrical 1,3,5-Triazine Derivatives and Their Biological Evaluation
  作者：Kunihiro Sumoto、Nobuko Mibu、Makoto Furutachi、Yusuke Inoue、Yuka Fujita、Yumemi Matsumoto、Yuki Kawano、Syoko Tomonaga、Junko Matsuyama、Kanae Yamada、Ryo Sato、Kazumi Yokomizo、Jian-Rong Zhou、Shunsuke Shimomura、Kaori Ota

  DOI：10.3987/com-19-14174

  日期：——

  unique mid-size multivalent symmetrical TAZ-related derivatives. Figure 1. Anti-HSV-1 active hybrid-type C2-symmetrrical TAZ derivative A RESULTS AND DISCUSSION For the preparation of various new target multivalent hybrid-type TAZ mid-size molecules (3), we used a conventional synthetic route consisting of stepwise coupling of intermediate TAZ derivatives (2) with various diaminoalkanes (1 → 2 → 3, see

  我们报告了一些新的 C2 对称多价杂合型分子的制备，该分子中具有亚甲基连接基团和 1,3,5-三嗪 (TAZ) 识别部分，我们还报告了其抗疱疹的生物学评价结果单纯形病毒 1 型（抗 HSV-1）活性和对 Vero 细胞的细胞毒活性。所有中等大小的 C2 对称多价杂合型分子（3a-2、3a-4、3b-2、3b-3、3b-4）均显示出相当高水平的抗 HSV-1 活性（EC50 = 7.6 ~ 95.6 μM) 对 Vero 细胞具有低水平的细胞毒性 (CC50 > 200 μM)。在测试的化合物中，杂合型 C2 对称多价分子 (3a-4) 似乎是寻找新的杂合型多价中等大小抗病毒化合物的有趣新线索。含碳水化合物的糖蛋白，具有高水平抗 HSV-1 活性的 C3 对称 TAZ 衍生物 13 的碳水化合物识别特性也促使我们研究这种新的独特的对称多价 TAZ 衍生物 A 和相关化合物，以寻找更有希望的新
• Hybrid Linker Mode C2-Symmetrical 1,3,5-Triazine Derivatives and Their Biological Evaluation
  作者：Kunihiro Sumoto、Shunsuke Shimomura、Kazumi Yokomizo、Jian-Rong Zhou、Kaori Ota、Nobuko Mibu、Makoto Furutachi

  DOI：10.3987/com-21-14549

  日期：——

  We report the preparation of some new multivalent hybrid-type C2-symmetrical molecules having a methylene linker group and 1,3,5-triazine (TAZ) moieties in the molecule and the results of biological evaluation of their anti-herpes simplex virus type 1 (anti-HSV-1) activity and cytotoxic activity against Vero cells. Some of the mid-sized C2-symmetrical multivalent hybrid-type molecules (3a) showed considerably

  我们报告了一些新的多价杂合型C 2对称分子的制备，该分子在分子中具有亚甲基连接基团和 1,3,5-三嗪 (TAZ) 部分，以及它们抗单纯疱疹病毒类型的生物学评价结果1（抗 HSV-1）活性和对 Vero 细胞的细胞毒活性。一些中等大小的C 2对称多价杂合型分子 ( 3a ) 显示出相当高水平的抗 HSV-1 活性 (EC 50 = 28.8 ~ 32.0 μ M) 和低水平的细胞毒性 (CC 50 = > 200 μ M) 对抗 Vero 细胞。在测试的混合型 TAZ 衍生物中，我们再次确认混合型C2-对称多价分子 ( 3a-4 ) 是寻找新的混合型多价中型抗病毒化合物的有趣候选者。
• Triazine-Based Vanilloid 1 Receptor Open Channel Blockers: Design, Synthesis, Evaluation, and SAR Analysis
  作者：Miquel Vidal-Mosquera、Asia Fernández-Carvajal、Alejandra Moure、Pierluigi Valente、Rosa Planells-Cases、José M. González-Ros、Jordi Bujons、Antonio Ferrer-Montiel、Angel Messeguer

  DOI：10.1021/jm200981s

  日期：2011.11.10

  The thermosensory transient receptor potential vanilloid 1 channel (TRPV1) is a polymodal receptor activated by physical and chemical stimuli. TRPV1 activity is drastically potentiated by proinflammatory agents released upon tissue damage. Given the pivotal role of TRPV1 in human pain, there is pressing need for improved TRPV1 antagonists, the development of which will require identification of new pharmacophore scaffolds. Uncompetitive antagonists acting as open-channel blockers might serve as activity-dependent blockers that preferentially modulate the activity of overactive channels, thus displaying fewer side effects than their competitive counterparts. Herein we report the design, synthesis, biological evaluation, and SAR analysis of a family of triazine-based compounds acting as TRPV1 uncompetitive antagonists. We identified the triazine 8aA as a potent, pure antagonist that inhibits TRPV1 channel activity with nanomolar efficacy and strong voltage dependency. It represents a new class of activity-dependent TRPV1 antagonists and may serve as the basis for lead optimization in the development of new analgesics.
• Some New C3- and Cs-Symmetrical Trialkylamino-substituted 1,3,5-Triazines and Their Biological Evaluation
  作者：Kunihiro Sumoto、Shunsuke Shimomura、Yusuke Inoue、Yuki Kawano、Yuka Fujita、Kanae Yamada、Yumemi Matsumoto、Kazumi Yokomizo、Jian-Rong Zhou、Kaori Ota、Nobuko Mibu、Makoto Furutachi

  DOI：10.3987/com-20-14308

  日期：——