N²,N²-dimethyl-6-methylsulfinyl-1,3,5-triazine-2,4-diamine | 1125364-78-4

• 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: N²,N²-dimethyl-6-methylsulfinyl-1,3,5-triazine-2,4-diamine
• 英文别名: 2-N,2-N-dimethyl-6-methylsulfinyl-1,3,5-triazine-2,4-diamine
• CAS: 1125364-78-4
• 化学式: C₆H₁₁N₅OS
• 分子量: 201.252
• InChiKey: ITCFGFDFDGBUKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 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：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²,N²-dimethyl-6-methylsulfinyl-1,3,5-triazine-2,4-diamine 、 2-丙基苯胺 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以72%的产率得到N²,N²-dimethyl-N⁴-(2-propylphenyl)-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  A novel metformin derivative, HL010183, inhibits proliferation and invasion of triple-negative breast cancer cells

  摘要：

  Mounting evidence suggests that metformin (N,N-dimethylbiguanide), a widely prescribed drug for the treatment of type II diabetes, exerts an anti-tumor effect on several cancers including breast cancer. Breast cancer has been estimated as one of the most commonly diagnosed types of cancer among women. In particular, triple-negative breast cancers are associated with poor prognosis and metastatic growth. In the present study, we synthesized a novel metformin derivative 5 (HL010183) and metformin salts, 9a, 9b, and 9c (metformin gamma-aminobutyric acid (GABA) salt, metformin pregabalin salt and metformin gabapentin salt), which exerted more potent inhibitory effects on the proliferation and invasiveness of Hs578T triple-negative breast carcinoma cells than metformin. Importantly, 5 showed approximately 100-fold more potent effects compared to metformin. In a triple-negative breast cancer xenograft model, 5 showed a comparable degree of inhibitory effect on in vivo tumor growth at the 100 mg/kg dose to that of metformin at 500 mg/kg. Our results clearly demonstrate that 5 exerts a potent anti-tumor effect both in vitro and in vivo, paving the way for a strategy for treatment of triple-negative breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.015
• 作为产物：
  描述：

  N,N-二甲基-6-(甲硫基)-1,3,5-三嗪-2,4-二胺 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N²,N²-dimethyl-6-methylsulfinyl-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  [EN] 1,3,5-TRIAZINE-2,4,6-TRIAMINE COMPOUND OR PHARMACEUTICAL ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  [FR] COMPOSÉ DE 1,3,5-TRIAZINE-2,4,6-TRIAMINE OU SON SEL PHARMACEUTIQUEMENT ACCEPTABLE, ET COMPOSITION PHARMACEUTIQUE LE COMPRENANT

  摘要：

  公开号：

  WO2009028891A3