N²,N²-Dimethyl-N⁴-(2-propylphenyl)-1,3,5-triazine-2,4,6-triamine HCl | 1429218-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N²,N²-Dimethyl-N⁴-(2-propylphenyl)-1,3,5-triazine-2,4,6-triamine HCl
• 英文别名: N2,N2-dimethyl-N4-(2-propylphenyl)-1,3,5-triazine-2,4,6-triamine hydrochloride；2-N,2-N-dimethyl-4-N-(2-propylphenyl)-1,3,5-triazine-2,4,6-triamine;hydrochloride
• CAS: 1429218-03-0
• 化学式: C₁₄H₂₀N₆*ClH
• 分子量: 308.814
• InChiKey: MNINIMANAGCJFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N²,N²-dimethyl-N⁴-(2-propylphenyl)-1,3,5-triazine-2,4,6-triamine 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以95%的产率得到N²,N²-Dimethyl-N⁴-(2-propylphenyl)-1,3,5-triazine-2,4,6-triamine HCl
  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

文献信息

• A novel metformin derivative, HL010183, inhibits proliferation and invasion of triple-negative breast cancer cells
  作者：Minsoo Koh、Jong-Cheol Lee、Changhee Min、Aree Moon

  DOI：10.1016/j.bmc.2013.02.015

  日期：2013.4

  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.