WG9001B | 1620164-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: WG9001B
• 英文别名: [[[5-(Diphosphonomethylamino)naphthalen-1-yl]amino]-phosphonomethyl]phosphonic acid；[[[5-(diphosphonomethylamino)naphthalen-1-yl]amino]-phosphonomethyl]phosphonic acid
• CAS: 1620164-74-0
• 化学式: C₁₂H₁₈N₂O₁₂P₄
• 分子量: 506.176
• InChiKey: CAMMZUPTZBEGGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  254
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1,5-萘二胺 在 盐酸 、 三甲基溴硅烷 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 WG9001B
  参考文献：
  名称：

  Synthesis and antiproliferative activity of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids

  摘要：

  A series of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids was synthesized in the reaction of triethylphosphite with isonitriles followed by hydrolysis or dealkylation. The in vitro anti-proliferative effect of all synthesized tetraphosphonic acids against MCF-7 breast cancer cells, J774E macrophages and HL-60 promyelocytic leukemia cells was determined. Three aromatic derivatives (5a, 5f and 5j) showed a similar or higher anti-proliferative activity than zoledronic acid. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.071

文献信息

• Biological effects of aromatic bis[aminomethylidenebis(phosphonic)] acids in osteoclast precursors in vitro
  作者：Anna Nasulewicz‐Goldeman、Waldemar Goldeman、Ewa Mrówczyńska、Joanna Wietrzyk

  DOI：10.1111/cbdd.13597

  日期：2019.10

  bone resorption by preventing osteoclast activity. Most clinically used BPs are hydroxybisphosphonates with the exception of incadronate, which belongs to the class of aminomethylidenebisphosphonic acids. The aim of this study was to evaluate the antiproliferative activity of two previously reported aminobisphosphonates (WG8185B2 and WG9001B) in combination with doxorubicin and cisplatin toward J774E

  含氮的双膦酸盐（N-BPs）通过阻止破骨细胞活性来抑制骨吸收。临床上大多数使用的BP是羟基双膦酸酯，但硬脂酸酯除外，其属于氨基亚甲基双膦酸类。这项研究的目的是评估两种先前报道的氨基双膦酸盐（WG8185B2和WG9001B）与阿霉素和顺铂联合对J774E细胞（体外破骨细胞前体模型）的抗增殖活性。WG8185B2和WG9001B BP增强了阿霉素和顺铂的细胞毒活性，尤其是在细胞抑制药前24小时使用时。研究的BPs的抗增殖作用与细胞周期进程的变化有关。WG8185B2导致S期的J774E细胞大量积聚，WG9001B导致G2 / M期的短暂停滞，随后S期的细胞百分比增加。此外，WG8185B2和WG9001B BP在破骨细胞前体中显示出增强的促凋亡活性，这通过caspase-3活性和凋亡细胞百分数的增加来体现。另外，两种化合物都影响J774E细胞的运动性。所检查的BP的确切分子作用机理尚待确定；
• Synthesis and antiproliferative activity of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids
  作者：Waldemar Goldeman、Anna Nasulewicz-Goldeman

  DOI：10.1016/j.bmcl.2014.05.071

  日期：2014.8

  A series of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids was synthesized in the reaction of triethylphosphite with isonitriles followed by hydrolysis or dealkylation. The in vitro anti-proliferative effect of all synthesized tetraphosphonic acids against MCF-7 breast cancer cells, J774E macrophages and HL-60 promyelocytic leukemia cells was determined. Three aromatic derivatives (5a, 5f and 5j) showed a similar or higher anti-proliferative activity than zoledronic acid. (C) 2014 Elsevier Ltd. All rights reserved.