4-(N-methyl-N-[(4-carbamoylfurazan-3-yl)methyl]amino)-1-hydroxybutylidene bis(phosphonic acid) | 1226460-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 4-(N-methyl-N-[(4-carbamoylfurazan-3-yl)methyl]amino)-1-hydroxybutylidene bis(phosphonic acid)
• 英文别名: [4-[(4-Carbamoyl-1,2,5-oxadiazol-3-yl)methyl-methylamino]-1-hydroxy-1-phosphonobutyl]phosphonic acid
• CAS: 1226460-45-2
• 化学式: C₉H₁₈N₄O₉P₂
• 分子量: 388.211
• InChiKey: LYOVRYZOAILBHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  221
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N-methyl-4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid 、 4-(bromomethyl)-1,2,5-oxadiazole-3-carboxamide 在 sodium hydroxide 、 盐酸 作用下， 以 水 、 乙腈 为溶剂， 以34%的产率得到4-(N-methyl-N-[(4-carbamoylfurazan-3-yl)methyl]amino)-1-hydroxybutylidene bis(phosphonic acid)
  参考文献：
  名称：

  Synthesis and preliminary pharmacological characterisation of a new class of nitrogen-containing bisphosphonates (N-BPs)

  摘要：

  A new series of bisphosphonates bearing either the nitrogen-containing NO-donor furoxan (1,2,5-oxadiazole 2-oxide) system or the related furazan (1,2,5-oxadiazole) in lateral chain has been developed. pK(a) values and affinity for hydroxyapatite were determined for all the compounds. The products were able to inhibit osteoclastogenesis on RAW 246.7 cells at 10 mu M concentration. The most active compounds were further assayed on human PBMC cells and on rat microsomes. Unlike most nitrogen-containing bisphosphonates which target farnesyl pyrophosphate synthase, experimental and theoretical investigations suggest that the activity of our derivatives may be related to different mechanisms. The furoxan derivatives were also tested for their ability to relax rat aorta strips in view of their potential NO-dependent vasodilator properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.058