4-nitrobenzyl methylenebis(N-(4-chlorobutyl)-N-methylphosphonamidate) | 1334149-62-0

• 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: 4-nitrobenzyl methylenebis(N-(4-chlorobutyl)-N-methylphosphonamidate)
• 英文别名: Phosphonamidic acid, P,Pa(2)-methylenebis[N-(4-chlorobutyl)-N-methyl-, P,Pa(2)-bis[(4-nitrophenyl)methyl] ester；4-chloro-N-[[[4-chlorobutyl(methyl)amino]-[(4-nitrophenyl)methoxy]phosphoryl]methyl-[(4-nitrophenyl)methoxy]phosphoryl]-N-methylbutan-1-amine
• CAS: 1334149-62-0
• 化学式: C₂₅H₃₆Cl₂N₄O₈P₂
• 分子量: 653.436
• InChiKey: XGDDLHOUDZFWKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-nitrobenzyl methylenebis(N-(4-chlorobutyl)-N-methylphosphonamidate) 在 sodium dithionite 作用下， 生成
  参考文献：
  名称：

  Bisphosphonamidate Clodronate Prodrug Exhibits Potent Anticancer Activity in Non-Small-Cell Lung Cancer Cells

  摘要：

  Bisphoshonates are used clinically to treat disorders of calcium metabolism, hypercalcemia and osteoporosis, and malignant bone disease. Although these agents are commonly used in cancer patients and have potential direct anticancer effects, their use for the treatment of extraskeletal disease is limited as a result of poor cellular uptake. We have designed and synthesized bisphosphonamidate prodrugs that undergo intracellular activation to release the corresponding bisphosphonate and require only two enzymatic activation events to unmask multiple negative charges. We demonstrate efficient bisphosphonamidate activation and significant enhancement in anticancer activity of two bisphosphonamidate prodrugs in vitro compared to the parent bisphosphonate. These data suggest a novel approach to optimizing the anticancer activities of commonly used bisphosphonates.

  DOI：

  10.1021/jm200521a
• 作为产物：
  描述：

  4-氯-N-甲基丁-1-胺盐酸盐 在 4-二甲氨基吡啶 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-nitrobenzyl methylenebis(N-(4-chlorobutyl)-N-methylphosphonamidate)
  参考文献：
  名称：

  [EN] BISPHOSPHONAMIDATE PRODRUGS AND USES THEREOF
  [FR] PROMÉDICAMENTS BISPHOSPHONAMIDATE ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2011139791A3

文献信息

• BISPHOSPHONAMIDATE PRODRUGS AND USES THEREOF
  申请人：Freel Meyers Caren Laura

  公开号：US20130090311A1

  公开（公告）日：2013-04-11

  Bisphosphonamidate prodrugs of therapeutic bisphosphonate compounds and uses thereof to treat diseases are described.
• US8772268B2
  申请人：——

  公开号：US8772268B2

  公开（公告）日：2014-07-08