N-(4-methylphenyl)aminoethylidenebisphosphonic acid

• 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: N-(4-methylphenyl)aminoethylidenebisphosphonic acid
• 英文别名: [2-(4-Methylanilino)-1-phosphonoethyl]phosphonic acid
• 化学式: C₉H₁₅NO₆P₂
• 分子量: 295.169
• InChiKey: HHHYSJINAKBFKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tetraethyl 2-(p-tolylamino)ethane-1,1-diyldiphosphonate 在 三甲基溴硅烷 作用下， 以 乙腈 为溶剂， 生成 N-(4-methylphenyl)aminoethylidenebisphosphonic acid
  参考文献：
  名称：

  Bisphosphonic acids as effective inhibitors ofMycobacterium tuberculosisglutamine synthetase

  摘要：

  Inhibition of glutamine synthetase (GS) is one of the most promising strategies for the discovery of novel drugs against tuberculosis. Forty-three bisphosphonic and bis-H-phosphinic acids of various scaffolds, bearing aromatic substituents, were screened against recombinant GS from Mycobacterium tuberculosis. Most of the studied compounds exhibited activities in micromolar range, with N-(3,5-dichlorophenyl)-2-aminoethylidenebisphoshonic acid, N-(3,5difluorophenyl)-2-aminoethylidene-bisphoshonic acid and N-(3,4-dichlorophenyl)-1-hydroxy1,1-ethanebisphosphonic acid showing the highest potency with kinetic parameters similar to the reference compound - L-methionine-S-sulfoximine. Moreover, these inhibitors were found to be much more effective against pathogen enzyme than against the human ortholog. Thus, with the bone-targeting properties of the bisphosphonate compounds in mind, this activity/selectivity profile makes these compounds attractive agents for the treatment of bone tuberculosis.

  DOI：

  10.3109/14756366.2015.1070846

文献信息

• ALFEREV I. S.; KOTLYAREVSKIJ I. L.; MIXALIN N. V.; NOVIKOVA V. M., IZV. AN CCCP CEP. XIM., 1980 HO 5, 1211-1212
  作者：ALFEREV I. S.、 KOTLYAREVSKIJ I. L.、 MIXALIN N. V.、 NOVIKOVA V. M.

  DOI：——

  日期：——
• Pharmaceutically active compounds and methods of use thereof
  申请人：Jiao Jin-An

  公开号：US20070155703A1

  公开（公告）日：2007-07-05

  The invention includes pharmaceutically active compounds and methods of treatment and pharmaceutical compositions that utilize or comprise one or more such compounds. Compounds of the invention are particularly useful for treatment or prophylaxis of undesired thrombosis.
• US6828312B2
  申请人：——

  公开号：US6828312B2

  公开（公告）日：2004-12-07
• US7199113B2
  申请人：——

  公开号：US7199113B2

  公开（公告）日：2007-04-03