1,4-二氨基丁基膦酸 | 20820-73-9

• 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
• 中文名称: 1,4-二氨基丁基膦酸
• 英文名称: 1,4-diaminobutylphosphonic acid
• 英文别名: 1,4-Diaminobutyl-phosphorigsaeure；(1,4-Diaminobutyl)phosphonic acid
• CAS: 20820-73-9
• 化学式: C₄H₁₃N₂O₃P
• 分子量: 168.133
• InChiKey: OBJPQOZOSRAWEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-二氨基丁基膦酸 、 2-甲基-2-疏基硫酸脲 在 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 以32%的产率得到1-amino-4-guanidinobutylphosphonic acid
  参考文献：
  名称：

  Synthesis of phosphorus-containing amino acid analogs as inhibitors of nitric oxide synthase

  摘要：

  Two series of alpha-amino phosphonic and alpha-amino phosphinic analogs of arginine were prepared and tested as inhibitors of nitric oxide synthase (NOS). Two of the analogs were found to possess inhibitory activity for the neuronal isoform of NOS. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00144-8
• 作为产物：
  描述：

  4-(1,3-二氧代异吲哚啉-2-基)丁醛 在 盐酸 、 氨基甲酸苄酯 、 三氯化磷 作用下， 生成 1,4-二氨基丁基膦酸
  参考文献：
  名称：

  In search of new anticancer drugs. 13. Phosphonic and phosphinic analogs of ornithine

  摘要：

  Phosphonic (4a,b) and phosphinic (5a-d) analogues of ornithine were synthesized and evaluated for their inhibitory activity against ornithine decarboxylase and against the lymphocytic leukemia P388. The title compounds possess a low degree of inhibition against rat liver ornithine decarboxylase as compared to alpha-(difluoromethyl)ornithine. Thus, compounds 4a and 5a inhibit by 40% the ornithine decarboxylase activity at a 5 mM concentration. The other derivatives are less potent. Compounds 4a, 4b, 5b, and 5d are inactive against P388 tumor in CD2F1 mice at doses of 50 and 150 mg/kg.

  DOI：

  10.1021/jm00147a041

文献信息

• Baylis, E. Keith; Campbell, Colin D.; Dingwall, John G., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2845 - 2853
  作者：Baylis, E. Keith、Campbell, Colin D.、Dingwall, John G.

  DOI：——

  日期：——
• Synthesis and Structure–Activity Relationships of Phosphonic Arginine Mimetics as Inhibitors of the M1 and M17 Aminopeptidases from <i>Plasmodium falciparum</i>
  作者：Komagal Kannan Sivaraman、Alessandro Paiardini、Marcin Sieńczyk、Chiara Ruggeri、Christine A. Oellig、John P. Dalton、Peter J. Scammells、Marcin Drag、Sheena McGowan

  DOI：10.1021/jm4005972

  日期：2013.6.27

  The malaria parasite Plasmodium falciparum employs two metallo-aminopeptidases, PfA-M1 and PfA-M17, which are essential for parasite survival. Compounds that inhibit the activity of either enzyme represent leads for the development of new antimalarial drugs. Here we report the synthesis and structure-activity relationships of a small library of phosphonic acid arginine mimetics that probe the SI pocket of both enzymes and map the necessary interactions that would be important for a dual inhibitor.
• In search of new anticancer drugs. 13. Phosphonic and phosphinic analogs of ornithine
  作者：George Sosnovsky、Jan Lukszo、Enrico Gravela、Maria Franca Zuretti

  DOI：10.1021/jm00147a041

  日期：1985.9

  Phosphonic (4a,b) and phosphinic (5a-d) analogues of ornithine were synthesized and evaluated for their inhibitory activity against ornithine decarboxylase and against the lymphocytic leukemia P388. The title compounds possess a low degree of inhibition against rat liver ornithine decarboxylase as compared to alpha-(difluoromethyl)ornithine. Thus, compounds 4a and 5a inhibit by 40% the ornithine decarboxylase activity at a 5 mM concentration. The other derivatives are less potent. Compounds 4a, 4b, 5b, and 5d are inactive against P388 tumor in CD2F1 mice at doses of 50 and 150 mg/kg.
• Synthesis of phosphorus-containing amino acid analogs as inhibitors of nitric oxide synthase
  作者：Marlon Cowart、Elizabeth A. Kowaluk、Kathy L. Kohlhaas、Karen M. Alexander、James F. Kerwin

  DOI：10.1016/0960-894x(96)00144-8

  日期：1996.5

  Two series of alpha-amino phosphonic and alpha-amino phosphinic analogs of arginine were prepared and tested as inhibitors of nitric oxide synthase (NOS). Two of the analogs were found to possess inhibitory activity for the neuronal isoform of NOS. (C) 1996 Elsevier Science Ltd.