(+)-N2,N5-二苯甲酰-L-鸟氨酸 | 495-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (+)-N2,N5-二苯甲酰-L-鸟氨酸
• 英文名称: di(benzoyl)-L-(+)-ornithine
• 英文别名: N,N'-di(benzoyl)ornithine；N²,N⁵-dibenzoyl-L-ornithine；N²,N⁵-Dibenzoyl-L-ornithin；L-Ornithursaeure；L-N²,N⁵-Dibenzoyl-ornithin；Dibenzoyl-L-ornithin；N(2),N(5)-dibenzoyl-L-ornithine；(2S)-2,5-dibenzamidopentanoic acid
• CAS: 495-46-5
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: NTRBNFOLBJWRAO-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-N2,N5-二苯甲酰-L-鸟氨酸 在 盐酸 作用下， 生成 N⁵-benzoyl-DL-ornithine
  参考文献：
  名称：

  Soerensen, Chemisches Zentralblatt, 1905, vol. 76, # II, p. 461

  摘要：

  DOI：
• 作为产物：
  描述：

  L-精氨酸 在 barium dihydroxide 、 sodium hydroxide 作用下， 生成 (+)-N2,N5-二苯甲酰-L-鸟氨酸
  参考文献：
  名称：

  Boon; Robson, Biochemical Journal, 1935, vol. 29, p. 2684,2688

  摘要：

  DOI：

文献信息

• Determination of Ornithine Conjugates of Some Carboxylic Acids in Birds by High-Performance Liquid Chromatography.
  作者：Kazuo IGARASHI、Ryo SUZUKI、Fumiyo KASUYA、Miyoshi FUKUI

  DOI：10.1248/cpb.40.2196

  日期：——

  A high-performance liquid chromatographic (HPLC) method for the determination of ornithine conjugation of some carboxylic acids in vitro has been developed. The ornithine conjugates of benzoic acid, p-nitrobenzoic acid, furancarboxylic acid and phenylacetic acid in an incubation mixture with kidney mitochondria were well separated on a reversed-phase C18 column using a mixture of 10 mM ammonium acetate buffer and methanol as the mobile phase. In addition, by varying the pH of the mobile phase and utilizing the absorption wavelengths (nm) of the conjugates it was possible to resolve and specifically detect each conjugate. The calibration curves were linear in the range of 0.2-16 μg/ml for all compounds and the detection limits were about 50 ng/ml except for the ornithine conjugate of phenyl acetic acid (S/N=2). The ornithine conjugatin of some carboxylic acids with chicken kidney mitochondria were determined by this assay method. The activity of ornithine conjugation of benzoic acid, furancarboxylic acid, p-nitrobenzoic acid and phenylacetic acid were 14.5, 5.5, 0.5 and 6.9 nmol/mg of protein, respectively. Moreover, the ornithine conjugation and the glycine conjugation of benzoic aicd were examined in birds and rodents. The ornithine conjugation was observed only in chicken (14.5 nmol/mg of protein) and mallard (0.99 nmol/mg of protein).

  研究人员开发了一种高效液相色谱（HPLC）方法，用于测定某些羧酸在体外的鸟氨酸共轭物。以10 mM乙酸铵缓冲液和甲醇的混合物为流动相，在C18反相色谱柱上分离了与肾线粒体培养混合液中的苯甲酸、对硝基苯甲酸、呋喃羧酸和苯乙酸的鸟氨酸共轭物。此外，通过改变流动相的 pH 值和利用共轭物的吸收波长（nm），可以分辨和特异性检测每种共轭物。除了苯乙酸的鸟氨酸共轭物（信噪比为 2）外，所有化合物的校准曲线在 0.2-16 μg/ml 范围内均呈线性，检测限约为 50 ng/ml。用这种检测方法测定了一些羧酸与鸡肾线粒体的鸟氨酸轭合物。苯甲酸、呋喃羧酸、对硝基苯甲酸和苯乙酸的鸟氨酸共轭活性分别为 14.5、5.5、0.5 和 6.9 nmol/mg（蛋白质）。此外，还研究了鸟类和啮齿动物体内苯甲酸的鸟氨酸共轭和甘氨酸共轭情况。仅在鸡肉（14.5 nmol/mg 蛋白质）和野鸭（0.99 nmol/mg 蛋白质）中观察到鸟氨酸共轭作用。
• S-2,.omega.-Diaminoalkyl dihydrogen phosphorothioates as antiradiation agents
  作者：James R. Piper、Lucy M. Rose、Thomas P. Johnston、Marie M. Grenan

  DOI：10.1021/jm00192a006

  日期：1979.6

  activity and involved the reduction of methyl 2,omega-bis(benzoylamino)alkanoates with lithium borohydride, debenzoylation-bromodehydroxylation, and reaction of the resulting 1-(bromomethyl)-1,omega-alkanediamine dihydrobromides with trisodium phosphorothioate. The products of an alternative route that involved the reduction of phthaloylated intermediates with sodium borohydride were racemic. Exploratory

  为了进一步比较放射防护硫代磷酸酯的结构活性，S-2，ω-二氨基烷基二氢硫代磷酸酯由L-2,4-二氨基丁酸，L-鸟氨酸，L-赖氨酸和DL-2,7-二氨基庚酸合成S-2，3-二氨基丙基二氢硫代磷酸酯的同系物（4），和S-2-[（ω-氨基烷基）氨基]乙基二氢硫代磷酸酯的同分异构体（例如1）。由探索性试验演变而来的优选途径保留了光学活性，并涉及用硼氢化锂还原2，ω-双（苯甲酰氨基）链烷酸甲酯，脱苯甲酰化-溴代羟基化反应以及所得的1-（溴甲基）-1，ω-链烷二胺的反应二氢溴化物与硫代磷酸三钠。涉及用硼氢化钠还原邻苯二甲酰化中间体的另一种途径的产物是外消旋的。N-（ω-烯基）邻苯二甲酰亚胺的探索性转化未能提供目标化合物的合适前体。在保护指数方面，当在全身伽马射线辐照之前对小鼠腹膜内施用时，这些同源物比母体硫代磷酸酯4具有更高的辐射防护性。衍生自L-赖氨酸的同系物也表现出良好的经口活性。在旋光活性同系物
• Polyfluorinated tripeptide thrombin inhibitors
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05391705A1

  公开（公告）日：1995-02-21

  This invention relates to novel polyfluorinated alkyl derivatives of certain tripeptides, to the methods for their preparation, the intermediates therefore, to their use in inhibiting thrombin and lung tryptase and in their end-use application as anti-coagulants useful in treating thrombophlebitis and coronary thrombosis and in the treatment of asthma.

  本发明涉及某些三肽的新型多氟烷基衍生物，其制备方法及其中间体，其在抑制凝血酶和肺内替普症方面的应用，以及其作为抗凝剂在治疗静脉炎和冠状动脉血栓形成以及治疗哮喘方面的最终应用。
• Thrombin inhibitors
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05563156A1

  公开（公告）日：1996-10-08

  This invention relates to novel polyfluorinated alkyl derivatives of certain tripeptides, to the methods for their preparation, the intermediates therefore, to their use in inhibiting thrombin and lung tryptase and in their end-use application as anti-coagulants useful in treating thrombophlebitis and coronary thrombosis and in the treatment of asthma.

  本发明涉及某些三肽的新型多氟烷基衍生物，以及它们的制备方法、中间体，以及它们在抑制凝血酶和肺组胺酶方面的用途，以及它们作为抗凝血剂在治疗静脉炎和冠状动脉血栓形成以及治疗哮喘方面的最终用途。
• Novel thrombin inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0503203A1

  公开（公告）日：1992-09-16

  This invention relates to novel polyfluorinated alkyl derivatives of certain tripeptides, to the methods for their preparation, the intermediates therefore, to their use in inhibiting thrombin and lung tryptase and in their end-use application as anti-coagulants useful in treating thrombophlebitis and coronary thrombosis and in the treatment of asthma and human immunodeficiency virus.

  本发明涉及某些三肽的新型多氟烷基衍生物、其制备方法、中间体、其在抑制凝血酶和肺胰蛋白酶方面的用途，以及其作为抗凝血剂在治疗血栓性静脉炎和冠状动脉血栓形成、治疗哮喘和人类免疫缺陷病毒方面的最终应用。