2-nitro-1-[(4S)-5-oxo-5-piperidin-1-yl-4-[[3-(trifluoromethyl)phenyl]sulfonylamino]pentyl]guanidine | 873584-04-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-nitro-1-[(4S)-5-oxo-5-piperidin-1-yl-4-[[3-(trifluoromethyl)phenyl]sulfonylamino]pentyl]guanidine
• CAS: 873584-04-4
• 化学式: C₁₈H₂₅F₃N₆O₅S
• 分子量: 494.495
• InChiKey: MTJKHWANAVZWII-HNNXBMFYSA-N

物化性质

• 沸点：
  650.2±65.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  171
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-nitro-1-[(4S)-5-oxo-5-piperidin-1-yl-4-[[3-(trifluoromethyl)phenyl]sulfonylamino]pentyl]guanidine 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以95%的产率得到N-[(S)-4-Guanidino-1-(piperidine-1-carbonyl)-butyl]-3-trifluoromethyl-benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis and evaluation of graftable thrombin inhibitors for the preparation of blood-compatible polymer materials

  摘要：

  我们合成了 N-α-(3-三氟甲基-苯磺酰基)-L-精氨酸（1）的哌嗪基酰胺衍生物，作为可嫁接的凝血酶抑制剂。对固定在 N-4 哌嗪基位置上的可变间隔臂可能对生物活性造成的干扰进行了体外评估（针对人类 α-凝血酶）和血液凝固试验。此外，还对凝血酶抑制剂复合物进行了分子建模（硅分析）和 X 射线衍射研究。通过湿化学处理将生物活性分子固定在聚对苯二甲酸丁二醇酯（PBT）和聚对苯二甲酸乙二醇酯（PET）膜上，并通过 XPS 分析进行评估。表面接枝抑制剂 1d 可减少改性表面血凝块的形成，从而改善膜的血液相容性。

  DOI：

  10.1039/b510239a
• 作为产物：
  描述：

  tert-butyl (S,E)-(5-(2-nitroguanidino)-1-oxo-1-(piperidin-1-yl)pentan-2-yl)carbamate 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-nitro-1-[(4S)-5-oxo-5-piperidin-1-yl-4-[[3-(trifluoromethyl)phenyl]sulfonylamino]pentyl]guanidine
  参考文献：
  名称：

  Synthesis and evaluation of a small library of graftable thrombin inhibitors derived from (l)-arginine

  摘要：

  Novel piperazinyl-amide derivatives of N-alpha-(aryl-sulfonyl)-L-arginine were synthesized as graftable thrombin inhibitors, in the context of biomaterials' design. The possible disturbance of biological activity due to a variable spacer-arm fixed on the N-4 piperazinyl position and the introduction of a trifluoromethyl group as XPS (X-ray Photoelectron Spectroscopy) tag on the sulfonamide moiety were evaluated in vitro against human alpha-thrombin. All the compounds of the library were found to be active at the micromolar level, as the reference TAME (N-tosyl-L-arginine methyl ester). The blood compatibilization improvement of poly(ethylene terephthalate) (PET) membrane, coated or grafted by wet chemistry treatment with one representative inhibitor of the library, was also evaluated, showing interesting decrease in blood clot formation. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.07.010

文献信息

• Synthesis and evaluation of a small library of graftable thrombin inhibitors derived from (l)-arginine
  作者：Claudio Salvagnini、Sonia Gharbi、Thierry Boxus、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.ejmech.2006.07.010

  日期：2007.1

  Novel piperazinyl-amide derivatives of N-alpha-(aryl-sulfonyl)-L-arginine were synthesized as graftable thrombin inhibitors, in the context of biomaterials' design. The possible disturbance of biological activity due to a variable spacer-arm fixed on the N-4 piperazinyl position and the introduction of a trifluoromethyl group as XPS (X-ray Photoelectron Spectroscopy) tag on the sulfonamide moiety were evaluated in vitro against human alpha-thrombin. All the compounds of the library were found to be active at the micromolar level, as the reference TAME (N-tosyl-L-arginine methyl ester). The blood compatibilization improvement of poly(ethylene terephthalate) (PET) membrane, coated or grafted by wet chemistry treatment with one representative inhibitor of the library, was also evaluated, showing interesting decrease in blood clot formation. (c) 2006 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and evaluation of graftable thrombin inhibitors for the preparation of blood-compatible polymer materials
  作者：Claudio Salvagnini、Catherine Michaux、Julie Remiche、Johan Wouters、Paulette Charlier、Jacqueline Marchand-Brynaert

  DOI：10.1039/b510239a

  日期：——

  Piperazinyl-amide derivatives of N-α-(3-trifluoromethyl-benzenesulfonyl)-L-arginine (1) were synthesized as graftable thrombin inhibitors. The possible disturbance of biological activity due to a variable spacer-arm fixed on the N-4 piperazinyl position was evaluated in vitro, against human α-thrombin, and in blood coagulation assay. Molecular modelling (in silico analysis) and X-ray diffraction studies of thrombin-inhibitor complexes were also performed. The fixation of bioactive molecules on poly(butylene terephthalate) (PBT) and poly(ethylene terephthalate) (PET) membranes was performed by wet chemistry treatment and evaluated by XPS analysis. Surface grafting of inhibitor 1d improved the membrane hemocompatibility by reducing blood clot formation on the modified surface.

  我们合成了 N-α-(3-三氟甲基-苯磺酰基)-L-精氨酸（1）的哌嗪基酰胺衍生物，作为可嫁接的凝血酶抑制剂。对固定在 N-4 哌嗪基位置上的可变间隔臂可能对生物活性造成的干扰进行了体外评估（针对人类 α-凝血酶）和血液凝固试验。此外，还对凝血酶抑制剂复合物进行了分子建模（硅分析）和 X 射线衍射研究。通过湿化学处理将生物活性分子固定在聚对苯二甲酸丁二醇酯（PBT）和聚对苯二甲酸乙二醇酯（PET）膜上，并通过 XPS 分析进行评估。表面接枝抑制剂 1d 可减少改性表面血凝块的形成，从而改善膜的血液相容性。