(12-{4-[(S)-2-amino-5-(N'-nitroguanidino)-pentanoyl]-piperazin-1-yl}-12-oxo-dodecyl)-carbamic acid 4-nitro-benzyl ester trifluoroacetate

• 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: (12-{4-[(S)-2-amino-5-(N'-nitroguanidino)-pentanoyl]-piperazin-1-yl}-12-oxo-dodecyl)-carbamic acid 4-nitro-benzyl ester trifluoroacetate
• 英文别名: (4-nitrophenyl)methyl N-[12-[4-[(2S)-2-amino-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoyl]piperazin-1-yl]-12-oxododecyl]carbamate;2,2,2-trifluoroacetic acid
• 化学式: C₂HF₃O₂*C₃₀H₄₉N₉O₈
• 分子量: 777.799
• InChiKey: IACCAJUDOBXRCZ-SNYZSRNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  284
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (12-{4-[(S)-2-amino-5-(N'-nitroguanidino)-pentanoyl]-piperazin-1-yl}-12-oxo-dodecyl)-carbamic acid 4-nitro-benzyl ester trifluoroacetate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 N-{(S)-1-[4-(12-Amino-dodecanoyl)-piperazine-1-carbonyl]-4-guanidino-butyl}-3-methyl-benzenesulfonamide; compound with acetic acid
  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
• 作为产物：
  描述：

  (12-{4-[(S)-2-tert-butoxycarbonylamino-5-(N'-nitroguanidino)-pentanoyl]-piperazin-1-yl}-12-oxo-dodecyl)-carbamic acid 4-nitro-benzyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到(12-{4-[(S)-2-amino-5-(N'-nitroguanidino)-pentanoyl]-piperazin-1-yl}-12-oxo-dodecyl)-carbamic acid 4-nitro-benzyl ester trifluoroacetate
  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