(R)-2-[(R)-2-((R)-2-Amino-3-sulfo-propionylamino)-3-sulfo-propionylamino]-2-[3-(2-{2-[3-(5-{5-[5-(4,6-diphenyl-pyridin-2-yloxy)-1,1-dimethyl-pentyl]-tetrazol-1-yl}-pentanoylamino)-propoxy]-ethoxy}-ethoxy)-propylcarbamoyl]-ethanesulfonic acid | 867061-94-7

• 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: (R)-2-[(R)-2-((R)-2-Amino-3-sulfo-propionylamino)-3-sulfo-propionylamino]-2-[3-(2-{2-[3-(5-{5-[5-(4,6-diphenyl-pyridin-2-yloxy)-1,1-dimethyl-pentyl]-tetrazol-1-yl}-pentanoylamino)-propoxy]-ethoxy}-ethoxy)-propylcarbamoyl]-ethanesulfonic acid
• 英文别名: (2R)-2-amino-3-[[(2R)-1-[[(2R)-1-[3-[2-[2-[3-[5-[5-[6-(4,6-diphenylpyridin-2-yl)oxy-2-methylhexan-2-yl]tetrazol-1-yl]pentanoylamino]propoxy]ethoxy]ethoxy]propylamino]-1-oxo-3-sulfopropan-2-yl]amino]-1-oxo-3-sulfopropan-2-yl]amino]-3-oxopropane-1-sulfonic acid
• CAS: 867061-94-7
• 化学式: C₄₉H₇₂N₁₀O₁₇S₃
• 分子量: 1169.37
• InChiKey: JEQGLDYVEOKCMQ-LMMYJMGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  79
• 可旋转键数：
  39
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  424
• 氢给体数：
  8
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (R)-2-[(R)-2-((R)-2-Amino-3-sulfo-propionylamino)-3-sulfo-propionylamino]-2-[3-(2-{2-[3-(5-{5-[5-(4,6-diphenyl-pyridin-2-yloxy)-1,1-dimethyl-pentyl]-tetrazol-1-yl}-pentanoylamino)-propoxy]-ethoxy}-ethoxy)-propylcarbamoyl]-ethanesulfonic acid 在 三异丙基硅烷 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.42h， 生成 (2R,5R,8R,11R)-2-amino-32-(5-(6-(4,6-diphenylpyridin-2-yloxy)-2-methylhexan-2-yl)-1H-tetrazol-1-yl)-3,6,9,12,28-pentaoxo-5,8,11-tris(sulfomethyl)-17,20,23-trioxa-4,7,10,13,27-pentaazadotriacontane-1-sulfonic acid
  参考文献：
  名称：

  Synthesis of Leukotriene B4 Antagonists Labeled with In-111 or Tc-99m to Image Infectious and Inflammatory Foci

  摘要：

  In previous studies we demonstrated that lipophilic Tc-99m-labeled LTB4 antagonist 1 (RP517) accumulated in infectious foci in rabbits, but hepatobiliary clearance hampered imaging of abdominal lesions. We now report the use of cysteic acid as a pharmacokinetic modifier to improve the water solubility and renal clearance of three hydrophilic analogues of 1. Divalent LTB4 antagonist 17 (DPC11870-11) is a DTPA conjugate for radiolabeling with In-111. Monovalent LTB4 antagonists 15 (BMS57868-88) and divalent LTB4 antagonist 18 (BMS5786881) are conjugated to bifunctional chelator HYNIC for radiolabeling with Tc-99m. The three compounds labeled efficiently with In-111 or Tc-99m with high radiochemical purity and specific activities. Scintigraphic images obtained in New Zealand White rabbits having acute intramuscular E. coli infection demonstrated that all agents were able to clearly visualize the abscess, and clearance was exclusively renal. The biodistribution of the Tc-99m-labeled LTB4 antagonists was affected by the coligands used with the HYNIC chelator and by the monovalent or divalent nature of the receptor binding moiety. The best scintigraphic images were obtained with monovalent HYNIC conjugate 15 using tricine and isonicotinic acid as coligands with HYNIC for coordination with Tc-99m.

  DOI：

  10.1021/jm050383h
• 作为产物：
  描述：

  在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以1.01 g的产率得到(R)-2-[(R)-2-((R)-2-Amino-3-sulfo-propionylamino)-3-sulfo-propionylamino]-2-[3-(2-{2-[3-(5-{5-[5-(4,6-diphenyl-pyridin-2-yloxy)-1,1-dimethyl-pentyl]-tetrazol-1-yl}-pentanoylamino)-propoxy]-ethoxy}-ethoxy)-propylcarbamoyl]-ethanesulfonic acid
  参考文献：
  名称：

  Synthesis of Leukotriene B4 Antagonists Labeled with In-111 or Tc-99m to Image Infectious and Inflammatory Foci

  摘要：

  In previous studies we demonstrated that lipophilic Tc-99m-labeled LTB4 antagonist 1 (RP517) accumulated in infectious foci in rabbits, but hepatobiliary clearance hampered imaging of abdominal lesions. We now report the use of cysteic acid as a pharmacokinetic modifier to improve the water solubility and renal clearance of three hydrophilic analogues of 1. Divalent LTB4 antagonist 17 (DPC11870-11) is a DTPA conjugate for radiolabeling with In-111. Monovalent LTB4 antagonists 15 (BMS57868-88) and divalent LTB4 antagonist 18 (BMS5786881) are conjugated to bifunctional chelator HYNIC for radiolabeling with Tc-99m. The three compounds labeled efficiently with In-111 or Tc-99m with high radiochemical purity and specific activities. Scintigraphic images obtained in New Zealand White rabbits having acute intramuscular E. coli infection demonstrated that all agents were able to clearly visualize the abscess, and clearance was exclusively renal. The biodistribution of the Tc-99m-labeled LTB4 antagonists was affected by the coligands used with the HYNIC chelator and by the monovalent or divalent nature of the receptor binding moiety. The best scintigraphic images were obtained with monovalent HYNIC conjugate 15 using tricine and isonicotinic acid as coligands with HYNIC for coordination with Tc-99m.

  DOI：

  10.1021/jm050383h