(R)-3-(1H-indol-3-yl)-2-(4-nitrobenzenesulfonylamino)propionic acid | 140645-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-(1H-indol-3-yl)-2-(4-nitrobenzenesulfonylamino)propionic acid
• 英文别名: (2R)-3-(1H-indol-3-yl)-2-[(4-nitrophenyl)sulfonylamino]propanoic acid
• CAS: 140645-38-1
• 化学式: C₁₇H₁₅N₃O₆S
• 分子量: 389.389
• InChiKey: KJJXWLQWLLITGC-MRXNPFEDSA-N

物化性质

• 沸点：
  690.1±65.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  154
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-3-(1H-indol-3-yl)-2-(4-nitrobenzenesulfonylamino)propionic acid 在 N-羟基-7-氮杂苯并三氮唑 、 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成 (R)-2-{4-[(2-fluoropyridine-4-carbonyl)amino]benzenesulfonylamino}-3-(1H-indol-3-yl)propionic acid
  参考文献：
  名称：

  Design, Synthesis, and Initial Evaluation of a High Affinity Positron Emission Tomography Probe for Imaging Matrix Metalloproteinases 2 and 9

  摘要：

  The activity of matrix metalloproteinases (MMPs) is elevated locally under many pathological conditions. Gelatinases MMP2 and MMP9 are of particular interest because of their implication in angiogenesis, cancer cell proliferation and metastasis, and atherosclerotic plaque rupture. The aim of this study was to identify and develop a selective gelatinase inhibitor for imaging active MMP2/MMP9 in vivo. We synthesized a series of N-sulfonylamino acid derivatives with low to high nanomolar inhibitory potencies. (R)-2-(4-(4-Fluorobenzamido)phenylsulfonamido)-3-(1H-indol-3-yl)propanoic acid (7) exhibited the best in vitro binding properties: MMP2 IC50 = 1.8 nM, MMP9 IC50 = 7.2 nM. Radiolabeling of 7 with no carrier added F-18-radioisotope was accomplished starting from iodonium salts as precursors. The radiochemical yield strongly depended on the iodonium counteranion (ClO4- > Br- > TFA(-) > tosylate). F-18-7 was obtained in up to 20% radiochemical yield (decay corrected), high radiochemical purity, and >90 GBq/mu mol specific radioactivity. The radiolabeled compound showed excellent stability in vitro and in mice in vivo.

  DOI：

  10.1021/jm400156p
• 作为产物：
  描述：

  D-tryptophan hydrochloride 、 对硝基苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以52%的产率得到(R)-3-(1H-indol-3-yl)-2-(4-nitrobenzenesulfonylamino)propionic acid
  参考文献：
  名称：

  Design, Synthesis, and Initial Evaluation of a High Affinity Positron Emission Tomography Probe for Imaging Matrix Metalloproteinases 2 and 9

  摘要：

  The activity of matrix metalloproteinases (MMPs) is elevated locally under many pathological conditions. Gelatinases MMP2 and MMP9 are of particular interest because of their implication in angiogenesis, cancer cell proliferation and metastasis, and atherosclerotic plaque rupture. The aim of this study was to identify and develop a selective gelatinase inhibitor for imaging active MMP2/MMP9 in vivo. We synthesized a series of N-sulfonylamino acid derivatives with low to high nanomolar inhibitory potencies. (R)-2-(4-(4-Fluorobenzamido)phenylsulfonamido)-3-(1H-indol-3-yl)propanoic acid (7) exhibited the best in vitro binding properties: MMP2 IC50 = 1.8 nM, MMP9 IC50 = 7.2 nM. Radiolabeling of 7 with no carrier added F-18-radioisotope was accomplished starting from iodonium salts as precursors. The radiochemical yield strongly depended on the iodonium counteranion (ClO4- > Br- > TFA(-) > tosylate). F-18-7 was obtained in up to 20% radiochemical yield (decay corrected), high radiochemical purity, and >90 GBq/mu mol specific radioactivity. The radiolabeled compound showed excellent stability in vitro and in mice in vivo.

  DOI：

  10.1021/jm400156p

文献信息

• Guanidine
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0468231B1

  公开（公告）日：1994-09-21
• US5260307A
  申请人：——

  公开号：US5260307A

  公开（公告）日：1993-11-09
• US5393760A
  申请人：——

  公开号：US5393760A

  公开（公告）日：1995-02-28
• US5532232A
  申请人：——

  公开号：US5532232A

  公开（公告）日：1996-07-02
• US5583133A
  申请人：——

  公开号：US5583133A

  公开（公告）日：1996-12-10