3-(6-aminohexyl)-5-fluoro-1H-indole oxalate | 1256348-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(6-aminohexyl)-5-fluoro-1H-indole oxalate
• 英文别名: 6-(5-fluoro-1H-indol-3-yl)hexan-1-amine;oxalic acid
• CAS: 1256348-76-1
• 化学式: C₂H₂O₄*C₁₄H₁₉FN₂
• 分子量: 324.352
• InChiKey: UEGKOGZLNUGOCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(6-azidohexyl)-5-fluoro-1H-indole 、 草酸 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 、 乙醚 为溶剂， 以20%的产率得到3-(6-aminohexyl)-5-fluoro-1H-indole oxalate
  参考文献：
  名称：

  3-ALKYL-5-FLUOROINDOLE DERIVATIVES AS MYELOPEROXIDASE INHIBITORS

  摘要：

  该发明涉及一个化合物，其化学式为（Ia），其中n为2到10之间的整数，R1和R2分别代表从氢、C1-C10烷基、C3-C10环烷基和氨基烷基组成的基团，或者R1和R2与它们所连接的氮原子一起形成一个由四到十个成员的杂环，R5在每个n个单位中独立地代表从氢、C1-C10烷基、卤素、烷氧基、氨基烷基和烷基氨基组成的基团；或其药学上可接受的盐，但排除5-氟色胺，用于治疗或预防神经炎性疾病或紊乱。该发明还涉及一种制药组合物，一种抑制髓过氧化物酶酶活性的方法，以及一种抑制低密度脂蛋白氧化的方法。

  公开号：

  US20120122948A1

文献信息

• Structure-Based Design, Synthesis, and Pharmacological Evaluation of 3-(Aminoalkyl)-5-fluoroindoles as Myeloperoxidase Inhibitors
  作者：Jalal Soubhye、Martine Prévost、Pierre Van Antwerpen、Karim Zouaoui Boudjeltia、Alexandre Rousseau、Paul G. Furtmüller、Christian Obinger、Michel Vanhaeverbeek、Jean Ducobu、Jean Nève、Michel Gelbcke、Franc¸ois Dufrasne

  DOI：10.1021/jm1009988

  日期：2010.12.23

  Oxidized low-density lipoproteins (LDLs) accumulate in the vascular wall and promote local inflammation, which contributes to the progression of the atheromatous plaque. The key role of myeloperoxidase (MPO) in this process is related to its ability to modify APO B-100 in the intima and at the surface of endothelial cells. A series of 3-(aminoalkyl)-5-fluoroindole analogues was designed and synthesized by exploiting the structure-based docking of 5-fluorotryptamine, a known MPO inhibitor. In vitro assays were used to study the effects of these compounds on the inhibition of MPO-mediated taurine chlorination and oxidation of LDLs. The kinetics of the interaction between the MPO redox intermediates, Compounds I and II, and these inhibitors was also investigated. The most potent molecules possessed a 4- or 5-carbon aminoalkyl side chain and no substituent on the amino group. The mode of binding of these analogues and the mechanism of inhibition is discussed with respect to the structure of MPO and its halogenation and peroxidase cycles.
• 3-ALKYL-5-FLUOROINDOLE DERIVATIVES AS MYELOPEROXIDASE INHIBITORS
  申请人：Soubhye Jalal

  公开号：US20120122948A1

  公开（公告）日：2012-05-17

  The invention relates to a compound of formula (Ia) wherein n is an integer between 2 and 10, R 1 and R 2 independently represent a substituent selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl and aminoalkyl, or R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form a four to ten-membered heterocycle, R 5 represents independently in each of the n units a substituent selected from the group consisting of hydrogen, C 1 -C 10 alkyl, halogen, alkoxy, aminoalkyl and alkylamino; or a pharmaceutically acceptable salt thereof, with the proviso that the 5-fluorotryptamine is excluded, for the treatment or the prophylaxis of neuroinflammatory diseases or disorders. The invention also relates to a pharmaceutical composition, a method for inhibiting myeloperoxidase enzyme activity, to a method for inhibiting Low density lipoproteins oxidation.

  该发明涉及一个化合物，其化学式为（Ia），其中n为2到10之间的整数，R1和R2分别代表从氢、C1-C10烷基、C3-C10环烷基和氨基烷基组成的基团，或者R1和R2与它们所连接的氮原子一起形成一个由四到十个成员的杂环，R5在每个n个单位中独立地代表从氢、C1-C10烷基、卤素、烷氧基、氨基烷基和烷基氨基组成的基团；或其药学上可接受的盐，但排除5-氟色胺，用于治疗或预防神经炎性疾病或紊乱。该发明还涉及一种制药组合物，一种抑制髓过氧化物酶酶活性的方法，以及一种抑制低密度脂蛋白氧化的方法。