4-hydroxy-6-iodo-8-methyl-2-oxo-1H-quinoline-3-carboxylic acid | 908006-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-hydroxy-6-iodo-8-methyl-2-oxo-1H-quinoline-3-carboxylic acid
• CAS: 908006-04-2
• 化学式: C₁₁H₈INO₄
• 分子量: 345.093
• InChiKey: HGDVEGOTEYVKNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-iodo-8-methyl-2-oxo-1H-quinoline-3-carboxylic acid 在 三氯氧磷 作用下， 生成
  参考文献：
  名称：

  Addressing species specific metabolism and solubility issues in a quinoline series of oral PDE4 inhibitors

  摘要：

  Species specific conversion of the lead PDE4 inhibitor 1 to the quinolone 3 was identified as the major route of metabolism in the cynomolgus monkey. Modification of the template to give the cinnoline 9 retained potency and selectivity, and greatly improved the pharmacokinetic pro. le in the cynomolgus monkey compared with 1. Additional SAR studies aimed at improving the solubility of 9 are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.010
• 作为产物：
  描述：

  C₁₅H₁₆INO₄ 在 三氟乙酸 作用下， 以70%的产率得到4-hydroxy-6-iodo-8-methyl-2-oxo-1H-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Addressing species specific metabolism and solubility issues in a quinoline series of oral PDE4 inhibitors

  摘要：

  Species specific conversion of the lead PDE4 inhibitor 1 to the quinolone 3 was identified as the major route of metabolism in the cynomolgus monkey. Modification of the template to give the cinnoline 9 retained potency and selectivity, and greatly improved the pharmacokinetic pro. le in the cynomolgus monkey compared with 1. Additional SAR studies aimed at improving the solubility of 9 are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.010

文献信息

• QUINOLONE BASED COMPOUNDS EXHIBITING PROLYL HYDROXYLASE INHIBITORY ACTIVITY, AND COMPOSITIONS, AND USES THEREOF
  申请人：Amgen, Inc.

  公开号：EP1960363A2

  公开（公告）日：2008-08-27
• [EN] 2-QUINOLONE COMPOUNDS AS INHIBITORS OF PHOSPHODIESTERASES<br/>[FR] COMPOSÉS DE 2-QUINOLONE COMME INHIBITEURS DES PHOSPHODIESTÉRASES
  申请人：GLAXO GROUP LTD

  公开号：WO2006089689A1

  公开（公告）日：2006-08-31

  [EN] There is provided according to the invention novel compounds of formula (I) or pharmaceutically acceptable solvates thereof.
  [FR] La présente invention concerne de nouveaux composés de la formule (I) ou des solvates pharmaceutiquement acceptables de ceux-ci.
• [EN] QUINOLONE BASED COMPOUNDS EXHIBITING PROLYL HYDROXYLASE INHIBITORY ACTIVITY, AND COMPOSITIONS, AND USES THEREOF<br/>[FR] COMPOSES A BASE DE QUINOLONE PRESENTANT UNE ACTIVITE INHIBITRICE DE PROLYLE HYDROXYLASE, ET LEURS COMPOSITIONS ET UTILISATIONS
  申请人：AMGEN INC

  公开号：WO2007070359A2

  公开（公告）日：2007-06-21

  [EN] This invention relates to new quinolone based compounds that exhibit prolyl hydroxylase inhibitory activity. This invention also relates to methods of increasing HIF levels or activity in a subject or treating a condition associated with HIF levels or activity in a subject by administering to the subject at least one quinolone based compound. This invention further involves assays for the detection of a hydroxyproline residue in a HIF molecule.
  [FR] La présente invention concerne de nouveaux composés à base de quinolone qui présentent une activité inhibitrice de prolyle hydroxylase. Cette invention concerne en outre des procédés d'augmentation des taux ou de l'activité de HIF chez un sujet ou de traitement d'un état associé aux taux ou à l'activité de HIF chez un sujet par administration au sujet d'au moins un composé à base de quinolone. Cette invention met en oevre en outre des essais pour la détection d'un résidu hydroxyproline dans une molécule de HIF.