6-氯-5-(4-氯苯基)-3-吡啶羧酸 | 1012792-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-氯-5-(4-氯苯基)-3-吡啶羧酸
• 英文名称: 6-chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid
• 英文别名: 6-chloro-5-(4-chloro-phenyl)-nicotinic acid；6-Chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid；6-chloro-5-(4-chlorophenyl)pyridine-3-carboxylic acid
• CAS: 1012792-56-1
• 化学式: C₁₂H₇Cl₂NO₂
• 分子量: 268.099
• InChiKey: CNOSIRGQGQQTCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氯-5-(4-氯苯基)-3-吡啶羧酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 5-(4-chlorophenyl)-6-(cyclopropylmethoxy)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide
  参考文献：
  名称：

  6-Alkoxy-5-aryl-3-pyridinecarboxamides, a New Series of Bioavailable Cannabinoid Receptor Type 1 (CB1) Antagonists Including Peripherally Selective Compounds

  摘要：

  We identified 6-alkoxy-5-aryl-3-pyridinecarboxamides as potent CB1 receptor antagonists with high selectivity over CB2 receptors. The series was optimized to reduce lipophilicity compared to rimonabant to achieve peripherally active molecules with minimal central effects. Several compounds that showed high plasma exposures in rats were evaluated in vivo to probe the contribution of central vs peripheral CB1 agonism to metabolic improvement. Both rimonabant and 14g, a potent brain penetrant CB1 receptor antagonist, significantly reduced the rate of body weight gain. However, 14h, a molecule with markedly reduced brain exposure, had no significant effect on body weight. PK studies confirmed similarly high exposure of both 14h and 14g in the periphery but 10-fold lower exposure in the brain for 14h. On the basis of these data, which are consistent with reported effects in tissue-specific CB1 receptor KO mice, we conclude that the metabolic benefits of CB1 receptor antagonists are primarily centrally mediated as originally believed.

  DOI：

  10.1021/jm4010708
• 作为产物：
  描述：

  5-溴-6-羟基烟酸 在 喹啉 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 lithium hydroxide monohydrate 、 sodium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 5.25h， 生成 6-氯-5-(4-氯苯基)-3-吡啶羧酸
  参考文献：
  名称：

  6-Alkoxy-5-aryl-3-pyridinecarboxamides, a New Series of Bioavailable Cannabinoid Receptor Type 1 (CB1) Antagonists Including Peripherally Selective Compounds

  摘要：

  We identified 6-alkoxy-5-aryl-3-pyridinecarboxamides as potent CB1 receptor antagonists with high selectivity over CB2 receptors. The series was optimized to reduce lipophilicity compared to rimonabant to achieve peripherally active molecules with minimal central effects. Several compounds that showed high plasma exposures in rats were evaluated in vivo to probe the contribution of central vs peripheral CB1 agonism to metabolic improvement. Both rimonabant and 14g, a potent brain penetrant CB1 receptor antagonist, significantly reduced the rate of body weight gain. However, 14h, a molecule with markedly reduced brain exposure, had no significant effect on body weight. PK studies confirmed similarly high exposure of both 14h and 14g in the periphery but 10-fold lower exposure in the brain for 14h. On the basis of these data, which are consistent with reported effects in tissue-specific CB1 receptor KO mice, we conclude that the metabolic benefits of CB1 receptor antagonists are primarily centrally mediated as originally believed.

  DOI：

  10.1021/jm4010708

文献信息

• 3-Pyridinecarboxamide derivatives as HDL-cholesterol raising agents
  申请人：Andjelkovic Mirjana

  公开号：US20080085906A1

  公开（公告）日：2008-04-10

  The present invention relates to a method of raising HDL cholesterol comprising administering to a patient in need thereof a compound of the formula wherein A, G, R 1 to R 8 and R 17 are as defined in the description.

  本发明涉及一种提高HDL胆固醇的方法，包括向需要的患者施用以下公式的化合物： 其中A、G、R1至R8和R17如描述中所定义。
• HETEROARYLMETHYL AMIDES
  申请人：Hebeisen Paul

  公开号：US20120065212A1

  公开（公告）日：2012-03-15

  The present invention relates to compounds of the formula wherein A 1 , A 2 , A 3 and R 1 to R 8 are defined in the description, and to pharmaceutically acceptable salts thereof, their manufacture, pharmaceutical compositions containing them and their use as medicaments for the treatment and/or prophylaxis of diseases which can be treated with HDL-cholesterol raising agents, such as particularly dyslipidemia, atherosclerosis and cardiovascular diseases.

  本发明涉及以下公式的化合物，其中A1、A2、A3和R1至R8在描述中有定义，并且其药用盐，其制备，含有它们的药物组合物以及它们作为药物用于治疗和/或预防可用高密度脂蛋白胆固醇升高剂治疗的疾病，例如特别是血脂异常、动脉粥样硬化和心血管疾病。
• [EN] HETEROARYLMETHYL AMIDES<br/>[FR] HÉTÉROARYLMÉTHYL-AMIDES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012032018A1

  公开（公告）日：2012-03-15

  The present invention relates to compounds of the formula I wherein A1, A2, A3 and R1 to R8 are defined in the description, and to pharmaceutically acceptable salts thereof, their manufacture, pharmaceutical compositions containing them and their use as medicaments for the treatment and/or prophylaxis of diseases which can be treated with HDL-cholesterol raising agents, such as particularly dyslipidemia, atherosclerosis and cardiovascular diseases.

  本发明涉及公式I中的化合物，其中A1、A2、A3和R1至R8在描述中有定义，以及其药用盐，其制备方法，含有它们的药物组合物以及它们作为药物用于治疗和/或预防可以用HDL-胆固醇升高剂治疗的疾病，如特别是脂质代谢异常、动脉粥样硬化和心血管疾病。
• 5-PHENYL-NICOTINAMIDE DERIVATIVES
  申请人：Hebeisen Paul

  公开号：US20080070931A1

  公开（公告）日：2008-03-20

  The present invention relates to compounds of the formula wherein R 1 to R 8 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors.

  本发明涉及公式中的化合物，其中R1至R8如描述和索赔中定义，并且其药用盐。这些化合物可用于治疗和/或预防与CB1受体调节相关的疾病。
• Design, Synthesis, and Evaluation of Novel Auxin Mimic Herbicides
  作者：Chi-Linh Do-Thanh、Jose J. Vargas、Joseph W. Thomas、Gregory R. Armel、Michael D. Best

  DOI：10.1021/acs.jafc.6b00675

  日期：2016.5.11

  applications. Herein, we describe the design and multistep synthesis of ten compounds bearing combinations of functional groups commonly associated with auxin-type properties. Following synthesis, these compounds were tested against multiple weed species as well as sweet corn. In general, while these structures were not quite as active as commercial auxin mimic herbicides, multiple compounds exhibited broadleaf

  由于植物生长素作为植物生长的主要调节剂的关键作用，因此人们对开发具有生长素样特性的化合物进行生长管理和杂草防治应用产生了极大的兴趣。本文中，我们描述了十个带有通常与生长素类型性质相关的官能团组合的化合物的设计和多步合成。合成后，针对多种杂草以及甜玉米对这些化合物进行了测试。通常，虽然这些结构不像市售的生长素模拟除草剂那么活跃，但多种化合物在甜玉米中表现出阔叶杂草活性并同时具有选择性（玉米）L.var。糖）。此外，在结构发生细微变化时观察到差异结果，从而洞察了活动所需的结构特性。