3-(5-bromo-6-methoxynaphthalen-2-yl)pyridine | 869120-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(5-bromo-6-methoxynaphthalen-2-yl)pyridine
• 英文别名: 3-(5-Bromo-6-methoxy-2-naphthyl)pyridine
• CAS: 869120-20-7
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: ZVOWEWSHEFYCIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-6-methoxynaphthalen-2-yl)pyridine 、 4-氟苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以77%的产率得到3-[5-(4-Fluorophenyl)-6-methoxynaphthalen-2-yl]pyridine
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling studies of novel ACD- and ABD-ring steroidomimetics as inhibitors of CYP17

  摘要：

  Two novel classes of non-steroidal substrate mimetics were synthesised and examined for their potency as inhibitors of human CYP17. Selected compounds were tested for inhibition of hepatic CYP enzymes 3A4, 1A2, 2C9 and 2C19. The most promising compound 15 showed a good inhibition of the target enzyme (31% and 66% at 0.2 and 2 mu M, respectively), and little inhibition of the most important hepatic enzyme CYP3A4 (6% and 19% inhibition at 0.2 and 2 mu M, respectively) and the key enzyme of glucocorticoid biosynthesis CYP11B1 (3% and 23% inhibition at 0.2 and 2 mu M, respectively). Docking studies revealed that this compound does not assume the same binding mode as steroidal ligands. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.079
• 作为产物：
  描述：

  1,6-二溴-2-甲氧基萘 、 3-吡啶硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以25%的产率得到3-(5-bromo-6-methoxynaphthalen-2-yl)pyridine
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling studies of novel ACD- and ABD-ring steroidomimetics as inhibitors of CYP17

  摘要：

  Two novel classes of non-steroidal substrate mimetics were synthesised and examined for their potency as inhibitors of human CYP17. Selected compounds were tested for inhibition of hepatic CYP enzymes 3A4, 1A2, 2C9 and 2C19. The most promising compound 15 showed a good inhibition of the target enzyme (31% and 66% at 0.2 and 2 mu M, respectively), and little inhibition of the most important hepatic enzyme CYP3A4 (6% and 19% inhibition at 0.2 and 2 mu M, respectively) and the key enzyme of glucocorticoid biosynthesis CYP11B1 (3% and 23% inhibition at 0.2 and 2 mu M, respectively). Docking studies revealed that this compound does not assume the same binding mode as steroidal ligands. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.079

文献信息

• Heteroaryl-Substituted Naphthalenes and Structurally Modified Derivatives:  Selective Inhibitors of CYP11B2 for the Treatment of Congestive Heart Failure and Myocardial Fibrosis
  作者：Marieke Voets、Iris Antes、Christiane Scherer、Ursula Müller-Vieira、Klaus Biemel、Catherine Barassin、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1021/jm0503704

  日期：2005.10.1

  a novel strategy for the treatment of congestive heart failure and myocardial fibrosis. In this study the synthesis and biological evaluation of heteroaryl-substituted naphthalenes and quinolines (1-31) is described. Key step for the preparation of the compounds was a Suzuki cross-coupling. Activity of the compounds was determined in vitro using human CYP11B2 and selectivity was evaluated toward the

  最近，我们提出抑制醛固酮合酶（CYP11B2）作为一种治疗充血性心力衰竭和心肌纤维化的新策略。在这项研究中，描述了杂芳基取代的萘和喹啉（1-31）的合成和生物学评估。制备化合物的关键步骤是铃木交叉偶联。使用人CYP11B2在体外确定化合物的活性，并评估对人类固醇生成酶CYP11B1，CYP19和CYP17的选择性。已鉴定出大量的CYP11B2高活性和选择性抑制剂。活性最高的抑制剂是6-氰基化合物8（IC50 = 3 nM），显示出竞争性的抑制类型（K（i）值= 1.9 nM）。发现6-乙氧基衍生物5是最具选择性的CYP11B2抑制剂（IC50 = 12 nM； K（i）值= 8 nM; CYP11B1 IC50 = 5419 nM；选择性因子= 451），显示没有对人CYP3A4（50 nM）和CYP2D6（20 nM）的抑制作用。使用我们的同源性建模的CYP11B2结构与所选化合物进行了
• Selective Inhibitors of Human Corticosteroid Synthases
  申请人：Hartmann Rolf W.

  公开号：US20090221591A1

  公开（公告）日：2009-09-03

  The invention relates to compounds for selectively inhibiting human corticosteroid synthases CYP1 1 B1 and CYP1 1 B2, and to the production and use thereof for treating hypercortisolism, diabetes mellitus, hyperaldosteronism, cardiac insufficiency, myocardial fibrosis, depression, age-related cognitive decline and metabolic syndrome.

  本发明涉及用于选择性抑制人类皮质类固醇合成酶CYP11B1和CYP11B2的化合物，以及其生产和用于治疗高皮质醇症，糖尿病，高醛固酮症，心力衰竭，心肌纤维化，抑郁症，年龄相关认知衰退和代谢综合征。
• SELEKTIVE HEMMSTOFFE HUMANER CORTICOIDSYNTHASEN
  申请人：Universität des Saarlandes

  公开号：EP1853261B1

  公开（公告）日：2017-01-11
• US9271963B2
  申请人：——

  公开号：US9271963B2

  公开（公告）日：2016-03-01
• [DE] SELEKTIVE HEMMSTOFFE HUMANER CORTICOIDSYNTHASEN<br/>[EN] SELECTIVE INHIBITORS OF HUMAN CORTICOSTEROID SYNTHASES<br/>[FR] INHIBITEURS SELECTIFS DE SYNTHASES DE CORTICOIDES HUMAINES
  申请人：UNIV SAARLAND

  公开号：WO2006092430A1

  公开（公告）日：2006-09-08

  [EN] The invention relates to compounds for selectively inhibiting human corticosteroid synthases CYP1 1 B1 and CYP1 1 B2, and to the production and use thereof for treating hypercortisolism, diabetes mellitus, hyperaldosteronism, cardiac insufficiency, myocardial fibrosis, depression, age-related cognitive decline and metabolic syndrome.
  [FR] L'invention concerne des composés d'inhibition sélective de synthases de corticoïdes humaines CYP1 1 B1 et CYP1 1 B2, leur fabrication et leur utilisation dans le traitement de l'hypercortisolisme, du diabète sucré, de l'hyperaldostéronisme, de l'insuffisance cardiaque, de la fibrose du myocarde, de la dépression, de défaillances cognitives séniles et du syndrome métabolique.
  [DE] Die Erfindung betrifft Verbindungen zur selektiven Hemmung der humanen Corticoidsynthasen CYP1 1 B1 und CYP1 1 B2, deren Herstellung und Verwendung zur Behandlung von Hypercortisolismus, Diabetes mellitus, Hyperaldosteronismus, Herzinsuff izienz, Myokardfibrose, Depression, altersbedingten kognitiven Einbußen und des metabolischen Syndroms.