2-(吡啶-4-甲基)-2,3-二氢-1H-茚-5-醇 | 154932-75-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 2-(吡啶-4-甲基)-2,3-二氢-1H-茚-5-醇
• 中文别名: 2-(吡啶基-4-甲基)-2,3-二氢-1H-茚-5-醇
• 英文名称: 2-Pyridin-4-ylmethyl-indan-5-ol
• 英文别名: 2-(pyridin-4-ylmethyl)-2,3-dihydro-1H-inden-5-ol
• CAS: 154932-75-9
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: OQVIVKTTYYDAGR-UHFFFAOYSA-N

物化性质

• 沸点：
  415.7±40.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  5-甲氧基-1-茚酮 在 palladium on activated charcoal 哌啶 、 甲醇 、 氢氧化钾 、 氢气 、 三溴化硼 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 11.5h， 生成 2-(吡啶-4-甲基)-2,3-二氢-1H-茚-5-醇
  参考文献：
  名称：

  Aromatase Inhibitors. Syntheses and Structure-Activity Studies of Novel Pyridyl-Substituted Indanones, Indans, and Tetralins

  摘要：

  The (E)-2-(4-pyridylmethylene)-1-indanones (E)-1-(E)-5[(E)-1, H; (E);2, 4-OCH3; (E)-3, 5-OCH3; (E)-4, 4-OH; (E)-5,5-OH] were obtained by aldol condensation of the corresponding 1-indanones with 4-pyridinecarboxaldehyde, and in case of the OH compound (E)-4 subsequent ether cleavage of (E)-2. The synthesis of the (Z)-isomers (Z)-1-(Z)-3 [(Z)-1, H; (Z)-2, 4-OCH3; (Z)-3, 5-OCH3] was accomplished by UV irradiation of the corresponding (E)-isomers. Catalytic hydrogenation of (E)-1-(E)-3 gave the 2-(4-pyridylmethyl)-1-indanones 6-8 (6, H; 7, 4-OCH3; 8, 5-OCH3). The 2-(4-pyridylmethyl)-substituted indans 11-13 (11, H; 12, 4-OCH3; 13, 5-OCH3) and the tetralins 16-19 (16, H; 17, 5-OCH3; 18, 6-OCH3; 19, 7-OCH3) were obtained by reduction of the corresponding ketones using N2H4/KOH. The 2-(4-pyridylmethyl)-substituted indanones 9 (4-OH) and 10 (5-OH), indans 14 (4-OH) and 15 (5-OH), and tetralins 20-22 (20, 5-OH; 21, 6-OH; 22, 7-OH) were synthesized by ether cleavage of the corresponding OCH3 compounds. All compounds showed inhibition of human placental aromatase exhibiting relative potencies from 0.9 [(E)-4] to 163 [18; aminoglutethimide (AC) potency E 1]. Compounds 13 and 18 showed competitive type of inhibition and a type II difference spectrum, indicating the interaction of the pyridyl-N with the central Fe(III) ion of the cytochrome P450 heme component. Only the OH-substituted indans and tetralins inhibited bovine adrenal desmolase with maximum activity shown by 20 and 22 (12% inhibition, 25 mu M; AG, 53 % inhibition, 25 mu M). In vivo, however, all tested aromatase inhibitors (6, 8, 10, 14, 15, 18 and 20) were less active than AG concerning the inhibition of the uterotrophic activity of androstenedione (6, 8, 10, 15), the reduction of the plasma estradiol concentration (14, 20), and the mammary carcinoma (MC) inhibiting properties (18, 20; androstenedione-stimulated juvenile rats, pregnant mares' serum gonadotropin-primed rats as well as dimethylbenzanthracene-induced MC of the Sprague-Dawley rat, postmenopausal experiment). Since no affinity to the estrogen receptor was demonstrated (20), estrogenic effects as a cause for the poor tumor inhibiting activity have to be excluded.

  DOI：

  10.1021/jm00035a007

文献信息

• 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。
• Selective inhibitors of human corticosteroid syntheses
  申请人：Hartmann Rolf

  公开号：US20090105278A1

  公开（公告）日：2009-04-23

  The invention relates to compounds for selectively inhibiting human corticosteroid syntheses CYP11B1 and CYP11B2, to the production thereof and to their use for treating hypercortisolism and diabetes mellitus or insufficiency of the heart and myocardial fibrosis.

  本发明涉及用于选择性抑制人类皮质类固醇合成CYP11B1和CYP11B2的化合物，其制备方法以及它们用于治疗高皮质醇症和糖尿病或心脏功能不全和心肌纤维化的应用。
• 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 SYNTHESES<br/>[FR] INHIBITEURS SELECTIFS DES CORTICOIDE-SYNTHASES HUMAINES
  申请人：UNIV SAARLAND

  公开号：WO2006008316A2

  公开（公告）日：2006-01-26

  Die Erfindung betrifft Verbindungen zur selektiven Hemmung der humanen Corticoidsynthasen CYP11B1 und CYP11B2, deren Herstellung und Verwendung zur Behandlung von Hypercortisolismus und Diabetes mellitus bzw. Herzinsuffizienz und Myokardfibrose.