7-Hydroxy-2-pyridin-4-ylmethyl-3,4-dihydro-2H-naphthalen-1-one | 135075-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 7-Hydroxy-2-pyridin-4-ylmethyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 7-hydroxy-2-(pyridin-4-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 135075-35-3
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: XWSFHWMUYSQTSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  7-Hydroxy-2-pyridin-4-ylmethyl-3,4-dihydro-2H-naphthalen-1-one 在 glycopeptide chiral stationary phase containing ristocetin 作用下， 以 乙醇 、 正己烷 、 三乙胺 为溶剂， 生成 (R)-7-Hydroxy-2-pyridin-4-ylmethyl-3,4-dihydro-2H-naphthalen-1-one 、 (S)-7-Hydroxy-2-pyridin-4-ylmethyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  正相模式下使用 HPLC 对几种四氢萘酮衍生物在大环抗生素手性固定相上的对映体拆分的比较研究

  摘要：

  五种取代的 2-(4-吡啶基烷基)-1-四氢萘酮衍生物的对映体拆分已在三种大环糖肽抗生素手性固定相即 Chiro-biotic R、T 和 V 色谱柱上实现。使用的流动相是己烷-乙醇-三乙胺（12:8:0.01，v/v/v）。Chirobiotic T 的流速分别为 1 mL/min，Chirobiotic R 和 V 的流速分别为 2 mL/min。UV检测在254nm处进行，所报道的四氢萘酮衍生物的解析对映异构体的a值在Chirobiotic R上为1.32至2.51，在Chirobiotic T上为2.02至2.88，在Chirobiotic V上为1.55至2.54 Rs 的值分别在 Chirobiotic R 的 1.00 至 2.50 范围内，Chirobiotic T 的 1.00 至 1.95 和 Chirobiotic V 的 1.00 至 1.60。

  DOI：

  10.1002/1521-4184(200107)334:7<258::aid-ardp258>3.0.co;2-g
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 palladium on activated charcoal 哌啶 、 氢气 、 三溴化硼 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 7-Hydroxy-2-pyridin-4-ylmethyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  New aromatase inhibitors. Synthesis and biological activity of pyridyl-substituted tetralone derivatives

  摘要：

  The (E)-2-(4-pyridylmethylene)-1-tetralones 1-7 (1, H; 2, 5-OCH3; 3, 6-OCH3; 4, 7-OCH3; 5, 5-OH; 6, 6-OH; 7, 7-OH) were obtained by aldol condensation of the corresponding 1-tetralones with 4-pyridinecarboxaldehyde, and in the case of the OH compounds 5 and 7 subsequent ether cleavage of the OCH3-substituted 2-(4-pyridylmethylene)-1-tetralones. Catalytic hydrogenation of 1-4 gave the 2-(4-pyridylmethyl)-1-tetralones 8-11 (8, H; 9, 5-OCH3; 10, 6-OCH3; 11, 7-OCH3). Subsequent ether cleavage of 9-11 led to the corresponding OH compounds 12-14 (12, 5-OH; 13, 6-OH; 14, 7-OH). The enantiomers of 11 and 12 were separated semipreparatively by HPLC on triacetylcellulose. All compounds (1-14) showed an inhibition of human placental aromatase exhibiting relative potencies from 2.2 to 213 [compounds 6 and (+)-12, respectively; aromatase inhibitory potency of aminoglutethimide (AG) = 1]. The compounds exhibited no or only a weak inhibition of desmolase [cholesterol side chain cleavage enzyme; maximum activity shown by 12, 23 % inhibition (25-mu-M); AG, 53 % inhibition (25-mu-M)]. In vivo, however, the compounds were not superior to AG as far as the reduction of the plasma estradiol concentration and the mammary carcinoma (MC) inhibiting properties are concerned (PMSG-primed SD rats as well as DMBA-induced MC of the SD rat, pre- and postmenopausal experiments, and the transplantable MXT-MC of the BD2F1 mouse). This is due to a fast decrease of the plasma E2 concentration inhibiting effect as could be shown by a kinetic experiment. In addition, select compounds inhibited rat ovarian aromatase much less than human placental aromatase (12, factor of 10). Estrogenic effects as a cause for the poor in vivo activity of the test compounds could be excluded, since they did not show affinity for the estrogen receptor.

  DOI：

  10.1021/jm00113a004

文献信息

• New aromatase inhibitors. Synthesis and biological activity of pyridyl-substituted tetralone derivatives
  作者：Herbert Bayer、Christine Batzl、Rolf W. Hartman、Albrecht Mannschreck

  DOI：10.1021/jm00113a004

  日期：1991.9

  The (E)-2-(4-pyridylmethylene)-1-tetralones 1-7 (1, H; 2, 5-OCH3; 3, 6-OCH3; 4, 7-OCH3; 5, 5-OH; 6, 6-OH; 7, 7-OH) were obtained by aldol condensation of the corresponding 1-tetralones with 4-pyridinecarboxaldehyde, and in the case of the OH compounds 5 and 7 subsequent ether cleavage of the OCH3-substituted 2-(4-pyridylmethylene)-1-tetralones. Catalytic hydrogenation of 1-4 gave the 2-(4-pyridylmethyl)-1-tetralones 8-11 (8, H; 9, 5-OCH3; 10, 6-OCH3; 11, 7-OCH3). Subsequent ether cleavage of 9-11 led to the corresponding OH compounds 12-14 (12, 5-OH; 13, 6-OH; 14, 7-OH). The enantiomers of 11 and 12 were separated semipreparatively by HPLC on triacetylcellulose. All compounds (1-14) showed an inhibition of human placental aromatase exhibiting relative potencies from 2.2 to 213 [compounds 6 and (+)-12, respectively; aromatase inhibitory potency of aminoglutethimide (AG) = 1]. The compounds exhibited no or only a weak inhibition of desmolase [cholesterol side chain cleavage enzyme; maximum activity shown by 12, 23 % inhibition (25-mu-M); AG, 53 % inhibition (25-mu-M)]. In vivo, however, the compounds were not superior to AG as far as the reduction of the plasma estradiol concentration and the mammary carcinoma (MC) inhibiting properties are concerned (PMSG-primed SD rats as well as DMBA-induced MC of the SD rat, pre- and postmenopausal experiments, and the transplantable MXT-MC of the BD2F1 mouse). This is due to a fast decrease of the plasma E2 concentration inhibiting effect as could be shown by a kinetic experiment. In addition, select compounds inhibited rat ovarian aromatase much less than human placental aromatase (12, factor of 10). Estrogenic effects as a cause for the poor in vivo activity of the test compounds could be excluded, since they did not show affinity for the estrogen receptor.
• A Comparative Study of the Enantiomeric Resolution of Several Tetralone Derivatives on Macrocyclic Antibiotic Chiral Stationary Phases Using HPLC under Normal Phase Mode
  作者：Hassan Y. Aboul-Enein、Imran Ali

  DOI：10.1002/1521-4184(200107)334:7<258::aid-ardp258>3.0.co;2-g

  日期：2001.7

  The enantiomeric resolution of five substituted 2‐(4‐pyridylalkyl)‐1‐ tetralone derivatives has been achieved on three macrocyclic glycopeptide antibiotic chiral stationary phases namely, Chiro‐biotic R, T, and V columns. The mobile phase used was hexane‐ethanol‐ triethylamine (12:8:0.01, v/v/v). The flow rates were 1 mL/min for Chirobiotic T and 2 mL/min for Chirobiotic R and V respectively. The UV

  五种取代的 2-(4-吡啶基烷基)-1-四氢萘酮衍生物的对映体拆分已在三种大环糖肽抗生素手性固定相即 Chiro-biotic R、T 和 V 色谱柱上实现。使用的流动相是己烷-乙醇-三乙胺（12:8:0.01，v/v/v）。Chirobiotic T 的流速分别为 1 mL/min，Chirobiotic R 和 V 的流速分别为 2 mL/min。UV检测在254nm处进行，所报道的四氢萘酮衍生物的解析对映异构体的a值在Chirobiotic R上为1.32至2.51，在Chirobiotic T上为2.02至2.88，在Chirobiotic V上为1.55至2.54 Rs 的值分别在 Chirobiotic R 的 1.00 至 2.50 范围内，Chirobiotic T 的 1.00 至 1.95 和 Chirobiotic V 的 1.00 至 1.60。