6-(4-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one | 169192-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(4-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 3,4-Dihydro-6-(4-fluorophenyl)-1(2H)-naphthalenone；6-(4-fluorophenyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 169192-34-1
• 化学式: C₁₆H₁₃FO
• 分子量: 240.277
• InChiKey: ADAQQUVWDOFOQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one 、 4-溴吡啶 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 以44%的产率得到6-(4-fluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling of Abiraterone Analogues: Novel CYP17 Inhibitors for the Treatment of Prostate Cancer

  摘要：

  Abiraterone, a steroidal cytochrome P450 17alpha-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent prostate cancer. Since steroidal compounds often show side effects attributable to their structure, we have tried to replace the sterane scaffold by nonsteroidal core structures. The design and synthesis of 20 new abiraterone mimetics are described. Their activities have been tested with recombinant human CYP17 expressed in E. coli. Promising compounds were further evaluated for selectivity against CYP11B1, CYP11B2, and the hepatic CYP3A4. Compounds 19 and 20 showed comparable activity to abiraterone (IC50 values of 144 and 64 nM vs 72 nM) and similar or even better selectivity against the other CYP enzymes. Selected compounds were also docked into our homology model, and the same binding modes as for abiraterone were found.

  DOI：

  10.1021/jm800355c
• 作为产物：
  描述：

  4-氟苯硼酸 、 5-氧代-5,6,7,8-四氢萘-2-基 三氟甲烷磺酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 8.0h， 以89%的产率得到6-(4-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling of Abiraterone Analogues: Novel CYP17 Inhibitors for the Treatment of Prostate Cancer

  摘要：

  Abiraterone, a steroidal cytochrome P450 17alpha-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent prostate cancer. Since steroidal compounds often show side effects attributable to their structure, we have tried to replace the sterane scaffold by nonsteroidal core structures. The design and synthesis of 20 new abiraterone mimetics are described. Their activities have been tested with recombinant human CYP17 expressed in E. coli. Promising compounds were further evaluated for selectivity against CYP11B1, CYP11B2, and the hepatic CYP3A4. Compounds 19 and 20 showed comparable activity to abiraterone (IC50 values of 144 and 64 nM vs 72 nM) and similar or even better selectivity against the other CYP enzymes. Selected compounds were also docked into our homology model, and the same binding modes as for abiraterone were found.

  DOI：

  10.1021/jm800355c

文献信息

• Tetracyclic compound
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05646283A1

  公开（公告）日：1997-07-08

  This invention relates to a novel tetracyclic compound represented by formula (I): ##STR1## or its pharmacologically-acceptable salt. The compound of this invention has strong immunosuppressive activity, and is useful as an immunosuppressive agent and as an agent for treating autoimmune disease.

  本发明涉及一种新型四环化合物，其化学式为(I): ##STR1## 或其药学上可接受的盐。该化合物具有强烈的免疫抑制活性，可作为免疫抑制剂和治疗自身免疫性疾病的药物。
• NOVEL TETRACYCLIC COMPOUND
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0721942A1

  公开（公告）日：1996-07-17

  A novel tetracyclic compound represented by general formula (I) or a pharmacologically acceptable salt thereof. It has a potent immunosuppressive activity and is useful as an immunosuppressant and a remedy for autoimmune diseases.

  一种由通式（I）代表的新型四环化合物或其药理学上可接受的盐。 它具有强效的免疫抑制活性，可用作免疫抑制剂和自身免疫性疾病的治疗药物。
• TETRACYCLIC COMPOUND
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0721942B1

  公开（公告）日：2002-06-05
• US5646283A
  申请人：——

  公开号：US5646283A

  公开（公告）日：1997-07-08
• Synthesis, Biological Evaluation, and Molecular Modeling of Abiraterone Analogues: Novel CYP17 Inhibitors for the Treatment of Prostate Cancer
  作者：Mariano A. E. Pinto-Bazurco Mendieta、Matthias Negri、Carsten Jagusch、Ursula Müller-Vieira、Thomas Lauterbach、Rolf W. Hartmann

  DOI：10.1021/jm800355c

  日期：2008.8.1

  Abiraterone, a steroidal cytochrome P450 17alpha-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent prostate cancer. Since steroidal compounds often show side effects attributable to their structure, we have tried to replace the sterane scaffold by nonsteroidal core structures. The design and synthesis of 20 new abiraterone mimetics are described. Their activities have been tested with recombinant human CYP17 expressed in E. coli. Promising compounds were further evaluated for selectivity against CYP11B1, CYP11B2, and the hepatic CYP3A4. Compounds 19 and 20 showed comparable activity to abiraterone (IC50 values of 144 and 64 nM vs 72 nM) and similar or even better selectivity against the other CYP enzymes. Selected compounds were also docked into our homology model, and the same binding modes as for abiraterone were found.