3-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1yl)pyridine hydrochloride | 1051380-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1yl)pyridine hydrochloride
• 英文别名: 3-[5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]pyridine;hydrochloride
• CAS: 1051380-44-9
• 化学式: C₂₀H₁₆FN*ClH
• 分子量: 325.813
• InChiKey: CZHBHMYFEKBMAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(5-(4-fluorophenyl)-3-H-inden-1yl)pyridine hydrochloride 在 palladium hydroxide on carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 以99%的产率得到3-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1yl)pyridine hydrochloride
  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

• PHARMACOPHORES, COMPOUNDS AND METHODS HAVING APPLICATION IN THE TREATMENT OF CANCER THROUGH INHIBITION OF CYP17A1 AND CYP19A1
  申请人：Mangosuthu University Of Technology

  公开号：EP3365819A2

  公开（公告）日：2018-08-29
• [EN] PHARMACOPHORES, COMPOUNDS AND METHODS HAVING APPLICATION IN THE TREATMENT OF CANCER THROUGH INHIBITION OF CYP17A1 AND CYP19A1<br/>[FR] PHARMACOPHORES, COMPOSÉS ET PROCÉDÉS AYANT UNE APPLICATION DANS LE TRAITEMENT DU CANCER PAR INHIBITION DE CYP17A1 ET CYP19A1
  申请人：MANGOSUTHU UNIV OF TECH

  公开号：WO2017070718A1

  公开（公告）日：2017-04-27

  The invention provides compounds for use as medicaments, which act by inhibiting CYP17A1 and CYP19A1 enzymes. The compounds have particular application in the treatment of cancer especially prostate cancer and breast cancer. The compounds have the formula: [Chem. 1] wherein: R is independently selected from the group consisting of optionally substituted arylamide; optionally substituted alkylarylamide; optionally substituted aryl carboxamide; optionally substituted cyanopiperidine; optionally substituted oxopiperidine; optionally substituted N-(pyridin-3-yl); optionally substituted pyridin-3-yl; optionally substituted pyrazole-4-carboxamide; optionally substituted pyrimidin-4-ylcarboxamide; optionally substituted pyrimidin-4-ylcarboxamide; optionally substituted 1H-pyrrol-2-ylcarboxamide; optionally substituted morpholin carboxamide; optionally substituted 1H-indazol-3-ylcarboxamide; optionally substituted 5-cyanopiperidin-3-ylcarboxamide; optionally substituted quinolin-7-yl; optionally substituted pyrazin-2-ylcarboxamide; optionally substituted 1H-1,3-benzodiazole-6-carboxamide; and optionally substituted 3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-ylcarboxamide; Each R1, R2, R3, R4, R5 is independently selected from the group consisting of H; OH; a halogen atom; OCH3; and NH2; and X is independently selected from the group consisting of O, H and OH. Some of the compounds are claimed per se and the invention also encompasses pharmaceutically acceptable salts, solvates, hydrates, primary metabolites and prodrugs thereof.
• 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.