6-[1-hydroxy-1-(1-methyl-1H-imidazol-5-yl)ethyl]-N-methylnaphthalene-2-carboxamide | 1346155-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-[1-hydroxy-1-(1-methyl-1H-imidazol-5-yl)ethyl]-N-methylnaphthalene-2-carboxamide
• 英文别名: 6-[1-hydroxy-1-(3-methylimidazol-4-yl)ethyl]-N-methylnaphthalene-2-carboxamide
• CAS: 1346155-91-6
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: CWOCSWWXAHRGJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴-2-萘甲酸 在 正丁基锂 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 6-[1-hydroxy-1-(1-methyl-1H-imidazol-5-yl)ethyl]-N-methylnaphthalene-2-carboxamide
  参考文献：
  名称：

  1,1-Diarylalkenes as anticancer agents: Dual inhibitors of tubulin polymerization and phosphodiesterase 4

  摘要：

  A series of 1,1-diarylalkene derivatives were prepared to optimize the properties of CC-5079 (1), a dual inhibitor of tubulin polymerization and phosphodiesterase 4 (PDE4). By using the 3-ethoxy-4-methoxyphenyl PDE4 pharmacophore as one of the aromatic rings, a significant improvement in PDE4 inhibition was achieved. Compound 28 was identified as a dual inhibitor with potent PDE4 (IC(50) = 54 nM) and antitubulin activity (HCT-116 IC(50) = 34 nM and tubulin polymerization IC(50) similar to 1 mu M). While the nitrile group at the alkene terminus was generally required for potent antiproliferative activity, its replacement was tolerated if there was a hydroxyl or amino group on one of the aryl rings. Conveniently, this group could also serve as a handle for amino acid derivatization to improve the compounds' solubility. The glycinamide analog 45 showed significant efficacy in the HCT-116 xenograft model, with 64% inhibition of tumor growth upon dosing at 20 mg/kg qd. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.068

文献信息

• Compositions and methods for treatment of prostate carcinoma
  申请人：Pellficure Pharmaceuticals, Inc.

  公开号：US10093620B2

  公开（公告）日：2018-10-09

  Disclosed herein are 1,4-naphthoquinone analogs, pharmaceutical compositions that include one or more of such 1,4-naphthoquinone analogs, and methods of treating and/or ameliorating diseases and/or conditions associated with a cancer, such as prostate cancer with such 1,4-naphthoquinone analogs. Also included are combination therapies wherein a 1,4-naphthoquinone analog disclosed herein, and a hormone therapy agent are provided to a subject suffering from a condition such as cancer.

  本文公开了1,4-萘醌类似物、包括一种或多种此类1,4-萘醌类似物的药物组合物，以及用此类1,4-萘醌类似物治疗和/或改善与癌症（如前列腺癌）相关的疾病和/或病症的方法。还包括组合疗法，其中向患有癌症等疾病的受试者提供本文公开的 1,4-萘醌类似物和激素治疗剂。
• NOVEL THERAPY FOR PROSTATE CARCINOMA
  申请人：Pellficure Pharmaceuticals, Inc.

  公开号：EP2968219A1

  公开（公告）日：2016-01-20
• 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
• COMPOSITIONS AND METHODS FOR TREATMENT OF PROSTATE CARCINOMA
  申请人：Pellficure Pharmaceuticals, Inc.

  公开号：US20170283374A1

  公开（公告）日：2017-10-05

  Disclosed herein are 1,4-naphthoquinone analogs, pharmaceutical compositions that include one or more of such 1,4-naphthoquinone analogs, and methods of treating and/or ameliorating diseases and/or conditions associated with a cancer, such as prostate cancer with such 1,4-naphthoquinone analogs. Also included are combination therapies wherein a 1,4-naphthoquinone analog disclosed herein, and a hormone therapy agent are provided to a subject suffering from a condition such as cancer.
• PHARMACEUTICAL COMPOSITIONS OF 5-HYDROXY-2-METHYLNAPHTHALENE-1,4-DIONE
  申请人：PellFiCure Pharmaceuticals, Inc.

  公开号：US20180221306A1

  公开（公告）日：2018-08-09

  Disclosed herein are pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1,4-dione. Also disclosed are methods of treating diseases and/or conditions associated with a cancer, such as prostate cancer with such pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1,4-dione. The disclosed pharmaceutical compositions may provide improved dosage for oral administration to patients in the clinic. The disclosed pharmaceutical compositions may provide improved stability and/or shelf life.