6-(3,4-dihydro-1H-isoquinoline-2-yl)-N-(4-methylpyridine-2-yl)nicotinamide | 1258160-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3,4-dihydro-1H-isoquinoline-2-yl)-N-(4-methylpyridine-2-yl)nicotinamide
• 英文别名: 6-(3,4-dihydro-1H-isoquinolin-2-yl)-N-(4-methylpyridin-2-yl)pyridine-3-carboxamide
• CAS: 1258160-95-0
• 化学式: C₂₁H₂₀N₄O
• 分子量: 344.416
• InChiKey: NHTWVPAXAZNUMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(3,4-dihydro-1H-isoquinoline-2-yl)-N-(4-methylpyridine-2-yl)nicotinamide 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 5.0h， 以21%的产率得到6-(3,4-dihydro-1H-isoquinoline-2-yl)-N-methyl-N-(4-methylpyridine-2-yl)nicotinamide
  参考文献：
  名称：

  SAR Based Design of Nicotinamides as a Novel Class of Androgen Receptor Antagonists for Prostate Cancer

  摘要：

  Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.

  DOI：

  10.1021/jm3014103
• 作为产物：
  描述：

  6-氯烟酸 在 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 48.0h， 生成 6-(3,4-dihydro-1H-isoquinoline-2-yl)-N-(4-methylpyridine-2-yl)nicotinamide
  参考文献：
  名称：

  SAR Based Design of Nicotinamides as a Novel Class of Androgen Receptor Antagonists for Prostate Cancer

  摘要：

  Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.

  DOI：

  10.1021/jm3014103

文献信息

• [EN] NEW NICOTINAMIDE DERIVATIVES WITH ANTI-ANDROGEN EFFECTS, PROCESSES OF PREPARING, AND ANTIANDROGENS COMPRISING THE SAME<br/>[FR] NOUVEAUX DÉRIVÉS DE NICOTINAMIDE AYANT DES EFFETS ANTI-ANDROGÉNIQUES, PROCÉDÉS DE PRÉPARATION, ET ANTI-ANDROGÈNES LES COMPRENANT
  申请人：UNIV NAT CHONNAM IND FOUND

  公开号：WO2010143803A2

  公开（公告）日：2010-12-16

  Provided are novel nicotinamide derivatives and pharmaceutically acceptable salts thereof with anti-androgen effects, preparing processes of the same and antiandrogens containing the same as active ingredients. More particularly, the said nicotinamide derivatives have anti-androgen activity, so that they can be effectively used as a preventive or therapeutic agent for androgen-related diseases such as prostatic disease, androgenic alopecia and acne.
• SAR Based Design of Nicotinamides as a Novel Class of Androgen Receptor Antagonists for Prostate Cancer
  作者：Su Hui Yang、Chin-Hee Song、Hue Thi My Van、Eunsook Park、Daulat Bikram Khadka、Eun-Yeung Gong、Keesook Lee、Won-Jea Cho

  DOI：10.1021/jm3014103

  日期：2013.4.25

  Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.