3,3'-dimethylene-2-(2'-pyridyl)indole | 119273-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,3'-dimethylene-2-(2'-pyridyl)indole
• 英文别名: 6,11-Dihydro-5H-pyrido[2,3-a]carbazole
• CAS: 119273-99-3
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: VKGPXNDBUOYUSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3'-dimethylene-2-(2'-pyridyl)indole 在 palladium on activated charcoal 作用下， 以 硝基苯 为溶剂， 以77%的产率得到11H-pyrido[2,3-a]carbazole
  参考文献：
  名称：

  Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds

  摘要：

  Methylation of 2-(2'-pyridyl)indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'-indolenylidene)-1,2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3,3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'-quinolinyl)pyrrole. The importance of the connectivity to pyridine is examined by considering three possible regioisomers, only two of which show tautomeric behavior. The tautomers show strong solvatochromic dependence and good linear behavior. The indoles absorb at shorter wavelengths and are strongly emitting while the tautomers show a strong bathochromic shift and emit only weakly; the salts exhibit intermediate behavior. NMR properties are consistent with contributions from a dipolar and uncharged resonance form while MO calculations indicate that the indole is about 40 kcal/mol more stable than its tautomer.

  DOI：

  10.1021/jo980134j
• 作为产物：
  描述：

  N-[(E)-6,7-dihydro-5H-quinolin-8-ylideneamino]aniline 以65%的产率得到
  参考文献：
  名称：

  THUMMEL, RANDOLPH P.;HEGDE, VIDYADHAR, J. ORG. CHEM., 54,(1989) N, C. 1720-1725

  摘要：

  DOI：

文献信息

• Antimalarial Dibenzannulated Medium-Ring Keto Lactams
  作者：Rongguo Ren、Xiaofang Wang、Derek A. Leas、Christian Scheurer、Sarah Hoevel、Monica Cal、Gong Chen、Longjin Zhong、Kasiram Katneni、Thao Pham、Rahul Patil、Diptesh Sil、Matthias J. Walters、Thomas T. Schulze、Andrew J. Neville、Yuxiang Dong、Sergio Wittlin、Marcel Kaiser、Paul H. Davis、Susan A. Charman、Jonathan L. Vennerstrom

  DOI：10.1021/acsinfecdis.3c00245

  日期：2023.10.13

  with IC50 values ranging from 80 to 200 nM. These keto lactams are converted into their poorly soluble 4(1H)-quinolone transannular condensation products in vitro in culture medium and in vivo in mouse blood. The similar antiplasmodial potencies of three keto lactam–quinolone pairs suggest that the quinolones likely contribute to the antimalarial activity of the lactams.

  我们发现二苯甲醛化中环酮内酰胺 （11,12-二氢-5H-二苯并[b，g]氮杂-6,13-二酮）是一种新的抗疟化学型。其中大多数样品的色谱 LogD7.4 值范围为 <0 至 3，且动力学溶解度良好（pH 值为 6.5 时为 12.5 至 >100 μg/mL）。该系列中极性较强的化合物 （<2 的 LogD7.4 值） 具有最佳的代谢稳定性 （人肝微粒体中 CLint 值为 <50 μL/min/mg 蛋白质）。大多数化合物具有较低的细胞毒性，IC50 值为 >30 μM，抗疟原虫活性与细胞毒性之间没有相关性。四种最有效的化合物的恶性疟原虫 IC50 值为 4.2 至 9.4 nM，体外选择性指数为 670 至 >12,000。它们对其他三种原生动物病原体（布鲁氏锥虫罗得西亚锥虫、克氏锥虫和多氏利什曼原虫）的效力低 4 个数量级以上，但对刚地弓形虫的效力相对较高，IC50 值范围为 80
• Polyaza-cavity shaped molecules. 14. Annelated 2-(2'-pyridyl)indoles, 2,2'-biindoles, and related systems
  作者：Randolph P. Thummel、Vidyadhar Hegde

  DOI：10.1021/jo00268a040

  日期：1989.3
• THUMMEL, RANDOLPH P.;HEGDE, VIDYADHAR, J. ORG. CHEM., 54,(1989) N, C. 1720-1725
  作者：THUMMEL, RANDOLPH P.、HEGDE, VIDYADHAR

  DOI：——

  日期：——
• Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds
  作者：Feiyue Wu、Jon Hardesty、Randolph P. Thummel

  DOI：10.1021/jo980134j

  日期：1998.6.1

  Methylation of 2-(2'-pyridyl)indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'-indolenylidene)-1,2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3,3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'-quinolinyl)pyrrole. The importance of the connectivity to pyridine is examined by considering three possible regioisomers, only two of which show tautomeric behavior. The tautomers show strong solvatochromic dependence and good linear behavior. The indoles absorb at shorter wavelengths and are strongly emitting while the tautomers show a strong bathochromic shift and emit only weakly; the salts exhibit intermediate behavior. NMR properties are consistent with contributions from a dipolar and uncharged resonance form while MO calculations indicate that the indole is about 40 kcal/mol more stable than its tautomer.