4-氨基喹啉-7-甲腈 | 1253790-96-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 4-氨基喹啉-7-甲腈
• 英文名称: 4-aminoquinoline-7-carbonitrile
• CAS: 1253790-96-3
• 化学式: C₁₀H₇N₃
• mdl: MFCD08063215
• 分子量: 169.186
• InChiKey: ULOMPSGOQQSFAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为产物：
  描述：

  间氨基苯甲腈 在 ammonium hydroxide 、 sodium hydroxide 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 二苯醚 、 水 为溶剂， 反应 4.25h， 生成 4-氨基喹啉-7-甲腈
  参考文献：
  名称：

  Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

  摘要：

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.040

文献信息

• Quinoline derivatives
  申请人：——

  公开号：US20030158179A1

  公开（公告）日：2003-08-21

  Compounds of formula I 1 as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 , R 2 , R 3 , A 1 and A 2 have the significance given in claim 1, can be used in the form of pharmaceutical preparations for the treatment or prevention of arthritis, cardiovascular diseases, diabetes, renal failure, eating disorders and obesity.

  具有I1式的化合物以及其药学上可接受的盐和酯，其中R1、R2、R3、A1和A2具有权利要求1中给定的含义，可用于制备药物制剂，用于治疗或预防关节炎、心血管疾病、糖尿病、肾功能衰竭、进食障碍和肥胖症。
• QUINOLINE DERIVATIVES
  申请人：Klug G. Michael

  公开号：US20060063758A1

  公开（公告）日：2006-03-23

  Compounds of formula I as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 , R 2 , R 3 , A 1 and A 2 have the significance given in claim 1, can be used in the form of pharmaceutical preparations for the treatment or prevention of arthritis, cardiovascular diseases, diabetes, renal failure, eating disorders and obesity.

  式I的化合物及其药学上可接受的盐和酯，其中R1、R2、R3、A1和A2具有权利要求1中所给定的含义，可以用作制备药物制剂，用于治疗或预防关节炎、心血管疾病、糖尿病、肾功能衰竭、进食障碍和肥胖症。
• US6787558B2
  申请人：——

  公开号：US6787558B2

  公开（公告）日：2004-09-07
• US7012073B2
  申请人：——

  公开号：US7012073B2

  公开（公告）日：2006-03-14
• US7064134B2
  申请人：——

  公开号：US7064134B2

  公开（公告）日：2006-06-20