3,5-dimethoxy-4-ethylbenzonitrile | 78025-98-6

• 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: 3,5-dimethoxy-4-ethylbenzonitrile
• 英文别名: 4-Ethyl-3,5-dimethoxybenzonitrile
• CAS: 78025-98-6
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: GOLDUADICZGKEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxy-4-ethylbenzonitrile 在 镍 甲酸 、 potassium tert-butylate 、 sodium methylate 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 31.5h， 生成 2,4-diamino-5-(4'-ethyl-3',5'-dimethoxybenzyl)pyrimidine
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 5. 3',5'-Dimethoxy-4'-substituted-benzyl analogs of trimethoprim

  摘要：

  Forty trimethoprim analogues in which the para substituent in the benzene ring was varied were prepared for antibacterial evaluation. All were very potent inhibitors of Escherichia coli dihydrofolate reductase. The similarity of their inhibitory activities strongly suggested that the side chains beyond the first two atoms were not in contact with the enzyme. However, among 38 ether derivatives which varied widely in their bulk and lipophilicity, very few approached trimethoprim in their broad-spectrum in vitro antibacterial activity. The 4'-methyl and 4'-ethyl analogues and the allyloxy and gamma-chloropropoxy ethers had activities fairly close to that of trimethoprim. The two ethers were chosen for further evaluation in vivo. Neither compound quite matched trimethoprim in efficacy in mice, and their half-lives, as well as that of the beta-methoxyethoxy analogue, were found to be shorter in dogs.

  DOI：

  10.1021/jm00140a005
• 作为产物：
  描述：

  2,6-二甲氧基苯乙酮 在 palladium on activated charcoal 1,4-二氧六环 、 Cu₂(CN)2 、 氰化钠 、 氨 、 氢气 、 溴 、 亚硝酸 、 ferric nitrate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 5.0h， 生成 3,5-dimethoxy-4-ethylbenzonitrile
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 5. 3',5'-Dimethoxy-4'-substituted-benzyl analogs of trimethoprim

  摘要：

  Forty trimethoprim analogues in which the para substituent in the benzene ring was varied were prepared for antibacterial evaluation. All were very potent inhibitors of Escherichia coli dihydrofolate reductase. The similarity of their inhibitory activities strongly suggested that the side chains beyond the first two atoms were not in contact with the enzyme. However, among 38 ether derivatives which varied widely in their bulk and lipophilicity, very few approached trimethoprim in their broad-spectrum in vitro antibacterial activity. The 4'-methyl and 4'-ethyl analogues and the allyloxy and gamma-chloropropoxy ethers had activities fairly close to that of trimethoprim. The two ethers were chosen for further evaluation in vivo. Neither compound quite matched trimethoprim in efficacy in mice, and their half-lives, as well as that of the beta-methoxyethoxy analogue, were found to be shorter in dogs.

  DOI：

  10.1021/jm00140a005

文献信息

• ROTH, B.;AIG, E.;RAUCKMAN, B. S.;STRELITZ, J. Z.;PHILLIPS, A. P.;FERONE, +, J. MED. CHEM., 1981, 24, N 8, 933-941
  作者：ROTH, B.、AIG, E.、RAUCKMAN, B. S.、STRELITZ, J. Z.、PHILLIPS, A. P.、FERONE, +

  DOI：——

  日期：——
• 2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 5. 3',5'-Dimethoxy-4'-substituted-benzyl analogs of trimethoprim
  作者：Barbara Roth、Edward Aig、Barbara S. Rauckman、Justina Z. Strelitz、Arthur P. Phillips、Robert Ferone、S. R. M. Bushby、Carl W. Sigel

  DOI：10.1021/jm00140a005

  日期：1981.8

  Forty trimethoprim analogues in which the para substituent in the benzene ring was varied were prepared for antibacterial evaluation. All were very potent inhibitors of Escherichia coli dihydrofolate reductase. The similarity of their inhibitory activities strongly suggested that the side chains beyond the first two atoms were not in contact with the enzyme. However, among 38 ether derivatives which varied widely in their bulk and lipophilicity, very few approached trimethoprim in their broad-spectrum in vitro antibacterial activity. The 4'-methyl and 4'-ethyl analogues and the allyloxy and gamma-chloropropoxy ethers had activities fairly close to that of trimethoprim. The two ethers were chosen for further evaluation in vivo. Neither compound quite matched trimethoprim in efficacy in mice, and their half-lives, as well as that of the beta-methoxyethoxy analogue, were found to be shorter in dogs.