1-氯-1-甲氧基-3-(4-甲氧基苯基)丙烷 | 122901-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-氯-1-甲氧基-3-(4-甲氧基苯基)丙烷
• 英文名称: 1-Chloro-1-methoxy-3-(4-methoxyphenyl)propane
• 英文别名: 1-(3-Chloro-3-methoxypropyl)-4-methoxybenzene
• CAS: 122901-02-4
• 化学式: C₁₁H₁₅ClO₂
• 分子量: 214.692
• InChiKey: DMUNYBFRORPFPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-氯-1-甲氧基-3-(4-甲氧基苯基)丙烷 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,8-Dihydroxy-10-[3-(4-methoxyphenyl)propylidene]anthracen-9-one
  参考文献：
  名称：

  Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase

  摘要：

  The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of 1,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10(-7) M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.

  DOI：

  10.1021/jm00077a015
• 作为产物：
  描述：

  3-(p-methoxyphenyl)propanal dimethylacetal 在 氯化亚砜 、 乙酰氯 作用下， 生成 1-氯-1-甲氧基-3-(4-甲氧基苯基)丙烷
  参考文献：
  名称：

  Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase

  摘要：

  The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of 1,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10(-7) M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.

  DOI：

  10.1021/jm00077a015

文献信息

• Lifetimes of oxocarbenium ions in aqueous solution from common ion inhibition of the solvolysis of .alpha.-azido ethers by added azide ion
  作者：Tina L. Amyes、William P. Jencks

  DOI：10.1021/ja00202a033

  日期：1989.9

  Determination des constantes de vitesse d'hydration des ions oxocarbeniums intermediaires. Effet des substituants

  Determination des constantes de vitesse d'hydration des ions oxocarbeniums intermediaires。替代物的作用
• Concerted bimolecular substitution reactions of acetal derivatives of propionaldehyde and benzaldehyde
  作者：Tina L. Amyes、William P. Jencks

  DOI：10.1021/ja00202a034

  日期：1989.9
• Absence of a common ion effect on the hydrolysis of an .alpha.-azido ether of an aliphatic aldehyde
  作者：Tina L. Amyes、William P. Jencks

  DOI：10.1021/ja00219a063

  日期：1988.5
• 10-SUBSTITUTED 1,8-DIHYDROXY-9(10H) ANTHRACENONE PHARMACEUTICALS
  申请人：TEVA PHARMACEUTICAL INDUSTRIES LTD.

  公开号：EP0664780A1

  公开（公告）日：1995-08-02
• US5426197A
  申请人：——

  公开号：US5426197A

  公开（公告）日：1995-06-20