4-[4-(4-甲基哌嗪-1-基)丁氧基]苯甲醛 | 919088-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[4-(4-甲基哌嗪-1-基)丁氧基]苯甲醛
• 英文名称: 4-[4-(4-Methyl-piperazin-1-yl)-butoxy]-benzaldehyde
• 英文别名: 4-[4-(4-Methylpiperazin-1-yl)butoxy]benzaldehyde；4-[4-(4-methylpiperazin-1-yl)butoxy]benzaldehyde
• CAS: 919088-63-4
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: WFNABXNQTTUSHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[4-(4-甲基哌嗪-1-基)丁氧基]苯甲醛 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 (2E,5E)-2,5-bis(4-(4-(4-methylpiperazin-1-yl)butoxy)benzylidene)cyclopentanone dihydrochloride
  参考文献：
  名称：

  Synthesis of novel monocarbonyl curcuminoids, evaluation of their efficacy against MRSA, including ex vivo infection model and their mechanistic studies

  摘要：

  In continuation of our effort to improve the physiological stability and the antibacterial activity of curcuminoids against drug-resistant bacteria, a series of novel monocarbonyl curcuminoids were synthesized and screened for antibacterial activity against S. aureus and E. coli strains. These curcuminoids showed potent antibacterial activity against both methicillin-sensitive and methicillin-resistant strains of S. aureus with MIC values 2-8 and 4-16 mu g/mL, respectively. They also exhibited moderate potency against E. coll. strains. The four most active curcuminoids (7d, 7i, 7m, and 7p) were on further investigation found to be very stable under physiological conditions, non-hemolytic, and non-toxic toward mammalian cells up to 150 mu g/mL concentration. Mechanistic studies revealed that these curcuminoids displayed potent bactericidal activity by targeting cell membranes. Further, in an ex vivo mammalian co-culture infection model study, remarkably, the curcuminoids 7i and 7p were able to clear the internalized bacteria in mammalian cells and the activity was found to be superior to conventional antibiotics such as vancomycin and linezolid. Therefore, the present study affords us water-soluble, stable, non-toxic curcuminoids that may serve as lead molecules for development as antibacterial agents against MRSA infections. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112276
• 作为产物：
  描述：

  N-甲基哌嗪 、 4-(4-chlorobutoxy)benzaldehyde 在 sodium carbonate 、 potassium iodide 作用下， 以 正丁醇 为溶剂， 生成 4-[4-(4-甲基哌嗪-1-基)丁氧基]苯甲醛
  参考文献：
  名称：

  Identification of 2-arylbenzimidazoles as potent human histamine H4 receptor ligands

  摘要：

  A series of 2-arylbenzimidazoles was synthesized and found to bind with high affinity to the human histamine H(4) receptor. Structure-activity relationships were investigated through library preparation and evaluation as well as traditional medicinal chemistry approaches, leading to the discovery of compounds with single-digit nanomolar affinity for the H(4) receptor.

  DOI：

  10.1016/j.bmcl.2006.08.117

文献信息

• Synthesis of novel monocarbonyl curcuminoids, evaluation of their efficacy against MRSA, including ex vivo infection model and their mechanistic studies
  作者：Gagandeep、Prince Kumar、Shamseer Kulangara Kandi、Kasturi Mukhopadhyay、Diwan S. Rawat

  DOI：10.1016/j.ejmech.2020.112276

  日期：2020.6

  In continuation of our effort to improve the physiological stability and the antibacterial activity of curcuminoids against drug-resistant bacteria, a series of novel monocarbonyl curcuminoids were synthesized and screened for antibacterial activity against S. aureus and E. coli strains. These curcuminoids showed potent antibacterial activity against both methicillin-sensitive and methicillin-resistant strains of S. aureus with MIC values 2-8 and 4-16 mu g/mL, respectively. They also exhibited moderate potency against E. coll. strains. The four most active curcuminoids (7d, 7i, 7m, and 7p) were on further investigation found to be very stable under physiological conditions, non-hemolytic, and non-toxic toward mammalian cells up to 150 mu g/mL concentration. Mechanistic studies revealed that these curcuminoids displayed potent bactericidal activity by targeting cell membranes. Further, in an ex vivo mammalian co-culture infection model study, remarkably, the curcuminoids 7i and 7p were able to clear the internalized bacteria in mammalian cells and the activity was found to be superior to conventional antibiotics such as vancomycin and linezolid. Therefore, the present study affords us water-soluble, stable, non-toxic curcuminoids that may serve as lead molecules for development as antibacterial agents against MRSA infections. (C) 2020 Elsevier Masson SAS. All rights reserved.
• Identification of 2-arylbenzimidazoles as potent human histamine H4 receptor ligands
  作者：Alice Lee-Dutra、Kristen L. Arienti、Daniel J. Buzard、Michael D. Hack、Haripada Khatuya、Pragnya J. Desai、Steven Nguyen、Robin L. Thurmond、Lars Karlsson、James P. Edwards、J. Guy Breitenbucher

  DOI：10.1016/j.bmcl.2006.08.117

  日期：2006.12

  A series of 2-arylbenzimidazoles was synthesized and found to bind with high affinity to the human histamine H(4) receptor. Structure-activity relationships were investigated through library preparation and evaluation as well as traditional medicinal chemistry approaches, leading to the discovery of compounds with single-digit nanomolar affinity for the H(4) receptor.