(2E,5E)-2,5-bis(4-(4-(azepan-1-yl)butoxy)-3-methoxybenzylidene)cyclopentanone | 1416896-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,5E)-2,5-bis(4-(4-(azepan-1-yl)butoxy)-3-methoxybenzylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis[[4-[4-(azepan-1-yl)butoxy]-3-methoxy-phenyl]methylene]cyclopentanone；(2E,5E)-2,5-bis[[4-[4-(azepan-1-yl)butoxy]-3-methoxyphenyl]methylidene]cyclopentan-1-one
• CAS: 1416896-83-7
• 化学式: C₄₁H₅₈N₂O₅
• 分子量: 658.922
• InChiKey: IRHXVOMOVNMQBR-ZRBLUKEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2E,5E)-2,5-bis(4-(4-(azepan-1-yl)butoxy)-3-methoxybenzylidene)cyclopentanone 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2E,5E)-2,5-bis(4-(4-(azepan-1-yl)butoxy)-3-methoxybenzylidene)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：

  4-(4-bromobutoxy)-3-methoxybenzaldehyde 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 (2E,5E)-2,5-bis(4-(4-(azepan-1-yl)butoxy)-3-methoxybenzylidene)cyclopentanone
  参考文献：
  名称：

  姜黄素新单羰基类似物的合成，抗疟活性和细胞毒性潜力

  摘要：

  已经设计，合成并测试了一系列姜黄素的新型单羰基类似物，它们针对Molt4，HeLa，PC3，DU145和KB癌细胞系的活性。其中六个类似物显示出对这些细胞系的有效细胞毒性，IC 50值低于1μM，优于美国FDA批准的阿霉素。在体外抗疟疾筛选中，还发现几种类似物对恶性疟原虫的CQ耐药（W2克隆）和CQ敏感（D6）菌株均具有活性。这种活性水平需要进一步研究这些化合物作为抗癌药和抗疟药的发展。

  DOI：

  10.1016/j.bmcl.2012.11.004

文献信息

• Synthesis, antimalarial activity and cytotoxic potential of new monocarbonyl analogues of curcumin
  作者：Sunny Manohar、Shabana I. Khan、Shamseer Kulangara Kandi、Kranthi Raj、Guojing Sun、Xiaochuan Yang、Angie D. Calderon Molina、Nanting Ni、Binghe Wang、Diwan S. Rawat

  DOI：10.1016/j.bmcl.2012.11.004

  日期：2013.1

  A series of novel monocarbonyl analogues of curcumin have been designed, synthesized and tested for their activity against Molt4, HeLa, PC3, DU145 and KB cancer cell lines. Six of the analogues showed potent cytotoxicity towards these cell lines with IC50 values below 1 μM, which is better than doxorubicin, a US FDA approved drug. Several analogues were also found to be active against both CQ-resistant

  已经设计，合成并测试了一系列姜黄素的新型单羰基类似物，它们针对Molt4，HeLa，PC3，DU145和KB癌细胞系的活性。其中六个类似物显示出对这些细胞系的有效细胞毒性，IC 50值低于1μM，优于美国FDA批准的阿霉素。在体外抗疟疾筛选中，还发现几种类似物对恶性疟原虫的CQ耐药（W2克隆）和CQ敏感（D6）菌株均具有活性。这种活性水平需要进一步研究这些化合物作为抗癌药和抗疟药的发展。
• 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.