4-((6-methyl-2-oxo-2H-chromen-4-yl)methoxy)benzaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-((6-methyl-2-oxo-2H-chromen-4-yl)methoxy)benzaldehyde
• 英文别名: 4-(6-methyl-2-oxo-2H-chromen-4-ylmethoxy)-benzaldehyde；4-(6-methyl-2-oxo-2H-chromen-4-ylmethoxy)benzaldehyde；4-[(6-methyl-2-oxochromen-4-yl)methoxy]benzaldehyde
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: NRRFKFXOTBDXKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((6-methyl-2-oxo-2H-chromen-4-yl)methoxy)benzaldehyde 、 2-氨基苯硫醇 以 二甲基亚砜 为溶剂， 反应 8.0h， 以92%的产率得到4-(4-benzothiazol-2-yl-phenoxymethyl)-6-methyl-chromen-2-one
  参考文献：
  名称：

  The Synthesis and Biological Evaluation of Regioisomeric Benzothiazolyl Coumarins

  摘要：

  Various 4-aryloxymethylcoumarins have been obtained by the r.t. allylic substitution with formylphenols. These have been further reacted with o-aminothiophenol resulting in the formation of a benzothiazole skeleton. These compounds have been synthesised with a view to study their potential as microbial growth inhibitors. Comparative studies on the spectral and antimicrobial activities have also been carried out.

  DOI：

  10.1080/10426500600614550
• 作为产物：
  描述：

  对羟基苯甲醛 、 6-methyl-4-bromomethylcoumarin 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.5h， 生成 4-((6-methyl-2-oxo-2H-chromen-4-yl)methoxy)benzaldehyde
  参考文献：
  名称：

  新型氮杂环丁酮衍生物的合成、体外抗菌和细胞毒性研究

  摘要：

  开发新型抗菌药物在现代制药行业中变得越来越重要。由 4-溴甲基香豆素 1a-e 合成了一系列新型 3-氯-4-[4-(2-oxo-2H-chromen-4-基甲氧基)苯基]-1-苯基氮杂环丁烷-2-ones 5a-o 和4-芳基亚氨基甲基苯酚 3a-c。筛选了这些化合物对两种革兰氏阳性菌（金黄色葡萄球菌和万古霉素耐药肠球菌）和两种革兰氏阴性菌（大肠杆菌和痢疾志贺氏菌）的体外抗菌活性以及对烟曲霉、白色念珠菌和青霉菌的抗真菌活性. 结果表明，化合物 5c、5f、5h、5j 和 5m 对一组微生物显示出极好的活性。还进行了盐水虾生物测定以研究它们的体外细胞毒性和两种化合物，5h 和 5m 分别具有 LD50 = 7.154×10-4 M 和 5.782×10-4 M，显示出对卤虫的有效细胞毒活性。讨论了香豆素部分中氯基团的存在及其对抗菌、抗真菌和细胞毒活性的影响。所有新合成的化合物均通过元素分析

  DOI：

  10.1002/ardp.200900188

文献信息

• Synthesis,<i>in-vitro</i>Antimicrobial and Cytotoxic Studies of Novel Azetidinone Derivatives
  作者：Rangappa S. Keri、Kallappa M. Hosamani、Harisha S. Reddy、Ramya V. Shingalapur

  DOI：10.1002/ardp.200900188

  日期：2010.3.4

  brine‐shrimp bioassay was also carried out to study their in‐vitro cytotoxic properties and two compounds, 5h and 5m, possessing LD50 = 7.154×10–4 M and 5.782×10–4 M, respectively, displayed potent cytotoxic activity against Artemia salina. The presence of a chlorine group in the coumarin moiety, its effect on their antibacterial, antifungal, and cytotoxic activities is discussed. All newly synthesized

  开发新型抗菌药物在现代制药行业中变得越来越重要。由 4-溴甲基香豆素 1a-e 合成了一系列新型 3-氯-4-[4-(2-oxo-2H-chromen-4-基甲氧基)苯基]-1-苯基氮杂环丁烷-2-ones 5a-o 和4-芳基亚氨基甲基苯酚 3a-c。筛选了这些化合物对两种革兰氏阳性菌（金黄色葡萄球菌和万古霉素耐药肠球菌）和两种革兰氏阴性菌（大肠杆菌和痢疾志贺氏菌）的体外抗菌活性以及对烟曲霉、白色念珠菌和青霉菌的抗真菌活性. 结果表明，化合物 5c、5f、5h、5j 和 5m 对一组微生物显示出极好的活性。还进行了盐水虾生物测定以研究它们的体外细胞毒性和两种化合物，5h 和 5m 分别具有 LD50 = 7.154×10-4 M 和 5.782×10-4 M，显示出对卤虫的有效细胞毒活性。讨论了香豆素部分中氯基团的存在及其对抗菌、抗真菌和细胞毒活性的影响。所有新合成的化合物均通过元素分析
• RETRACTED: 2-Azetidinone derivatives: Design, synthesis, in vitro anti-microbial, cytotoxic activities and DNA cleavage study
  作者：Rangappa S. Keri、Kallappa M. Hosamani、Ramya V. Shingalapur、Harisha R. Seetharama Reddy

  DOI：10.1016/j.ejmech.2009.09.011

  日期：2009.12

  A novel series of 3-chloro-4-[4-(2-oxo-2H-chromen-4-ylmethoxy)-phenyl]-1-phenyl-azetidin-2-one derivatives (5a-j) have been synthesized from 4-aryloxymethylcoumarins (la-e) and 4-aryliminomethylphenols (3a-b). The title compounds were screened for their in vitro anti-bacterial and anti-fungal activities. Results revealed that, compounds (5c), (5f), (5h) and (5j) showed excellent anti-microbial activity against a panel of microorganisms. Brine shrimp bioassay was also carried out to study their in vitro cytotoxic properties among which (5h) and (5j) displayed potent cytotoxic activity against Artemia salina. The DNA cleavage activity of some compounds was studied by agarose gel electrophoresis method. All synthesized compounds were characterized using IR, H-1 NMR, C-13 NMR, MS and elemental analysis. (C) 2009 Elsevier Masson SAS. All rights reserved.
• A facile and expeditious approach for the synthesis of 2-azetidinone derivatives via a multicomponent reaction
  作者：Rangappa S. Keri、Kallappa M. Hosamani

  DOI：10.1007/s00706-010-0342-0

  日期：2010.8

  New organic reactions allow chemical transformations which were previously unknown. Therefore, new reactions are important contributions to progress in the field of organic synthesis. Herein, we are reporting a simple, one-pot, efficient three-component synthesis of novel 3-chloro-4-[4-(2-oxo-2H-chromen-4-ylmethoxy)phenyl]-1-phenylazetidin-2-one derivatives using 4-(2-oxo-2H-chromen-4-ylmethoxy)benzaldehydes, anilines, and chloroacetyl chloride in the presence of triethyl amine as a catalyst under different conditions. Taking into account environmental and economic considerations, the protocol presented here has the merits of simple operation, convenient work-up, being environmentally benign, and providing good yields. The synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, MS, and elemental analysis.
• Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety
  作者：Rangappa S. Keri、Kallappa M. Hosamani、Ramya V. Shingalapur、Mallinath H. Hugar

  DOI：10.1016/j.ejmech.2010.02.048

  日期：2010.6

  A novel series of 4-[4-(6-phenyl-pyrimidin-4-yl)-phenoxymethyl]-chromen-2-ones [5-7(a e)] were synthesized from various 4-bromomethyl coumarins 1(a e). The synthesized compounds were screened for In-vivo analgesic and anti-pyretic activities at a dose of 25 and 100 mg/kg body weight (b w), respectively. Among them, compounds 5(d), 6(c) and 7(d) exhibited significant analgesic activity comparable with standard drug analgin using Tail-flick model. Compounds 5(a) and 7(a d) showed significant anti-pyretic activities comparable with standard drug aspirin using yeast-induced pyrexia model. DNA cleavage study by agarose gel electrophoresis method was also studied. Qualitative SAR studies indicate that, compounds with amino group at 2-position of pyrimidine ring enhances analgesic and anti-pyretic activities and compounds with hydroxyl and till group at 2-position of pyrimidine ring increase DNA cleavage activities.
• The Synthesis and Biological Evaluation of Regioisomeric Benzothiazolyl Coumarins
  作者：K. Shivashankar、Manohar V. Kulkarni、Lokesh A. Shastri、Vijaykumar P. Rasal、Sandur V. Rajendra

  DOI：10.1080/10426500600614550

  日期：2006.9.1

  Various 4-aryloxymethylcoumarins have been obtained by the r.t. allylic substitution with formylphenols. These have been further reacted with o-aminothiophenol resulting in the formation of a benzothiazole skeleton. These compounds have been synthesised with a view to study their potential as microbial growth inhibitors. Comparative studies on the spectral and antimicrobial activities have also been carried out.