10-oxiranylmethyl-9-oxo-9,10-dihydro-acridine-4-carboxylic acid | 1167990-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-oxiranylmethyl-9-oxo-9,10-dihydro-acridine-4-carboxylic acid
• 英文别名: 10-(Oxiran-2-ylmethyl)-9-oxoacridine-4-carboxylic acid
• CAS: 1167990-20-6
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: SCESBQRFSISFDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10-oxiranylmethyl-9-oxo-9,10-dihydro-acridine-4-carboxylic acid 、 二乙胺 反应 0.12h， 以67%的产率得到10-(3-diethylamino-2-hydroxypropyl)-9-oxo-9,10-dihydroacridine-4-carboxylic acid
  参考文献：
  名称：

  Targeting efflux pumps—In vitro investigations with acridone derivatives and identification of a lead molecule for MDR modulation

  摘要：

  To search multi drug resistance modulators, acridones carrying hydroxyl amine substituent at N-10 and COOH/Cl at C-4 were investigated for their interactions with the three components of efflux pump viz. P-gp, ATP, and Mg2+. Experimental and theoretical results indicated that the compounds with COOH group at C-4 interact with P-gp and Mg2+ while other set of compounds with Cl at C-4 interact with ATP and Mg2+. Spot assay and R6G influx/efflux assay of compound 3 using Candida albicans showed decrease in the fungal growth and efflux of R6G, respectively, in presence of compound 3 suggesting the suitability of this compound for MDR modulation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.003
• 作为产物：
  描述：

  羟甲基环丙烷 、 4-羧基-9-茚酮 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 以65%的产率得到10-oxiranylmethyl-9-oxo-9,10-dihydro-acridine-4-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and evaluations of acridone derivatives using Candida albicans—Search for MDR modulators led to the identification of an anti-candidiasis agent

  摘要：

  In order to search for MDR modulators, rationally designed acridone derivatives were investigated for their effect on influx or efflux of Rhodamine6G (R6G) in CAI4 cells. Results of these investigations indicate that in presence of compound 12, inhibition of growth of CAI4 cells and also an increased influx/efflux of R6G in CAI4 cells have been observed. This seems to be occurring due to the cell wall rupturing of Candida albicans. Compound 12 may be a suitable candidate for candidiasis therapy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.026

文献信息

• Design, synthesis and evaluations of acridone derivatives using Candida albicans—Search for MDR modulators led to the identification of an anti-candidiasis agent
  作者：Palwinder Singh、Jatinder Kaur、Bhawna Yadav、Sneha Sudha Komath

  DOI：10.1016/j.bmc.2009.04.026

  日期：2009.6

  In order to search for MDR modulators, rationally designed acridone derivatives were investigated for their effect on influx or efflux of Rhodamine6G (R6G) in CAI4 cells. Results of these investigations indicate that in presence of compound 12, inhibition of growth of CAI4 cells and also an increased influx/efflux of R6G in CAI4 cells have been observed. This seems to be occurring due to the cell wall rupturing of Candida albicans. Compound 12 may be a suitable candidate for candidiasis therapy. (C) 2009 Elsevier Ltd. All rights reserved.
• Targeting efflux pumps—In vitro investigations with acridone derivatives and identification of a lead molecule for MDR modulation
  作者：Palwinder Singh、Jatinder Kaur、Bhawna Yadav、Sneha Sudha Komath

  DOI：10.1016/j.bmc.2010.05.003

  日期：2010.6.15

  To search multi drug resistance modulators, acridones carrying hydroxyl amine substituent at N-10 and COOH/Cl at C-4 were investigated for their interactions with the three components of efflux pump viz. P-gp, ATP, and Mg2+. Experimental and theoretical results indicated that the compounds with COOH group at C-4 interact with P-gp and Mg2+ while other set of compounds with Cl at C-4 interact with ATP and Mg2+. Spot assay and R6G influx/efflux assay of compound 3 using Candida albicans showed decrease in the fungal growth and efflux of R6G, respectively, in presence of compound 3 suggesting the suitability of this compound for MDR modulation. (C) 2010 Elsevier Ltd. All rights reserved.