3-methoxy-9-methyl-5,6-dihydrobenzo[c]acridine | 72019-94-4

• 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: 3-methoxy-9-methyl-5,6-dihydrobenzo[c]acridine
• 英文别名: 3-methoxy-9-methyl-5,6-dihydro-benz[c]acridine；3-Methoxy-9-methyl-5,6-dihydro-benz[c]acridin
• CAS: 72019-94-4
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: VSAMVXZUAGQMSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-甲氧基-1-萘满酮 在 氢氧化钾 作用下， 生成 3-methoxy-9-methyl-5,6-dihydrobenzo[c]acridine
  参考文献：
  名称：

  Buu-Hoi et al., Journal of the Chemical Society, 1952, p. 279

  摘要：

  DOI：

文献信息

• Microwave-assisted one-pot synthesis of steroid–quinoline hybrids and an evaluation of their antiproliferative activities on gynecological cancer cell lines
  作者：Ádám Baji、András Gyovai、János Wölfling、Renáta Minorics、Imre Ocsovszki、István Zupkó、Éva Frank

  DOI：10.1039/c6ra03910c

  日期：——

  Novel D- and A-ring-fused quinolines in the estrone and 5α-androstane series were efficiently synthesized from the corresponding β-chlorovinyl aldehydes with different arylamines in DMF under microwave irradiation. The rates of the one-pot catalyst-free syntheses and the yields of the desired products were found to be affected significantly by the electronic and steric character of the substituents

  在微波辐射下，由DMF中相应的β-氯乙烯基醛与不同的芳基胺合成了雌酮和5α-雄烷酮系列的新型D-环和A-环稠合喹啉。发现一锅无催化剂合成的速率和所需产物的产率受到苯胺上取代基的电子和空间特性以及甾烷骨架的环D和A的不同反应性的显着影响。所有合成的化合物都在人宫颈癌（C33A，HeLa和SiHa）和乳腺癌（MCF-7，MDA-MB-231，MDA-MB-361和T47D）癌细胞系中进行了体外测试，以研究其在肝癌中的抗增殖活性。体外。通过流式细胞术，caspase-3活性测定和显微镜技术获得了最有效的化合物14c的细胞周期阻滞和细胞凋亡诱导的证据。
• A microwave promoted solvent-free approach to steroidal quinolines and their in vitro evaluation for antimicrobial activities
  作者：Shyamalee Gogoi、Kommuri Shekarrao、Aparajita Duarah、Tarun C. Bora、Sanjib Gogoi、Romesh C. Boruah

  DOI：10.1016/j.steroids.2012.08.008

  日期：2012.11

  The preparation of A-ring and D-ring fused steroidal quinolines is described from one-pot reaction of steroidal beta-bromovinylaldehydes and arylamines in solvent-free and catalyst-free condition under microwave irradiation. The antimicrobial activities of the compounds were tested by agar diffusion assay and broth macro dilution method. Compounds 7a, 7e and 7g-h showed promising in vitro activity when tested against fungal pathogen Aspergillus niger whereas compounds 7e-h and 7j showed promising activity when tested against fungal pathogen Candida albicans. Compounds 7c and 7f showed potent inhibition against the growth of Gram negative bacteria Pseudomonas aeruginosa and compounds 7e, 7g-h and 7j inhibited the growth of tested Gram positive bacteria Bacillus subtilis and Staphylococcus aureus. (C) 2012 Elsevier Inc. All rights reserved.