N-[3,3,6,6-tetramethyl-1,8-dioxo-9-(2,3,4-trimethoxyphenyl)-4,5,7,9-tetrahydro-2H-acridin-10-yl]pyridine-4-carboxamide | 1292782-02-5

• 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: N-[3,3,6,6-tetramethyl-1,8-dioxo-9-(2,3,4-trimethoxyphenyl)-4,5,7,9-tetrahydro-2H-acridin-10-yl]pyridine-4-carboxamide
• CAS: 1292782-02-5
• 化学式: C₃₂H₃₇N₃O₆
• 分子量: 559.662
• InChiKey: LDZYDWFSBODKIT-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  异烟肼 、 5,5-二甲基-1,3-环己二酮 、 2,3,4-三甲氧基苯甲醛 在 4-十二烷基苯磺酸 作用下， 以 水 为溶剂， 以76%的产率得到N-[3,3,6,6-tetramethyl-1,8-dioxo-9-(2,3,4-trimethoxyphenyl)-4,5,7,9-tetrahydro-2H-acridin-10-yl]pyridine-4-carboxamide
  参考文献：
  名称：

  Microwave assisted one-pot synthesis of highly potent novel isoniazid analogues

  摘要：

  A series of novel isoniazid (INH) analogues were synthesized by microwave assisted one pot reaction of INH, various benzaldehydes and dimedone in water with catalytic amount of DBSA. The synthesized compounds were evaluated for their anti-TB activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant Mycobacterium tuberculosis (MDR-TB). Among the 29 compounds, compound N-[9-[2-(benzyloxy)phenyl]-3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-10(1H)-acridinyl] isonicotinamide (12) inhibited MTB with MIC of <0.17 mu M and MDR-TB with MIC of 0.69 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.122

文献信息

• Microwave assisted one-pot synthesis of highly potent novel isoniazid analogues
  作者：Thimmappa H. Manjashetty、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2011.01.122

  日期：2011.4

  A series of novel isoniazid (INH) analogues were synthesized by microwave assisted one pot reaction of INH, various benzaldehydes and dimedone in water with catalytic amount of DBSA. The synthesized compounds were evaluated for their anti-TB activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant Mycobacterium tuberculosis (MDR-TB). Among the 29 compounds, compound N-[9-[2-(benzyloxy)phenyl]-3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-10(1H)-acridinyl] isonicotinamide (12) inhibited MTB with MIC of <0.17 mu M and MDR-TB with MIC of 0.69 mu M. (C) 2011 Elsevier Ltd. All rights reserved.