N,N-bs(4,6-dimethyl-3-oxo-2,3-dihydroisothiazolo[5,4-b]pyridin-2-ylmethyl)-N-3,4-methylenodioxybenzylamine | 1449783-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N,N-bs(4,6-dimethyl-3-oxo-2,3-dihydroisothiazolo[5,4-b]pyridin-2-ylmethyl)-N-3,4-methylenodioxybenzylamine
• 英文别名: 2-[[1,3-Benzodioxol-5-ylmethyl-[(4,6-dimethyl-3-oxo-[1,2]thiazolo[5,4-b]pyridin-2-yl)methyl]amino]methyl]-4,6-dimethyl-[1,2]thiazolo[5,4-b]pyridin-3-one；2-[[1,3-benzodioxol-5-ylmethyl-[(4,6-dimethyl-3-oxo-[1,2]thiazolo[5,4-b]pyridin-2-yl)methyl]amino]methyl]-4,6-dimethyl-[1,2]thiazolo[5,4-b]pyridin-3-one
• CAS: 1449783-99-6
• 化学式: C₂₆H₂₅N₅O₄S₂
• 分子量: 535.648
• InChiKey: KJMQKLTZFTZFNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧基苄胺 、 2-hydroxymethyl-4,6-dimethylisothiazolo[5,4-b]pyridin-3(2H)-one 以 乙醇 为溶剂， 反应 2.0h， 以48.5%的产率得到N,N-bs(4,6-dimethyl-3-oxo-2,3-dihydroisothiazolo[5,4-b]pyridin-2-ylmethyl)-N-3,4-methylenodioxybenzylamine
  参考文献：
  名称：

  Synthesis of novel isothiazolopyridines and their in vitro evaluation against Mycobacterium and Propionibacterium acnes

  摘要：

  In this paper we describe synthesis, structures and some physicochemical properties of 20 isothiazolopyridines 8-13 substituted differently into an isothiazole ring as well as their in vitro antibacterial assays against Mycobacterium tuberculosis H37Rv, Mycobacterium fortuitum PCM 672 and Propionibacterium acnes PCM 2400. Compound 13a was found to be the most active derivative against M. tuberculosis H37Rv, demonstrating 100% growth inhibition of microorganisms in the primary screen (minimum inhibitory concentration [MIC] 6.25 mu g/mL). Nineteen of the prepared compounds were evaluated against M. fortuitum PCM 672 and P. acnes PCM 2400 and only compounds 9 and 12d exhibited excellent activity against individual strains of microorganisms with MIC90 <1 mu g/mL. The inhibitory action of the remaining isothiazolopyridines towards the tested strains of the microorganism was low, absent, or a non-linear correlation prohibited accurate determination of MIC values. Unexpectedly, seven of the remaining isothiazolopyridines tested against M. fortuitum and P. acnes stimulated growth of the microorganisms in the range 10-50% or even more (10b) under experimental conditions. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.027

文献信息

• Synthesis of novel isothiazolopyridines and their in vitro evaluation against Mycobacterium and Propionibacterium acnes
  作者：Wiesław Malinka、Piotr Świątek、Małgorzata Śliwińska、Bogumiła Szponar、Andrzej Gamian、Zbigniew Karczmarzyk、Andrzej Fruziński

  DOI：10.1016/j.bmc.2013.06.027

  日期：2013.9

  In this paper we describe synthesis, structures and some physicochemical properties of 20 isothiazolopyridines 8-13 substituted differently into an isothiazole ring as well as their in vitro antibacterial assays against Mycobacterium tuberculosis H37Rv, Mycobacterium fortuitum PCM 672 and Propionibacterium acnes PCM 2400. Compound 13a was found to be the most active derivative against M. tuberculosis H37Rv, demonstrating 100% growth inhibition of microorganisms in the primary screen (minimum inhibitory concentration [MIC] 6.25 mu g/mL). Nineteen of the prepared compounds were evaluated against M. fortuitum PCM 672 and P. acnes PCM 2400 and only compounds 9 and 12d exhibited excellent activity against individual strains of microorganisms with MIC90 <1 mu g/mL. The inhibitory action of the remaining isothiazolopyridines towards the tested strains of the microorganism was low, absent, or a non-linear correlation prohibited accurate determination of MIC values. Unexpectedly, seven of the remaining isothiazolopyridines tested against M. fortuitum and P. acnes stimulated growth of the microorganisms in the range 10-50% or even more (10b) under experimental conditions. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.