1-(2,4-difluorophenyl)pentane-1,4-dione | 908292-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,4-difluorophenyl)pentane-1,4-dione
• CAS: 908292-39-7
• 化学式: C₁₁H₁₀F₂O₂
• 分子量: 212.196
• InChiKey: BONKZRWFJIXXEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,4-difluorophenyl)pentane-1,4-dione 在 溶剂黄146 、 gadolinium(III) trifluoromethanesulfonate 作用下， 以 水 、 乙腈 为溶剂， 反应 6.5h， 生成 (5R)-5-(azidomethyl)-3-(4-(4-((1-(2-bromo-5-fluorophenyl)-5-(2,4-difluorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)oxazolidin-2-one
  参考文献：
  名称：

  Anti-tubercular agents. Part 7: A new class of diarylpyrrole–oxazolidinone conjugates as antimycobacterial agents

  摘要：

  In an effort to discover new anti-tubercular agents, a series of new diarylpyrrole oxazolidinone conjugates have been designed and synthesized. The anti-tubercular activity of these new conjugates (4a-n and 5a-d) against Mycobacterium tuberculosis H(37)Rv and drug resistance strains such as M. tuberculosis Rif(R) and M. tuberculosis XDR are discussed, wherein compound 4i has been found to be the most potent amongst the series. MTT assay was performed on the active conjugates of the series (4b-f, 4i and 5c) against mouse macrophage (J-774) cells to evaluate cytotoxic effects and selective index values. In addition, these conjugates (4a-n and 5a-d) are also tested against a panel of Gram-positive and Gram-negative bacterial strains. The docking studies have been carried out to provide some insight into the mechanism of action for this class of compounds. (C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.03.027
• 作为产物：
  描述：

  2,4-二氟苯甲醛 、 丁烯酮 在 三乙胺 作用下， 反应 5.0h， 生成 1-(2,4-difluorophenyl)pentane-1,4-dione
  参考文献：
  名称：

  Anti-tubercular agents. Part 7: A new class of diarylpyrrole–oxazolidinone conjugates as antimycobacterial agents

  摘要：

  In an effort to discover new anti-tubercular agents, a series of new diarylpyrrole oxazolidinone conjugates have been designed and synthesized. The anti-tubercular activity of these new conjugates (4a-n and 5a-d) against Mycobacterium tuberculosis H(37)Rv and drug resistance strains such as M. tuberculosis Rif(R) and M. tuberculosis XDR are discussed, wherein compound 4i has been found to be the most potent amongst the series. MTT assay was performed on the active conjugates of the series (4b-f, 4i and 5c) against mouse macrophage (J-774) cells to evaluate cytotoxic effects and selective index values. In addition, these conjugates (4a-n and 5a-d) are also tested against a panel of Gram-positive and Gram-negative bacterial strains. The docking studies have been carried out to provide some insight into the mechanism of action for this class of compounds. (C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.03.027

文献信息

• Antimycobacterial Agents. Novel Diarylpyrrole Derivatives of BM212 Endowed with High Activity toward Mycobacterium tuberculosis and Low Cytotoxicity
  作者：Mariangela Biava、Giulio Cesare Porretta、Giovanna Poce、Sibilla Supino、Delia Deidda、Raffaello Pompei、Paola Molicotti、Fabrizio Manetti、Maurizio Botta

  DOI：10.1021/jm0602662

  日期：2006.8.1

  On the basis of suggestions derived either from a pharmacophoric model for antitubercular agents or from a structure-activity relationship analysis of many pyrroles previously described by us, we report here the design and synthesis of new analogues of 1,5-(4-chlorophenyl)-2-methyl-3-(4-methylpiperazin-1-yl)methyl-1H- pyrrole (BM212). Various substituents with different substitution patterns were added to both positions 1 and 5 of the pyrrole nucleus to evaluate their influence on the activity toward Mycobacterium tuberculosis (MTB) and atypical mycobacteria. Biological data showed that, although some nontuberculosis mycobacterial strains were found to be sensitive, MIC values were higher than those found toward MTB. The best compound (1-(4-fluorophenyl)-2-methyl-3-(thiomorpholin-4-yl)methyl-5-(4-methylphenyl)-1H-pyrrole, 5) possessed a MIC of 0.4 mu g/mL (better than BM212 and streptomycin) and a very high protection index (160), better than BM212, isoniazid, and streptomycin ( 6, 128, and 128, respectively). Finally, molecular modeling studies were performed to rationalize the activity of the new compounds in terms of both superposition onto a pharmacophoric model for antitubercular compounds and their hydrophobic character.
• Anti-tubercular agents. Part 7: A new class of diarylpyrrole–oxazolidinone conjugates as antimycobacterial agents
  作者：Ahmed Kamal、P. Swapna、Rajesh V.C.R.N.C. Shetti、Anver Basha Shaik、M.P. Narasimha Rao、Farheen Sultana、Inshad Ali Khan、Sandeep Sharma、Nitin Pal Kalia、Sunil Kumar、Bagul Chandrakant

  DOI：10.1016/j.ejmech.2013.03.027

  日期：2013.6

  In an effort to discover new anti-tubercular agents, a series of new diarylpyrrole oxazolidinone conjugates have been designed and synthesized. The anti-tubercular activity of these new conjugates (4a-n and 5a-d) against Mycobacterium tuberculosis H(37)Rv and drug resistance strains such as M. tuberculosis Rif(R) and M. tuberculosis XDR are discussed, wherein compound 4i has been found to be the most potent amongst the series. MTT assay was performed on the active conjugates of the series (4b-f, 4i and 5c) against mouse macrophage (J-774) cells to evaluate cytotoxic effects and selective index values. In addition, these conjugates (4a-n and 5a-d) are also tested against a panel of Gram-positive and Gram-negative bacterial strains. The docking studies have been carried out to provide some insight into the mechanism of action for this class of compounds. (C) 2013 Published by Elsevier Masson SAS.