3-[2-(4-Fluorophenyl)hydrazinyl]-5,5-dimethylcyclohex-2-en-1-one | 1371632-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[2-(4-Fluorophenyl)hydrazinyl]-5,5-dimethylcyclohex-2-en-1-one
• CAS: 1371632-05-1
• 化学式: C₁₄H₁₇FN₂O
• 分子量: 248.3
• InChiKey: WVMWVCCMVVGZBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-(4-Fluorophenyl)hydrazinyl]-5,5-dimethylcyclohex-2-en-1-one 、 2,6-二氯喹啉-3-甲醛 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 以74%的产率得到2-amino-4-(2,6-dichloro(3-quinolyl))-7,7-dimethyl-5-oxo-1-(4-fluorophenylamino)-1,4,6,7,8-pentahydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  New N-arylamino biquinoline derivatives: Synthesis, antimicrobial, antituberculosis, and antimalarial evaluation

  摘要：

  A new series of N-arylamino biquinoline derivatives 5a-x were synthesized by reaction of 2-chloro-3-formyl quinolines 2a-d with malononitrile and various enhydrazinoketones 4a-f in absolute ethanol. The newly synthesized compounds were evaluated for their in vitro antimicrobial activity against a representative panel of pathogenic strains and antituberculosis activity against Mycobacterium tuberculosis H37Rv. Compounds Sh and Ss exhibited excellent antibacterial activity and some of the compounds demonstrated moderate antituberculosis activities compared with the first line drugs. The compounds were evaluated in vitro for their activity against the growth of Plasmodium falciparum, the malaria causing parasite. Some of them showed antimalarial activity with IC50 values as low as 0.005-0.009 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.004
• 作为产物：
  描述：

  4-氟苯肼盐酸盐 、 5,5-二甲基-1,3-环己二酮 以 水 为溶剂， 反应 6.0h， 生成 3-[2-(4-Fluorophenyl)hydrazinyl]-5,5-dimethylcyclohex-2-en-1-one
  参考文献：
  名称：

  Green synthesis and pharmacological screening of polyhydroquinoline derivatives bearing a fluorinated 5-aryloxypyrazole nucleus

  摘要：

  绿色合成，生物评价和带有氟化5-芳氧吡唑核的多羟基喹啉骨架的结构活性关系研究。

  DOI：

  10.1039/c5ra00388a

文献信息

• New N-arylamino biquinoline derivatives: microwave-assisted synthesis and their antimicrobial activities
  作者：Nimesh M. Shah、Manish P. Patel、Ranjan G. Patel

  DOI：10.1007/s00044-012-0031-0

  日期：2013.1

  A new series of N-arylamino biquinoline derivatives 5a–x were synthesized under microwave irradiation technique in good yields compared with conventional method and screened for their antimicrobial activity. All the synthesized compounds have been established by elemental analysis, IR, 1H NMR, 13C NMR and mass spectral data. In vitro antimicrobial activity was carried out against three Gram-positive

  与常规方法相比，在微波辐射技术下以高收率合成了一系列新的N-芳基氨基联喹啉衍生物5a – x，并对其抗菌活性进行了筛选。通过元素分析，IR，1 H NMR，13 C NMR和质谱数据确定了所有合成的化合物。对三种革兰氏阳性菌（枯草芽孢杆菌，破伤风梭菌，肺炎链球菌），三种革兰氏阴性菌（大肠杆菌，鼠伤寒沙门氏菌，霍乱弧菌）进行了体外抗菌活性）和两种真菌（烟曲霉，白色念珠菌）采用肉汤微量稀释法。在研究的化合物中，化合物5u对肺炎链球菌和伤寒沙门氏菌显示出有希望的抗菌活性。
• Green synthesis and pharmacological screening of polyhydroquinoline derivatives bearing a fluorinated 5-aryloxypyrazole nucleus
  作者：Sharad C. Karad、Vishal B. Purohit、Dipak K. Raval、Piyush N. Kalaria、Jemin R. Avalani、Parth Thakor、Vasudev R. Thakkar

  DOI：10.1039/c5ra00388a

  日期：——

  Green synthesis, biological evaluation and SAR study of polyhydroquinoline scaffold bearing fluorinated 5-aryloxypyrazole nucleus is discussed.

  绿色合成，生物评价和带有氟化5-芳氧吡唑核的多羟基喹啉骨架的结构活性关系研究。
• New N-arylamino biquinoline derivatives: Synthesis, antimicrobial, antituberculosis, and antimalarial evaluation
  作者：Nimesh M. Shah、Manish P. Patel、Ranjan G. Patel

  DOI：10.1016/j.ejmech.2012.05.004

  日期：2012.8

  A new series of N-arylamino biquinoline derivatives 5a-x were synthesized by reaction of 2-chloro-3-formyl quinolines 2a-d with malononitrile and various enhydrazinoketones 4a-f in absolute ethanol. The newly synthesized compounds were evaluated for their in vitro antimicrobial activity against a representative panel of pathogenic strains and antituberculosis activity against Mycobacterium tuberculosis H37Rv. Compounds Sh and Ss exhibited excellent antibacterial activity and some of the compounds demonstrated moderate antituberculosis activities compared with the first line drugs. The compounds were evaluated in vitro for their activity against the growth of Plasmodium falciparum, the malaria causing parasite. Some of them showed antimalarial activity with IC50 values as low as 0.005-0.009 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.