新型5-官能化吡唑：合成、表征及药理筛选
Novel 5-functionalized-pyrazoles: Synthesis, characterization and pharmacological screening.
作者信息
Doddaramappa Shridevi D, Lokanatha Rai K M, Srikantamurthy Ningaiah, Chethan Javarasetty
机构信息
Department of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India.
Department of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India.
出版信息
Bioorg Med Chem Lett. 2015 Sep 1;25(17):3671-5. doi: 10.1016/j.bmcl.2015.06.050. Epub 2015 Jun 18.
In the present study a series of O-substituted pyrazoles 7(a-f) and N-substituted pyrazoles 9(a-f) were synthesized via phase-transfer catalyzed reaction of ethyl 5-(bromomethyl)-1,3-diphenyl-1H-pyrazole-4-carboxylate 5 with various oxygen and nitrogen containing compounds in presence of tetrabutylammonium bromide (TBAB) in THF. The compound 5 was obtained by the efficient bromination with N-bromosuccinimide (NBS) in presence of a catalytic amount of azoiso-bis-butyro nitrile (AIBN) in refluxing CCl4. The synthesized compounds were evaluated for their in vitro antimicrobial and antidiabetic activity and were compared with standard drugs. Among the synthesized compounds, compound 9b emerged as an excellent antimicrobial and antidiabetic agent. Newly synthesized compounds were characterized by analytical and spectral (IR, (1)H NMR, (13)C NMR and LC-MS) methods.
在本研究中，通过5-(溴甲基)-1,3-二苯基-1H-吡唑-4-羧酸乙酯5与各种含氧化合物和含氮化合物在四丁基溴化铵（TBAB）存在下于四氢呋喃中进行相转移催化反应，合成了一系列O-取代吡唑7(a - f)和N-取代吡唑9(a - f)。化合物5是通过在催化量的偶氮二异丁腈（AIBN）存在下，于回流的四氯化碳中用N-溴代琥珀酰亚胺（NBS）进行有效溴化反应制得。对合成的化合物进行了体外抗菌和抗糖尿病活性评估，并与标准药物进行了比较。在合成的化合物中，化合物9b表现为一种优异的抗菌和抗糖尿病药物。通过分析和光谱（红外光谱、¹H核磁共振、¹³C核磁共振和液相色谱 - 质谱）方法对新合成的化合物进行了表征。
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