Kallitsakis Michael G, Carotti Angelo, Catto Marco, Peperidou Aikaterini, Hadjipavlou-Litina Dimitra J, Litinas Konstantinos E
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece.
Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari "Aldo Moro", V. Orabona 4, I-70125 Bari, Italy.
Open Med Chem J. 2017 Nov 30;11:196-211. doi: 10.2174/1874104501711010196. eCollection 2017.
The 1,3-dipolar cycloaddition reactions of nitrile oxides formed (in the presence of NCS and EtN) from the oximes of (purin-9-yl)acetaldehyde or (coumarinyloxy)acetaldehyde with allyloxycoumarins or 9-allylpurines, respectively resulted in 3,5-disubstituted isoxazolines. The similar reactions of propargyloxycoumarins or 9-propargylpurines led to 3,5-disubstituted isoxazoles by treatment with PIDA and catalytic amount of TFA.
The new compounds were tested as antioxidant agents and inhibitors of soybean lipoxygenase LO, AChE and MAO-B.
The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds and presented LO inhibitory activity.
Compound e presents an antioxidant significant profile combining anti-LO, anti-AChE and anti-MAO-B activities.
（嘌呤 - 9 - 基）乙醛肟或（香豆素氧基）乙醛肟分别与烯丙氧基香豆素或9 - 烯丙基嘌呤在NCS和EtN存在下形成的腈氧化物的1,3 - 偶极环加成反应分别生成3,5 - 二取代异恶唑啉。炔丙氧基香豆素或9 - 炔丙基嘌呤的类似反应通过用PIDA和催化量的TFA处理生成3,5 - 二取代异恶唑。
对新化合物进行了作为抗氧化剂以及大豆脂氧合酶LO、乙酰胆碱酯酶和单胺氧化酶B抑制剂的测试。
大多数化合物表现出显著的羟自由基清除活性。化合物 和 表现出脂氧合酶抑制活性。
化合物e呈现出具有抗氧化、抗脂氧合酶、抗乙酰胆碱酯酶和抗单胺氧化酶B活性的显著特性。
