三氟甲基取代内亚磺酰胺衍生物的构建及抑菌活性研究

Synthesis and antifungal activity of trifluoromethyl substituted sultimderivatives

摘要

亚磺酰胺作为多用途的合成中间体,对药物化学有着较大的利用价值。通过丁炔二酸二甲酯与三氟甲基α,β-不饱和N-(R)叔丁基亚磺酰基酮亚胺的[3+2]环加成反应,开发了一种简洁的合成三氟甲基内亚磺酰胺的策略。该反应以SnCl₂作为催化剂,乙腈和甲苯作混合溶剂(V_乙腈/V_甲苯=4/1),在回流温度下以中上产率(49%~82%)得到内亚磺酰胺。采用菌丝生长速率法测定了所得化合物的抑菌活性,结果表明多数所得化合物对尖孢镰刀菌均有中等的抑制率,部分所得化合物对金黄壳囊孢菌表现出中等至良好的抑菌活性,大部分化合物对立枯丝核菌的抑制率并不理想。

Abstract

Sulfinamide, as a versatile synthetic intermediate, has significant value in pharmaceutical chemistry. A concise and direct synthetic strategy for the construction of trifluoromethylated sultim have been developed via[3+2] cycloaddition reaction of dimethyl acetylenedicarboxylate and trifluoromethyl α,β-unsaturated N-(R)-tert-butyl sulfinylketoimines. The reaction affords the sultim in mid to good yields (49%~82%) under reflux. And SnCl₂ as a catalyst, acetonitrile and toluene as mixed solvent (V_acetonitrile/V_toluene=4/1). The antifungal activity of the compound was determined using the mycelial growth rate method. Most of the obtained compounds showed moderate inhibition rates against Fusarium oxysporum, while some compounds exhibited moderate to good antibacterial activity against Cytospora chrysosperma. However, the inhibition rates of most compounds against Rhizoctonia solani were not ideal.

关键词

环加成反应 / 内亚磺酰胺 / 抑菌活性

Key words

cycloaddition reaction / sultim / fungicidal activity

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基金资助

新疆生产建设兵团指导性计划项目 (2022ZD021,2022ZD067)