Medicinal and Natural Product Laboratory, Department of Chemistry, Chandigarh University, Gharuan, Mohali 140413, Punjab, India.
Department of Chemistry and Biochemistry, University of Nevada Las Vegas, 4505 S. Maryland Parkway, Box 454003, Las Vegas, NV 89154, USA.
Molecules. 2024 Sep 30;29(19):4655. doi: 10.3390/molecules29194655.
In the present report, we have described the synthesis of N-aminopolyhydroquinoline (N-PHQ) derivatives using highly efficient -cyclodextrin (-CD) as a catalyst by the Hantzsch condensation of substituted aromatic aldehydes, dimedone, and hydrazine hydrate in one pot. The reactions were completed in a shorter time without the generation of any other byproduct. The synthesized N-PHQs were washed thoroughly with distilled water and recrystallized with ethanol to get highly purified products (as crystals). The structure of the synthesized N-PHQs was established by using advanced spectroscopic techniques FT-IR, NMR (H, C, DEPT, COSY, and HSQC), ESI-MS, and Elemental Analyzer. The N-PHQs derivatives demonstrated moderate to excellent resistance against the tested strains (both fungal as well as bacterial). The presence of polar groups, which are able to form H-bonds, attached to the phenyl ring -NO ( and , and -OMe ( and ) exhibits excellent activity, which is comparable to standard drugs, amoxicillin and fluconazole.
在本报告中,我们描述了使用高效的β-环糊精(β-CD)作为催化剂,通过取代芳香醛、二亚甲基酮和水合肼的 Hantzsch 缩合反应一锅法合成 N-氨基金刚烷(N-PHQ)衍生物。反应在更短的时间内完成,没有生成任何其他副产物。合成的 N-PHQ 用蒸馏水彻底洗涤,并通过乙醇重结晶得到高纯度产物(晶体)。通过使用先进的光谱技术 FT-IR、NMR(H、C、DEPT、COSY 和 HSQC)、ESI-MS 和元素分析,确定了合成的 N-PHQ 的结构。N-PHQ 衍生物表现出对测试菌株(真菌和细菌)的中等至优异的抗性。带有极性基团(能够形成氢键)的苯基环上的取代基 -NO (和 )和 -OMe (和 )表现出优异的活性,与标准药物阿莫西林和氟康唑相当。