Second generation of primaquine ureas and bis-ureas as potential antimycobacterial agents
| Autor: | Branka Zorc, Ivana Perković, Josef Jampilek, Kristina Pavić, Hana Michnová, Zrinka Rajić |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
medicine.drug_class
Alcohol Microbial Sensitivity Tests Primaquine 010402 general chemistry Antimycobacterial 01 natural sciences Medicinal chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound Aminolysis primaquine urea aminoalcohol antimycobacterial activity Drug Discovery medicine Urea Phenol Physical and Theoretical Chemistry Molecular Biology Semicarbazide Trifluoromethyl Benzotriazole 010405 organic chemistry Organic Chemistry Mycobacterium tuberculosis General Medicine Anti-Bacterial Agents 0104 chemical sciences chemistry Information Systems |
| Zdroj: | Molecular Diversity. 23:657-667 |
| ISSN: | 1573-501X 1381-1991 |
| DOI: | 10.1007/s11030-018-9899-z |
| Popis: | Here, we describe design and synthesis of twelve novel compounds bearing primaquine motif and hydroxy- or halogenamine linked by an urea or bis-urea spacer. Preparation of ureas 3a-f started with the conversion of primaquine to benzotriazolide 2 and aminolysis of the later compound by 4-(2-aminoethyl)phenol or amino alcohols bearing fluorine atom, cycloalkyl or trifluoromethyl group under microwave irradiation. The four-step sequence leading to bis-ureas 6a-f included preparation of benzotriazolide 2 and two intermediates, semicarbazide 4 and benzotriazole bis-urea 5, which upon aminolysis with the same aminophenol or amino alcohols gave the title compounds. Antimycobacterial screening detected three active compounds against Mycobacterium marinum and M. tuberculosis, namely 3b, 3f and 6f, derived from cyclobutyl amino alcohol or amino phenol. |
| Databáze: | OpenAIRE |
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