ArticleMolecular diversity2019
Second generation of primaquine ureas and bis-ureas as potential antimycobacterial agents.
Article in Molecular diversity, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
6 citing papers in PubMed.
- Host-Mediated Antimicrobial Effects and NLRP3 Inflammasome Modulation by Caulerpin and Its Derivatives in Macrophage Models of Mycobacterial Infections.Microorganisms · 2025Article
- Evaluation of the Anti-Mycobacterial and Anti-Inflammatory Activities of the New Cardiotonic Steroid γ-Benzylidene Digoxin-15 in Macrophage Models of Infection.Microorganisms · 2025Article
- Design, Synthesis and Biological Activities of (Thio)Urea Benzothiazole Derivatives.International journal of molecular sciences · 2023Review
- Synthesis and Biological Importance of 2-(thio)ureabenzothiazoles.Molecules (Basel, Switzerland) · 2022Review
- Enantioselective Interactions of Anti-Infective 8-Aminoquinoline Therapeutics with Human Monoamine Oxidases A and B.Pharmaceuticals (Basel, Switzerland) · 2021Article
- Primaquine derivatives: Modifications of the terminal amino group.European journal of medicinal chemistry · 2019Review
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
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.
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Registered trials
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