Synthesis and antiplasmodial evaluation of 1H-1,2,3-triazole grafted 4-aminoquinoline-benzoxaborole hybrids and benzoxaborole analogues

Saini, Anu; Kumar, Sumit; Raj, Raghu; Chowdhary, Shefali; Gendrot, Mathieu; Mosnier, Joël; Fonta, Isabelle; Pradines, Bruno; Kumar, Vipan

doi:10.1016/j.bioorg.2021.104733

Cited by 21 publications

(22 citation statements)

References 32 publications

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“…The other cycloaddition partner, acetylenic intermediate 4, was generated by O-alkylation of 2-bromo-3-hydroxybenzaldehyde 3 with propargyl bromide (1.5 equiv.) and Clinically approved quinoline (red) and 1,2,3-triazole (blue) containing drugs (some structures of quinolone-and triazole-based hybrids reported in the literature (a-f) [9][10][11][12][13][14]); and the structure of the compound (cyan, 5) reported in this paper. Square: synthesis of 1,2,3-triazoles using click chemistry.…”

Section: Resultsmentioning

confidence: 90%

“…For the 13 C-NMR signals, the disappearance of the characteristic peaks of acetylenic group at 77.4 and 76.7 ppm, and the appearance of the C-13 methylene signal at 61.6 ppm and C-11 vinylic signal at 126.6 ppm were the proposed relevant characteristics to recognize the synthesis of a triazole moiety.…”

Section: Resultsmentioning

confidence: 99%

“…Heteronuclear single quantum coherence spectroscopy (HSQC) was also used to assign 13 C signals of compound 5, as shown in Table S1 (see Supplementary Materials for 2D spectra, Figures S5 and S6).…”

Section: Resultsmentioning

confidence: 99%

“…Figure 1. Clinically approved quinoline (red) and 1,2,3-triazole (blue) containing drugs (some structures of quinolone-and triazole-based hybrids reported in the literature (a-g) [9][10][11][12][13][14]); and the structure of the compound (cyan, 5) reported in this paper. Square: synthesis of 1,2,3-triazoles using click chemistry.…”

Section: Introductionmentioning

confidence: 91%

“…Previously, we reported the synthesis of a novel 4-amino-7-chloroquinoline-based 1,2,3-triazole hybrid g by Cu(I)-catalyzed azide-alkyne cycloaddition (click chemistry) [12]. Recently, a library of 1,2,3-triazoles 4-aminoquinoline-benzoxaborole derivatives was synthesized [13], and our recent interest in boron derivatives [14] advanced further studies on similar derivatives.…”

Section: Introductionmentioning

confidence: 99%

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2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde

Yun

Xie

et al. 2022

Molbank

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The 1,2,3-triazole ring system can be easily obtained by copper-catalyzed click reaction of azides with alkynes. 1,2,3-Triazole exhibits a myriad of biological activities, including antimalarial, antibacterial, and antiviral activities. We herein reported the synthesis of quinoline-based [1,2,3]-triazole hybrid via Cu(I)-catalyzed click reaction of 4-azido-7-chloroquinoline with alkyne derivative of 2-bromobenzaldehyde. The compound was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV), and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro against two different normal cell lines. Preliminary studies attempted to evaluate its interaction with Delta RBD of spike protein of SARS-CoV-2 by bio-layer interferometry. Finally, the drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties.

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

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2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde

Yun

Xie

et al. 2022

Molbank

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Exploring the Recent Pioneering Developments of Small Molecules in Antimalarial Drug Armamentarium: A Chemistry Prospective Appraisal

Bagratee,

Prawlall,

Ndlovu

et al. 2024

Chemistry & Biodiversity

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Malaria is a very destructive and lethal parasitic disease that causes significant mortality worldwide, resulting in the loss of millions of lives annually. The uncontrolled intake of antimalarial drugs often employed in clinical settings has resulted in the emergence of numerous strains of plasmodium that are resistant to these drugs, including multidrug‐resistant strains. Hence, there is an urgent need for developing unique classes of antimalarial drugs that function with distinct mechanisms of action. In this context, the design and development of hybrid compounds that combine pharmacophoric properties from different lead molecules into a single unit gives a unique perspective towards further development of malaria drugs in the next generation. In light of this, we have reviewed the progress of hybrid antimalarial agents from 2021 up to the present. This manuscript presents a comprehensive overview of the latest advancements in the medicinal chemistry pertaining to small molecules, with a specific focus on their potential as antimalarial agents. This review explores a variety of physiologically active compounds that have been described in the literature in order to lay a strong foundation for the logical design and eventual identification of antimalarial drugs based on lead frameworks.

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Biannual Account of Anti‐malarial Agents reported in 2021 and 2022: A Comprehensive Coverage

Dhameliya,

Patel,

Kathuria

et al. 2024

ChemistrySelect

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Malaria remains a severe infectious disease caused by Plasmodium parasites among the primarily afflicting impoverished populations. According to World Health Organization (WHO) report, there were an estimated 247 million malarial cases globally, resulting in approximately 6,19,000 fatalities. Particularly prevalent in tropical and subtropical regions, the development of drug resistance has exacerbated this public health challenge. Consequently, there has been a concrete effort to explore novel compounds with anti‐malarial properties. In continuation of our previous works, this review focuses on heterocyclic compounds documented in 2021 and 2022, including artemisinin, benzimidazole, benzofuran, β‐lactam, coumarin, furan, indole, morpholine, piperazine, pyrimidine, quinoline, triazole, etc. highlighting their efficacy, structural characteristics, in vitro and in vivo activities, among other relevant aspects for the broad interest of medicinal chemists working on the design and development of novel anti‐malarial agents.

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Synthesis and antiplasmodial evaluation of 1H-1,2,3-triazole grafted 4-aminoquinoline-benzoxaborole hybrids and benzoxaborole analogues

Cited by 21 publications

References 32 publications

2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde

2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde

Exploring the Recent Pioneering Developments of Small Molecules in Antimalarial Drug Armamentarium: A Chemistry Prospective Appraisal

Biannual Account of Anti‐malarial Agents reported in 2021 and 2022: A Comprehensive Coverage

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