A novel synthetic approach for the synthesis of pyrano[3,2-c] quinolone-3carbaldehydes by using modified Vilsmeier Haack reaction, as potent antimicrobial agents

Zaman, Ashhar-uz; Ahmad, Awais; Pervaiz, Muhammad; Ahmad, S.; Kiran, Shumaila; Khan, Misbahul Ain; Gulzar, Tahsin; Kamal, Tahseen

doi:10.1016/j.molstruc.2018.11.030

Cited by 27 publications

(19 citation statements)

References 42 publications

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“…The potential interactions of the lipophilic components (lipoproteins, liposaccharides, and phospholipids) of these hydrogels with the bacterial cell walls may be electrostatic as well as hydrophobic (Ahmed et al, 2016; Zykwinska et al, 2018). Hence, the microorganisms adsorb and immobilized onto the surface of the hydrogels, and even the hydrogel may enter into the cells via the cytoplasmic membrane and binds to the ribosome of bacteria to disrupt protein synthesis and hinder microbial activity (Kamal, Ul‐islam, Khan, & Asiri, 2015; Zaman et al, 2019). Our discussion is also supported by the water contact angle measurement.…”

Section: Resultsmentioning

confidence: 99%

“…Hydrogels can heal wounds quickly due to inheritable properties of hydrophilicity, moisture preservation, oxygenation, fibroblast proliferation, and antibacterial activity. Modern research has developed various medicines to revolutionize the medical system of care, cure, and treatment for wound healing applications (Liu et al, 2018; Zaman et al, 2019). Thus, novel medicines/formulations of hydrogels were produced, which showed controlled release and no side effects during wound healing.…”

Section: Introductionmentioning

confidence: 99%

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Novel functional antimicrobial and biocompatible arabinoxylan/guar gum hydrogel for skin wound dressing applications

Khan

Raza

Razak

et al. 2020

J Tissue Eng Regen Med

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It is a challenging task to develop active biomacromolecular wound dressing materials that are biocompatible and possesses antibacterial properties against the bacterial strains that cause severe skin disease. This work is focused on the preparation of a biocompatible and degradable hydrogel for wound dressing application using arabinoxylan (ARX) and guar gum (GG) natural polymers. Fourier transform infrared spectroscopy (FT-IR) confirmed that both ARX and GG interacted well with each other, and their interactions further increased with the addition of crosslinker tetraethyl orthosilicate. Scanning electron microscope (SEM) micrographs showed uniform porous morphologies of the hydrogels. The porous morphologies and uniform interconnected pores are attributed to the increased crosslinking of the hydrogel. Elastic modulus, tensile strength, and fracture strain of the hydrogels significantly improved (from ATG-1 to ATG-4) with crosslinking. Degradability tests showed that hydrogels lost maximum weight in 7 days. All the samples showed variation in swelling with pH. Maximum swelling was observed at pH 7. The hydrogel samples showed good antibacterial activity against Pseudomonas aeruginosa (Gram-negative) and Staphylococcus aureus (Gram-positive) in PBS, good drug release profile (92% drug release), and nontoxic cellular behavior. The cells not only retained their cylindrical morphologies onto the hydrogel but were also performing their normal activities. It is, therefore, believed that as-developed hydrogel could be a potential material for wound dressing application.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel functional antimicrobial and biocompatible arabinoxylan/guar gum hydrogel for skin wound dressing applications

Khan

Raza

Razak

et al. 2020

J Tissue Eng Regen Med

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show abstract

“…Fused 8‐quinoline‐pyranone carbaldehyde scaffolds are designed to possess antibacterial potencies. [ 44 ] Disappointing antibacterial results are obtained, wherein a low zone of inhibition is observed. In this regard, 6‐bromoquinoline analog 69 (Figure 11) is the most significant inhibitor of E. coli with a zone of inhibition of 14.2 mm, yet inferior as compared with rifampicin (20.25 mm).…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…Moderate antifungal properties (48–56%) have been observed for the quinoline analogs connected with pyrazole aldehyde motif against C. albicans ATCC 10231 strain, compared with ketoconazole (100%). [ 40 ] The antifungal activity of pyranone aldehyde‐fused quinoline molecules revealed modest Aspergillus flavus inhibitory potency (13.2 mm) of compound 69 , [ 44 ] whereas other derivatives possessed inferior properties. Also, deteriorated antifungal effects are seen in the case of A. niger and A. alternata fungal strains for all evaluated derivatives.…”

Section: Antifungal Activitymentioning

confidence: 99%

Recent update on antibacterial and antifungal activity of quinoline scaffolds

Dorababu¹

2020

Archiv der Pharmazie

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Although most of the heterocycles have been reported to possess a significant pharmacological activity, only a few of them, namely quinoline derivatives, have exhibited the finest biological activities. Despite the few medicinal properties of the plain quinoline molecule, its derivatives exhibit diverse pharmacological properties such as anticancer, anti‐inflammatory, antibacterial, antiviral, antifungal, antiprotozoal activities, and so on. The potential antimicrobial properties of the quinoline derivatives are evident from the decades of research on these derivatives. Owing to limitations like drug resistance, high cost, severe side effects, and less bioavailability of previously synthesized antimicrobial agents, these drugs have become obsolete in recent years. Hence, the design of more efficient antimicrobial drugs must be given topmost priority. A breakthrough in drug discovery is a must to prevent malevolent microbial diseases. Addressing all these issues, researchers have been continuously contributing to antimicrobial drug discovery. Herein, a short description of the pharmacology of antimicrobial agents such as antibacterials and antifungals synthesized recently is provided. The versatile derivatization of the quinoline moiety leading to significant antimicrobial potencies is discussed, considering the structure–activity relationship.

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“…1,2 Due to the remarkable application value in chemistry, formylation of arene has attracted much interest of organic chemists. Traditionally, the most classical methods include Vilsmeier-Haack, [3][4][5] Duff reaction, [6][7][8] Reimer Tiemann, 9,10 Rieche 11 and Friedel-Crafts acylations. 12,13 Nevertheless, these reactions generally require excess strong bases or acids in workup processes and are unfriendly to the environment.…”

Section: Introductionmentioning

confidence: 99%

Metal-free selective aryl C–H formylation co-controlled by 1,2,3-triazole and hydroxyl using DMSO as formyl source

Liu

et al. 2019

J Chem Sci

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A novel synthetic approach for the synthesis of pyrano[3,2-c] quinolone-3carbaldehydes by using modified Vilsmeier Haack reaction, as potent antimicrobial agents

Cited by 27 publications

References 42 publications

Novel functional antimicrobial and biocompatible arabinoxylan/guar gum hydrogel for skin wound dressing applications

Novel functional antimicrobial and biocompatible arabinoxylan/guar gum hydrogel for skin wound dressing applications

Recent update on antibacterial and antifungal activity of quinoline scaffolds

Metal-free selective aryl C–H formylation co-controlled by 1,2,3-triazole and hydroxyl using DMSO as formyl source

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