Quinoxaline-PABA bipartite hybrid derivatization approach: Design and search for antimicrobial agents

Patel, Harun; Bhardwaj, Varun; Sharma, Poonam; Noolvi, Malleshappa N.; Lohan, Sandeep; Bansal, Sumit; Sharma, Amit

doi:10.1016/j.molstruc.2019.02.074

Cited by 28 publications

(26 citation statements)

References 22 publications

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“…Low pH values potentiate this action. Analogous conclusions about adjunctive/synergistic activity were obtained for antivirotics [1][2][3]6]. It has also exhibited multiple antiviral and antioxidant actions.…”

Section: Introductionmentioning

confidence: 58%

“…In addition to PABA "non-imine" cytotoxic derivatives [1,5,12,44], Farooq et al [18] discovered N-alkylisatin-3-iminobenzoic acids, i.e., Schiff bases of substituted isatin and PABA, as potential cytotoxic/antileukemic agents with IC 50 for human normal as well as cancer cell lines comparable to our the most active molecules. Thus, the formation of Schiff bases could convert non-toxic PABA to moderate cytotoxic agents, depending on the carbonyl compound used.…”

Section: Cytotoxicitymentioning

confidence: 96%

“…However, PABA is neither essential nor biosynthesized in mammals. It is produced by symbiotic bacteria, especially Escherichia coli and absorbed from dietary intake [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

“…It has also exhibited multiple antiviral and antioxidant actions. PABA and its derivatives have been utilized as active constituents in sunscreens to protect against UVB irradiation, i.e., scavengers of reactive oxygen species [1][2][3]. PABA demonstrated also properties of cytoprotective agents [7] and direct anticoagulants [2].…”

Section: Introductionmentioning

confidence: 99%

“…PABA hybrid compounds have been reported as potential antimicrobial agents. PABA has been linked with other bioactive scaffolds involving NH 2 group via amide bond [15], as a secondary amine [1] or ureido moiety [16]. The derivatives of PABA showed improved radical scavenging properties and also enhanced toxicity for cancer cells [5].…”

Section: Introductionmentioning

confidence: 99%

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4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents

et al. 2019

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4-aminobenzoic acid (PABA), an essential nutrient for many human pathogens, but dispensable for humans, and its derivatives have exhibited various biological activities. In this study, we combined two pharmacophores using a molecular hybridization approach: this vitamin-like molecule and various aromatic aldehydes, including salicylaldehydes and 5-nitrofurfural, via imine bond in one-step reaction. Resulting Schiff bases were screened as potential antimicrobial and cytotoxic agents. The simple chemical modification of non-toxic PABA resulted in constitution of antibacterial activity including inhibition of methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 15.62 µM), moderate antimycobacterial activity (MIC ≥ 62.5 µM) and potent broad-spectrum antifungal properties (MIC of ≥ 7.81 µM). Some of the Schiff bases also exhibited notable cytotoxicity for cancer HepG2 cell line (IC 50 ≥ 15.0 µM). Regarding aldehyde used for the derivatization of PABA, it is possible to tune up the particular activities and obtain derivatives with promising bioactivities.

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Section: Introductionmentioning

confidence: 58%

Section: Cytotoxicitymentioning

confidence: 96%

“…However, PABA is neither essential nor biosynthesized in mammals. It is produced by symbiotic bacteria, especially Escherichia coli and absorbed from dietary intake [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents

et al. 2019

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An Expeditious One‐Pot Two‐Component Synthesis of Quinoxaline Derivatives in Natural Deep Eutectic Solvents (NADESs)

et al. 2023

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A facile and eco‐friendly sustainable synthesis of functionalized quinoxaline derivatives from 1,2‐diaminobenzenes and 2‐bromoacetophenones via a one‐pot two‐component reaction using choline chloride (ChCl): glycerol as a bio‐renewable DES has been developed. In this protocol, nucleophilic 1,2‐diaminobenzenes are mixed with phenacyl bromides or 3‐(bromoacetyl) coumarin to produce quinoxaline derivatives in a high yield (up to 96 %), with a clean reaction profile without the use of a solvent or catalyst at ambient temperature (80 °C). The presence of DES is proven to be essential for assuring efficient transformation, as the product yield was extremely low with a slow reaction profile in the absence of this media. The DES media could be recycled and reused up to five times without losing its efficiency or affecting the chemical yield of the reaction. In the showcase study, the reaction was also scaled up to the gram scale (10 mmol scale), revealing the synthetic potential of the current approach. A DFT calculation has been also performed to probe the mechanism and reversal of the regioselectivity in the products formation.

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A Review on Multipurpose Potential of Bioactive Heterocycle Quinoxaline

2023

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In last few decades, nitrogen‐containing heterocycles have maintained their status as an important core of FDA‐approved drugs and medicinally active compounds. Quinoxaline is one such class of nitrogen‐containing scaffold that has become a subject of extensive research as it possess a plethora of biological activities. Molecular hybridization is a versatile and rational approach to drug design that involves the combination of two bioactive molecules possessing distinct intrinsic activity into a single scaffold for enhancing their therapeutic potential. In view of this, the advancement and potential of quinoxaline hybrids bearing thiazole, triazole, oxadiazole, pyrrolizines, pyrazole, etc. have attracted the keen attention of researchers to explore their therapeutic ability against different biological targets. The present review includes the research in the recent years (2018–2023) and addresses the graceful advancements in the studies related to quinoxaline‐based small molecules including their synthetic routes, biological activities and structure‐activity relationships. We anticipate that this review article will provide comprehensive knowledge of pharmacological importance of quinoxaline analogues and will fulfill the need of scientific community in designing and developing efficacious novel molecules.

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Quinoxaline-PABA bipartite hybrid derivatization approach: Design and search for antimicrobial agents

Cited by 28 publications

References 22 publications

4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents

4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents

An Expeditious One‐Pot Two‐Component Synthesis of Quinoxaline Derivatives in Natural Deep Eutectic Solvents (NADESs)

A Review on Multipurpose Potential of Bioactive Heterocycle Quinoxaline

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