Evaluation of novel<i>N</i>′-(3-hydroxybenzoyl)-2-oxo-2<i>H</i>-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors

Jesumoroti, Omobolanle J.; Faridoon,; Mnkandhla, Dumisani; Isaacs, Michelle; Hoppe, Heinrich C.; Klein, Rosalyn

doi:10.1039/c8md00328a

Cited by 16 publications

(13 citation statements)

References 27 publications

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“…In the same year, Jesumoroti and co-workers approached the problem from another point of view, both regarding the target and the origin of the coumarin derivatives [117]. First of all, a different viral target was chosen, HIV-1 IN, which is essential for a stable infection.…”

Section: Antiviral Activitymentioning

confidence: 99%

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An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

249

156

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Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

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Section: Antiviral Activitymentioning

confidence: 99%

“…Coumarin derivatives synthesized by Jesumoroti and co-workers[117]. Prenylated coumarins from Manilkara zapota.…”

mentioning

confidence: 99%

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An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

249

156

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“…Klein and co‐workers exploited a scaffold hopping approach to develop a series of 2‐oxo‐2H‐chromene‐3‐carbohydrazides (e. g., 95 ), many of which were found to possess nanomolar‐range inhibitory activity against integrase, comparable to that of chicoric acid, with negligible cytotoxicity . In a related study, Kaye and co‐workers generated a small library of 4‐arylimino‐3‐hydroxybutanoic acids ( 96 ), which displayed moderate albeit encouraging integrase inhibitory activity …”

Section: Anti‐hiv Agentsmentioning

confidence: 99%

Recent Highlights in Anti‐infective Medicinal Chemistry from South Africa

Veale

Müller

2020

ChemMedChem

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Global advancements in biological technologies have vastly increased the variety of and accessibility to bioassay platforms, while simultaneously improving our understanding of druggable chemical space. In the South African context, this has resulted in a rapid expansion in the number of medicinal chemistry programmes currently operating, particularly on university campuses. Furthermore, the modern medicinal chemist has the advantage of being able to incorporate data from numerous related disciplines into the medicinal chemistry process, allowing for informed molecular design to play a far greater role than previously possible. Accordingly, this review focusses on recent highlights in drug-discovery programmes, in which South African medicinal chemistry groups have played a substantive role in the design and optimisation of biologically active compounds which contribute to the search for promising agents for infectious disease.

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“…Compounds derived from coumarins and quinoline have been tested against various viruses (McKee et al, 2020;Mishra et al, 2020). Quinolines have recently been used in experimental treatments for SARS-CoV-2 infected persons in several countries (Arshad et al, 2020;Lopez et al, 2020;Mori et al, 2020) and it has been proposed that coumarins inhibit the replication of several viruses including influenza (Pavurala et al, 2018), HIV (Jesumoroti et al, 2019), Dengue (Coulerie et al, 2013), Chikungunya (Hwu et al, 2019), hepatitis (Hwu et al, 2008) and filoviruses (EBOLA, Marburgvirus (MARV) and Cuevavirus) (Liu et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

In Silico Study of Coumarins and Quinolines Derivatives as Potent Inhibitors of SARS-CoV-2 Main Protease

et al. 2021

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The pandemic that started in Wuhan (China) in 2019 has caused a large number of deaths, and infected people around the world due to the absence of effective therapy against coronavirus 2 of the severe acute respiratory syndrome (SARS-CoV-2). Viral maturation requires the activity of the main viral protease (Mpro), so its inhibition stops the progress of the disease. To evaluate possible inhibitors, a computational model of the SARS-CoV-2 enzyme Mpro was constructed in complex with 26 synthetic ligands derived from coumarins and quinolines. Analysis of simulations of molecular dynamics and molecular docking of the models show a high affinity for the enzyme (∆Ebinding between −5.1 and 7.1 kcal mol−1). The six compounds with the highest affinity show Kd between 6.26 × 10–6 and 17.2 × 10–6, with binding affinity between −20 and −25 kcal mol−1, with ligand efficiency less than 0.3 associated with possible inhibitory candidates. In addition to the high affinity of these compounds for SARS-CoV-2 Mpro, low toxicity is expected considering the Lipinski, Veber and Pfizer rules. Therefore, this novel study provides candidate inhibitors that would allow experimental studies which can lead to the development of new treatments for SARS-CoV-2.

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Evaluation of novelN′-(3-hydroxybenzoyl)-2-oxo-2H-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors

Abstract: In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised.

Cited by 16 publications

References 27 publications

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Recent Highlights in Anti‐infective Medicinal Chemistry from South Africa

In Silico Study of Coumarins and Quinolines Derivatives as Potent Inhibitors of SARS-CoV-2 Main Protease

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