Recent progress in synthesis and application of furoxan

Yousef, Muhammad Abu; Matsubara, Ryosuke

doi:10.1039/d3ra00189j

Cited by 9 publications

(3 citation statements)

References 87 publications

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“…Their potencies are extremely modulable depending on the substituent in position 3 of the ring, and their NO-releasing ability can be abolished by the NO scavenger HbO 2 ++ . These properties have also been confirmed in animal studies, in which furoxans have been administered as antihypertensive molecules [77][78][79]. Concerning their flexibility as a pharmacological tool, the presence of electron-withdrawing groups on the ring, in particular at the 3-position, increases the rate and amount of NO production, but the exact mechanism is unknown and only speculative hypotheses have been proposed [28,80].…”

Section: No Donorsmentioning

confidence: 78%

Proteomics Studies Suggest That Nitric Oxide Donor Furoxans Inhibit In Vitro Vascular Smooth Muscle Cell Proliferation by Nitric Oxide-Independent Mechanisms

Lazzarato,

Bianchi,

Andolfo

et al. 2023

Molecules

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Physiologically, smooth muscle cells (SMC) and nitric oxide (NO) produced by endothelial cells strictly cooperate to maintain vasal homeostasis. In atherosclerosis, where this equilibrium is altered, molecules providing exogenous NO and able to inhibit SMC proliferation may represent valuable antiatherosclerotic agents. Searching for dual antiproliferative and NO-donor molecules, we found that furoxans significantly decreased SMC proliferation in vitro, albeit with different potencies. We therefore assessed whether this property is dependent on their thiol-induced ring opening. Indeed, while furazans (analogues unable to release NO) are not effective, furoxans’ inhibitory potency parallels with the electron-attractor capacity of the group in 3 of the ring, making this effect tunable. To demonstrate whether their specific block on G1-S phase could be NO-dependent, we supplemented SMCs with furoxans and inhibitors of GMP- and/or of the polyamine pathway, which regulate NO-induced SMC proliferation, but they failed in preventing the antiproliferative effect. To find the real mechanism of this property, our proteomics studies revealed that eleven cellular proteins (with SUMO1 being central) and networks involved in cell homeostasis/proliferation are modulated by furoxans, probably by interaction with adducts generated after degradation. Altogether, thanks to their dual effect and pharmacological flexibility, furoxans may be evaluated in the future as antiatherosclerotic molecules.

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Section: No Donorsmentioning

confidence: 78%

Proteomics Studies Suggest That Nitric Oxide Donor Furoxans Inhibit In Vitro Vascular Smooth Muscle Cell Proliferation by Nitric Oxide-Independent Mechanisms

Lazzarato,

Bianchi,

Andolfo

et al. 2023

Molecules

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“…As a result, when R1 and R2 are different from one another, two regioisomers occur. The oxygen atom on the ring is traditionally numbered one, the nitrogen atom with the oxygen atom outside of the ring is numbered two, and the other atoms are numbered three, four, and five in that order [127]. Until now, several benzofuroxans derivatives with activity against MTB have been reported, however there are a few who presented excellent activity against MTB [128].…”

Section: Pretomanidmentioning

confidence: 99%

Advances in Diagnostics and Drug Discovery against Resistant and Latent Tuberculosis Infection

Shleider Carnero Canales,

Marquez Cazorla,

Furtado Torres

et al. 2023

Pharmaceutics

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Latent tuberculosis infection (LTBI) represents a subclinical, asymptomatic mycobacterial state affecting approximately 25% of the global population. The substantial prevalence of LTBI, combined with the risk of progressing to active tuberculosis, underscores its central role in the increasing incidence of tuberculosis (TB). Accurate identification and timely treatment are vital to contain and reduce the spread of the disease, forming a critical component of the global strategy known as “End TB.” This review aims to examine and highlight the most recent scientific evidence related to new diagnostic approaches and emerging therapeutic treatments for LTBI. While prevalent diagnostic methods include the tuberculin skin test (TST) and interferon gamma release assay (IGRA), WHO’s approval of two specific IGRAs for Mycobacterium tuberculosis (MTB) marked a significant advancement. However, the need for a specific test with global application viability has propelled research into diagnostic tests based on molecular diagnostics, pulmonary immunity, epigenetics, metabolomics, and a current focus on next-generation MTB antigen-based skin test (TBST). It is within these emerging methods that the potential for accurate distinction between LTBI and active TB has been demonstrated. Therapeutically, in addition to traditional first-line therapies, anti-LTBI drugs, anti-resistant TB drugs, and innovative candidates in preclinical and clinical stages are being explored. Although the advancements are promising, it is crucial to recognize that further research and clinical evidence are needed to solidify the effectiveness and safety of these new approaches, in addition to ensuring access to new drugs and diagnostic methods across all health centers. The fight against TB is evolving with the development of more precise diagnostic tools that differentiate the various stages of the infection and with more effective and targeted treatments. Once consolidated, current advancements have the potential to transform the prevention and treatment landscape of TB, reinforcing the global mission to eradicate this disease.

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“…Although ozonolysis of alkenes was discovered in the mid-19th century, its mechanism was firmly established only at the end of the 20th century. − This textbook recipe for converting alkenes to carbonyl compounds is quite complex from the mechanistic perspective. − The classic alkene ozonolysis is a remarkable sequence of three pericyclic reactions (two [3 + 2] cycloadditions and a cycloreversion) that stops upon the arrival to stereoelectronically stabilized secondary ozonides (Figure ). Interestingly, the relatively unexplored ozonolysis of CN bonds can continue to include the fourth pericyclic step, i.e., another thermodynamically favorable cycloreversion ( vide infra ). − …”

Section: Introductionmentioning

confidence: 99%

Interrupted Dance of Five Heteroatoms: Reinventing Ozonolysis to Make Geminal Alkoxyhydroperoxides from C═N Bonds

Yaremenko,

Fomenkov,

Budekhin

et al. 2024

J. Org. Chem.

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Four heteroatoms dance in the cascade of four pericyclic reactions initiated by ozonolysis of C�N bonds. Switching from imines to semicarbazones introduces the fifth heteroatom that slows this dance, delays reaching the thermodynamically favorable escape path, and allows efficient interception of carbonyl oxides (Criegee intermediates, CIs) by an external nucleophile. The new three-component reaction of alcohols, ozone, and oximes/semicarbazones greatly facilitates synthetic access to monoperoxyacetals (alkoxyhydroperoxides).

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Recent progress in synthesis and application of furoxan

Abstract: This review summarizes the recent advances in the synthesis and application of furoxan molecules, with special attention to the synthetic strategy of the post-ring introduction of substituents (PRIS).

Cited by 9 publications

References 87 publications

Proteomics Studies Suggest That Nitric Oxide Donor Furoxans Inhibit In Vitro Vascular Smooth Muscle Cell Proliferation by Nitric Oxide-Independent Mechanisms

Proteomics Studies Suggest That Nitric Oxide Donor Furoxans Inhibit In Vitro Vascular Smooth Muscle Cell Proliferation by Nitric Oxide-Independent Mechanisms

Advances in Diagnostics and Drug Discovery against Resistant and Latent Tuberculosis Infection

Interrupted Dance of Five Heteroatoms: Reinventing Ozonolysis to Make Geminal Alkoxyhydroperoxides from C═N Bonds

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