☆ 4.6 Review

Recent progress in synthesis and application of furoxan

RSC ADVANCES (2023)

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Article Chemistry, Medicinal

Synthesis and biological evaluation of novel hybrids of phenylsulfonyl furoxan and phenstatin derivatives as potent anti-tumor agents

Xin Huang et al.

Summary: This study developed a series of furoxan-based NO-releasing arylphenones derivatives by introducing an efficient NO donor, furoxan moiety, into the microtubule-interfering agent phenstatin. The synthesized compounds showed moderate to potent anti-tumor activities against various human cancer cell lines. Compound 15h displayed the most potent activities against both chemo-sensitive and resistant cancer cell lines, exhibiting anti-angiogenesis, colony formation inhibition, cell cycle arrest, and apoptosis induction effects. In a nude mice xenograft model, 15h significantly inhibited the growth of paclitaxel-resistant tumors with low toxicity, indicating its potential as a therapeutic agent for chemo-resistant cancers.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2022)

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Article Biochemistry & Molecular Biology

Second generation β-elemene nitric oxide derivatives with reasonable linkers: potential hybrids against malignant brain glioma

Renren Bai et al.

Summary: This study introduces furoxan nitric oxide (NO) donors into the structure of beta-elemene to improve its anti-tumor activity. The synthesized compounds effectively release NO and demonstrate significant anti-proliferative effects on tumor cell lines. In an orthotopic glioma model, one of the compounds continuously suppresses tumor growth.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2022)

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Article Chemistry, Medicinal

Design, synthesis and biological activity evaluation of novel scopoletin-NO donor derivatives against MCF-7 human breast cancer in vitro and in vivo

Nairong Yu et al.

Summary: Eleven new scopoletin derivatives were synthesized and evaluated for their antiproliferative activity against human breast cancer cells, among which compound 18e exhibited the most potent effect. It was found that 18e could inhibit the growth of MCF-7 cells by blocking the cell cycle at the G(2)/M phase and regulating the expressions of apoptosis proteins. This compound may serve as a promising anticancer agent against MCF-7 human breast cancer through its unique mechanisms of action.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

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Article Chemistry, Organic

Furoxan Incorporation into C-H Bonds Enabling Nitrogen-Containing Functional Group Installation into the Same

Chenlu Dong et al.

Summary: A novel C-C bond forming method has been developed, allowing for the incorporation of a furoxan ring into various types of C-H bonds. This method not only provides a concise route to alkylated furoxan derivatives, but also offers an efficient strategy for inserting nitrogen-containing functional groups into C-H bonds via transformation of the resulting furoxan ring.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Multidisciplinary Sciences

Design, synthesis and biological evaluation of N-oxide derivatives with potent in vivo antileishmanial activity

Leandro da Costa Clementino et al.

Summary: Leishmaniasis is a neglected disease affecting 12 million people mainly in developing countries. The synthesized compound 4f showed promising antileishmanial activity, possibly acting through a dual mechanism against L. infantum.

PLOS ONE (2021)

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Review Biochemistry & Molecular Biology

Anti-Tumor Drug Discovery Based on Natural Product β-Elemene: Anti-Tumor Mechanisms and Structural Modification

Ziqiang Bai et al.

Summary: Beta-elemene, extracted from Curcuma wenyujin, is a natural product with broad anti-tumor activities. Its main molecular mechanism includes inhibiting tumor growth, inducing apoptosis, enhancing chemoradiotherapy sensitivity, among others. However, its lipophilicity and low bioavailability hinder its application, prompting researchers to seek better beta-elemene-derived anti-tumor drugs through structural modifications.

MOLECULES (2021)

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Article Chemistry, Medicinal

Discovery of β-carboline-(phenylsulfonyl)furoxan hybrids as potential anti-breast cancer agents

Xu Hu et al.

Summary: The study focused on the cytotoxicity properties of beta-carboline alkaloids and designed thirty beta-carboline-(phenylsulfonyl)furoxan hybrids. Among them, the derivative 13h showed promising inhibitory effects on breast cancer cells and could potentially be further explored as an antimetastatic agent.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2021)

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Article Chemistry, Organic

Borylfuroxans: Synthesis and Applications

Weibin Xie et al.

Summary: In this study, we report a novel synthesis method for borylfuroxans through the reaction of sulfonylfuroxans with Lewis base-ligated boranes under radical conditions. Additionally, we demonstrate the transformation of borylfuroxans to a variety of 1,2-dioximes and their derivatives.

ORGANIC LETTERS (2021)

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Article Biochemistry & Molecular Biology

Tuning NO release of organelle-targeted furoxan derivatives and their cytotoxicity against lung cancer cells

Federica Sodano et al.

Summary: This study investigated a set of hybrid compounds with different nitric oxide (NO) releasing capacities, composed of 3-R-substituted furoxan moieties linked to a mitochondrial probe, rhodamine B. Strong electron-withdrawing groups at the 3-position of the furoxan showed high cytotoxicity likely due to their high NO-releasing properties and ability to inhibit cellular proteins by covalent binding. The most interesting product was identified as the rhodamine hybrid containing 3-SO2C6H5 substituted furoxan moiety, showing high cytotoxicity over the entire concentration range tested.

BIOORGANIC CHEMISTRY (2021)

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Article Biochemistry & Molecular Biology

Synthesis and biological evaluation of NO-donor containing photosensitizers to induce ferroptosis of cancer cells

Xiuhan Guo et al.

Summary: Researchers found that the PS-NO photosensitizers containing NO donors have stronger antitumor activity compared to chlorin e6, and can increase the levels of NO and ROS in cells. Additionally, the addition of the ferroptosis inhibitor Ferrostatin-1 significantly reduces the photodynamic activity of PS-NO and the levels of NO and ROS in cells.

BIOORGANIC CHEMISTRY (2021)

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Review Chemistry, Organic

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Leonid L. Fershtat et al.

Summary: Five-membered heterocyclic N-oxides have significant potential applications in medicinal chemistry and advanced materials science, with recent research focusing on novel methods for their synthesis and functionalization, including transition-metal-catalyzed and metal-free protocols. The transformations of these hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also explored.

SYNTHESIS-STUTTGART (2021)

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Review Chemistry, Multidisciplinary

1,2,5-Oxadiazole-Based High-Energy-Density Materials: Synthesis and Performance

Leonid L. Fershtat et al.

CHEMPLUSCHEM (2020)

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Article Chemistry, Medicinal

Design, synthesis and apoptosis-related antiproliferative activities of chelidonine derivatives

Xueyan Huang et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2020)

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Article Chemistry, Organic

Modular Synthesis of Carbon-Substituted Furoxans via Radical Addition Pathway. Useful Tool for Transformation of Aliphatic Carboxylic Acids Based on Build-and-Scrap Strategy

Ryosuke Matsubara et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Multidisciplinary

Synthesis and Antitumor Evaluation of Novel Hybrids of Phenylsulfonylfuroxan and Estradiol Derivatives

Qi Wan et al.

CHEMISTRYOPEN (2020)

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Article Chemistry, Organic

Synthesis and Synthetic Application of Chloro- and Bromofuroxans

Ryosuke Matsubara et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Review Urology & Nephrology

Review of a Potential Novel Approach for Erectile Dysfunction: Light-Controllable Nitric Oxide Donors and Nanoformulations

Yuji Hotta et al.

SEXUAL MEDICINE REVIEWS (2020)

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Article Chemistry, Organic

N-Oxide-Controlled Chemoselective Reduction of Nitrofuroxans

Leonid L. Fershtat et al.

SYNTHESIS-STUTTGART (2019)

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Article Oncology

Furoxans and tocopherol analogs-furoxan hybrids as anticancer agents

Florencia Perez et al.

ANTI-CANCER DRUGS (2019)

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Article Chemistry, Multidisciplinary

A Fluorescent Naphthalenediimide-Alkoxyfuroxan Photoinduced Nitric Oxide Donor

Christopher Peter Seymour et al.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2019)

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Article Chemistry, Medicinal

Design, synthesis and biological evaluation of novel furoxan-based coumarin derivatives as antitumor agents

Zhuo Zhang et al.

MEDICINAL CHEMISTRY RESEARCH (2018)

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Article Chemistry, Organic

Synthesis of sulfonyloxy furoxans via hydroxyfuroxan ammonium salts

Ryosuke Matsubara et al.

TETRAHEDRON (2018)

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Article Chemistry, Medicinal

Discovery of novel antitumor nitric oxide-donating β-elemene hybrids through inhibiting the PI3K/Akt pathway

Jichao Chen et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2017)

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Article Chemistry, Medicinal

Potent Inhibition of Nitric Oxide-Releasing Bifendate Derivatives against Drug-Resistant K562/A02 Cells in Vitro and in Vivo

Xiaoke Gu et al.

JOURNAL OF MEDICINAL CHEMISTRY (2017)

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Article Chemistry, Organic

Photosensitization of Fluorofuroxans and Its Application to the Development of Visible Light-Triggered Nitric Oxide Donor

Christopher Peter Seymour et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Direct introduction of cyano group on furoxan ring

Lorenzo Annaratone et al.

MENDELEEV COMMUNICATIONS (2017)

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Article Chemistry, Organic

Synthesis of alkynyl furoxans. Rare carbon-carbon bond-forming reaction on a furoxan ring

Ryosuke Matsubara et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

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Article Chemistry, Organic

Study on the Photoinduced Nitric-Oxide-Releasing Ability of 4-Alkoxy Furoxans

Ryosuke Matsubara et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Review Chemistry, Multidisciplinary

Overcoming the Achilles' heel of photodynamic therapy

Wenpei Fan et al.

CHEMICAL SOCIETY REVIEWS (2016)

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Article Chemistry, Organic

Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions

Leonid L. Fershtat et al.

TETRAHEDRON LETTERS (2016)

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Article Chemistry, Organic

Fluorofuroxans: Synthesis and Application as Photoinduced Nitric Oxide Donors

Akihiro Ando et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Chemistry, Organic

Mechanism of Thiol-Induced Nitrogen(II) Oxide Donation by Furoxans: a Quantum-Chemical Study

Oleg N. Burov et al.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2015)

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Article Chemistry, Organic

Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives

Leonid L. Fershtat et al.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2015)

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Article Chemistry, Multidisciplinary

Design of hetarylthiofuroxans by nucleophilic substitution of NO2 group in nitrofuroxans

Leonid L. Fershtat et al.

MENDELEEV COMMUNICATIONS (2015)

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Article Biochemistry & Molecular Biology

Synthesis and antitumor evaluation of novel hybrids of phenylsulfonylfuroxan and epiandrosterone/dehydroepiandrosterone derivatives

Yaoqing Huang et al.

STEROIDS (2015)

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Article Chemistry, Organic

An efficient access to (1H-tetrazol-5-yl)furoxan ammonium salts via a two-step dehydration/[3+2]-cycloaddition strategy

Leonid L. Fershtat et al.

TETRAHEDRON (2015)

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Article Microbiology

Leishmanicidal Activities of Novel Synthetic Furoxan and Benzofuroxan Derivatives

Luiz Antonio Dutra et al.

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY (2014)

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Article Chemistry, Multidisciplinary

Dinitrogen Trioxide-Mediated Domino Process for the Regioselective Construction of 4-Nitrofuroxans from Acrylic Acids

Leonid L. Fershtat et al.

HETEROATOM CHEMISTRY (2014)

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Review Biochemistry & Molecular Biology

Hybrid Molecules Incorporating Natural Products: Applications in Cancer Therapy, Neurodegenerative Disorders and Beyond

M. Decker

CURRENT MEDICINAL CHEMISTRY (2011)

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Review Chemistry, Multidisciplinary

Light-controlled nitric oxide delivering molecular assemblies

Salvatore Sortino

CHEMICAL SOCIETY REVIEWS (2010)

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Article Chemistry, Medicinal

Structure Mechanism Insights and the Role of Nitric Oxide Donation Guide the Development of Oxadiazole-2-Oxides as Therapeutic Agents against Schistosomiasis

Ganesha Rai et al.

JOURNAL OF MEDICINAL CHEMISTRY (2009)

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Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene Boryl Radicals: A New Class of Boron-Centered Radical

Shau-Hua Ueng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

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Article Chemistry, Multidisciplinary

An unexpected transformation of 3,4-bis(isocyanato)furoxan into 3,3′-bi(1,2,4-oxadiazol-5-one)

Igor V. Ovchinnikov et al.

MENDELEEV COMMUNICATIONS (2009)

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Article Chemistry, Multidisciplinary

Complexes of borane and N-heterocyclic carbenes:: A new class of radical hydrogen atom donor

Shau-Hua Ueng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Article Chemistry, Organic

Ultrafast study of the photochemistry of 2-azidonitrobenzene

RD McCulla et al.

ORGANIC LETTERS (2006)

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Review Chemistry, Medicinal

Pharmacological properties of furoxans and benzofuroxans: Recent developments

H Cerecetto et al.

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2005)

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Article Chemistry, Applied

Synthesis of condensed nitrofuroxanes using hydroxylamine

OR Klyuchnikov et al.

RUSSIAN JOURNAL OF APPLIED CHEMISTRY (2004)

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Article Chemistry, Multidisciplinary

Crystal packing: An examination of the packing of molecules approximately isosteric with 4,5-dichlorophthalic anhydride

D Britton et al.

HELVETICA CHIMICA ACTA (2003)

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Article Chemistry, Organic

Unsymmetrically substituted furoxans. Part 18. Smiles rearrangement in furoxan systems and in related furazans

D Boschi et al.

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (2001)

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