1,2,5-Oxadiazole N-oxide derivatives as potential anti-cancer agents: synthesis and biological evaluation. Part IV

Boiani, Mariana; Cerecetto, Hugo; González, Mercedes; Risso, Mariela; Olea‐Azar, Claudio; Piro, Oscar E.; Castellano, Eduardo E.; Ceráin, Adela López de; Ezpeleta, Olga; Monge‐Vega, Antonio

doi:10.1016/s0223-5234(01)01265-x

Cited by 59 publications

(30 citation statements)

References 27 publications

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“…96, 131.58, 128.56, 127.57, 125.79, 112.91, 110.01, 77.03, 32.66; ESI-MS (m/z): 211.1 [M+H] + ; which was in agreement with those reported in the literature (Boiani et al, 2001).…”

Section: General Procedures For Synthesis Of Compoundsupporting

confidence: 90%

Preparation and Antitumor Activity of a Tamibarotene-Furoxan Derivative

Wang¹,

Duan²,

Li³

et al. 2014

Asian Pacific Journal of Cancer Prevention

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Multi-target drug design, in which drugs are designed as single molecules to simultaneously modulate multiple physiological targets, is an important strategy in the field of drug discovery. QT-011, a tamibarotene-furoxan derivative, was here prepared and proposed to exert synergistic effects on antileukemia by releasing nitric oxide and tamibarotene. Compared with tamibarotene itself, QT-011 displayed stronger antiproliferative effects on U937 and HL-60 cells and was more effective evaluated in a nude mice U937 xenograft model in vivo. In addition, QT-011 could release nitric oxide which might contribute to the antiproliferative activity. Autodocking assays showed that QT-011 fits well with the hydrophobic pocket of retinoic acid receptors. Taken together, these results suggest that QT-011 might be a highly effective derivative of tamibarotene and a potential candidate compound as antileukemia agent.

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“…96, 131.58, 128.56, 127.57, 125.79, 112.91, 110.01, 77.03, 32.66; ESI-MS (m/z): 211.1 [M+H] + ; which was in agreement with those reported in the literature (Boiani et al, 2001).…”

Section: General Procedures For Synthesis Of Compoundsupporting

confidence: 90%

Preparation and Antitumor Activity of a Tamibarotene-Furoxan Derivative

Wang¹,

Duan²,

Li³

et al. 2014

Asian Pacific Journal of Cancer Prevention

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“…Similar to the nitro pharmacophore of antitrypanosomal drugs, the N-oxide moiety of the quinoxaline could produce parasitic damage through the production of radical species affecting the redox metabolism. 15 As previously described, 17 the absence of the Noxide moiety produces a decrease in the antiepimastigote activity, thereby confirming that this group plays a key role in the mechanism of QDO antitrypanosomal activity. 18 Based on this idea, and in the search for more selective and less toxic anti-Chagas drugs, our synthesis group, led by professor Monge, has synthesized different series of quinoxaline-1,4-di-N-oxide derivatives, with a great variety of substituents in positions 2, 3, 6 and 7 ( Figure 2).…”

Section: Figure 1 Nifurtimox and Benznidazole Structuressupporting

confidence: 72%

Quinoxaline 1,4-di-N-oxide Derivatives: Interest in the Treatment of Chagas Disease

Moreno‐Viguri¹,

Pérez‐Silanes²

2013

Revista Virtual De Química

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Resumo: Mais de 100 milhões de pessoas estão em risco de contrair a doença de Chagas. Estima-se que em 2008, mais de 10.000 pessoas morreram devido a esta patologia. Apesar de a doença ter sido descoberta há mais de 100 anos, ainda é preciso encontrar tratamento seguro e eficaz. Portanto, novos fármacos eficazes contra a doença de Chagas necessitam urgentemente serem descobertos. Derivados de quinoxalina apresentam interessantes propriedades biológicas (anti-infecciosa, citotóxica, anti-candida, anti-protozoário) e a avaliação de suas propriedades farmacológicas ainda está em andamento. Com respeito a isso, nós estamos há mais de uma década em busca de agentes anti-chagásicos. Nesta revisão mostramos nosso trabalho em andamento para identificação de novos agentes anti-T. cruzi com o padrão estrutural quinoxalina-di-N-óxido e apresentamos a relação estrutura-atividade observada entre as diferentes substituições nas posições C-2, C-3, C-6 e C-7 do anel da quinoxalina.Palavras-chave: Doença de Chagas; Trypanosoma cruzi; 1,4-di-N-óxido Quinoxalinas. AbstractsMore than 100 million people are at risk of contracting Chagas disease. It is estimated that in 2008, Chagas disease was responsible for the death of more than 10,000 people. Despite the fact that there are more than 100 years since the disease was discovered, safe and effective treatments still have to be found. Therefore, new drugs active against Chagas disease are urgently required. Quinoxaline derivatives show very interesting biological properties (antiinfective, cytotoxic, anticandida, antiprotozoal) and evaluation of their medicinal chemistry is still in progress. In this regard, we have spent more than a decade in the search for antiChagasic agents. In this review, we summarize our on-going work to identify new anti-T. cruzi agents with the quinoxaline-di-N-oxide scaffold. We present the structure-activity relationship observed among the different substitutions in C-2, C-3, C-6 and C-7 position of the quinoxaline ring.

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“…Compounds F.12,F.13,and F.14 showed moderate cytotoxicity, though the phenyl furoxan derivatives displayed greater activity than methyl furoxan derivatives. Chemical modifications of these structures yielded F.15, which is a hybrid NORM incorporating a DNA-intercalator (Cerecetto et al 2000), and F.16, which was the most cytotoxic agent reported (Boiani et al 2001). The DNA-intercalating bioactive carrier failed to enhance the toxicity of the warhead.…”

Section: Furoxans and Benzofuroxansmentioning

confidence: 99%

Nitric Oxide-Releasing Molecules for Cancer Therapy and Chemoprevention

Anand

Thatcher

2010

Nitric Oxide (NO) and Cancer

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The Nobel Prize for Medicine and Physiology in 1998 to Furchgott, Ignarro, and Murad provided a new impetus to research in prodrugs of the messenger molecule, nitric oxide (NO). Although more famously known for its cardiovascular roles in the treatment of angina (nitrates) and more recently erectile dysfunction (Viagra R ), NO has been extensively researched within the realm of cancer biology. This review briefly highlights the various chemical classes of NO donors with potential utility in cancer chemotherapy and chemoprevention. These molecules release NO upon bioactivation and thus engender the therapeutic rationale of using them in a clinical setting. Bearing these factors in mind, and in the light of current research findings, special emphasis is given to a newer generation of NORMs (nitric oxide-releasing molecules), viz., NONOates, NO-NSAIDs, and furoxans.

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1,2,5-Oxadiazole N-oxide derivatives as potential anti-cancer agents: synthesis and biological evaluation. Part IV

Cited by 59 publications

References 27 publications

Preparation and Antitumor Activity of a Tamibarotene-Furoxan Derivative

Preparation and Antitumor Activity of a Tamibarotene-Furoxan Derivative

Quinoxaline 1,4-di-N-oxide Derivatives: Interest in the Treatment of Chagas Disease

Nitric Oxide-Releasing Molecules for Cancer Therapy and Chemoprevention

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