Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment

Nortcliffe, Andrew; Ekström, Alexander; Black, James R.; Ross, James A.; Habib, Fouad K.; Botting, Nigel P.; O’Hagan, David

doi:10.1016/j.bmc.2013.12.014

Cited by 33 publications

(29 citation statements)

References 21 publications

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“…Synthesis of furoxan-sulindac hybrids. [59] Reagentsa nd conditions:a )EDCI·HCl, DMAP( cat. ), CH 2 Cl 2 ,RT, 3h,8 3-93 %.…”

Section: Discussionmentioning

confidence: 99%

“…Furoxan–sulindac hybrids 105 a , b were readily synthesized through coupling of alcohols 106 a , b with sulindac 107 (Scheme ). Both compounds exhibited high levels of NO production and significant cytotoxic activity against prostate cancer cell lines, even in the nanomolar range …”

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

“…Both compounds exhibited high levels of NO production and significant cytotoxic activity against prostate cancer cell lines, even in the nanomolar range. [59] There are numerous examples of furoxan-based hybrids incorporating one of the well-known anticancer drugs,e ither approvedo ru nder clinical trials (such as gemcitabine, cisplatin, doxorubicine, pemetrexed, etc. ), which possess cytotoxic activity against varioush uman cancer cell lines superior to parent drugs and that are less toxic toward normal cells.…”

Section: Introductionmentioning

confidence: 99%

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Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Ферштат

Махова

2017

ChemMedChem

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The molecular hybridization of different compounds with known pharmacological activity is a particularly prominent approach for the design of potential drugs with improved pharmacokinetic profiles. Much attention over the last decade has been focused on the synthesis of hybrid structures with a nitric oxide (NO)-donor framework, as NO is a ubiquitous and crucial regulator of cellular metabolism, affecting various physiological and pathophysiological processes. 1,2,5-Oxadiazole 2-oxides (furoxans), which are capable of exogenous NO release in the presence of thiol cofactors, are an important class of prospective NO donors. As such, a wide range of hybrid compounds that combine a furoxan ring with various pharmacologically active structures have been created. This review focuses on recent results in the synthesis and pharmacological activity of furoxan-based hybrids. Special attention is given to chemo- and regioselective methods used in the preparation of these hybrid structures, and the role of synergistic effects on their pharmacological activity, associated with the furoxan fragment.

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“…Synthesis of furoxan-sulindac hybrids. [59] Reagentsa nd conditions:a )EDCI·HCl, DMAP( cat. ), CH 2 Cl 2 ,RT, 3h,8 3-93 %.…”

Section: Discussionmentioning

confidence: 99%

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Ферштат

Махова

2017

ChemMedChem

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“…It not only can regulate various physiological functions in the living organisms via the NO release, but also can make a coupling reaction with a variety of the known drugs and the activated compounds. Thus it has potential applications in new drug research [3,4] . Praziquante is a kind of new anti-schistosomal drug, and NO that released from praziquante can effectively kill schistosoma and its eggs [5,6] .…”

Section: Introductionmentioning

confidence: 99%

A Potential Anti-schistosomal Agent Containing 1,2,5-Oxadiazole-2-oxide and Praziquante Moieties

Wang¹,

Zhang²

2015

Proceedings of the 3rd International Conference on Material, Mechanical and Manufacturing Engineering

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“…18 The incorporation of the furoxan ring as a potential NO donor with drug candidates of known pharmacological activity, especially anticancer, has been recently used by many research groups. [19][20][21][22][23][24][25][26] In present work we have aimed to synthesize the heterocyclic structures comprising furoxan ring coupled with various functionally substituted heterocyclic fragments and to carry out an evaluation of their cytotoxic activity and NO-donor capability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization and cytotoxic activity of heterocyclic compounds containing the furoxan ring

Larin¹,

Ферштат²,

Аникина³

et al. 2017

Arkivoc

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A direct approach to the synthesis of previously unknown 1H-1,2,3-triazolylfuroxans, involving nucleophilic substitution of the nitro group in nitrofuroxans followed by catalytic [3+2] cycloaddition of intermediate azidofuroxans to 1,3-ketoesters, is reported. The scope of the triazolylfuroxans was additionally diversified through a number of transformations of the functional groups attached to the 1,2,3-triazole ring. The cytotoxic activity of the newly synthesized triazolylfuroxans and of previously reported hetarylfuroxans was studied. The NO-donor capability of selected synthesized hetarylfuroxans was measured by the Griess reaction using a spectrophotometric technique.

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Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment

Cited by 33 publications

References 21 publications

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

A Potential Anti-schistosomal Agent Containing 1,2,5-Oxadiazole-2-oxide and Praziquante Moieties

Synthesis, structural characterization and cytotoxic activity of heterocyclic compounds containing the furoxan ring

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