Analgesic activity of cyclic imides: 1,8-naphthalimide and 1,4,5,8-naphthalenediimide derivatives

Andricopulo, Adriano D.; Müller, Luciane; Filho, Valdir Cechinel; Cani, Graziela S; Roos, Juliana F; Corrêa, Rogério; Santos, Adair R.S.; Nunes, Ricardo José; Yunes, Rosendo A.

doi:10.1016/s0014-827x(00)00027-6

Cited by 64 publications

(21 citation statements)

References 4 publications

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“…Compound 4 underwent a Beckmann rearrangement with AlCl 3 with ring enlargement and the formation of the lactam 5. N An attempt at the dehydrogenation of compound 5 by the action of Pd/C led to 2-hydroxy-1-azapyrene (6). The amide 5 was then converted into the thioamide 7; quaternization of the latter followed by reduction of the methylthio derivative gave the amine 8.…”

Section: Azapyrenesmentioning

confidence: 99%

Synthesis of aza-and polyazapyrenes (Review)

Боровлев

Демидов

2008

Chem Heterocycl Comp

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Published data on methods for the synthesis of mono-, di-, tri-, and tetraazapyrenes are reviewed.It is theoretically possible to envisage about 300 isomeric aza-and polyazapyrenes with the nitrogen atoms at various positions around the periphery of the pyrene ring and also many mono-and dications with a bridging positively charged nitrogen atom. At present, according to our data, only a small number of these aromatic nitrogen heterocycles have been synthesized.The attention paid to azapyrenes is due both to theoretical aspects (aromaticity, thermodynamic stability, the mechanism of electrophilic and nucleophilic substitution, the stability of the radical-ions, etc.) and to the results of applied studies. In particular, the change of the biological activity with the inclusion of nitrogen atoms in the pyrene ring, i.e., the transition from pyrene to its aza and polyaza analogs, is of undoubted interest. Thus, whereas the monoazapyrenes found in natural subjects [1-4] exhibit mutagenic and carcinogenic activity [5] the derivatives of the most investigated 4(9)-and 2,7-diazapyrenes exhibit analgesic [6] and antiviral and antibacterial [4] activity, and also anticancer activity [8][9][10]. The mechanism of such activity is usually attributed to their known ability to act as intercalators [11][12][13][14][15][16][17][18][19][20]. Polyazapyrenes are actively used in supramolecular chemistry for the construction of molecular devices [21], compounds with topological bonding [22], molecules of the "host-guest" type [23], and macrocomplexes with the cations of transitional metals [24,25].In this review the generally accepted substitutive aza nomenclature [26] is used for these compounds, although other names were used in the earlier papers.

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Section: Azapyrenesmentioning

confidence: 99%

Synthesis of aza-and polyazapyrenes (Review)

Боровлев

Демидов

2008

Chem Heterocycl Comp

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“…Observou-se ainda a importância de grupos substituintes elétron-doadores (como metila e metoxila) no aumento da atividade analgésica. Alguns destes compostos mostraram-se muito mais ativos que o ácido acetil salicílico e o acetaminofeno 75,76 .…”

Section: Esquema 19unclassified

Aspectos químicos e potencial terapêutico de imidas cíclicas: uma revisão da literatura

Filho¹,

Campos²,

Corrêa³

et al. 2003

Quím. Nova

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Recebido em 15/4/02; aceito em 19/7/02 CHEMICAL ASPECTS AND THERAPEUTIC POTENTIAL OF CYCLIC IMIDES: A REVIEW. Cyclic imides consists of an important family of organic compounds with therapeutic potential. In this review, emphasis will be given to the chemical and biological aspects of several sub-classes of this family, incluing maleimides, succinimides, glutarimides, naphtalimides, etc. Additionally, will be focused the contribution of our research group in this field.Keywords: cyclic imides; synthesis; biological activities. INTRODUÇÃOA necessidade do desenvolvimento de novos fármacos, que sejam efetivos contra algumas patologias ainda sem tratamento adequado, e que possam substituir os existentes, porém a custos menores e dotados de menores efeitos adversos, tem impulsionado a comunidade científica a novas e incessantes pesquisas nesta área. A síntese orgânica tem contribuído significativamente neste aspecto, sendo responsável por cerca de 75% dos fármacos existentes no mercado farmacêutico 1,2 . Cabe ressaltar, porém, que muitos destes fármacos são oriundos de protótipos advindos de produtos naturais, especialmente de plantas, que têm, ao longo dos anos, possibilitado a descoberta de inúmeras moléculas bio-ativas 3-6 .Muitas classes de compostos orgânicos têm demonstrado promissores efeitos biológicos e a literatura científica relata um crescimento significativo de novas moléculas com potência similar ou superior àquela de um fármaco, sendo que muitos deles encontram-se em estudos pré-clínicos e clínicos avançados e pormenorizados. Entre estas substâncias, pode-se inserir as imidas cíclicas, alvo desta revisão.As imidas cíclicas são compostos que contém o grupo -CO-N(R)-CO-, sendo R um átomo de hidrogênio, grupo alquila ou grupo arila. Tais compostos podem ser divididos em sub-classes, incluindo as maleimidas, succinimidas, glutarimidas, ftalimidas, naftalimidas, etc., e seus respectivos derivados. Em 1970, Hargreaves e colaboradores 7 publicaram uma revisão abordando vários aspectos químicos, industriais e biológicos das imidas cíclicas. Nos últimos anos, esta classe de compostos tem ressurgido e atraído a atenção da comunidade científica, devido, principalmente, às suas potencialidades terapêuticas. Como exemplo, podemos citar o caso da talidomida (1) que apesar dos significativos efeitos adversos do passado, ocasionando praticamente 100% de teratogenicidade, mesmo em doses clí-nicas modestas, sendo sua indicação específica para uso na gravidez 8 , os recentes estudos têm evidenciado um possível uso desta substância para o tratamento de várias patologias incluindo o câncer 9-11 .Os departamentos de Química e Farmacologia da UFSC e o Núcleo de Investigações Químico-Farmacêuticas da UNIVALI iniciaram os estudos com esta classe de compostos a partir da descoberta do alcalóide natural filantimida (2), isolado das partes aéreas do Phyllanthus sellowianus 12 . Este composto, derivado da glutarimida, apresentou moderado efeito antimicrobiano 13 , antiespasmódico 14 e analgésico 15,16 , sendo então usado como mode...

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“…They exhibit diverse biological activities including anticancer [1], antibacterial [2], anti trypanosomal [3], analgesic [4], photobiological [5], antinociceptive [6] potency. Some naphthalimide derivatives such as amonafide and elinafide have been on the clinical trials stage for the treatment of cancer [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and fluorescence study of Naphthalimide-Coumarin, Naphthalimide-Luminol conjugates

Reddy

2014

J Fluoresc

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Fluorescent naphthalimide-coumarin and naphthalimide-luminol conjugates were prepared by nucleophilic substitution reaction. The synthesized conjugates were characterized by (1)H-NMR, (13)C-NMR, mass and IR spectra. The absorption and fluorescence of these conjugates revealed that naphthalimide-luminol conjugates are more fluorescent than the naphthalimide-coumarin conjugates. In proton accepting DMSO solvent the fluorescence of the conjugates was quenched, while in proton donating ethanol solvent enhanced fluorescence was noticed. Based on the excitation maxima and fluorescence maxima it was found that in naphthalimide-coumarin conjugates coumarin acting as donor and naphthalimide acting as acceptor where as in naphthalimide-luminol conjugates naphthalimide acts as donor and luminol acts as acceptor.

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Analgesic activity of cyclic imides: 1,8-naphthalimide and 1,4,5,8-naphthalenediimide derivatives

Cited by 64 publications

References 4 publications

Synthesis of aza-and polyazapyrenes (Review)

Synthesis of aza-and polyazapyrenes (Review)

Aspectos químicos e potencial terapêutico de imidas cíclicas: uma revisão da literatura

Synthesis and fluorescence study of Naphthalimide-Coumarin, Naphthalimide-Luminol conjugates

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