Fluorescent Symmetric Phenazines from the Reactions of β-Lapachone and Nor-β-lapachone with Ammoniating Agents

Pinto, Antônio V.; Pinto, Cleverson N.; Pinto, Maria do Carmo F. R.; Emery, Flávio da Silva; Moura, Kelly C. G. de; Carvalho, C. A. A. de; Brinn, Ira M.

doi:10.1039/a906357i

Cited by 7 publications

(3 citation statements)

References 9 publications

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“…Pinto and collaborators [39] described the synthesis of several dimeric phenazines, with phenazines 3a and 4a (see diagram 3) showing great promise in photochemical studies as potential fluorescent probes [40]. These authors reported the synthesis of phenazine 5a derived from -lapachone, and its high activity against the infectious trypomastigote form of T. cruzi.…”

Section: Experimental and Theoretical Results For Some Of The Studiedmentioning

confidence: 99%

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Theoretical Evaluation and Classifications of Potential Antimalarial Phenazine Compounds

Silva¹,

Cerqueira²,

Silva³

et al. 2011

LOC

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This study demonstrates a methodology for evaluating the theoretical antimalarial potential of 18 phenazine derivatives, some of which have no known biological activities. Semi-empirical, density functional and statistical methods for analytical data treatment were used to establish a quantitative structure-activity relationship (QSAR). A set of 16 descriptors were obtained. Theoretical tools regarding inferential statistics were used to analyze and interpret the information necessary for the application of a multivariate analysis. We classified four types of phenazines into distinct clusters taking into account including planarity, ring-attached substituents, geometric arrangement and conjugation effects, energy maps as well as frontier orbitals energies. The experimental data and crystallochemical analysis obtained in the present study were able to substantiate the chemo-theoretical analysis. Our classifications agree well with experimental evidence regarding compounds that have already been studied. it would also be desirable to conduct new experimental studies in order to further evaluate the predicting capability of our calculations.

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Section: Experimental and Theoretical Results For Some Of The Studiedmentioning

confidence: 99%

“…The BCD tricycle was extensively studied by several researchers [39,44], who concluded that these types of phenazine have antimalarial properties [14].…”

Section: Experimental and Theoretical Results For Some Of The Studiedmentioning

confidence: 99%

Theoretical Evaluation and Classifications of Potential Antimalarial Phenazine Compounds

Silva¹,

Cerqueira²,

Silva³

et al. 2011

LOC

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“…91 Melhores resultados foram alcançados quando a glicina foi substituída por CH 3 CO 2 NH 4 ou HCO 2 NH 4 , em vários solventes e sob diferentes condições. 92 Pinto e colaboradores relataram a síntese da fenazina 63 de ivada da β-lapachona com atividade contra a forma infecciosa tripomastigota de T. cruzi, nove vezes maior (ED 50 / h de , ±9, μ ol.L -1 ) que o cristal violeta (ED 50 / h de ± μ ol.L -1 ). 78 Esta su st ia foi o tida at avés da eaç o da βlapachona com quatro equivalentes de anilina (Esquema 14) e teve sua estrutura confirmada por difração de raios X. Esquema 14.…”

Section: Figura 12 Exemplo De Fenazinas Isoladas De Fontes Naturaisunclassified

ß-Lapachone: Medicinal chemistry significance and structural modifications

Ferreira¹,

Gonzaga²,

Santos³

et al. 2010

Revista Virtual De Química

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This mini-review describes the work of Brazilian researchers who started the investigations about lapachol and -lapachone, a natural product of inspiring a series of papers on new substances with anticancer activity, trypanocidal, antinflammatory, tuberculostatics and antimalarial. Among these studies, we report some of the most important structural changes made in the carbonyl functions of these naphthoquinones, presenting the main results achieved in medicinal chemistry.

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ChemInform Abstract: Fluorescent Symmetric Phenazines from the Reactions of β‐Lapachone and Nor‐β‐lapachone with Ammoniating Agents.

Pinto

et al. 2000

ChemInform

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Fluorescent Symmetric Phenazines from the Reactions of β-Lapachone and Nor-β-lapachone with Ammoniating Agents. -Phenazines (II), (III), (V), and (VI) exhibit high, solvent dependent, fluorescence quantum yields, making them possibly useful in laser studies. -(PINTO, ANTONIO V.; PINTO, CLEVERSON N.; PINTO, MARIA DO CARMO F. R.; EMERY, FLAVIO S.; DE MOURA, KELLY C. G.; CARVALHO, CARLOS EDUARDO M.; BRINN, IRA M.; J.

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Fluorescent Symmetric Phenazines from the Reactions of β-Lapachone and Nor-β-lapachone with Ammoniating Agents

Cited by 7 publications

References 9 publications

Theoretical Evaluation and Classifications of Potential Antimalarial Phenazine Compounds

Theoretical Evaluation and Classifications of Potential Antimalarial Phenazine Compounds

ß-Lapachone: Medicinal chemistry significance and structural modifications

ChemInform Abstract: Fluorescent Symmetric Phenazines from the Reactions of β‐Lapachone and Nor‐β‐lapachone with Ammoniating Agents.

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