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Relevant academic research and scientific papers

Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives

9- and 10-membered macrolactones bearing benzo and diazine rings were obtained by chemoselective ozonolysis of dihydrofuran and pyran 1,4-diazaphenathrene derivatives. This is the first example of preparation of macrolactones by chemoselective ozonolysis of an enol double bond shared by aromatic and heterocyclic rings.

Chemistry of lapachol - Syntheses of some new biogenetically related naphthoquinones, naphthoquinone dimers, naphthaquinoxaline and naphtha-azaquinoxaline derivatives from lapachol

The present short review focus on chemical transformations of lapachol to a large number of biogenetically related lapachol conegeners, dimers and heterocyclic analogues that have been achieved in our laboratory during more than two decades. Conversion of lapachol to stenocarpoquinone-B, rhinacanthin-A, β-(l-hydroxyisopropanyl)-dihydrofurano-1,2-naphthoquinone, stenocarpoquinone-A, dehydro-α-lapachone and dehydro-β-lapachone by the reaction with m-chloroperbenzoic acid; dehydroiso-α-lapachone, dehydroiso-β-lapachone, dehydro-α-lapachone, α-lapachone and β-lapachone by the reaction with aqueous NaNO2 and glacial AcOH; adenophyllone, quadrllone and dehydro-α-lapachone by the reaction with boiling pyridine; naphthaquinoxaline and naphtha-azaquinoxaline derivatives by the reaction with 1,2-diamines and dialkyltin dilapacholates by the reaction with dialkyltin diisopropoxides have been accomplished. Notably the syntheses of rhinacanthin-A, β-(1-hydroxyisopropanyl)-dihydrofurano-1,2-naphthoquinone, dehydroiso-α-lapachone, dehydroiso-β-lapachone, adenophyllone and quadrllone have been reported for the first time from our group starting from lapachol. The synthesis of novel naphthaquinoxaline and azaquinoxaline derivatives from lapachol has been additional interesting results of this investigation.

A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis

We report here an alternative to the MCPBA or ozonolysis-based oxidation methods of quinoxaline-featuring compounds prepared from beta-lapachones. The use of peracetic acid allowed a simple preparation of the corresponding macrolactones by cleavage of the ring system. These lactones were evaluated for their antimycobacterial potential and compound 4 turned out to have an MIC of 0.62 μg per mL on Mycocabteriumtuberculosis H37Rv. These results justify further research into its value as a potential lead for an original treatment of tuberculosis.

Reaction of β-lapachone with 1,2-diamines: Facile synthesis of novel tetracyclic pyrazines

The reactions of β-lapachone (1) with 1,2-diaminoethane (2) and 1,2-diaminopropane (4) gave the tetracyclic pyrazine derivatives (3) and mixtures of (5) and (6), respectively, while reaction with o-phenylene diamine (7) gave the quinoxaline derivative (8). The structure of pyrazine derivative (3) is confirmed by single-crystal X-ray diffraction study. Copyright Taylor & Francis Group, LLC.

Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line

Catalyst/HypoGen pharmacophore modeling approach and three-dimensional quantitative structure-activity relationship (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to explain the cytotoxic activity of a set of 51 natural and synthesized naphthoquinone derivatives tested in human promyelocytic leukemia HL-60 cell line. The computational models have facilitated the identification of structural elements of the ligands that are key for antitumoral properties. The four most salient features of the highly active β-cycled-pyran-1,2-naphthoquinones [0.1 μM 50 0.6 μM] are the hydrogen-bond interactions of the carbonyl groups at C-1 (HBA1) and C-2 (HBA2), the hydrogen-bond interaction of the oxygen atom of the pyran ring (HBA3), and the interaction of methyl groups (HYD) at the pyran ring with a hydrophobic area at the receptor. The moderately active 1,4-naphthoquinone derivatives accurately fulfill only three of these features. The results of our study provide a valuable tool in designing new and more potent cytotoxic analogues.