Design and functionalization of bioactive benzoxazines. An unexpected <i>ortho</i>-substitution effect

Arendt-Pindel, Agata; Marszałek-Harych, Aleksandra; Gębarowska, Elżbieta; Gębarowski, Tomasz; Jędrzkiewicz, Dawid; Pląskowska, Elżbieta; Zalewski, Dariusz; Gulia, Nurbey; Szafert, Sławomir; Ejfler, Jolanta

doi:10.1039/c8nj06440g

Cited by 14 publications

(12 citation statements)

References 27 publications

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“…The isomers represent a different arrangement of the methyl and cyclohexyl substituents occurring on the nitrogen atom. The crystallographic data reveal that all bond lengths and angles are in the normal ranges and comparable to reported neutral ones (for details of the X-ray data, see Tables S1 and S2 ), 14 , 21 , 32 but it should be emphasized that this is the first example of ionic 1,3-benzoxazine in the literature. The heterocyclic ring presents a preferential distorted semichair conformation, making it possible for the oxazine ring to undergo ring-opening polymerization (ROP).…”

Section: Resultssupporting

confidence: 72%

“…Although benzoxazine monomers possess rich molecular design flexibility, which enables the synthesis of polybenzoxazines with tailor-made properties, − some features are still being analyzed and require detailed studies in order to obtain polybenzoxazines with predictable fixed properties. On the other hand, they also have some disadvantages, such as low solubility, a high curing temperature, low fracture toughness, and a sometimes expensive fabricating process, which would require some improvements to be introduced into the monomer design on the synthesis level.…”

Section: Introductionmentioning

confidence: 99%

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N-Activated 1,3-Benzoxazine Monomer as a Key Agent in Polybenzoxazine Synthesis

et al. 2020

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A novel and successful application of ring-closing reactions of aminophenols has been proposed for the formation of a new type of 1,3-benzoxazine ionic derivatives. The optimization of the reaction and detailed computational studies have been reported for the estimation of heterocyclic ring stability and its further transformation, which is crucial in the polymerization process. The molecular structure of the obtained compounds has been fully characterized by applying X-ray analysis and spectroscopic methods. The novel benzoxazines undergo an intriguing thermal reaction leading to classical benzoxazines and chloroalkanes, which is the first step of transformation before polymerization. To gain more insights into the transformation behavior of ionic benzoxazine derivatives, the Fourier transform infrared (FT-IR) spectra of gaseous products were recorded in experiments with near simultaneous FT-IR/TGA measurements. The combination of thermogravimetry with FT-IR spectroscopy enables the quantitative and qualitative characterization of thermal transformation products and clarification of the reaction mechanism. The experimental data have been verified by applying DFT(B3LYP) and DFT(M062x) theoretical studies.

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Section: Resultssupporting

confidence: 72%

Section: Introductionmentioning

confidence: 99%

N-Activated 1,3-Benzoxazine Monomer as a Key Agent in Polybenzoxazine Synthesis

et al. 2020

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“…The DSC results of H,tBu Bx C12 were presented previously. 46 The common future of ionic benzoxazines [ H,tBu Bx dC12 ]Cl, [ H,tBu Bx dMx ]Cl, and [ dtBu Bx dMx ]Cl is the presence of an endothermic effect preceding an exothermic effect. In the case of ionic benzoxazine [ H,tBu Bx dC12 ]Cl, the maximum exothermic peak is located at lower temperatures than for its neutral H,tBu Bx C12 derivative.…”

Section: Resultsmentioning

confidence: 99%

Novel Latent Catalyst for Ring-Opening Polymerization of 1,3-Benzoxazines Triggered by a Dual Ionic/Non-ionic Monomer Partnership

et al. 2023

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We report unraveling the catalytic effect of N-activated benzoxazine monomers on the ring-opening polymerization of simple 1,3-benzoxazine. A novel series of ionic and neutral benzoxazine monomer couples were synthesized and thoroughly characterized using cutting-edge X-ray and spectroscopic techniques. Specially designed monomers act as latent catalyst systems that remain dormant at room temperature but become activated during heating. This two-stage process involves the detachment of chloroalkane and the opening of the oxazine ring, significantly reducing the ROP temperature. To shed new light on the catalytic performance of ionic monomers, simultaneous Fourier transform infrared and thermogravimetry measurements were conducted, providing a comprehensive understanding of the thermal transformation products and revealing the immense catalytic potential and effectiveness of ionic benzoxazines.

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“…The activity assessment was performed according to the National Cancer Institute guidelines for screening human tumour lines and based on the basis of our own studies [ 69 ]. Tumour cell lines and normal human cells cultured in a suitable medium containing 5% fetal serum were used for the study.…”

Section: Methodsmentioning

confidence: 99%

In Vitro Evaluation of Antiprotozoal Properties, Cytotoxicity Effect and Anticancer Activity of New Essential-Oil Based Phytoncide Mixtures

et al. 2023

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Protozoa, in both humans and animals, are one of the leading causes of disease. International programmes introduced in many countries have helped reduce the incidence of disease. However, it has recently become increasingly difficult to achieve the goals set for the coming years. One of the main reasons for this, as with other pathogenic organisms, such as bacteria and fungi, is the increasing resistance to current methods of treating and preventing infection. Therefore, new therapies with high efficacy are needed. In the present study, the novel mixtures of essential oils (EOs), clove, garlic, Ceylon cinnamon, and rosemary with organic acids (acetic, propionic, lactic) and metal ions (Cu, Mn, Zn) were tested against five selected model protozoa (Euglena gracilis, Gregarina blattarum, Amoeba proteus, Paramecium caudatum, Pentatrichomonas hominis). The cytotoxicity and potential anticancer activity of the obtained combinations were tested on the human fibroblasts (NHDF) and human cancer cell lines (A549, MCF7, LoVo, HT29). All of the mixtures showed very good antiprotozoal properties. The most efficient were the combination of clove and rosemary essential oils, mixtures of acids, and Mn ions. The LD50 values were in the range of 0.001–0.006% and the LD100 values were 0.002–0.008%. All of the tested mixtures did not show cytotoxicity against normal cells, but did show growth inhibition against cancer cell lines. The most cytotoxic against cancer cells were combinations with cinnamon essential oil. Nevertheless, the proposed combinations containing essential oils, organic acids, and metal ions have high antiprotozoal activity, with low toxicity to healthy human cells.

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Design and functionalization of bioactive benzoxazines. An unexpected ortho-substitution effect

Abstract: A family of o, p- and N-functionalized dihydro-2H-benzo-1,3-oxazines was synthesized and characterized.

Cited by 14 publications

References 27 publications

N-Activated 1,3-Benzoxazine Monomer as a Key Agent in Polybenzoxazine Synthesis

N-Activated 1,3-Benzoxazine Monomer as a Key Agent in Polybenzoxazine Synthesis

Novel Latent Catalyst for Ring-Opening Polymerization of 1,3-Benzoxazines Triggered by a Dual Ionic/Non-ionic Monomer Partnership

In Vitro Evaluation of Antiprotozoal Properties, Cytotoxicity Effect and Anticancer Activity of New Essential-Oil Based Phytoncide Mixtures

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