Camphor nitroimine: a key building block in unusual transformations and its applications in the synthesis of bioactive compounds

Silva, Emerson Teixeira da; Santos, Luciano da Silva; Andrade, Gabriel Fernandes de; Rosa, Emerson Joaquim Rodrigues; Souza, Marcus V. N. de

doi:10.1007/s11030-021-10341-0

Cited by 4 publications

(1 citation statement)

References 79 publications

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“…With cellular senescence, an important discovery was that most senescent cells undergo alteration to produce the "senescence-associated secretory phenotype" (SASP) (Coppe et al, 2010;Birch & Gil, 2020). The SASP involves the production of a complex array of chemokines, cytokines, growth factors, and proteases, which cause significant effects on neighboring cells, even including conversion into new senescent cells by way of the so-called "bystander" effect (Zheng et al, 2017;da Silva et al, 2022). Many of the impacts of the SASP appear to be negative: it promotes chronic inflammation, which is an essential contributor to a wide range of age-related diseases.…”

Section: Factors Influencing Cellular Senescence and Immune Cellsmentioning

confidence: 99%

Cellular aging and immunity

Zhelavskyi¹,

Kernychnyi²,

Dmytriv

et al. 2022

Ukr. Jour. of Vet. and Agr. Sci.

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Science is constantly evolving and updated with current data on cell biology. The cellular aging phenomenon should be considered an evolutionary mechanism of the biological regulation of all living organisms. Factors initiating cellular aging are variable. Each cell type can respond differently to the activation factors of cellular aging. In recent decades, science has been supplemented with new data that provide a deeper understanding of cellular and molecular mechanisms of cellular aging and the formation of immune homeostasis. There is a real prospect of using effective means of its regulation. In recent years, scientists have come close to discovering the mechanisms of cellular aging. Factors and mechanisms of cell regeneration are more deeply revealed. Scientists are also better aware of the phylogeny and ontogenesis of immune processes and the role of immune factors in developing pathologies. Researchers are increasingly focusing on modern diagnostic methods and xenotherapy. However, the specific factors of immunoregulation and the interaction of microphages, macrophages, and lymphocytes with other body cells are not yet fully understood. Accordingly, this requires further in-depth study. This review reviews the current literature on cellular aging and its regulatory mechanisms. The authors also present the results of their research on the mechanisms of immune responses in reproductive pathology. They draw parallels with modern scientific theories and interpret research. We will also focus on the issues that need to be addressed in the near future for the progressive development of this field of science. Thus, the study of the mechanisms of cellular aging and the development of effective means of hay therapy today requires further painstaking work. Despite significant advances in preclinical studies, many questions remain about the practical use of the drugs. This is especially true in the medicine of oncology, neurology, and cardiology. Nevertheless, scientists will be able to use pharmacological agents to influence cell division, differentiation, and determination in the future. We also hope to have developed effective means of immunotherapy of diseases. The molecular mechanisms of cell aging and mediators involved in the mechanisms of cell aging and death are being studied in detail. The field of research contains countless fascinating studies that are sure to be discovered.

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Section: Factors Influencing Cellular Senescence and Immune Cellsmentioning

confidence: 99%

Cellular aging and immunity

Zhelavskyi¹,

Kernychnyi²,

Dmytriv

et al. 2022

Ukr. Jour. of Vet. and Agr. Sci.

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The Reaction of Fenchone and Camphor Hydrazones with 5‐Acyl‐4‐Pyrones as a Method for the Synthesis of New Polycarbonyl Conjugates: Tautomeric Equilibrium and Antiviral Activity

Viktorova,

Obydennov,

Kovaleva

et al. 2024

Chemistry & Biodiversity

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Selective synthesis of polycarbonyl conjugates of (+)‐fenchone and (+)‐camphor was carried out (44–91 % yields) via the ring‐opening transformation of 5‐acyl‐4‐pyrones with hydrazones of the corresponding monoterpenoids. A strong influence of the hydrazone fragment on the observed tautomeric equilibrium of the tricarbonyl system was shown. Although the major tautomer of the conjugates is the acyclic polycarbonyl form, the camphor‐based conjugates undergo new type of ring‐chain tautomerism, diketoenaminone‐dihydropyridone equilibrium, and predominantly exist in the cyclic dihydropyridone form in DMSO‐d6. The polyketones can undergo intramolecular cyclization to form N‐amino‐4‐pyridones in high selectivity. In vitro screening for activity against the influenza virus H1 N1 and vaccinia virus was estimated for the obtained conjugates. The (+)‐fenchone derivatives demonstrated the higher activity against vaccinia virus than camphor derivatives. The conjugate, which was prepared from diethyl isochelidonate and hydrazone (+)‐fenchone, showed the highest activity against vaccinia virus (SI=17).

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Synthesis and Anti-bacterial Activity Evaluation against Mycobacterium tuberculosis of New Quinoline Derivatives Coupled with the Camphor Nucleus

de Andrade,

da Silva,

Lourenço

et al. 2024

LOC

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Background: Tuberculosis is a serious infectious disease caused by Mycobacterium tuberculosis (Mtb), also known as Koch’s bacillus. The involvement of latent forms and resistant strains has aggravated the situation, making the disease a serious public health problem. Objective: The objective of the study was to synthesize and evaluate ten new compounds containing camphor nucleus coupled to quinolinic derivatives as probable inhibitors of sensitive and resistant strains of Mtb growth. Methods: The synthesis of the final compounds, 3a-e and 4a-e, was based on the use of intermediates previously obtained, in which the coupling of the camphor nucleus to quinoline derivatives was carried out via a convergent route, which resulted in good yields (50-80%). All the final compounds were fully characterized, and the 3-dimensional molecular structure of compound 4c was determined. The anti-mycobacterial activities of all compounds against Mtb strains were evaluated and the cytotoxicity test was conducted using the in vitro microplate procedure with broth microdilution assay (MTT). Results: Compound 3e was the most active against sensitive and resistant strains, with a minimal inhibitory concentration (MIC) of 9.5 M, similar to ethambutol, a first-line drug used against the tuberculosis. The most active compound 3e was selected for the potential activity against Vero cells and it displayed no cytotoxicity at a concentration near the MIC value. Conclusion: The final compounds were obtained in good yields, with derivative 3e being the most promising with high activity and low cytotoxicity. Such findings open new perspectives for drug development based on the incorporation of camphor nucleus in selected compounds.

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Camphor nitroimine: a key building block in unusual transformations and its applications in the synthesis of bioactive compounds

Cited by 4 publications

References 79 publications

Cellular aging and immunity

Cellular aging and immunity

The Reaction of Fenchone and Camphor Hydrazones with 5‐Acyl‐4‐Pyrones as a Method for the Synthesis of New Polycarbonyl Conjugates: Tautomeric Equilibrium and Antiviral Activity

Synthesis and Anti-bacterial Activity Evaluation against Mycobacterium tuberculosis of New Quinoline Derivatives Coupled with the Camphor Nucleus

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