A one Step Synthesis of 4-Methyl-3,4-Dihydro-2H,5H-Pyrano[3,2-C]Quinolin-2,5[6H]- Diones and Their Biological Activities

Abstract Cyclic and polycyclic compounds containing moieties such as imidazole, pyrazole, isoxazole, thiazoline, oxazine, indole, benzothiazole and benzoxazole benzimidazole are prized molecules because of the various pharmaceutical properties that they display. This led Prof. Landor and co-workers to engage in the synthesis of several of them such as alkylimidazolenes, oxazolines, thiazolines, pyrimidopyrimidines, pyridylpyrazoles, benzoxazines, quinolines, pyrimidobenzimidazoles and pyrimidobenzothiazolones. This review covers the synthesis of biologically active heterocyclic compounds by the Michael addition and the double Michael addition of various amines and diamines on allenic nitriles, acetylenic nitriles, hydroxyacetylenic nitriles, acetylenic acids and acetylenic aldehydes. The heterocycles were obtained in one step reaction and in most cases, did not give side products. A brief discussion on the biological activities of some heterocycles is also provided.

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A New Method for the Synthesis of 2-Substituted Benzoxazoles from 2-Nitrophenol Derivatives and Aldehydes

JST: Engineering and Technology for Sustainable Development ◽

10.51316/jst.151.etsd.2021.31.3.8 ◽

2021 ◽

Vol 31 (3) ◽

pp. 43-46

Keyword(s):

Biological Activities ◽

Catalyst System ◽

Biologically Active ◽

New Method ◽

Redox Catalyst ◽

High Pressure High Temperature ◽

One Step ◽

High Yields ◽

Strong Acids ◽

Single Reaction

Benzoxazole derivatives are one of the compounds with many interesting biological activities. Conventional methods are often performed under complex conditions using strong acids, expensive metal catalysts, requiring high pressure, high temperature, and under microwave irradiation. In this study, we reported a new method of benzoxazole synthesis with redox catalyst using FeCl3.6H2O and sulfur. This is a suitable, efficient, readily available and environmentally friendly catalyst system for redox and condensation reactions in one step at 100 oC. Applying this new method, we have synthesized eight 2-arylbenzoxazole derivatives with high yields (calculated according to 2-nitrophenol). This research is an important step forward in the synthesis of biologically active compounds containing the benzoxazole framework from readily available starting materials in a single reaction.

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4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents

Biomolecules ◽

10.3390/biom10010009 ◽

2019 ◽

Vol 10 (1) ◽

pp. 9 ◽

Cited By ~ 3

Author(s):

Martin Krátký ◽

Klára Konečná ◽

Jiří Janoušek ◽

Michaela Brablíková ◽

Ondřej Janďourek ◽

...

Keyword(s):

Schiff Bases ◽

Biological Activities ◽

Aromatic Aldehydes ◽

Antimycobacterial Activity ◽

Cytotoxic Agents ◽

Aminobenzoic Acid ◽

Human Pathogens ◽

Essential Nutrient ◽

One Step ◽

Imine Bond

4-aminobenzoic acid (PABA), an essential nutrient for many human pathogens, but dispensable for humans, and its derivatives have exhibited various biological activities. In this study, we combined two pharmacophores using a molecular hybridization approach: this vitamin-like molecule and various aromatic aldehydes, including salicylaldehydes and 5-nitrofurfural, via imine bond in one-step reaction. Resulting Schiff bases were screened as potential antimicrobial and cytotoxic agents. The simple chemical modification of non-toxic PABA resulted in constitution of antibacterial activity including inhibition of methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 15.62 µM), moderate antimycobacterial activity (MIC ≥ 62.5 µM) and potent broad-spectrum antifungal properties (MIC of ≥ 7.81 µM). Some of the Schiff bases also exhibited notable cytotoxicity for cancer HepG2 cell line (IC50 ≥ 15.0 µM). Regarding aldehyde used for the derivatization of PABA, it is possible to tune up the particular activities and obtain derivatives with promising bioactivities.

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Tetrahydrofuranylmethylamines: An efficient and simple one-step synthesis and biological activities

Journal of Heterocyclic Chemistry ◽

10.1002/jhet.5570400523 ◽

2003 ◽

Vol 40 (5) ◽

pp. 895-900 ◽

Cited By ~ 3

Author(s):

Marcus Limbeck ◽

Daniela Gündisch

Keyword(s):

Biological Activities ◽

One Step

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Enzyme mediated synthesis of hybrid polyedric gold nanoparticles

Scientific Reports ◽

10.1038/s41598-021-81751-1 ◽

2021 ◽

Vol 11 (1) ◽

Author(s):

Célia Arib ◽

Jolanda Spadavecchia ◽

Marc Lamy de la Chapelle

Keyword(s):

Gold Nanoparticles ◽

Self Assembly ◽

Manganese Superoxide Dismutase ◽

Protein Complexes ◽

Biological Activities ◽

Production Method ◽

Cellular Mechanisms ◽

Manganese Superoxide ◽

Gold Salts ◽

One Step

AbstractLarge protein complexes carry out some of the most complex activities in biology1,2. Such structures are often assembled spontaneously through the process of self-assembly and have characteristic chemical or biological assets in the cellular mechanisms3. Gold-based nanomaterials have attracted much attention in many areas of chemistry, physics and biosciences because of their size- and shape-dependent optic, electric, and catalytic properties. Here we report for the first time a one step synthesis in which Manganese Superoxide Dismutase protein plays a key role in the reduction of gold salts via the use of a Good's buffer (HEPES) to produce gold nanoparticles, compared to other proteins as catalase (CAT) and bovine serum albumin (BSA).We prove that this effect is directly related with the biological activities of the proteins that have an effect on the gold reduction mechanisms. Such synthesis route also induces the integration of proteins directly in the AuNPs that are intrinsically safe by design using a one-step production method. This is an important finding that will have uses in various applications, particularly in the green synthesis of novel nanomaterials.

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Lactoferrin Production from Bovine Milk or Cheese Whey

Journal of Engineering and Applied Sciences Technology ◽

10.47363/jeast/2020(2)103 ◽

2020 ◽

pp. 1-9

Author(s):

Jean-Paul Perraudin ◽

◽

Léo De Valck ◽

Keyword(s):

Bacterial Contamination ◽

Cheese Whey ◽

Biological Activities ◽

Bovine Milk ◽

Second Step ◽

Scale Production ◽

One Step ◽

High Level ◽

Industrial Scale Production

Today, the industrial scale production of lactoferrin is carried out in one step by extraction from bovine milk or whey. As the role of lactoferrin in the milk is to protect the liquid against the bacterial contamination binding the lipopolysaccharides (LPS) of those bacteria, it is not surprising that the lactoferrin extracted from milk is covered by bacterial LPS, losing the most part of its biological activities. It is absolutely crucial that the production of Lactoferrin consists to a two steps process. The first step consists to extract from milk or from whey a solution that we called lactenin which contains different molecules including lactoferrin, lactoperoxidase, angiogenin and some other minor components. The second step consists to purify the lactoferrin from the other components including the LPS. Only under such conditions, we could recuperate a high level pure molecule with all its biological activities as it is not done actually

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Isolation and characterization of jadomycin L from Streptomyces venezuelae ISP5230 for solid tumor efficacy studies

Pure and Applied Chemistry ◽

10.1351/pac-con-08-11-08 ◽

2009 ◽

Vol 81 (6) ◽

pp. 1041-1049 ◽

Cited By ~ 15

Author(s):

David L. Jakeman ◽

Stephanie N. Dupuis ◽

Cathy L. Graham

Keyword(s):

Natural Products ◽

Solid Tumor ◽

Culture Media ◽

Biological Activities ◽

Streptomyces Venezuelae ◽

Gram Positive Bacteria ◽

Isolation And Characterization ◽

One Step ◽

Efficacy Studies

Precursor-directed biosynthesis offers opportunities to modify natural products and obtain structurally complex metabolites without the need for chemical synthesis. However, such opportunities are limited owing to the inherent substrate specificity of biosynthetic enzymes. The jadomycins are a family of natural products produced by the soil microbe Streptomyces venezuelae ISP5230. Their biosynthesis contains one step that is potentially non-enzymatic, namely, the condensation of a biosynthetic aldehyde and an amino acid that leads to a uniquely substituted oxazolone ring. Variation of amino acids in the culture media enables the production of a wide array of substituted oxazolones. These analogs have been shown to have a variety of biological activities against cancer cell lines and also against Gram-positive bacteria. Herein, we report the first isolation and characterization of jadomycin L and jadomycin L aglycone from 8 L of bacterial culture for solid tumor efficacy studies.

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Glycosylation of 3-Hydroxyflavone, 3-Methoxyflavone, Quercetin and Baicalein in Fungal Cultures of the Genus Isaria

Molecules ◽

10.3390/molecules23102477 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2477 ◽

Cited By ~ 16

Author(s):

Monika Dymarska ◽

Tomasz Janeczko ◽

Edyta Kostrzewa-Susłow

Keyword(s):

Biological Activities ◽

Plant Secondary Metabolites ◽

Hydroxyl Group ◽

Flavonoid Glycosides ◽

Isaria Fumosorosea ◽

Green Areas ◽

Excellent Method ◽

One Step ◽

Kinetics Of ◽

Lower Silesia

Flavonoids are plant secondary metabolites with a broad spectrum of biological activities. In nature, they occur mainly in the form of glycosides, but their extraction is often difficult and expensive, as is chemical synthesis. We have shown that biotransformations are an excellent method for obtaining flavonoid glycosides. We are the first team to describe the use of Isaria microorganisms in biotransformations of flavonoid compounds. In the present study as biocatalysts, we used one strain of Isaria fumosorosea KCH J2 isolated from a spider carcass in green areas of Wroclaw and two strains of I. farinosa (J1.4 and J1.6) isolated from insects found in already unused mines in Lower Silesia. The substrates were 3-hydroxyflavone, 3-methoxyflavone, quercetin (3,3′,4′,5,7-pentahydroxyflavone), and baicalein (5,6,7-trihydroxyflavone). For all the substrates that were used in this study, we obtained 4-O-methylglucopyranosides. In the case of substrates with a hydroxyl group in the third position, O-β-d-glucopyranosides were also formed. Isoquercetin that was obtained by biotransformation was used as a substrate to check the kinetics of the formation of flavonoid 4-O-methylglucopyranosides in I. fumosorosea KCH J2 culture. We did not observe the attachment of the methyl group to glucose unit in isoquercetin. Our finding suggest that the attachment of 4-O-methylglucopyranose occurs in one step.

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Orthogonal Functionalization of Nanodiamond Particles after Laser Modification and Treatment with Aromatic Amine Derivatives

Nanomaterials ◽

10.3390/nano8110908 ◽

2018 ◽

Vol 8 (11) ◽

pp. 908

Author(s):

Justyna Fraczyk ◽

Adam Rosowski ◽

Beata Kolesinska ◽

Anna Koperkiewcz ◽

Anna Sobczyk-Guzenda ◽

...

Keyword(s):

Aromatic Amines ◽

Biological Activities ◽

Laser System ◽

Average Power ◽

Average Laser Power ◽

One Step ◽

Ft Ir ◽

Amine Groups ◽

Ir And Raman

A laser system with a wavelength of 1064 nm was used to generate sp2 carbon on the surfaces of nanodiamond particles (NDPs). The modified by microplasma NDPs were analysed using FT-IR and Raman spectroscopy. Raman spectra confirmed that graphitization had occurred on the surfaces of the NDPs. The extent of graphitization depended on the average power used in the laser treatment process. FT-IR analysis revealed that the presence of C=C bonds in all spectra of the laser-modified powder. The characteristic peaks for olefinic bonds were much more intense than in the case of untreated powder and grew in intensity as the average laser power increased. The olefinized nanodiamond powder was further functionalized using aromatic amines via in situ generated diazonium salts. It was also found that isokinetic mixtures of structurally diverse aromatic amines containing different functional groups (acid, amine) could be used to functionalize the surfaces of the laser-modified nanoparticles leading to an amphiphilic carbon nanomaterial. This enables one-step orthogonal functionalization and opens the possibility of selectively incorporating molecules with diverse biological activities on the surfaces of NDPs. Modified NDPs with amphiphilic properties resulting from the presence carboxyl and amine groups were used to incorporate simultaneously folic acid (FA-CONH-(CH2)5-COOH) and 5(6)-carboxyfluorescein (FL-CONH-(CH2)2-NH2) derivatives on the surface of material under biocompatible procedures.

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