scholarly journals Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol

2020 ◽  
Vol 16 ◽  
pp. 2322-2331
Author(s):  
Ekaterina E Stepanova ◽  
Maksim V Dmitriev ◽  
Andrey N Maslivets
Keyword(s):  
Biological Activity ◽  
Acute Toxicity ◽  
Synthetic Approach ◽  
Biological Assays ◽  
Synthetic Approaches ◽  
New Compounds

Two synthetic approaches to enaminones fused to 1,4-benzothiazin-2-one moiety, which can be interesting in studies on biological activity, chemosensors, and fluorescence, were developed via the reaction of furan-2,3-diones or acylpyruvic acids in the presence of carbodiimides with o-aminothiophenols. The target enaminones were formed together with pharmaceutically interesting 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones. A selective synthetic approach to 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones was developed via the solvent-switchable reaction of furan-2,3-diones with o-aminothiophenol. Preliminary biological assays (antimicrobial, acute toxicity) of the new compounds were carried out.

scholarly journals 1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo

2021 ◽  
Vol 22 (5) ◽  
pp. 2367
Author(s):  
Sen Yang ◽  
Chao-Li Ren ◽  
Tian-Yang Ma ◽  
Wen-Qian Zou ◽  
Li Dai ◽  
...  
Keyword(s):  
Biological Activity ◽  
Antifungal Activity ◽  
Acute Toxicity ◽  
High Activity ◽  
Broad Spectrum ◽  
Zebrafish Embryo ◽  
Thanatephorus Cucumeris ◽  
Low Toxicity ◽  
New Compounds ◽  
Better Than

To discover new compounds with broad spectrum and high activity, we designed a series of novel benzamides containing 1,2,4-oxadiazole moiety by bioisosterism, and 28 benzamides derivatives with antifungal activity were synthesized. These compounds were evaluated against four fungi: Botrytis cinereal, FusaHum graminearum, Marssonina mali, and Thanatephorus cucumeris. The results indicated that most of the compounds displayed good fungicidal activities, especially against Botrytis cinereal. For example, 10a (84.4%), 10d (83.6%), 10e (83.3%), 10f (83.1%), 10i (83.3%), and 10l (83.6%) were better than pyraclostrobin (81.4%) at 100 mg/L. In addition, the acute toxicity of 10f to zebrafish embryo was 20.58 mg/L, which was classified as a low-toxicity compound.

scholarly journals Synthesis and Biological Activity of Arylspiroborate Salts Derived from Caffeic Acid Phenethyl Ester

2015 ◽  
Vol 2015 ◽  
pp. 1-9 ◽  
Author(s):  
Martin J. G. Hébert ◽  
Andrew J. Flewelling ◽  
Trevor N. Clark ◽  
Natalie A. Levesque ◽  
Jacques Jean-François ◽  
...  
Keyword(s):  
Biological Activity ◽  
Caffeic Acid ◽  
Radical Scavenging ◽  
Antimicrobial Properties ◽  
Caffeic Acid Phenethyl Ester ◽  
Boron Compounds ◽  
Biological Assays ◽  
Radical Scavenging Ability ◽  
New Compounds ◽  
Human Polymorphonuclear Leukocytes

Two novel boron compounds containing caffeic acid phenethyl ester (CAPE) derivatives have been prepared and characterized fully. These new compounds and CAPE have been investigated for potential antioxidant and antimicrobial properties and their ability to inhibit 5-lipoxygenase and whether chelation to boron improves their biological activity. Sodium salt 4 was generally more active than ammonium salt 5 in the biological assays and surpassed the radical scavenging ability of CAPE. Compounds 4 and 5 were more active than CAPE and Zileuton in human polymorphonuclear leukocytes. These results clearly show the effectiveness of the synthesized salts as transporter of CAPE.

Click Reactions in Chemistry of Triterpenes - Advances Towards Development of Potential Therapeutics

2018 ◽  
Vol 25 (5) ◽  
pp. 636-658 ◽  
Author(s):  
Jan Pokorny ◽  
Lucie Borkova ◽  
Milan Urban
Keyword(s):  
Biological Activities ◽  
Synthetic Approach ◽  
Clinical Use ◽  
New Approach ◽  
Click Reactions ◽  
Drug Candidates ◽  
The Past ◽  
Low Toxicity ◽  
New Compounds ◽  
Potential Therapeutics

Triterpenoids are natural compounds with a large variety of biological activities such as anticancer, antiviral, antibacterial, antifungal, antiparazitic, antiinflammatory and others. Despite their low toxicity and simple availability from the natural resources, their clinical use is still severely limited by their higher IC50 and worse pharmacological properties than in the currently used therapeutics. This fact encouraged a number of researchers to develop new terpenic derivatives more suitable for the potential clinical use. This review summarizes a new approach to improve both, the activity and ADME-Tox properties by connecting active terpenes to another modifying molecules using click reactions. Within the past few years, this synthetic approach was well explored yielding a lot of great improvements of the parent compounds along with some less successful attempts. A large quantity of the new compounds presented here are superior in both activity and ADME-Tox properties to their parents. This review should serve the researchers who need to promote their hit triterpenic structures towards their clinical use and it is intended as a guide for the chemical synthesis of better drug candidates.

Synthesis and Biological Potentials of Quinoline Analogues: A Review of Literature

2019 ◽  
Vol 16 (7) ◽  
pp. 653-688 ◽  
Author(s):  
Leena Kumari ◽  
Salahuddin ◽  
Avijit Mazumder ◽  
Daman Pandey ◽  
Mohammad Shahar Yar ◽  
...  
Keyword(s):  
Biological Activity ◽  
Heterocyclic Compounds ◽  
Building Blocks ◽  
Vital Role ◽  
Review Of Literature ◽  
Drug Discovery Process ◽  
Active Compounds ◽  
Lead Compounds ◽  
Synthetic Approaches ◽  
Derivatives Of

Heterocyclic compounds are well known for their different biological activity. The heterocyclic analogs are the building blocks for synthesis of the pharmaceutical active compounds in the organic chemistry. These derivatives show various type of biological activity like anticancer, antiinflammatory, anti-microbial, anti-convulsant, anti-malarial, anti-hypertensive, etc. From the last decade research showed that the quinoline analogs plays a vital role in the development of newer medicinal active compounds for treating various type of disease. Quinoline reported for their antiviral, anticancer, anti-microbial and anti-inflammatory activity. This review will summarize the various synthetic approaches for synthesis of quinoline derivatives and to check their biological activity. Derivatives of quinoline moiety plays very important role in the development of various types of newer drugs and it can be used as lead compounds for future investigation in the field of drug discovery process.

Prediction of Oral Acute Toxicity of Organophosphates Using QSAR Methods

2019 ◽  
Vol 16 ◽  
Author(s):  
Mina Kianpour ◽  
Esmat Mohammadinasab ◽  
Tahereh Momeni Esfahani
Keyword(s):  
Acute Toxicity ◽  
Molecular Descriptors ◽  
Back Propagation ◽  
Quantitative Structure Activity Relationship ◽  
Average Deviation ◽  
Qsar Models ◽  
Ann Models ◽  
Similar Class ◽  
New Compounds ◽  
Oral Acute Toxicity

: The aim of the present study was to develop quantitative structure-activity relationship (QSAR) models, based on molecular descriptors to predict the oral acute toxicity (LD50) of organophosphate compounds. The QSAR models based on genetic algorithm-multiple linear regression (GA-MLR) and back-propagation artificial neural network (BP-ANN) methods were proposed. The prediction experiment showed that the BP-ANN method was a reliable model for screening molecular descriptors, and molecular descriptors obtained by BP-ANN models could well characterize the molecular structure of each compound. It was indicated that among molecular descriptors to predict the LD50 (mgkg-1) of organophosphates, ALOGP2, RDF030u, RDF065p and GATS5m descriptors have more importance than the other descriptors. Also BP-ANN approach with the values of root mean square error (RMSE= 0.00168), square correlation coefficient (R2= 0.9999) and absolute average deviation (AAD=0.6981631) gave the best outcome, and the model predictions were in good agreement with experimental data. The proposed model may be useful for predicting LD50 (mgkg-1) of new compounds of similar class.

scholarly journals Two Ecdysteroids Isolated from Micropropagated Lychnis flos-cuculi and the Biological Activity of Plant Material

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 904
Author(s):  
Michał P. Maliński ◽  
Jaromir Budzianowski ◽  
Małgorzata Kikowska ◽  
Monika Derda ◽  
Marcelina M. Jaworska ◽  
...  
Keyword(s):  
Biological Activity ◽  
Acute Toxicity ◽  
Plant Material ◽  
Present Report ◽  
Root Extract ◽  
Methanolic Extracts ◽  
Comparable Activity ◽  
Antiamoebic Activity ◽  
Amoebicidal Activity

Genetically uniform plant material, derived from Lychnis flos-cuculi propagated in vitro, was used for the isolation of 20-hydroxyecdysone and polypodine B and subjected to an evaluation of the antifungal and antiamoebic activity. The activity of 80% aqueous methanolic extracts, their fractions, and isolated ecdysteroids were studied against pathogenic Acanthamoeba castellani. Additionally, a Microtox® acute toxicity assay was performed. It was found that an 80% methanolic fraction of root extract exerts the most potent amoebicidal activity at IC50 of 0.06 mg/mL at the 3rd day of treatment. Both ecdysteroids show comparable activity at IC50 of 0.07 mg/mL. The acute toxicity of 80% fractions at similar concentrations is significantly higher than that of 40% fractions. Crude extracts exhibited moderate antifungal activity, with a minimum inhibitory concentration (MIC) within the range of 1.25–2.5 mg/mL. To the best of our knowledge, the present report is the first to show the biological activity of L. flos-cuculi in terms of the antifungal and antiamoebic activities and acute toxicity. It is also the first isolation of the main ecdysteroids from L. flos-cuculi micropropagated, ecdysteroid-rich plant material.

scholarly journals Development of Antibacterial and Antifungal Triazole Chromium(III) and Cobalt(II) Complexes: Synthesis and Biological Activity Evaluations

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 2013 ◽  
Author(s):  
Ricardo Murcia ◽  
Sandra Leal ◽  
Martha Roa ◽  
Edgar Nagles ◽  
Alvaro Muñoz-Castro ◽  
...  
Keyword(s):  
Electrical Conductivity ◽  
Biological Activity ◽  
Melting Point ◽  
Inhibitory Concentration ◽  
Vero Cells ◽  
Visible Spectroscopy ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial And Antifungal ◽  
New Compounds

In this work, six complexes (2–7) of Cr(III) and Co(II) transition metals with triazole ligands were synthesized and characterized. In addition, a new ligand, 3,5-bis(1,2,4-triazol-1-ylmethyl)toluene (1), was synthesized and full characterized. The complexes were obtained as air-stable solids and characterized by melting point, electrical conductivity, thermogravimetric analysis, and Raman, infrared and ultraviolet/visible spectroscopy. The analyses and spectral data showed that complexes 3–7 had 1:1 (M:L) stoichiometries and octahedral geometries, while 2 had a 1:2 (M:L) ratio, which was supported by DFT calculations. The complexes and their respective ligands were evaluated against bacterial and fungal strains with clinical relevance. All the complexes showed higher antibacterial and antifungal activities than the free ligands. The complexes were more active against fungi than against bacteria. The activities of the chromium complexes against Candida tropicalis are of great interest, as they showed minimum inhibitory concentration 50 (MIC50) values between 7.8 and 15.6 μg mL−1. Complexes 5 and 6 showed little effect on Vero cells, indicating that they are not cytotoxic. These results can provide an important platform for the design of new compounds with antibacterial and antifungal activities.

scholarly journals Synthesis, Characterization and Biological Activity Study of New Compounds Tetrazole Derivatives Azo-Schiff Base

2019 ◽  
Vol 25 (103) ◽  
pp. 68-89
Author(s):  
Hiba Ibrahim Abdulla AL-Joubory ◽  
Khalid Mohamad Motny Al-janaby
Keyword(s):  
Biological Activity ◽  
Schiff Base ◽  
Pathogenic Bacteria ◽  
Diazonium Salt ◽  
Aldehyde Group ◽  
Spectroscopic Techniques ◽  
Phenyl Hydrazine ◽  
Ft Ir ◽  
New Compounds ◽  
Tetrazole Derivatives

This work included synthesis of azo dye (H1) by the reaction of diazonium salt to sulfacetamide with 4-hydroxy benzaldehyde at (0-5) oC  and synthesis of schiff base (H2-H6) through reaction substituted aromatic amine (aniline, 4-nitro aniline, 4-chloro aniline, 4-amino benzoic acid and phenyl hydrazine)  with aldehyde group in azo compound (H1) in ethanol compounds (H2-H6) and tetrazole derivatives prepared by reaction schiff base with sodium azide in ethanol compounds (H7-H11) and characterization by using spectroscopic techniques Uv/Vis, FT-IR, C.H.N. and H1-NMR of some the prepared compounds using DMSO-d6 a solvent, in addition melting point and determination a purity of TLC, and this work consists a study of biological activity for the some prepared compounds against four types of pathogenic bacteria and know to be resistant to anti biotic.

scholarly journals Synthesis, characterization and acute toxicity of new Schiff base derived from phenylethyl amine and 2-hydroxy naphthaldehyde

2019 ◽  
Vol 10 (1) ◽  
pp. 26-29
Author(s):  
Ibtihal Hassan Hatim ◽  
Wasfi Aboud Al-Masoudi ◽  
Rashad Fadhil Ghadhban
Keyword(s):  
Body Weight ◽  
Schiff Base ◽  
Nmr Spectroscopy ◽  
Acute Toxicity ◽  
Elemental Analysis ◽  
Good Yield ◽  
Mice Model ◽  
Base Derivative ◽  
New Compounds

There is an urgent need for the design and development of new and safer drugs, this has attracted organic chemists to synthesize new compounds with potential of biological and chemotherapeutic activities. Here we report, the condensation of phenylethylamine with 2-hydroxy naphthaldehyde yielded Schiff base derivative in good yield. Characterization of synthesized compound was carried by elemental analysis, IR, 1H-, 13C- and HSQC-NMR spectroscopy. The toxicity of the synthesized compound was determined using Balb/c mice model. Dixon’s up and down method was found to have an LD50 of 827.2 mg/kg of body weight, moderate toxicity.

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

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