scholarly journals Ultrasound-Accelerated Amide Coupling Reactions Directed toward the Synthesis of 1-Acetyl-3-carboxamide-β-carboline Derivatives of Biological Importance

SynOpen ◽  
2017 ◽  
Vol 01 (01) ◽  
pp. 0008-0010 ◽  
Author(s):  
N. Sharma ◽  
P. Kumari ◽  
P. Sharma ◽  
N. Bhagat ◽  
S. Bhagat
Keyword(s):  
Reaction Time ◽  
Carboxylic Acid ◽  
Aromatic Amines ◽  
Coupling Reactions ◽  
Biological Importance ◽  
Amide Coupling ◽  
Derivatives Of

Several biologically important 1-acetyl-3-carboxamide-β-carboline derivatives were rapidly synthesized by ultrasound-promoted amide coupling of 1-acetyl-9H-pyrido[3,4-b]indole-3-carboxylic acid with substituted aromatic amines. The major advantages of the proposed method are that use of ultrasound irradiations afforded the desired products in a drastically reduced reaction time and in excellent yields compared with conventional stirring.

scholarly journals Synthesis of β-Amino Carbonyl Compounds via the Iodine-Alumina Catalyzed Three-Component Coupling Reaction under Microwave Irradiation

2011 ◽  
Vol 2011 ◽  
pp. 1-7 ◽  
Author(s):  
Mantu Rajbangshi ◽  
Md. Rumum Rohman ◽  
Icydora Kharkongor ◽  
Hormi Mecadon ◽  
Bekington Myrboh
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Carbonyl Compounds ◽  
Aromatic Amines ◽  
Coupling Reaction ◽  
Environmentally Friendly ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Key Features ◽  
Operational Simplicity

Iodine-alumina was employed as a catalyst in the coupling reactions of aldehydes, enolizable ketones, or 1,3-dicarbonyls with methyl carbamate or aromatic amines under microwave irradiation to afford β-amino carbonyl compounds in good-to-excellent yields. The key features of this environmentally friendly methodology are its operational simplicity, mild reaction conditions, and less reaction time.

The Reaction of N-Trimethylsilyl-Substituted Heteroarylamines with Esters and Thioesters: An Efficient Protocol To Access Diheteroarylamides

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1779-1790
Author(s):  
Ana Koperniku ◽  
Maryam Zamiri ◽  
David Grierson
Keyword(s):  
Parallel Synthesis ◽  
Amide Bond ◽  
Coupling Reactions ◽  
Trimethylsilyl Derivative ◽  
Vacuum Filtration ◽  
Bond Forming ◽  
Compound Libraries ◽  
Amide Coupling ◽  
Derivatives Of

The S-benzyl thioester and methyl ester derivatives of a representative 4-pyridinone-based carboxylic acid were sufficiently activated to react efficiently in amide coupling reactions with the amide anion generated in situ from the N-trimethylsilyl derivative of different weakly nucleophilic heteroarylamines. In acetonitrile as solvent, the precipitated diheteroarylamide products were isolated in pure form by vacuum filtration. This simple amide bond forming protocol can be readily adapted to the parallel synthesis of compound libraries.

Peptide synthesis with 1-Aminocyclopropane-1-carboxylic acid

1981 ◽  
Vol 34 (11) ◽  
pp. 2431 ◽  
Author(s):  
FHC Stewart
Keyword(s):  
Amino Acid ◽  
Carboxylic Acid ◽  
Peptide Synthesis ◽  
Steric Effect ◽  
Coupling Reactions ◽  
Open Chain ◽  
Leucine Enkephalin ◽  
Active Ester ◽  
Peptide Derivatives ◽  
Derivatives Of

Peptide derivatives of 1-aminocyclopropane-1-carboxylic acid have been synthesized by model active ester coupling reactions in order to compare the steric effect of this plant amino acid with that of its open-chain congener 2-methylalanine. An analogue of leucine-enkephalin containing the alicyclic amino acid has also been prepared.

scholarly journals Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1813
Author(s):  
László Kollár ◽  
Ádám Erdélyi ◽  
Haroon Rasheed ◽  
Attila Takács
Keyword(s):  
Synthetic Method ◽  
Selective Synthesis ◽  
Varied Structure ◽  
Biological Importance ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Derivatives Of

The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance.

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

Synlett ◽  
2021 ◽  
Author(s):  
Tran Quang Hung ◽  
Tuan Thanh Dang ◽  
Peter Langer ◽  
Ha Nam Do ◽  
Nguyen Minh Quan ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Coupling Reactions ◽  
Carbazole Derivatives ◽  
High Yields

AbstractAn efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

scholarly journals Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

2021 ◽  
Vol 11 (3) ◽  
pp. 1180
Author(s):  
Kinga Paruch ◽  
Łukasz Popiołek ◽  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Malm ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Carboxylic Acid ◽  
Bacterial Infections ◽  
Acid Hydrazide ◽  
Antimicrobial Effect ◽  
In Vitro Antimicrobial Activity ◽  
Research Goal ◽  
New Compounds ◽  
Derivatives Of

Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.

Some Basic Derivatives of 3-Methylflavone-8-carboxylic Acid

1960 ◽  
Vol 2 (3) ◽  
pp. 263-269 ◽  
Author(s):  
Paolo Da Re ◽  
Lucia Verlicchi ◽  
Ivo Setnikar
Keyword(s):  
Carboxylic Acid ◽  
Derivatives Of

scholarly journals Hyperbranched Molecular Structures with Potential Antiviral Activity: Derivatives of 5,6-Dihydroxyindole-2-Carboxylic Acid

Molecules ◽  
2006 ◽  
Vol 11 (12) ◽  
pp. 968-977 ◽  
Author(s):  
Mario Sechi ◽  
Fabio Casu ◽  
Ilaria Campesi ◽  
Stefano Fiori ◽  
Alberto Mariani
Keyword(s):  
Carboxylic Acid ◽  
Antiviral Activity ◽  
Molecular Structures ◽  
Derivatives Of

„IN SILICO“ PREDICTION OF PHARMACOKINETIC PROPERTIES AND DRUGLIKENESS OF NOVEL THIOUREA DERIVATIVES OF NAPROXEN

2021 ◽  
Author(s):  
Nikola V. Nedeljković ◽  
◽  
Vladimir D. Dobričić ◽  
Marina Ž. Mijajlović ◽  
Gordana P. Radić ◽  
...  
Keyword(s):  
Blood Brain Barrier ◽  
Aromatic Amines ◽  
Gastrointestinal Absorption ◽  
Skin Permeability ◽  
Thiourea Derivatives ◽  
Barrier Permeability ◽  
Brain Barrier Permeability ◽  
Pharmacokinetic Properties ◽  
Inhibitory Potential ◽  
Derivatives Of

Masking the carboxyl group of naproxen with other functional groups may be a promising strategy to decrease its gastrointestinal toxicity. Thiourea moiety has been described as an important pharmacophore in a variety of pharmacologically active compounds, including anti-inflammatory, antiviral, anticancer, hypoglycemic and antimicrobial agents. Our research group has previously designed twenty novel thiourea derivatives of naproxen, containing amino acids (glycine, L-alanine, β-alanine, L-valine and L-phenylalanine – compounds 1,2,3,4 and 5, respectively), their methyl (6–10) and ethyl esters (11–15), as well as aromatic amines (16–20). Pharmacokinetic properties and druglikeness of these compounds were predicted using SwissADME web tool (http://www.swissadme.ch/). Predicted pharmacokinetic properties include potential for gastrointestinal absorption, blood-brain barrier permeability, skin permeability, transport mediated by P-glycoproteins and enzyme inhibitory potential. Druglikeness was evaluated using Lipinski’s, Ghose’s, Veber’s, Egan’s and Muegge’s rules, as well as on the basis of bioavailability score. All tested compounds had high-predicted gastrointestinal absorption and low blood-brain barrier permeability. Also, derivatives 2, 4, 7, 9, 10, 12, 14, 15 and 18 were predicted to be substrates for P-glycoprotein. Derivatives with aromatic amines (16–20) showed inhibitory potential against all tested CYP isoforms. Derivative 19 had the highest, while derivative 13 demonstrated the lowest predicted skin permeability. Finally, derivatives 1–12, except 5 and 10, have druglike structures, since they obey to all imposed rules.

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