Synthesis, Antibacterial and Antitubercular Activities of Some 5H-Thiazolo[3,2-a]pyrimidin-5-ones and Sulfonic Acid Derivatives

A series of 5H-thiazolo[3,2-a]pyrimidin-5-ones were synthesized by the cyclization reactions of S-alkylated derivatives in concentrated H2SO4. Upon treatment of S-alkylated derivatives at different temperatures, intramolecular cyclization to 7-(substituted phenylamino)-5H-thiazolo[3,2-a]pyrimidin-5-ones or sulfonation of cyclized products to sulfonic acid derivatives occurred. The structures of the target compounds were confirmed by IR, 1H-NMR, 13C-NMR and HRMS studies. The compounds were evaluated for their preliminary in vitro antibacterial activity against some Gram-positive and Gram-negative bacteria and screened for antitubercular activity against Mycobacterium tuberculosis by the broth dilution assay method. Some compounds showed good antibacterial and antitubercular activities.

• Publication year

  2015

• Venue

  Molecules

• Publication date

  2015-09-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.3390/molecules200916419PMID 26378507PMCID 6332143
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Polysulfonation of PBI-based membranes for HT-PEMFCs: a possible way to maintain high proton transport at a low H3PO4 doping level

  2014cited by this paper
• Synthesis and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as dual binding site acetylcholinesterase inhibitors.

  2014cited by this paper
• Efficient Synthesis of New Functionalized 2-(Hetaryl)thiazoles

  2013cited by this paper
• Synthesis of 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one derivatives

  2013cited by this paper
• Laccase-catalyzed domino reaction between catechols and 6-substituted 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles for the synthesis of pyrimidobenzothiazole derivatives.

  2013cited by this paper
• Synthesis and Biological Studies of Novel Biphenyl-3,5-dihydro-2H- thiazolopyrimidines Derivatives

  2012cited by this paper
• Synthesis, characterization and biological evaluation of thiazolopyrimidine derivatives

  2012cited by this paper
• A Convenient, Rapid Microwave-Assisted Synthesis of 2-Substituted Phenyl-2,3-Dihydrobenzo[B][1,4]Thiazepine-3-Carboxamide Derivatives and Its Antimicrobial Activity

  2012cited by this paper
• Antituberculosis and antibacterial evaluations of some novel phenyl pyrazolone-substituted 1h-benzo[g]pyrazolo[3,4-b]quinoline-3-ylamine derivatives

  2012cited by this paper
• Substituted thiazoles V. synthesis and antitumor activity of novel thiazolo[2,3-b]quinazoline and pyrido[4,3-d]thiazolo[3,2-a]pyrimidine analogues.

  2012cited by this paper
• Design, synthesis and evaluation of clinafloxacin triazole hybrids as a new type of antibacterial and antifungal agents.

  2012cited by this paper
• Thiazolidione derivatives as novel antibiofilm agents: design, synthesis, biological evaluation, and structure-activity relationships.

  2011cited by this paper
• Anti-HSV-1 activity and mechanism of action of some new synthesized substituted pyrimidine, thiopyrimidine and thiazolopyrimidine derivatives.

  2010cited by this paper
• Thiazolopyrimidine Inhibitors of 2‐Methylerythritol 2,4‐Cyclodiphosphate Synthase (IspF) from Mycobacterium tuberculosis and Plasmodium falciparum

  2010cited by this paper
• 4-[1-(Substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]-benzenesulfonic acids: Synthesis, antimicrobial activity, QSAR studies, and antiviral evaluation

  2010cited by this paper
• Synthesis and antimicrobial studies of thiazolotriazinones.

  2010cited by this paper
• Thiazolopyrimidines without bridge-head nitrogen: thiazolo [4,5-d] pyrimidines

  2010cited by this paper
• Development of Novel Thiazolopyrimidines as CDC25B Phosphatase Inhibitors

  2009cited by this paper
• Synthesis, Pharmacophore Modeling, and Biological Evaluation of Novel 5H-Thiazolo[3,2-a]pyrimidin-5-one Derivatives as 5-HT2A Receptor Antagonists

  2008cited by this paper
• Antitumor studies. Part 4: Design, synthesis, antitumor activity, and molecular docking study of novel 2-substituted 2-deoxoflavin-5-oxides, 2-deoxoalloxazine-5-oxides, and their 5-deaza analogs.

  2008cited by this paper
• Synthesis and antimicrobial studies of novel dichlorofluorophenyl containing aminotriazolothiadiazines.

  2008cited by this paper
• Investigation into the regioisomeric composition of some fused pyrimidines: 1H NMR and theoretical studies

  2008cited by this paper
• A Novel Synthesis of Some New Pyrimidine and Thiazolopyrimidine Derivatives for Anticancer Evaluation

  2007cited by this paper
• Microbial screening of novel synthesized formazans having amide linkagesΦ

  2006cited by this paper
• Synthesis and Antimicrobial Activity of Some New 1,3-Diphenylpyrazoles Bearing Pyrimidine, Pyrimidinethione, Thiazolopyrimidine, Triazolopyrimidine, Thio-and Alkylthiotriazolop-Yrimidinone Moieties at the 4-Position

  2006cited by this paper
• Microbial Screening of Novel Synthesized Formazans Having Amide Linkages.

  2006cited by this paper
• Structural chemistry and properties of metal arenesulfonates

  2004cited by this paper
• Reactions with 2-Thiothymine; Selective Cyclization of S-Substituted 2-Thiothymine

  2003cited by this paper
• Keto-enol/enolate equilibria in the isochroman-4-one system. Effect of a beta-oxygen substituent.

  2001cited by this paper
• Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents.

  2000cited by this paper
• Structure-activity relationships of substituted 5H-thiazolo[3,2-a]pyrimidines as group 2 metabotropic glutamate receptor antagonists.

  1999cited by this paper
• Synthesis and anti-inflammatory activities of some thiazolo[3,2-a]pyrimidine derivatives.

  1999cited by this paper
• Synthesis and anti-HIV-1 activity of novel 2,3-dihydro-7H-thiazolo[3,2-a]pyrimidin-7-ones.

  1998cited by this paper
• Condensed Heterocyclic Compounds: Synthesis and Antiinflammatory Activity of Novel Thiazolo[3,2‐a]pyrimidines

  1998cited by this paper
• Enhancement of luminescence of europium(III) ions in water by use of synergistic chelation. Part 2. 1:1:1 complexes

  1996cited by this paper
• Syntheses and anti-inflammatory activity of novel oximes and O-acyloximes.

  1992cited by this paper
• Thiazolo[3,2-a]pyrimidine derivatives as calcium antagonists.

  1992cited by this paper
• New Thiazolo(3,2‐a)pyrimidine Derivatives, Synthesis and Structure‐ Activity Relationships.

  1992cited by this paper
• Condensed heterocycles: synthesis and antifungal activity of .pi.-deficient pyrimidines linked with .pi.-rich heterocycles

  1991cited by this paper
• Synthese und Reaktionen von 2-Arylhydrazono-2-cyan-N,N-dialkyl-acetamidinen

  1991cited by this paper
• Pteridines. Part XLI. Synthesis and properties of 6,7,8‐trimethyl‐4‐thiolumazine

  1989cited by this paper
• Pteridines. Part XLII. Synthesis and properties of 8‐substituted 2,4‐dithiolumazines

  1988cited by this paper
• Aminoketone enolisation: influence of increasing chain length on intramolecular catalysis

  1988cited by this paper
• Chlormethyl-substituierte Heterocyclen aus Chlortetrolsäuremethylester

  1988cited by this paper
• Synthesis of 6-anilino-2-thiouracils and their inhibition of human placenta iodothyronine deiodinase.

  1985cited by this paper
• Palladium-catalyzed polyhetero-Claisen rearrangement of 2-(allylthio)pyrimidin-4(3H)-ones

  1985cited by this paper
• 7-trans-(2-Pyridylethenyl)-5H-thiazolo[3,2-a]pyrimidine-5-ones: synthesis and pharmacological activity.

  1985cited by this paper
• Pyrylium-mediated transformations of natural products. Part 3. Synthesis of water-soluble pyrylium salts and their preparative reactions with amines

  1984cited by this paper
• 2‐Arylamino‐thiophen‐3‐carbonsäurederivate

  1984cited by this paper
• Taulomerism and Electronic Structure of Biological Pyrimidines

  1975cited by this paper
• Potential anticancer angents. II. Schiff bases from benzaldehyde nitrogen mustards.

  1968cited by this paper
• Potential anticancer agents. 4. Schiff bases from benzaldehyde nitrogen mustards.

  1968cited by this paper
• A new synthesis of thiazolo[3,2‐a] pyrimidinones

  1967cited by this paper
• The Structure of Certain Polyazaindenes. II. The Product from Ethyl Acetoacetate and 3-Amino-1,2,4-triazole

  1959cited by this paper
• Simple pyrimidines. Part II. 1:2-Dihydro-1-methylpyrimidines and the configuration of the N-methyluracils

  1955cited by this paper

• Hantzsch-Type Regioselective Synthesis of Novel Pentaza-5H-cyclopenta[b]anthracene-4,6-diones Based on 7-(phenylamino)-[1,2,4]triazolo[4,3-a]pyrimidin-5-ones Precursors

  2026cites this paper
• A simple, facile and greener route to thiazolo[3,2-c]pyrimidinones in semi-aqueous medium and their antibacterial properties

  2024cites this paper
• 6-Nitroazolo[1,5-a]pyrimidines and 6-Nitroazolo[5,1-c][1,2,4]triazines in the Nucleophilic Sulfation Reaction

  2024cites this paper
• Kinetic study on the degradation of Acid Red 88 azo dye in a constructed wetland-microbial fuel cell inoculated with Shewanella oneidensis MR-1

  2024cites this paper
• Synthetic approaches and biological evaluation of nitrogen bridgehead thiazolo[3,2-a]pyrimidines

  2024cites this paper
• Unveiling the antibacterial efficacy of thiazolo [3,2‐a] pyrimidine: Synthesis, molecular docking, and molecular dynamic simulation

  2024cites this paper
• An efficient organopromotor L‐arginine facilitated synthesis of thiazolo[3,2‐a]pyrimidine derivatives in EtOH:H2O solvent

  2023cites this paper
• Characterization, DFT calculations and antimicrobial assays of some novel nanoparticles mixed ligand complexes of 5-cyano-6-phenyl-2-thiouracil in presence of 1,10-phenanthroline

  2023cites this paper
• Thiazolopyrimidines: A Retrospective Study of Synthesis, Structure-Activity Relationship and Diverse Pharmacological Actions

  2022cites this paper
• Thiazolopyrimidine Scaffold as a Promising Nucleus for Developing Anticancer Drugs: a Review in Last Decade.

  2022cites this paper
• Efficient and green synthesis of novel hexahydro-5H-thiazolo[2',3':2,3]pyrimido[4,5-b]quinoline derivatives

  2022cites this paper
• Synthesis, spectral characterization, DFT-Computational analyses on Novel 4-nitrobenzenaminium benzenesulfonate (4NBASA) crystal

  2022cites this paper
• Design, Synthesis, and Anti-mycobacterial Evaluation of New 3,5-Disubstituted-pyrazole-1-carbothioamides

  2022cites this paper
• Three-Component One-Pot Construction of 2-Aryl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidines Using Solid Calcium Carbide as a Surrogate of Gaseous Acetylene.

  2022cites this paper
• Synthesis and spectral characterization of some new thiazolopyrimidine derivatives

  2021cites this paper
• Pharmacophore Modeling, Design, and Synthesis of Potent Antihypertensives, Oxazolo/thiazolo-[3,2-a]-pyrimidin-3(2H)-one, and 1,5-Dihydroimidazo-[1,2-a]-pyrimidin-3(2H)-one Derivatives: A Pilot Trial.

  2020cites this paper
• Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues

  2020cites this paper
• An efficient microwave-promoted three-component synthesis of thiazolo[3,2-a]pyrimidines catalyzed by SiO2–ZnBr2 and antimicrobial activity evaluation

  2019cites this paper
• Synthesis and antitumor activity of isolongifoleno[7,8‐d]thiazolo[3,2‐a]pyrimidine derivatives via enhancing ROS level

  2019cites this paper
• Synthesis of Some New Thiazolo[3,2‐ a ]pyrimidine Derivatives and Their Applications as Disperse Dyes

  2019cites this paper
• Synthesis and biological screening of new thiazolo[4,5-d]pyrimidine and dithiazolo[3,2-a:5',4'-e]pyrimidinone derivatives as antimicrobial, antiquorum-sensing and antitumor agents.

  2018cites this paper
• Synthesis, spectroscopic characterization and computational chemical study of 5-cyano-2-thiouracil derivatives as potential antimicrobial agents

  2018cites this paper
• Antitubercular Activity and Synergistic Study of Novel Pyrazole Derivatives

  2018cites this paper
• Synthesis and Biological Evaluation of New Dipyridylpteridines, Lumazines, and Related Analogues

  2017cites this paper
• Synthesis and characterization of some novel 7-(aryl)-3-phenyl-6-(1H-tetrazol-5-yl)-5H-thiazolo[3,2-a]pyrimidin-5-one derivatives

  2017cites this paper
• Regioselective Bromination of 2-Iodomethyl-2,3-Dihydrothiazolo[3,2-a]pyrimidin-5-one

  2016cites this paper
• Crystal structure of 2-(4-methoxyphenyl)-1,3-thiazolo[4,5-b]pyridine, C13H10N2OS

  2016cites this paper