Synthesis, characterization, and biological activities of 4-imino-3-arylazo-4H-pyrimido[2,1-b][1,3]benzothiazole-2-oles

Erişkin, Selinay; Şener, Nesrin; Yavuz, Serkan; Şener, İzzet

doi:10.1007/s00044-014-0962-8

Cited by 23 publications

(12 citation statements)

References 18 publications

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“…This work is the continuation of our previous studies . We report here synthesis of 7‐imino‐3‐phenylazo‐6‐arylazo‐2‐methyl‐4 H ‐pyrazolo[1,5‐a]pyrimidine‐5‐ole derivatives 4(a‐m) .…”

Section: Resultsmentioning

confidence: 79%

Synthesis, Characterization, Solvatochromic Properties, and Antimicrobial‐radical Scavenging Activities of New Diazo Dyes Derived from Pyrazolo[1,5‐a]pyrimidine

Şener

Erişkin

Yavuz

et al. 2017

Journal of Heterocyclic Chem

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5‐Amino‐3‐methyl‐4‐phenylazo‐1H‐pyrazole and ethyl cyanoacetate reacted in solvent‐free media at 150°C to produce 7‐amino‐3‐phenylazo‐2‐methyl‐4H‐pyrazolo[1,5‐a]pyrimidine‐5‐one (3). A series of aromatic amines was coupled using this compound (3) and nitrous acid to produce new pyrazolo[1,5‐a] pyrimidine derivatives with two arylazo groups 4(a‐m). The structures of these dyes were determined via UV–vis, Fourier transform infrared, proton nuclear magnetic resonance, high‐resolution mass spectral data, and elemental analysis. After synthesis, the solvent and acid–base effects of the dyes were investigated within the UV–vis region. The antimicrobial properties of the dyes were also studied. All dyes exhibited activity against Gram‐positive and Gram‐negative bacteria, and even against fungi. The results were compared to conventional reference results from the antibiotics ciprofloxacin and ketoconazole. Antioxidant potentials were analyzed using in vitro antioxidant models on the basis of DPPH (1,1‐diphenyl‐2‐picrylhydrazyl) radical scavenging activities. Most of the compounds exhibited excellent antioxidant activities. In particular, compound 4b had a higher activity than Vitamin C.

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Section: Resultsmentioning

confidence: 79%

Synthesis, Characterization, Solvatochromic Properties, and Antimicrobial‐radical Scavenging Activities of New Diazo Dyes Derived from Pyrazolo[1,5‐a]pyrimidine

Şener

Erişkin

Yavuz

et al. 2017

Journal of Heterocyclic Chem

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“…The UV-vis spectrum indicated two peaks at 386 and 263 nm that corresponded to n-π* (N=N azo group) and π-π* transitions (phenyl groups), respectively. [27] The thermal decomposition of the azo-dye ligand involved three decomposition steps. The first one started at 35 C and finished at 455 C, which involved the removal of C 6 H 5 and C 6 H 5 N molecules (found 35.43% and calcd = 35.07%).…”

Section: Characterization Of Azo-dye Ligand (H 2 L)mentioning

confidence: 99%

Metal complexes of tetradentate azo‐dye ligand derived from 4,4′‐oxydianiline: Preparation, structural investigation, biological evaluation and MOE studies

Deghadi

Mahmoud

Mohamed

2020

Applied Organom Chemis

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The Cr (III), Mn (II), Fe (III), Co (II), Ni (II), Cu (II) and Cd (II) complexes were prepared by reaction of its metal chlorides with new azo‐dye ligand (H2L). The ligand derived from 4,4′‐oxydianiline and 2‐amino‐4‐chlorophenol was synthesized in a 1:2 molar ratio. The structure of the ligand and its metal complexes was investigated using different tools such as elemental analysis (C, H, N and M), molar conductivity, IR, UV–vis, 1H‐NMR, mass spectrometry and thermogravimetric and differential thermogravimetric studies. The data showed that the ligand acted as a N,N,O,O‐binegative tetradentate ligand. All metal complexes had a octahedral structure as depicted by spectral and elemental analyses. The conductivity data showed the electrolytic nature of the Cr (III) and Fe (III) complexes while the other complexes were nonelectrolytes. Thermal analysis studies showed the decomposition of the complexes in four to five steps with the weight loss of hydrated water in the first decomposition step followed by the coordinated water and ligand molecules. Biological activity was tested for the prepared compounds against four bacterial species (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa) and against two fungal species (Aspergillus fumigatus and Candida albicans). Also, all complexes were screened for anticancer activities against a breast cancer (MCF‐7) cell line. The [Co(L)(H2O)2] complex showed the lowest IC50 value. Molecular docking is a key tool in computer drug design. Therefore, investigation of protein receptors and ligand interaction plays a vital role in the design of structurally based drugs. As a result, docking studies were investigated for H2L ligand, [Mn(L)(H2O)2] and [Ni(L)(H2O)2] complexes with 5KBC, 3V7B and 4G9M receptors.

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“…There are few reports available concerning the synthesis of pyrimidothiazoles or pyrimidoimidazole‐imino and/or pyrimidoimidazole‐one derivatives . 4‐Imino‐3,4‐dihydro‐2 H ‐pyrimido[2,1‐ b ][1,3]benzothiazole‐2‐one has been synthesized by the reaction of 2‐aminobenzothiazole with ethyl cyanoacetate in either ethoxide/ethanol or phosphoric acid as well as under neat conditions , or with bis(methylthio)methylene malononitrile in dimethylformamide (DMF)/K 2 CO 3 .…”

Section: Introductionmentioning

confidence: 99%

Regioselectivity in the Reaction of 2‐Aminobenzothiazoles and 2‐Aminobenzimidazoles with Enaminonitriles and Enaminones: Synthesis of Functionally Substituted Pyrimido[2,1‐b][1,3]benzothiazole and Pyrimido[1,2‐a]benzimidazole Derivatives

Alnajjar

Abdelkhalik

Riad

et al. 2018

Journal of Heterocyclic Chem

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A variety of new polyfunctionally substituted benzo[d]pyrimido[2,1‐b][1,3]thiazole and benzo[4,5]imidazo[1,2‐a]pyrimidine derivatives have been synthesized. The general synthetic procedure used for this purpose involves the condensation of 2‐aminobenzothiazole and 2‐aminobenzimidazole with a variety of enaminonitriles, enaminones, and acrylaldehyde. The regioselectivity for initial attack of either endocyclic ring nitrogen or exocyclic amino group was studied and rationalized for. It has been concluded that ring nitrogen is the most reactive cite in acidic medium, and cyclic intermediate can also be isolated, attesting to this conclusion upon cyclization. However, in basic or neutral medium, the exocyclic amino group was found to be the most reactive center. All structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthetic route whenever possible.

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Synthesis, characterization, and biological activities of 4-imino-3-arylazo-4H-pyrimido[2,1-b][1,3]benzothiazole-2-oles

Cited by 23 publications

References 18 publications

Synthesis, Characterization, Solvatochromic Properties, and Antimicrobial‐radical Scavenging Activities of New Diazo Dyes Derived from Pyrazolo[1,5‐a]pyrimidine

Synthesis, Characterization, Solvatochromic Properties, and Antimicrobial‐radical Scavenging Activities of New Diazo Dyes Derived from Pyrazolo[1,5‐a]pyrimidine

Metal complexes of tetradentate azo‐dye ligand derived from 4,4′‐oxydianiline: Preparation, structural investigation, biological evaluation and MOE studies

Regioselectivity in the Reaction of 2‐Aminobenzothiazoles and 2‐Aminobenzimidazoles with Enaminonitriles and Enaminones: Synthesis of Functionally Substituted Pyrimido[2,1‐b][1,3]benzothiazole and Pyrimido[1,2‐a]benzimidazole Derivatives

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