Synthesis and anti-inflammatory activities of some thiazolo[3,2-a]pyrimidine derivatives

Tozkoparan, Birsen; Ertan, Mevlüt; Kelicen, Pelin; Demirdamar, R.

doi:10.1016/s0014-827x(99)00068-3

Cited by 204 publications

(146 citation statements)

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“…The spectra also exhibited a broad signal in the region 8-10, which was due to two NH protons. 13 C NMR spectra of the thiones (1a-5d) gave further support to the reported structures, showing signals attributable to CS (177-178), ϾCH (55-56), and ϭCH-(99-100).…”

supporting

confidence: 74%

“…The molecular formula, molecular weight (MW), melting point, % yield and elemental analysis, 1 H NMR, 13 C NMR of all the synthesized compounds are given below: 1H, d, ϾCH-), 5.41 (1H, d, ϭCH-), 3.73 (3H, s, -OCH 3 ), 8.9 (1H, brs, -NH), 9.6 (1H, brs, -NH). 13 …”

Section: Chemical Datamentioning

confidence: 99%

“…5,6) The study of nitrogen-containing heterocycles in pesticide chemistry has the history of more than 40 years. [7][8][9][10][11][12][13] The development of efficient and straightforward methods for the synthesis of heterocyclic compounds represents a broad area of organic chemistry. 14,15) Structures containing such units often play an essential role due to their biological activity, particularly in cancer and virus research.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and insecticidal activity of 3,4-dihydropyrimidine-2(1H)-thiones against the pulse beetle, Callosobruchus chinensis

et al. 2011

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A series of twenty substituted 3,4-dihydropyrimidine derivatives were prepared and characterized by TLC, IR, 1 H NMR, 13 C NMR spectroscopic data and elemental analysis. These were screened for insecticidal activity by the film residue method against the pulse beetle (adzuki bean weevil, Callosobruchus chinensis). 4-(2Ј-Chlorophenyl)-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione (LC 50 0.00201 mg/cm 2 ), 4-(2Ј-chlorophenyl)-6-p- Many of these have been proved to be herbicides 31,32) and fungicides. 33,34) In view of the wide range of biological activities observed in pyrimidine derivatives, it was aimed to test their insecticidal activities. In this paper we report the synthesis, characterization and insecticidal activity of a series of 3,4-dihydropyrimidine-2(1H )-thione derivatives. The compounds were tested against the pulse beetle (adzuki bean weevil, Callosobruchus chinensis) taking organophosphate (OP) insecticide dichlorvos 35) as standard test compounds to search for a new compound having insecticidal activity. Materials and Methods Instruments and reagentsAll the chemicals used were purchased from Sigma-Aldrich (India). Reactions were monitored by thin layer chromatography (TLC) on precoated Merck silica gel 60F 254 (India), the spots were visualized either by UV or by iodine vapor and were further purified by column chromatography (60-120 mesh). Melting points were determined on a melting point apparatus. Infra Red (IR) spectra were recorded on a PerkinElmer model 2000 FT-IR spectrophotometer (UK) as KBr pellets, and values are expressed as n˜(cm Ϫ1 ). The 1 H NMR and 13 C NMR spectra were recorded on a Bruker 400 MHz spectrometer (Germany) using tetramethylsilane (TMS) as an internal standard. The chemical shift was recorded on a d scale. Elemental analysis was performed using a EURO elemental analyzer (Italy), and the data of C, H and N were within 0.4% of the calculated values. Chemical synthesis 2.1 General procedure for the preparation of 4,6-diphenyl-3,4-dihydropyrimidine-2(1H)-thione derivativesA mixture of chalcone (0.001 mol), thiourea (0.001 mol) and KOH (6.5 g) in 25 mL methanol was refluxed for 3 hr. Completion of the reaction was monitored by TLC (hexane : ethyl acetate, 7 : 3 v/v). The reaction product was concentrated and cooled; and the precipitate was filtered off and recrystallized

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supporting

confidence: 74%

Section: Chemical Datamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and insecticidal activity of 3,4-dihydropyrimidine-2(1H)-thiones against the pulse beetle, Callosobruchus chinensis

et al. 2011

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“…As one type of those heterocyclic rings, 5H-thiazolo[3,2-a]pyrimidin-5-ones are considered a promising class of bioactive heterocyclic compounds having a wide range of biological activities such as anti-inflammatory 4,5 . These compounds also have Anti-hypertensive 6 , antifungal 7 , antibiofilm 8 , antibacterial 9 , antiviral 10 , antioxidant 11 , antitumor 12,13 , anti-HIV 14 , calcium channel blocking 15 , antitubercular 16 activities. Apart from this our research group also newly synthesize earlier some potent biologically active compounds like antimicrobial 17 , anti tubercular agents 18 .…”

Section: Introductionmentioning

confidence: 99%

Thiazolo[3,2-a] pyrimidin-5-ones: Design, Synthesis and Antimicrobial Evaluation

Zine¹,

Jadhav²,

Dixit³

et al. 2017

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Bacterial and fungal infections represent one of the most common health problem that cause functional disability and other complications. Upcoming needs for the clinical drugs candidates for the improvement signifies an exciting and challenging approach to improve the clinical effectiveness of current drugs in the development of new therapeutic approaches. In the existing report, we here report our results for extensive SAR study of novel thiazolo pyrimidin-5-ones derivatives, synthesis, antibacterial and antifungal activity. We are happy to display our most active compounds 5a, 5d, 5e, 5i owned incredible antimicrobial and antifungal potency. Altogether, compound 5i was found to be a lead candidate, displayed maximum potency in both antifungal and antibacterial segments. These findings recommend the prospective to explore this series as antimicrobial and anti-fungal agents.

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TheBiginelli Dihydropyrimidine Synthesis

2004

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The cyclocondensation of suitable CH‐acidic carbonyl compounds, aldehydes, and urea‐type blocks under acidic conditions provides multifunctionalized derivatives. The discovery of this three‐component condensation process was made by Biginelli in 1893, therefore this reaction is called the “Biginelli reaction,” “Biginelli condensation,” or the “Biginelli dihydropyrimidine synthesis.” While the early examples of this cyclocondensation process typically involved a beta‐ketoester, aromatic aldehyde, and urea, the scope has now been extended considerably by variation of three building blocks, allowing access to a large number of multifunctionalized pyridmidine derivatives. The importance of multicomponent reactions in combinatorial chemistry has generated a renewed interest in the Biginelli reaction and the number of patents and publications on this subject is growing. In this chapter, all three‐component condensations involving suitable CH‐acidic carbonyl compounds, aldehydes, and urea‐type building blocks following the Biginelli concept are covered. Therefore, reactions involving 1,3‐diketones or nitroacetone as building blocks leading to dihydropyrimides that follow the discussed substitution pattern are included in contrast to earlier articles. Patents are only cited if they contain information not otherwise available.

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Synthesis and anti-inflammatory activities of some thiazolo[3,2-a]pyrimidine derivatives

Cited by 204 publications

References 7 publications

Synthesis and insecticidal activity of 3,4-dihydropyrimidine-2(1H)-thiones against the pulse beetle, Callosobruchus chinensis

Synthesis and insecticidal activity of 3,4-dihydropyrimidine-2(1H)-thiones against the pulse beetle, Callosobruchus chinensis

Thiazolo[3,2-a] pyrimidin-5-ones: Design, Synthesis and Antimicrobial Evaluation

TheBiginelli Dihydropyrimidine Synthesis

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