Design and synthesis of some substituted 1H-pyrazolyl-thiazolo[4,5-d]pyrimidines as anti-inflammatory–antimicrobial Agents

Bekhit, Adnan A.; Fahmy, Hesham; Rostom, Sherif A. F.; Baraka, Azza

doi:10.1016/s0223-5234(02)00009-0

Cited by 208 publications

(41 citation statements)

References 22 publications

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“…Therefore, the synthesis and selective functionalization of pyrazoleshas been thefocus of active research over theyears [1][2][3]. A survey of the literature reveals that some pyrazoles have been employed as antileukemic [4,5], antitumor [6, 7], anti-proliferative agents [8], anti-inflammatory and antimicrobial agents [9,10]. Schiff base ligands synthesized from pyrazole rings have also been employed in adiverse range of applications.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-(3-chloro-phenyl)-5-methyl-4-[1-(5-methyl-4-ptolyl- thiazol-2-ylimino)-ethyl]-2,4-dihydro-pyrazol-3-one, C23H-ClN4OS

Thakar

Friedrich

Joshi³

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialAs olution of 4-acetyl-2-(3-chloro-phenyl)-5-methyl-2,4-dihydro-pyrazol-3-one (1.0 g, 3.99 mmol) in methanol (30 mL) was added to asolution of 5-methyl-4-p-tolyl-thiazol-2-ylamine (0.815 g, 3.99 mmol) in methanol (20 mL) under an inert atmosphere. The reaction mixture was refluxed for three hours. Completion of the reaction was monitored by silica TLC using hexane/ethyla cetate (8:2).T he reaction was allowed to cool to room temperature and then stirred overnight. Ayellow precipitete formed which wast hen filtered and washed with methanol (10 mL). Thec rude product, which was purified by crystallization from ethanol gave brown crystals. (1.22 g, 70% yield). M.p. = 451-452 K. Crystals suitable for X-ray diffraction were obtained by slow evaporation of the title compound from ad ichloromethane:hexane solution at room temperature. Experimental detailsAll Hatomswere positioned geometrically and allowed to ride on their respective parent atoms. The absorpton correction was based on fitting afunction to the empirical transmission surface as sampled by multiple equvalent measurements [14]. DiscussionThe pyrazole ring is aprominent structural motif found in numerous pharmaceutically active compounds. This is mainly due to the easy preparation and the important pharmacological activity. Therefore, the synthesis and selective functionalization of pyrazoleshas been thefocus of active research over theyears [1][2][3]. A survey of the literature reveals that some pyrazoles have been employed as antileukemic [4,5], antitumor [6, 7], anti-proliferative agents [8], anti-inflammatory and antimicrobial agents [9,10]. Schiff base ligands synthesized from pyrazole rings have also been employed in adiverse range of applications. We previously have reported the synthesis of the title structure and from NMR deduced that the Schiff base is present as the keto-imine tautomeric form [11]. Thediffraction data in this report clearly indicates that the nitrogen atom from 2-aminothiazole exists as a secondaryamine. Theketo-amine tautomeric formrather than the keto-imine predominates in the solid state. There areseveral examples from thel iterature wheret hish as been observed previously [12,13]. In the crystal lattice as ingle intramolcular hydrogen bonding arrangement is observed i.e. N3-H3···O1 3.0132(13) Å (Fig.).

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-(3-chloro-phenyl)-5-methyl-4-[1-(5-methyl-4-ptolyl- thiazol-2-ylimino)-ethyl]-2,4-dihydro-pyrazol-3-one, C23H-ClN4OS

Thakar

Friedrich

Joshi³

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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“…IR spectra were taken on a Specord 71 IR spectrophotometer. NMR spectra were recorded in CDCl 3 or DMSO-d 6 on a Varian VXR 300, Varian Unity Plus 400, and a Bruker Avance DRX 500 spectrometer, TMS was used as the internal standard. Because of poor solubility of most compounds 7 and 11 in mentioned solvents, their 13 C NMR spectra were not obtained.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of some 2-imidoylimino-2,3-dihydro- thiazolo[4,5-d]pyrimidines

Rensky¹,

Zyabrev²

2015

Arkivoc

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The paper is concerned with chemistry of thiazolo [4,5-d]pyrimidine derivatives bearing a 1,3-diazapropenylidene fragment at position 2 and an oxygen or a mobile chlorine atom at position 7. These compounds are obtained in three steps: (i) cycloaddition of malononitrile to available 1,2,4-thiadiazol-5(2H)-imines to form N-(4-amino-5-cyanothiazol-2(3H)-ylidene)amidines; (ii) their acylation or condensation with DMF dimethyl acetal followed by; (iii) pyrimidine ring closure.

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“…Scheme 3 comprises the direct hydrazinolysis of compound 5 with hydrazine hydrate to give the corresponding 3-amino-2-hydrazino-7-methyl-thiazolo[3,2-a] pyrimidin-5-one (12). Structure of compound 12 is confirmed on the basis of elemental analyses and spectral data.…”

Section: Scheme 2 the Keto-enol Type Of Tautomerismmentioning

confidence: 99%

“…They receive diverse pharmacological applications such as anti-HIV (5,6) , antibacterial (7,8) , anticancer (9) , anti-inflammatory (10)(11)(12) , antimalarial (5) , antimicrobial (12,13) , anti-HSV-1 (14) and herbicidal (15) activities. Furthermore, some thiazolopyrimidines have been assigned as new acetylcholin esterase inhibitors, especially for the treatment of Alzheimer's disease (16) .…”

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Novel One-pot Synthesis of Thiazolo[3,2-a] Pyrimidin-5-one as a Key Compound for Poly Nuclear Heterocycles

2016

Egypt. J. Chem.

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-AMINO-2-hydroxy-7-methyl-thiazolo[3,2-a]pyrimidin-5-one (5) ….was synthesized by one-pot reaction from 2-bromo cyanoacetamide, ethyl acetoacetate and thiourea. The new 3-amino-2-hydrazino derivatives (15,18), 2-pyrazol-thiazolo [3,2-a] pyrimidin -5-ones )14,17,20) and 2-(4-arylidene) -pyrazol-thiazolo [3,2-a] pyrimidin-5-ones (22a-d) were synthesized through facile condensing procedures starting from 3-amino-2-hydrazino-7-methyl-thiazolo[3,2-a]pyrimidin-5-one (12). The newly synthesized products were characterized by their IR, ESI-MS, NMR and micro analytical data.

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Design and synthesis of some substituted 1H-pyrazolyl-thiazolo[4,5-d]pyrimidines as anti-inflammatory–antimicrobial Agents

Cited by 208 publications

References 22 publications

Crystal structure of 2-(3-chloro-phenyl)-5-methyl-4-[1-(5-methyl-4-ptolyl- thiazol-2-ylimino)-ethyl]-2,4-dihydro-pyrazol-3-one, C23H-ClN4OS

Crystal structure of 2-(3-chloro-phenyl)-5-methyl-4-[1-(5-methyl-4-ptolyl- thiazol-2-ylimino)-ethyl]-2,4-dihydro-pyrazol-3-one, C23H-ClN4OS

Synthesis of some 2-imidoylimino-2,3-dihydro- thiazolo[4,5-d]pyrimidines

Novel One-pot Synthesis of Thiazolo[3,2-a] Pyrimidin-5-one as a Key Compound for Poly Nuclear Heterocycles

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