Design and Synthesis of Some Substituted 1H‐Pyrazolyl‐thiazolo[4,5‐d]pyrimidines as Antiinflammatory—Antimicrobial Agents.

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

doi:10.1002/chin.200329129

Cited by 40 publications

(46 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…15 In method B, arylhydrazine hydrochlorides 14-18 reacted with ethoxymethylenemalononitrile in ethanol and the resulting 5-amino-1-aryl-1H-pyrazole-4-carbonitriles 19-23 were subjected to aprotic deamination with t-butyl nitrite in tetrahydrofuran to generate the key intermediates. 16,17 Finally, the targets 1-aryl-1H-pyrazole-4-carboximidamides derivatives 1-5 were obtained by the reaction of the key intermediates 24-28 with gaseous hydrochloric acid followed by treatment with ammonia.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and antileishmanial activity of new 1-aryl-1H-pyrazole-4-carboximidamides derivatives

Santos¹,

Gomes²,

Bernardino³

et al. 2011

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

A quimioterapia para as leishmanioses, doenças causadas por protozoários do gênero Leishmania, ainda permanece ineficiente em diversos tratamentos. Portanto, existe a necessidade de pesquisa por novos fármacos. Nesse trabalho, foram sintetizados derivados 1-aril-1H-pirazol-4-carboximidamidas, avaliadas as atividades leishmanicida e os efeitos citotóxicos in vitro, e realizado um estudo de relação estrutura-atividade (REA) com a série de compostos. O composto 2 apresentou um perfil de atividade que pode ser melhorado através de estratégias de modificação molecular da química medicinal.Chemotherapy for leishmaniasis, diseases caused by protozoa of the genus Leishmania, remains inefficient in several treatments. So there is a need to search for new drugs. In this work, we have synthesized 1-aryl-1H-pyrazole-4-carboximidamides derivatives and evaluated antileishmanial activities in vitro, as well as cytotoxic effects. Structure-activity relationship (SAR) studies were carried out with all the compounds of the series. Compound 2 showed an activity profile that can be improved through medicinal chemistry strategies.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and antileishmanial activity of new 1-aryl-1H-pyrazole-4-carboximidamides derivatives

Santos¹,

Gomes²,

Bernardino³

et al. 2011

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…Thiazolopyrimidines (D), the bioisostere analogues of the anticancer purines such as Thioguanine 8,9) (Lanvis ® ) (E), are potentially bioactive molecules reported to display significant anticancer and antimicrobial activities [10][11][12][13] (Fig. 1).…”

Section: 7)mentioning

confidence: 99%

Synthesis, Antitumor and Antimicrobial Testing of Some New Thiopyrimidine Analogues

Taher

Helwa

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

The synthesis of some new 4-chloro-pyrimidine-5-carbonitriles (3b-d), 4-substituted-amino-pyrimidine-5-carbonitriles (4a-g), trioxo and dioxo-thiazolo[3,2-a]pyrimidine-6-carbonitriles (5a-c and 6a-h) have been described. The obtained compounds were evaluated for their in-vitro antitumor activity. A single dose (10 µM) of the test compounds was used in the National Cancer Institute (NCI) 60 cell lines panel assay. Compounds 3c and 4f showed high inhibitory activity against leukemia, whereas, compounds 3b and 4d, g displayed moderate activity. On the other hand, all compounds were screened for their in-vitro antibacterial and antifungal activities. Compounds 3d and 4b exhibited significant antibacterial activity against Staphylococcus aureus. Compound 4e showed two folds inhibitory activity against Entrobacter aerogener compared with the reference drug Tobramycin.Key words thiopyrimidine derivative; synthesis; antitumor; antimicrobial activity Thiouracil, 5-Flurouracil 1) (A) and other pyrimidine compounds are important synthons in anticancer, antibacterial and antifungal chemotherapy.2-5) S-Alkylation (B) and N-alkylation (C) products of thiouracil analogues have been recently reported as novel antibacterial, and cytotoxic agents. 6,7)Thiazolopyrimidines (D), the bioisostere analogues of the anticancer purines such as Thioguanine 8,9) (Lanvis ® ) (E), are potentially bioactive molecules reported to display significant anticancer and antimicrobial activities [10][11][12][13] (Fig. 1). The development of potent and effective novel antineoplastic drugs is one of the most intensely persuaded goals of contemporary medicinal chemistry. In view of the biological significance of thiouracils and in continuation of our previous efforts in the synthesis of new thiouracils and uracil-related heterocycles, 7) we would like to report herein the synthesis of new thioxo-chloro-pyrimidines (3b-d), substituted-aminopyrimidines (4a-g) and thiazolopyrimidines (5a-c, 6a-h) and their antitumor, antimicrobial testing. Results and DiscussionChemistry The 6-chloro-pyrimidine derivatives 3a-d is used as a key precursor in the present study. They were synthesized using the reported method for compound 3a.14) (Chart 1). Thus compounds 1a-d was treated with alkyl halides to give the corresponding S-alkylated derivatives 2a-d followed by phosphoryl chloride treatment to afford 3a-d. The structure of the newly prepared compounds 3b-d was confirmed by elemental analyses and spectral data (IR, 1 H-NMR and MS). The IR spectra of these compounds showed the disappearance of both NH and C= O bands. 1 H-NMR spectra of compounds 3b-d showed the absence of NH signal. Moreover mass spectrum of compound 3c showed molecular ion peaks at m/z 307.05 (M + ) (33.17%) and 309.05 (M+ 2) (13.09%) in ratio 3 : 1 indicating the presence of chlorine atom.2-Alkylthio-6-aryl-4-substituted-aminopyrimidine-5-carbonitriles (4a-g) were prepared through direct reaction of 2-alkylthio-4-aryl-6-chloropyrimidine-5-carbonitrile with various amines, in the presence of potassiu...

show abstract

“…They are insoluble in water and chloroform. In the H 1 -NMRspectra of the synthesized compounds 5, the peak of the aromatic proton in the 9th position of the heterocycle is shifted downfields (10,(5)(6)(7)(8)(9)(10)(11)5) due to the influence of the spatially nearby sulphur atom in the thioxo-group in the first position. This fact, together with the methyl ester and amino group signals' disappearance in position 4 of compound 4, is evidence of the proposed structure.…”

Section: Chemistrymentioning

confidence: 99%

“…Compounds of these classes have been proved as potential bio-actives substances [2][3][4][5][9][10][11][12][13][14][15][16][17] . Some of described compounds showed antimicrobial activity [13][14][15][16][17] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobal activity of 5-oxo-1-tioxo-4,5-dihydro[1,3]thiazolo[3,4-a]quinazolines

O.Parkhomenko¹,

Kovalenko²,

Chernykh³

et al. 2006

Arkivoc

View full text Add to dashboard Cite

show abstract

Design and Synthesis of Some Substituted 1H‐Pyrazolyl‐thiazolo[4,5‐d]pyrimidines as Antiinflammatory—Antimicrobial Agents.

Cited by 40 publications

References 1 publication

Synthesis and antileishmanial activity of new 1-aryl-1H-pyrazole-4-carboximidamides derivatives

Synthesis and antileishmanial activity of new 1-aryl-1H-pyrazole-4-carboximidamides derivatives

Synthesis, Antitumor and Antimicrobial Testing of Some New Thiopyrimidine Analogues

Synthesis and antimicrobal activity of 5-oxo-1-tioxo-4,5-dihydro[1,3]thiazolo[3,4-a]quinazolines

Contact Info

Product

Resources

About