Synthesis of thiazolo[4,5-d]pyrimidine derivatives as potential antimicrobial agents

Habib, N. S.; Soliman, Raafat; El-Tombary, Alaa A.; El-Hawash, Soad A.M.; Shaaban, Omaima G.

doi:10.1007/bf02977319

Cited by 29 publications

(23 citation statements)

References 11 publications

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“…Pyrimidine derivatives have been reported as anti-microbial [3], analgesic, anti-viral, anti-inflammatory [4], anti-HIV [5], anti-tubercular [6], anti-tumour [7], anti-malarial [8], cardiovascular [9] agents. Pyrimidine derivatives have been found to exhibit cytostatic [10][11][12], immune modulating [13,14] and antibacterial properties [15][16][17][18][19][20][21]. In particular, studies concerning the synthesis of pyrimido [4,5-d]-1,3-oxazines [22] showing considerable similarity to quinoline chemotherapeutic agents with an antibacterial effect.…”

Section: Introductionmentioning

confidence: 99%

IR and <sup>1</sup>H NMR Spectral Studies of some 2-Amino-4-Isopropyl-6-Methoxy-N-Phenylpyrimidine-5-Carboxamides: Assessment of Substituent Effects

Arulkumaran¹,

Sundararajan²,

Manikandan³

et al. 2014

ILCPA

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A series of 2-Amino-4-isopropyl-6-methoxy-N-phenylpyrimidine-5-carboxamide compounds have been synthesized from various substituted dithioacetal and guanidine. The purities of these compounds were checked by their physical constants, UV, IR, NMR and MASS spectral data. The IR and 1 HNMR spectral data of these compounds have been correlated with Hammett sigma constants, F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effects of substituents on the spectral group frequencies have been discussed.

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Section: Introductionmentioning

confidence: 99%

IR and <sup>1</sup>H NMR Spectral Studies of some 2-Amino-4-Isopropyl-6-Methoxy-N-Phenylpyrimidine-5-Carboxamides: Assessment of Substituent Effects

Arulkumaran¹,

Sundararajan²,

Manikandan³

et al. 2014

ILCPA

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“…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%

“…[2][3][4][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).…”

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confidence: 99%

Synthesis, Antitumor and Antimicrobial Testing of Some New Thiopyrimidine Analogues

Taher

Helwa

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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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...

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“…Various pyrimidine derivatives were reported to exhibit diverse biological activities including antimicrobial, 1,2 antitubercular, 3 antifungal, 4 antiviral, 5 and antitumor effects. 6,7 Notably, polymethoxysubstituted diarylpyrimidines displayed dual antimicrobial-anticancer properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimitotic properties of ortho-substituted polymethoxydiarylazolopyrimidines

Chernyshova¹,

Tsyganov²,

Khrustalev³

et al. 2017

Arkivoc

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Ortho-substituted polymethoxydiarylazolopyrimidines were synthesized using polymethoxysubstituted benzaldehydes and acetophenones as starting material. X-ray crystallography data clearly confirmed that the subsequent cyclization of 3-amino-1,2,4-triazole with ketoaldehydes yielded polymethoxyphenylsubstituted 6,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines as single isomers. All compounds were evaluated in vivo using phenotypic sea urchin embryo assay. 6-(4-Methoxyphenyl)-7-(3,4,5-trimethoxyphenyl)pyrazolo [1,5-a]pyrimidine showed antimitotic microtubule destabilizing activity. The importance of aryl rings substituents in diaryltriazolopyrimidines for their antiproliferative antitubulin effect has been suggested.

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Synthesis of thiazolo[4,5-d]pyrimidine derivatives as potential antimicrobial agents

Cited by 29 publications

References 11 publications

IR and <sup>1</sup>H NMR Spectral Studies of some 2-Amino-4-Isopropyl-6-Methoxy-N-Phenylpyrimidine-5-Carboxamides: Assessment of Substituent Effects

IR and <sup>1</sup>H NMR Spectral Studies of some 2-Amino-4-Isopropyl-6-Methoxy-N-Phenylpyrimidine-5-Carboxamides: Assessment of Substituent Effects

Synthesis, Antitumor and Antimicrobial Testing of Some New Thiopyrimidine Analogues

Synthesis and antimitotic properties of ortho-substituted polymethoxydiarylazolopyrimidines

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