Synthesis and Biological Evaluation of Novel Isopropyl 2-thiazolopyrimidine-6-carboxylate Derivatives

Yalagala, Kotaiah; Krishna, N. Hari; Raju, K. Naga; Rao, C.V.; Jonnalagadda, Sreekantha B.; Maddila, Suresh

doi:10.5012/jkcs.2012.56.1.068

Cited by 12 publications

(3 citation statements)

References 14 publications

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“…Many studies have reported antibacterial activities of derivatives. The structure-activity relationships based on the literature results [27][28][29] indicated that fused pyrimidines, especially thiazolopyrimidine derivatives, have antibacterial activity. The obtained results indicated that the compounds bearing 2-(piperidin-1-yl) 4c and 2-(4-methylpiperidin-1-yl) 4d substituents show the highest sensitivity against Streptococcus equinus and Streptococcus pneumonia, respectively, compared with ceftriaxone and cefazolin as reference drugs, which may be due to the lipophilicity increase of the moiety, which has enhanced the pharmacological activity.…”

Section: Antibacterial Evaluationsmentioning

confidence: 99%

Synthesis, Characterisation, and in Vitro Antibacterial Evaluation of a New Class of 2-substituted-4-methyl-7,8-dihydro-5H-pyrimido[4,5-d]thiazolo[3,2-a] Pyrimidines

Etemadi

Shiri

Akbarzadeh

et al. 2016

Journal of Chemical Research

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The reaction of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine with 4,5-dihydrothiazol-2-amine in chloroform led to the formation of 2-chloro-4-methyl-7,8-dihydro-5H-pyrimido[4,5-d]thiazolo[3,2-a]pyrimidine (3). The true structure of the target compound was confirmed by density functional theory calculations of condensed Fukui indices. The substitution of the 2-Cl function in compound 3 with different secondary amines yielded 2-substituted-4-methyl-7,8-dihydro-5H-pyrimido[4,5-d]thiazolo[3,2-a]pyrimidines in good yields. The assigned products were tested for their potential antibacterial activity and the results indicated that a few derivatives are valuable compounds with great potential to be used as antibacterial agents.

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Section: Antibacterial Evaluationsmentioning

confidence: 99%

Synthesis, Characterisation, and in Vitro Antibacterial Evaluation of a New Class of 2-substituted-4-methyl-7,8-dihydro-5H-pyrimido[4,5-d]thiazolo[3,2-a] Pyrimidines

Etemadi

Shiri

Akbarzadeh

et al. 2016

Journal of Chemical Research

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“…These facts together with the powerful biological activity of pyrimidine moiety which is widely used as a key building block for pharmacological agent led us to bind these two interesting moieties and specifically its derivative thiazolopyrimidine hoping to build significant places in medicinal chemistry research .…”

Section: Introductionmentioning

confidence: 99%

New Benzimidazoles and Their Antitumor Effects with Aurora A Kinase and KSP Inhibitory Activities

El-All

Magd-El-Din

Ragab

et al. 2015

Archiv der Pharmazie

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A newly synthesized series of anticancer compounds comprising thiazolo[3,2-a]pyrimidine derivatives 6a-q bearing a benzimidazole moiety was produced via a one-pot reaction of N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-2-cyanoacetamide 5 with 2-aminothiazole and an appropriate aromatic aldehyde. Compound 7 was obtained via the reaction of 4-(1H-benzo[d]imidazol-2yl)benzenamide 1 with carbon disulphide and methyl iodide in the presence of concentrated aqueous solution of NaOH, then treated with o-phenylenediamine to give N-(4-1H-benzo[d]imidazol-2-yl)phenyl)-1H-benzo[d]imidazol-2-amine 8. The structures of the newly synthesized compounds were confirmed by analytical and spectroscopic measurements (IR, MS, and (1) H NMR). The synthesized products were screened and studied for their in vitro antitumor activity against three human cancer cell lines (namely colorectal cancer cell line HCT116, human liver cancer cell line HepG2, and human ovarian cancer cell line A2780) and their Aurora A kinase and KSP inhibitory activities. All newly synthesized compounds revealed marked results comparable with the standard drug CK0106023. The compounds 6e and 6k of the thiazolopyrimidine derivatives were the most active compounds when tested against the three cell lines in comparison with the standard drug CK0106023, and showed potent dual KSP and Aurora A kinase inhibition.

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“…11 In view of all these observations, we have undertaken the synthesis of some new derivatives of thiazolo [3,2-a]pyrimidines. The traditional methods 7,[12][13][14] to synthesize arylidene derivative involve the use of 1:1 mixture of acetic acid and acetic anhydride in presence of sodium acetate. But this method is not satisfactory with regard to the isolation of the products and also due to the drastic reaction conditions that are employed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some new derivatives of thiazolopyrimidines and hydrolysis of its arylidene derivative

2015

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Abstract.A new ammonium acetate-assisted, convenient and efficient procedure for the synthesis of arylidene derivatives of thiazolopyrimidine is described. The main advantages of this protocol is that it is economical, short reaction time, commonly available chemicals, and ease of isolation of products. In addition, a new series of thiazole-fused pyrimidines were synthesized and hydrolysis of one of its arylidene derivative studied. All the compounds were characterized by analytical and spectroscopic methods. Further, the structure of hydrolyzed product and two other compounds were confirmed by X-ray crystal structure analysis. The crystal structures are stabilized by intermolecular C-H. . .O, C-H. . .N, C-H. . . π and π . . . π weak interactions. The anti-microbial screening was done on the compounds in order to test their anti-bacterial and anti-fungal activities.

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Synthesis and Biological Evaluation of Novel Isopropyl 2-thiazolopyrimidine-6-carboxylate Derivatives

Cited by 12 publications

References 14 publications

Synthesis, Characterisation, and in Vitro Antibacterial Evaluation of a New Class of 2-substituted-4-methyl-7,8-dihydro-5H-pyrimido[4,5-d]thiazolo[3,2-a] Pyrimidines

Synthesis, Characterisation, and in Vitro Antibacterial Evaluation of a New Class of 2-substituted-4-methyl-7,8-dihydro-5H-pyrimido[4,5-d]thiazolo[3,2-a] Pyrimidines

New Benzimidazoles and Their Antitumor Effects with Aurora A Kinase and KSP Inhibitory Activities

Synthesis of some new derivatives of thiazolopyrimidines and hydrolysis of its arylidene derivative

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