Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety

Mavrova, Anelia Ts.; Wesselinova, Diana; Tsenov, Jordan A.; Lubenov, Lubomir A.

doi:10.1016/j.ejmech.2014.09.032

Cited by 42 publications

(26 citation statements)

References 23 publications

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“…Elemental analysis was undertaken with Elemental Vario EL III Carlo Erba 1108 analyser. Syntheses of the target compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were performed according to fig. 2, through following steps.…”

Section: Methodsmentioning

confidence: 99%

“…Triazole heterocycles is a building block of great value in drug candidates [8,9] and a large number of ring systems containing this heterocyclic core have been incorporated into a wide variety of therapeutically interesting drug compounds including antiinflammatory, CNS stimulants, sedatives, antianxiety [10,11] and antimycotic agents such as fluconazole, itraconazole and voriconazole [12,13] . The 1,2,4-triazole, as well found to exhibit antiasthmatic [14] , antiviral (ribavirin) [15] , antifungal (fluconazole) [16] , antimicrobial [17,18] , antibacterial [19][20][21] , insecticidal [22] , hypnotic [23] , cytotoxic [24] , antitubercular [25] and hypotensive [26,27] activities.…”

Section: Research Papermentioning

confidence: 99%

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Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents

Singh¹,

Kashaw²,

Mishra³

et al. 2018

pharmaceutical-sciences

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Section: Methodsmentioning

confidence: 99%

Section: Research Papermentioning

confidence: 99%

Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents

Singh¹,

Kashaw²,

Mishra³

et al. 2018

pharmaceutical-sciences

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“…9,10 The presence of pyrimidine ring in the basic building scaffolds of DNA and RNA modules (thymine, cytosine and uracil) is probably the reason of their diverse biological activities. 11 In addition, the tricyclic system, cycloalkylthieno [2,3-d]pyrimidine, which is considered to be a bioisostere of quinazoline, has been used as a core for the mechanism-based design and synthesis of a variety of compounds for anticancer therapy. [12][13][14][15][16] On the other hand, the 1,2,4-triazole heterocycle is of great value as a building block in the structure of several anticancer drug candidates.…”

Section: Introductionmentioning

confidence: 99%

“…[12][13][14][15][16] On the other hand, the 1,2,4-triazole heterocycle is of great value as a building block in the structure of several anticancer drug candidates. 11,17,18 Letrozole, Anastrozole and Ribavirin are representative examples of commercially available anticancer drugs containing triazole scaffolds (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Cytotoxicity of substituted[1]benzothieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidines

Botros¹,

Khalil²,

Kamel³

et al. 2017

ACSi

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A new series of 4-benzyl-6,7,8,9-tetrahydro[1]benzothieno [3,2-e] [1,2,4]triazolo [4,3-a]pyrimidines was synthesized motivated by the widely reported anticancer activity of thieno [2,3-d]pyrimidines and triazolothienopyrimidines. The in vitro cytotoxic activity of some selected compounds was evaluated against two human cell lines: prostate cancer (PC-3) and colon cancer (HCT-116). A preliminary study of the structure-activity relationship of the target compounds was discussed. Most of the synthesized compounds showed remarkable activity on the tested cell lines, while compound 16c had the highest potency against the PC-3 cell line with an IC 50 of 5.48 μM compared to Doxorubicin (IC 50 = 7.7 μM), the reference standard used in this study. On the other hand, 6c and 18c were the most active against HCT-116 (IC 50 = 6.12 and 6.56 μM, respectively) relative to IC 50 = 15.82 μM of the standard. Thus, some of the synthesized thienopyrimidine derivatives, specially 6c, 16c and 18c, have the potential to be developed into potent anticancer agents.

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“…Furthermore, thieno [2,3-d]pyrimidine derivatives show antibacterial (6) and antiproliferative activity (7). Also, chromene--3-carboxamide acts as an anti-Helicobacter pylori agent (8) and pyrazole derivatives have a specific effect with favorable antitumor activity (9).…”

mentioning

confidence: 99%

Synthesis and antitumor activity of some novel thiophene, pyrimidine, coumarin, pyrazole and pyridine derivatives

2017

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Synthesis and antitumor activity of some novel thiophene, pyrimidine, coumarin, pyrazole and pyridine derivatives 2-Cyano-N-(thiazol-2-yl) acetamide (2a) and 2-cyano-N-(oxazol-2-yl) acetamide (2b) were obtained via the reaction of ethyl cyanoacetate with either 2-aminothiazole (1a) or 2-aminooxazole (1b). The formed products were directed toward the reaction with cyclopentanone and elemental sulfur in the presence of triethylamine to give cyclopenta [b]thiophene derivatives (3a,b). The latter products were reacted with either ethyl cyanoacetate or malononitrile to form compounds 4a,b and 5a,b, respectively. Compounds 4a,b were aimed at synthesizing some heterocyclic compounds; thus internal cyclization reactions were introduced to form compounds 6a,b. Also, compounds 4a,b reacted with salicylaldehyde, hydrazine derivatives and either urea or thiourea to produce coumarin derivatives (7a,b), pyrazole derivatives (8a-d) and pyrimidine derivatives (9a-d), respectively. Reaction of either benzaldehyde or benzene diazonium chloride (11) with compounds 4a,b afforded compounds 10a,b and 12a,b, respectively. On the other hand, compounds 5a,b underwent internal cyclization to form pyrimidine derivatives 13a,b. Also, when compounds 5a,b reacted with either ethyl cyanoacetate or malononitrile, they gave pyridine derivatives (15a-d) through the formation of intermediates (14a-d). Finally, formation of fused pyrimidine derivatives (17a,b) was achieved through the reaction of compounds 5a,b and salicylaldehyde applying two different pathways. The first pathway used a catalytic amount of piperidine to form compounds 16a,b; the latter products underwent cyclization to give compounds 17a,b. The second pathway, using a catalytic amount of sodium ethoxide solution directly in one step, afforded compounds 17a,b. Structures of the newly synthesized compounds were established using IR, 1 H NMR, 13 C NMR and mass spectrometry and their antitumor activity was investigated. Some of these compounds showed promising inhibitory effects on three different cell lines. However, fused pyrimidine acetonitrile derivatives 6a and 6b exerted the highest inhibitory effect, comparable to that of doxorubicin.

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Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety

Cited by 42 publications

References 23 publications

Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents

Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents

Synthesis, Characterization and Cytotoxicity of substituted[1]benzothieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidines

Synthesis and antitumor activity of some novel thiophene, pyrimidine, coumarin, pyrazole and pyridine derivatives

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