Synthesis and Anticonvulsant Activity of 7(8)-Amino Derivatives of Condensed Thieno[3,2-d]Pyrimidines

Sirakanyan, S. N.; Akopyan, É. K.; Paronikyan, R. G.; Akopyan, A. G.; Ovakimyan, A. A.

doi:10.1007/s11094-016-1439-5

Cited by 21 publications

(30 citation statements)

References 6 publications

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“…Therefore, the chemical studies of each of thiophene, pyrimidine, triazole, thiazine, pyrrole, quinoxaline and imidazole nucleus play a significant role in the synthesis of a diversity of fused heterocyclic compounds having a wide range of biological and pharmacological activities. Accordingly, previous scientific studies confirmed that thienopyrimidine derivatives have various biological and pharmacological activities, such as antibiotics [ 3 ], antimicrobial [ 4 , 5 ], anticonvulsants [ 6 ], antiviral [ 7 ], antioxidant and antitumor agents [ 8 ], anticancer [ 9 ] and mitotic arrest of breast cancer [ 10 ], anti-inflammatory and analgesic activities [ 11 , 12 ], antiglaucoma agents [ 13 ], platelet aggregation inhibitors [ 14 ], anti-hyperlipidemia [ 15 ], antidepressant, anti-inflammatory and antimicrobial activities [ 16 ]. In addition, the thiazolopyrimidine, 1,2,4-triazolopy- rimidine and thienotriazolopyrimidinone derivatives possess such biological activities as anti-inflammatory and analgesic activity [ 17 , 18 ], antimicrobial [ 19 ] and anticancer activity through a potential of the enzyme (PARP-1) inhibition [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives

2021

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In this article, we showed the synthesis of new polycyclic aromatic compounds, such as thienotriazolopyrimidinones, N-(thienotriazolopyrimidine) acetamide, 2-mercapto-thienotriazolo-pyrimidinones, 2-(((thieno-triazolopyrimidine) methyl) thio) thieno-triazolopyrimidines, thieno-pyrimidotriazolo-thiazines, pyrrolo-triazolo-thienopyrimidines, thienopyrimido-triazolopyrrolo-quinoxalines, thienopyrimido-triazolo-pyrrolo-oxathiino-quinoxalinones, 1,4-oxathiino-pyrrolo- triazolothienopyrimidinones, imidazopyrrolotriazolothienopyrimidines and 1,2,4-triazoloimidazo- pyrrolotriazolothienopyrimidindiones, based on the starting material 2,3-diamino-6-benzoyl-5- methylthieno[2,3-d]pyrimidin-4(3H)-one (3). The chemical structures were confirmed using many spectroscopic ways (IR, 1H, 13C, −NMR and MS) and elemental analyses. A series of thiazine, imidazole, pyrrole, thienotriazolopyrimidine derivatives were synthesized and evaluated for their antiproliferative activity against four human cancer cell lines, i.e., CNE2 (nasopharyngeal), KB (oral), MCF-7 (breast) and MGC-803 (gastric) carcinoma cells. The compounds 20, 19, 17, 16 and 11 showed significant cytotoxicity against types of human cancer cell lines.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives

2021

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“…In continuation of our studies on the synthesis and biological activity of amino derivatives of fused thieno [3,2-d]pyrimidines (Sirakanyan et al 2014(Sirakanyan et al , 2016a, in this article we report the synthesis and antimicrobial activity of new 8-amino-5-isopropyl-2,2-dimethyl-10-(methylthio)-1,4-dihydro- 2Hpyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno [3,2-d] pyrimidines.…”

Section: Introductionmentioning

confidence: 95%

Synthesis and antimicrobial activity of new amino derivatives of pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidine

Sirakanyan¹,

Geronikaki

Spinelli

et al. 2018

An. Acad. Bras. Ciênc.

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Annulated thienopyrimidine derivatives attracted big interest of the scientific community due to their broad spectrum of biological activities among which are the inhibition of phosphodiesterase, antiproliferative and antimicrobial activities. As a continuation of our studies on the synthesis and biological activity of fused thieno[3,2-d]pyrimidine derivatives, the goal of this paper is the synthesis and study of the properties of compounds containing different heterocycles such as fused thieno[2,3-b]pyridine and tetrazolo[1,5-c]pyrimidine in the same molecule. Thus, starting from the ethyl 1-amino-5-isopropyl-8,8-dimethyl-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate 1, efficient methods for obtaining new 8-amino-5-isopropyl-2,2-dimethyl-10-(methylthio)-1,4-dihydro-2H-pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidines 6 and thieno[2,3-e]tetrazolo[1,5-c]pyrimidine 8 are described. The spectroscopic results showed that compound 8 in the solid state is exclusively in the tetrazolo tautomeric form, while in solution an azide-tetrazole equilibrium is present 8A/T. The possible antimicrobial activity of newly synthesized compounds against some gram-positive and gram-negative bacilli strains has been evaluated. The biological tests evidenced that some of them showed promising antimicrobial activity. Two compounds showed similar activity to the one of the used reference drug. The study of structure-activity relationships revealed that the activity of a compound depends mostly on the nature of substituent R1R2. According to the predicted docking studies our compounds could be DnaG inhibitors.

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“…Thieno [3,2-d]pyrimidine derivatives display a wide range of activities acting as anticonvulsants (9), antivirals (10), antibiotics (11), antiglaucoma agents (12) and platelet aggregation inhibitors (13). On the other hand, some 2-substituted-thieno [3,2-d]pyrimidine--4-ones are considered to exert antihyperlipidemic (14) and anti-inflammatory activity (15).…”

Section: Abstract: Thieno[32-d]pyrimidines Thienotriazolopyrimidinementioning

confidence: 99%

Synthesis and evaluation of antitumor activity of new 4-substituted thieno[3,2-d]pyrimidine and thienotriazolopyrimidine derivatives

Hafez

El‐Gazzar

2017

Acta Pharmaceutica

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3-Methyl-6-phenyl-2-thioxo-2,3-dihydrothieno[3,2-d]pyrimidin- 4(1H)-one (2), on treatment with phosphorous oxychoride, affored 4-chloro-3-methyl-6-phenyl -thieno[3,2-d]pyrimidine- 2(3H)-thione (3). A series of novel 6-phenyl-thieno[3,2-d]pyrimidine derivatives 4-9 bearing different functional groups were synthesized via treatment of compound 3 with different reagents. On the other hand, compound 2 was used to synthesize ethyl-[(3-methyl-6-phenyl-2-thioxo-2,3-dihydrothieno[ 3,2-d]pyrimidin-4-yl)-oxy]acetate (10), 2-hydrazinyl- -3-methyl-6-phenyl-thieno[3,2-d]pyrimidin-4(3H)-one (11), 3-methyl-2-(methyl-sulfanyl)-6-phenyl-thieno[3,2-d]pyrimidin- 4(3H)-one (12) and N-(phenyl)/4-chlorophenyl or methoxy- phenyl)-2-[(3-methyl-4-oxo-6-phenyl-3,4-dihydrothieno[ 3,2-d]pyrimidin-2-yl)-sulfanyl]-acetamide (13a-c). In addition, compound 12 was used to synthesize thieno[1,2,4] triazolopyrimidine derivatives 14 and 15 and 3-methyl-2-(methyl-sulfonyl)-6-phenyl-thieno[3,2-d]pyrimidin-4(3H)-one (16) through the reaction with the respective reagents. Moreover, the reaction of 16 with 4-phenylenediamine gave 2-[(4-aminophenyl)-amino]-3-methyl-6-phenyl-thieno[3,2-d] pyrimidin-4(3H)-one (17), which reacted with methanesulfonyl chloride to afford N-{4-[(3-methyl-4-oxo-6-phenyl-3H,4H- -thieno[3,2-d]pyrimidin-2-yl)-amino]phenyl}-methanesulfonamide (18). The majority of the newly synthesized compounds displayed potent anticancer activity, comparable to that of doxorubicin, on three human cancer cell lines, including the human breast adenocarcinoma cell line (MCF-7), cervical carcinoma cell line (HeLa) and colonic carcinoma cell line (HCT- 116). Compounds 18, 13b and 10 were nearly as active as doxorubicin whereas compounds 6, 7b and 15 exhibited marked growth inhibition, but still lower than doxorubicin.

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Synthesis and Anticonvulsant Activity of 7(8)-Amino Derivatives of Condensed Thieno[3,2-d]Pyrimidines

Cited by 21 publications

References 6 publications

Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives

Design, Synthesis and Anticancer Activity of New Polycyclic: Imidazole, Thiazine, Oxathiine, Pyrrolo-Quinoxaline and Thienotriazolopyrimidine Derivatives

Synthesis and antimicrobial activity of new amino derivatives of pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidine

Synthesis and evaluation of antitumor activity of new 4-substituted thieno[3,2-d]pyrimidine and thienotriazolopyrimidine derivatives

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