Recent Report on Thieno[2,3-<i>d</i>]pyrimidines. Their Preparation Including Microwave and Their Utilities in Fused Heterocycles Synthesis

Aly, Ashraf A.; Ishak, Esam A.; Ramadan, Mohamed; Germoush, Mousa O.; El‐Emary, Talaat I.; Al‐Muaikel, Nayef S.

doi:10.1002/jhet.1118

Cited by 20 publications

(12 citation statements)

References 75 publications

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“…Consequently, compound 14 reacted with ammonium thiocyanate to give the corresponding thienopyrimidinone derivative 21 , while nucleophilic addition of amino group in compound 14 on cyano function in 2‐(4‐(4‐chlorophenyl)thiazol‐2‐yl)acetonitrile 22 followed by intramolecular cyclization with removal of ethanol molecule yielded the corresponding thienopyrimidinone analogue 23 . Moreover, multicomponent reaction of 2‐aminoesters with mixture of substituted amines and triethyl orthoformate produced the corresponding thienopyrimidinone derivatives . So three‐component reaction of compound 14 , 4‐bromoaniline, and triethyl orthoformate gave the corresponding thienopyrimidinone derivative 24 as described in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Hassan

Husseiny

2019

Journal of Heterocyclic Chem

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In an attempt to establish novel candidate with promising anticancer activity, two derivatives of (benzo[d]thiazol‐2‐yl)thiophene backbone 1 and 14 were synthesized, and they further reacted with various chemical reagents to afford the corresponding substituted thiophene derivatives 6, 8, 10, 15, 17, and 20, thieno[3,2‐d]pyrimidine derivatives 2–5, 7, 9, 16, 21, 23, and 24, thieno[3,2‐b]pyridine derivatives 11–13, and thieno[3,2‐e][1,4]oxazepine derivative 18. Structures of prepared compounds were affirmed via spectral and elemental data. Among the obtained compounds, seven derivatives 2, 3, 4, 5, 11, 12, and 13 were chosen by National Cancer Institute, USA. Such compounds were screened for their antitumor activity versus 60 cancer cell lines in one‐dose (10 μmol) screening assay. The outcomes showed that all selected compounds exhibited moderate to high anticancer activity towards many cancer cell lines among which compounds 5 and 11 exerted potent antitumor activity against numerous malignant growth cell lines particularly Ovarian Cancer IGROV1.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Hassan

Husseiny

2019

Journal of Heterocyclic Chem

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“…The synthesis, reactions and biological effects of isomeric thienopyrimidines have been reviewed extensively [15][16][17][18][19][20][21][22][23][24]. Thieno pyrimidines have a great potential of application and were recognized as anticancer agents [25][26][27][28][29][30].…”

Section: Resultsmentioning

confidence: 99%

Spirocyclic thienopyrimidines: synthesis, new rearrangements under Vilsmeier conditions and in silico prediction of anticancer activity

et al. 2020

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Aim. To find novel anticancer lead molecules among easily available spiro-fused thieno[2,3-d] pyrimidines. Methods. Organic synthesis, spectral methods and molecular docking. Results. New spiro heterocycles were synthesized by condensation of 2-aminothiophene-3-carbonitriles with cyclic ketones via Gevald reaction. Other model spirocyclic compounds were prepared by the reaction of 3-aminothieno[2,3-b]pyridine-2-carboxamides with cyclohexanone under acidic conditions. According to the docking studies against the EGFR WT the synthesized compounds revealed good binding energies ranging from-8.4 to-10.2 kcal/mol. The compounds were tested as inhibitors of protein kinase CK; 7',8',9',10'-tetrahydro-1'H-spiro[cyclohexane-1,2'-pyrimido[4',5':4,5]thieno[2,3-b]quinolin]-4'(3'H)-one showed the best binding energy while be bound by a hydrogen bond to Val66 amino acid residue. This compound also showed good results as a potential inhibitor of B-Raf kinase. Conclusion. New spiro-fused thieno[2,3d]pyrimidines have been synthesized. The inhibition activity of novel compounds as potential inhibitors of the EGFR, CK2, FGFR1 and B-raf kinases was examined. We found that spirofused thieno[2,3-d]pyrimidines undergo the rearrangement under Vilsmeier-Haack conditions to afford hitherto undescribed thienopyrimidines and-quinolines. The docking studies revealed that the rearranged products do not tend to form hydrogen bonds with the kinase amino acid residues and show moderate binding energies. Therefore, in contrast to the spiro-fused thieno[2,3-d]pyrimidines, the rearranged products cannot be considered as perspective targets for further screening.

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“…In 2011, Abdalha and co-workers investigated and designed some interactions of 2-phenyl- [1,3]oxazin-4-one (BTO) 36 with various amines under MWI. From BTO, they synthesized several analogs through exotic combinations of groups and active moieties; for example, the fusion of BTO with hydrazine hydrate yielded the pyrimidine derivative 37 and P 2 S 5 thiazine-4-one derivative 38 accordingly.…”

Section: (Scheme 11)mentioning

confidence: 99%

Recent developments regarding the use of thieno[2,3-d]pyrimidin-4-one derivatives in medicinal chemistry, with a focus on their synthesis and anticancer properties

Bozorov

Zhao

Элмурадов

et al. 2015

European Journal of Medicinal Chemistry

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Recent Report on Thieno[2,3-d]pyrimidines. Their Preparation Including Microwave and Their Utilities in Fused Heterocycles Synthesis

Abstract: The review summarizes recent literatures dealing with the synthetic tools of thieno[2,3‐d]pyrimidine derivatives including their biological activities and their applications in the synthesis of heterocycles.

Cited by 20 publications

References 75 publications

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Spirocyclic thienopyrimidines: synthesis, new rearrangements under Vilsmeier conditions and in silico prediction of anticancer activity

Recent developments regarding the use of thieno[2,3-d]pyrimidin-4-one derivatives in medicinal chemistry, with a focus on their synthesis and anticancer properties

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