Synthesis, Characterization and Reactions of 4‐Hydrazino‐2‐methylpyrimidino[4′5′:4,5]thiazolo[3,2‐a]benzimidazole

El‐Wareth, Abd; Sarhan, Ahmed Aly Diaa Mohammed

doi:10.1002/jccs.200000177

Cited by 5 publications

(3 citation statements)

References 13 publications

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“…[22] Elemental analysis with spectral data (IR, 1 H NMR, and 13 C NMR) verified the structure of compound 11. [23,24] Upon treatment of compound 11 with an excess amount of triethyl orthoformate, [25] the ring closure has occurred to provide the respective triazolo[4,3-a]pyrimidine derivative 13. The IR spectrum of compound 12 revealed an absorption band at 2160 cm −1 assigned to the azide function, in addition to strong band characteristic for 1,5-disubstituted tetrazole ring at 1575 cm −1 , as well as an absorption band due to (N-N═N) moiety at 1338 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

“…These spectroscopic data are similar to those found for 1,5-disubstituted tetrazole in the literature. [23,24] Upon treatment of compound 11 with an excess amount of triethyl orthoformate, [25] the ring closure has occurred to provide the respective triazolo[4,3-a]pyrimidine derivative 13. Formation of pyrimido[2,1-c][1,2,4]triazinone derivative 14 was achieved through the reaction of compound 11 with ethyl 2-chloroacetoacetate in the presence SCHEME 2 Reagents and conditions: (i) NH 2 CH 2 CH 2 NH 2 /CS 2 , W.B.…”

Section: Resultsmentioning

confidence: 99%

“…N-(4-Imino-9-methyl-7phenylpyrido[3′,2′:4,5]thieno[3,2-d] pyrimidin-3(4H)-yl)benzamide(25) Compound 24 (0.41 g, 1 mmol) in N,Ndimethylformamide (9 mL) was heated under reflux for 1 hour. After being cooled, the separated solid was filtered off, washed with ethanol, left to dry, and crystallized from hexane to give a brown powder.…”

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Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine: Part 2

Hassan

Sarg

El‐Sebaey

2019

Journal of Heterocyclic Chem

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As a continuation of our research on developing anticancer agents and based on the proven proprieties of thieno[2,3-b]pyridines as anticancer, we have designed to synthesize novel thieno[2,3-b]pyridine derivatives that incorporate different biologically active heterocycles through various chemical reactions.All of the newly obtained compounds, compared with the standard anticancer drug (doxorubicin), were screened in vitro for their antitumor activity against hepatocellular carcinoma (HepG-2) and human breast cancer (MCF-7) cell lines. The results revealed that compounds 3, 7, 12, and 19 were found to be the most potent against both HepG-2 and MCF-7 cell lines exhibiting IC 50 values ranging from 3.67 to 11.50 and 5.13 to 11.80 μg/mL, respectively, among which compound 7 has a more potent activity than the reference drug doxorubicin against HepG-2 cell line, showing IC 50 value of 3.67 μg/mL (doxorubicin 4.65 μg/mL).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine: Part 2

Hassan

Sarg

El‐Sebaey

2019

Journal of Heterocyclic Chem

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Microwave-assisted synthesis of new pyrimido[4′,5′:4,5]thiazolo[3,2-a] benzimidazol-4(3H)-one derivatives in solvent-free condition

Davoodnia

Roshani

Nadim

et al. 2007

Chinese Chemical Letters

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Alternative Route for the Synthesis of New Derivatives of Benzimidazo[2′,1′:2,3] thiazolo[5,4-d]pyrimidine

Asghari

Bakavoli

Shiri

et al. 2015

Journal of Chemical Research

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The benzimidazole core is classified by medicinal chemists as one of the privileged sub-structures for drug design, in the light of the affinity they display for a variety of enzymes and protein receptors. 1 Benzimidazoles are very important compounds due to their wide spectrum of biological activities such as antioxidant, 2 antimicrobial, 3 antihypertensive, 4 antiviral, 5 antifungal, 6 antitumour, 7 antihepatitis B virus, 8 anticancer, 9 anticonvulsant, 10 analgesic 11 and antiinflammatory 12 activities.Also, diverse biological properties have been associated with thiazolobenzimidazole derivatives, including antibacterial, 13,14 antifungal, 15 antiinflammatory, 16 antiulcer, 17 antiviral, 18 anthelmintic 19 and anticancer activity 20,21 . An in vitro parasitological study showed that the heterocyclic 2-substituted-[1,3] thiazolo[3,2-a]benzimidazole-3(2H)-ones exhibit higher activity than albendazole against Trichinella spiralis. 22 Moreover, benzimidazothiazolopyrimidines as potential biologically active heterocycles have been the subject of recent studies. 23,24 The synthetic routes to these compounds are limited and mainly involve cyclocondensation of 3-amino-2,3-dihydrobenzimidazo[2,1-b]thiazole-2-carbonitrile with electrophilic reagents such as formamide, acetic anhydride, and orthoesters in combination with amines. 25 Derivatives of these compounds have also been prepared through nucleophilic substitution reactions of the chlorine and alkylthio substituents with different nucleophiles such as hydrazine, thiourea and amines. 23 The above observations prompted us to report an alternative route for the synthesis of new derivatives of benzimidazothiazolopyrimidines through the reaction of the pyrimidine ring with 2-mercaptobenzimidazole. Results and discussionThe starting material 5-bromo-2,4-dichloro-6-methylpyrimidine 1 was prepared according to the published method. 26 Treatment

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Synthesis, Characterization and Reactions of 4‐Hydrazino‐2‐methylpyrimidino[4′5′:4,5]thiazolo[3,2‐a]benzimidazole

Cited by 5 publications

References 13 publications

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine: Part 2

Synthesis and antitumor evaluation of some new derivatives and fused heterocyclic compounds derived from thieno[2,3‐b]pyridine: Part 2

Microwave-assisted synthesis of new pyrimido[4′,5′:4,5]thiazolo[3,2-a] benzimidazol-4(3H)-one derivatives in solvent-free condition

Alternative Route for the Synthesis of New Derivatives of Benzimidazo[2′,1′:2,3] thiazolo[5,4-d]pyrimidine

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