Synthetic applications of benzothiazole containing cyanoacetyl group

Fadda, Ahmed A.; Abdelrazek, Fathy M.; Mohamed, Khaled S.; Ghieth, Howayda Mohamed Mostafa; Etman, H. A.

doi:10.5155/eurjchem.1.2.90-95.32

Cited by 16 publications

(10 citation statements)

References 21 publications

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“…3‐Oxopentanedinitrile derivative 14 was utilized for preparation of various substituted five‐, six‐, and seven‐membered rings attached to the pyridothienopyrimidine nucleus via its treatment with hydroxylamine hydrochloride in N , N ‐dimethylformamide containing a catalytic amount of triethylamine, salicylaldehyde in ethanol and piperidine as a catalyst, and hydrazine hydrate in ethanol containing freshly fused sodium acetate to yield the corresponding 2(5‐aminoisoxazol‐3‐yl)acetonitrile 15 , 4 H ‐chromeno[2,3‐ b ]pyridin‐4‐one 16 , and 3,7‐diamino‐4 H ‐1,2‐diazepin‐5(6 H )one 17 derivatives, respectively. Spectroscopic data and elemental analyses of compounds 15 to 17 were in agreement with the predicted structures (see Section ).…”

Section: Resultsmentioning

confidence: 99%

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

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 IC50 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 IC50 value of 3.67 μg/mL (doxorubicin 4.65 μg/mL).

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Section: Resultsmentioning

confidence: 99%

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

Hassan

Sarg

El‐Sebaey

2019

Journal of Heterocyclic Chem

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“…Figure 1 We have now developed a novel, versatile and convenient approach to fused thiazolopyrimidine derivatives to which the third ring is attached bridging the N-3 and S-2 positions. Also, the present work is an extension of our ongoing efforts [30][31][32][33][34][35] towards the development and identification of new molecules via aimed to synthesized some novel thiazolo, thiazino, benzothiazepen, thiazepen derivatives and screen them for antimicrobial activities. Compound 4 was used as a key compound for this study and for further synthesis of other fused heterocycles.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Some New 1,2,3,4-Tetrahydropyrimidine-2-thione and Their Thiazolo[3,2-a]pyrimidine, Thiazino and Benzothiazepine Derivatives

Fadda

Bondock

Khalil

et al. 2013

J. Heterocyclic Chem.

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The starting N‐(2‐pyridyl)‐6‐methyl‐4‐phenyl‐2‐thioxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxamide (4) was used as a key intermediate for the synthesis of new 1,2,3,4‐tetrahydropyrimidine‐2‐thione and their thiazolo[3,2‐a]pyrimidine, thiazino and benzothiazipen derivatives. The reaction of 4 with haloketones in ethanol catalyzed by base afforded the corresponding thiophenopyrimidine and pyrimidothiazipine derivatives 5, 6, 7, 8, 9, 10. Methylation and formylation of 4 led to the pyrimidine derivatives 15 and 16, respectively. The preventative compounds were established on the basis of elemental and spectral data.

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“…Furthermore, various substituted benzothiazoles such as 2-aryl benzothiazoles have received much attention because of their unique structures and uses as radioactive amyloid imagining agents [25] and anticancer agents [26]. In continuation of our interest in the synthesis of heterocycles containing a benzothiazole moiety [27][28][29][30], we report herein a facile route to several new benzothiazole-fused heterocyclic systems. We present efficient synthesis of novel pyrido [2,1-b] [1,3] benzothiazole, pyrimidopyrido [2,1-b] [1,3]benzothiazole, and benzothiazolo[3,2-a] [1,8] naphthyridine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Efficient and convenient synthesis of pyrido [2,1-b]benzothiazole, pyrimidopyrido[2,1-b]benzothiazole and benzothiazolo[3,2-a][1,8]naphthyridine derivatives

Refat

Mohamed²

2015

Heterocyclic Communications

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Efficient and convenient synthesis of pyrido[2,1-b]benzothiazole, pyrimidopyrido[2,1-b] benzothiazole and benzothiazolo[3,2-a][1,8] naphthyridine derivatives Abstract: New 3-aryl-pyrido[2,1-b][1,3]benzothiazole derivatives 2a-e were synthesized in excellent yields via the reaction of benzothiazoleacetonitrile (1) with different aromatic aldehydes. The treatment of 2-(benzo[d]thiazol-2-yl)-3-(pyridin-4-yl)acrylonitrile (6) with malononitrile afforded 1-amino-3-(pyridin-4-yl)-3H-pyrido[2,1-b][1,3]benzothiazole-2,4-dicarbonitrile (7), which was allowed to react with a variety of reagents to provide pyrimido[5′,4′:5,6]pyrido[2,1-b][1,3]benzothiazole 8, 9 and [1,3]benzothiazolo[3,2-a][1,8] naphthyridine 10, 15 derivatives. All synthesized products were confirmed by elemental analysis, IR, 1 H-NMR, 13C-NMR, and mass spectral data.

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Synthetic applications of benzothiazole containing cyanoacetyl group

Cited by 16 publications

References 21 publications

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

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

Synthesis of Some New 1,2,3,4-Tetrahydropyrimidine-2-thione and Their Thiazolo[3,2-a]pyrimidine, Thiazino and Benzothiazepine Derivatives

Efficient and convenient synthesis of pyrido [2,1-b]benzothiazole, pyrimidopyrido[2,1-b]benzothiazole and benzothiazolo[3,2-a][1,8]naphthyridine derivatives

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