The reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activities

Mohareb, Rafat M.; El-Sharkawy, Karam Ahmed; Sherif, Sherif M.

doi:10.2478/v10007-008-0030-3

Cited by 8 publications

(17 citation statements)

References 23 publications

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“…On the other hand, the reaction of 5 with either malononitrile or ethyl cyanoacetate in DMF containing triethylamine gave the 1,5-dihydrobenzo [4,5]imidazo[1,2-a]pyridine derivatives 13a and 13b, respectively (Scheme 3).…”

Section: Chemistrymentioning

confidence: 99%

“…The presence of the 2-EtO group in 11b is responsible for its high potency. Considering the 7,8,9,10-tetrahydrobenzo [4,5]…”

Section: Structure Activity Relationshipmentioning

confidence: 99%

“…The obtained product was crystallized from ethanol to give greenish brown crystals. Phenyl-7,8,9,10-tetrahydrobenzo[ [4,5] …”

Section: General Procedures For the Synthesis Of The Imidazo [ [12-b]mentioning

confidence: 99%

“…The obtained product was crystallized from ethanol to give yellow crystals of 12a and orange crystals of 12b. General procedure for the synthesis of the benzo[ [4,5] …”

Section: General Procedures For the Synthesis Of The Benzylidene Derivmentioning

confidence: 99%

“…Omeprazole 3 and Pimobendan 4 that are therapeutically useful in the management of peptic ulcer and congestive heart failure, respectively. Many derivatives of benzimidazoles are well known for their antimicrobial, [5][6][7][8][9][10] anthelmintic, 11 antiviral, [12][13][14][15][16] and antifungal 17,18 activities. Since 1985 benzimidazole containing compounds have been reported as well known anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

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New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

Mohareb

Mohamed²,

Abdallah³

2016

ACSi

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The reaction of ethyl cyanoacetate with o-phenylenediamine gave the 2-cyanomethylbenzo[c]imidazole (1). The latter compound was used as the key starting material to synthesise biologically active heterocyclic derivatives. Thus, the reaction of 1 with cyclohexanone and either of benzaldehyde, 4-methoxybenzaldehyde or 4-chlorobenzaldehyde gave the annulated derivatives 2a-c, respectively. The antitumor evaluations of the newly synthesized products against the three cancer cell lines MCF-7 (breast adeno-carcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) showed that compounds 2b, 6, 11b, 11c, 12b, 16a, 16b and 18a exhibited optimal cytotoxic effect against cancer cell lines, with IC 50 values in the nM range. Bioactive compounds are often toxic to shrimp larvae. Thus, in order to monitor these chemicals in vivo lethality to shrimp larvae (Artemia salina), Brine-Shrimp Lethality Assay was used. Compounds 11b, 12b and 16b showed no toxicity against the tested organisms.

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Section: Chemistrymentioning

confidence: 99%

“…The presence of the 2-EtO group in 11b is responsible for its high potency. Considering the 7,8,9,10-tetrahydrobenzo [4,5]…”

Section: Structure Activity Relationshipmentioning

confidence: 99%

“…The obtained product was crystallized from ethanol to give greenish brown crystals. Phenyl-7,8,9,10-tetrahydrobenzo[ [4,5] …”

Section: General Procedures For the Synthesis Of The Imidazo [ [12-b]mentioning

confidence: 99%

“…The obtained product was crystallized from ethanol to give yellow crystals of 12a and orange crystals of 12b. General procedure for the synthesis of the benzo[ [4,5] …”

Section: General Procedures For the Synthesis Of The Benzylidene Derivmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

Mohareb

Mohamed²,

Abdallah³

2016

ACSi

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Synthesis and anticancer activity of novel 2-substituted pyranopyridine derivatives

et al. 2016

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A novel series of 2-aminopyranopyridine derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) were synthesized utilizing 2-chloro-4-(thiophen-2-yl)-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile (2) as a key starting compound. The structures of the newly synthesized compounds were confirmed on the basis of elemental analyses and infrared (IR), 1 H, 13 C-nuclear magnetic resonance (NMR) and mass spectra. Anticancer evaluation was carried out for the new derivatives against Hep-G2 (human liver carcinoma), MCF-7 (human breast carcinoma), Caco-2 (human colorectal adenocarcinoma) and HCT116 (human colorectal carcinoma) cell lines using doxorubicin as a reference drug. The biological results revealed that the compounds 12 and 14 exhibited more potent anticancer activity than the reference drug.

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Synthesis and Antimicrobial of Certain New Thiazolidinone, Thiazoline, and Thiophene Derivatives

Gouda

Berghot

Shoeib

et al. 2010

Phosphorus, Sulfur, and Silicon and the Related Elements

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The reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activities

Cited by 8 publications

References 23 publications

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

Synthesis and anticancer activity of novel 2-substituted pyranopyridine derivatives

Synthesis and Antimicrobial of Certain New Thiazolidinone, Thiazoline, and Thiophene Derivatives

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