Synthesis of Some New Quinoxalines and 1,2,4‐Triazolo[4,3‐<i>a</i>]‐quinoxalines for Evaluation of <i>in vitro</i> Antitumor and Antimicrobial Activities

El-Hawash, Soad A.M.; Habib, N. S.; Kassem, Mervat A.

doi:10.1002/ardp.200600061

Cited by 101 publications

(39 citation statements)

References 14 publications

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“…The structure modification of heterocyclic thioamides is an important task in organic synthesis. Triazolethioamide 3 displays an interesting tautomeric equilibrium between thiol (structure 3a ) and thione (structure 3b ) forms (Scheme ) ; consequently, it is amenable to structure modification by simple chemoselective alkylation reactions at the sulfur and nitrogen atoms.…”

Section: Resultsmentioning

confidence: 99%

Convenient Synthesis of Some Novel Pyridazinone‐Bearing Triazole Moieties

Rayes

Ali

Fathalla

2018

Journal of Heterocyclic Chem

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The chemoselective reactions of 2‐(5‐mercapto‐4‐phenyl‐4H‐[1,2,4]triazol‐3‐ylmethyl)‐6‐p‐tolyl‐4,5‐dihydro‐2H‐pyridazin‐3‐one (3) with different electrophiles were evaluated. Triazole 3 reacted with alkyl halides in the presence of triethylamine in alcohol to give the corresponding S‐substituted derivatives. On the basis of S‐chemoselective reactions of triazole 3, a series of amino acid 10a–d and dipeptide derivatives 12a–d were prepared via azide coupling of the corresponding hydrazides 9 and 15 with amino acid ester hydrochlorides, respectively. N‐Substituted triazoles 6a–c or 7a–d attached to pyridazin‐3‐one moiety were successfully formed by the reaction of 3 with activated acrylic acid derivatives or with amines. Antibacterial activities of the synthesized derivatives were investigated through correlation with Escherichia coli FabH inhibitory activities using molecular modeling docking software. The antimicrobial activity of synthesized compounds was evaluated, showing best inhibition zone for N‐substituted carboxylic acid 5a and N‐substituted nitrile 5c parallel to the molecular modeling studies.

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Section: Resultsmentioning

confidence: 99%

Convenient Synthesis of Some Novel Pyridazinone‐Bearing Triazole Moieties

Rayes

Ali

Fathalla

2018

Journal of Heterocyclic Chem

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“…3-Phenylquinoxaline-2(1 H )-thione ( 5 ) displays an interesting tautomeric equilibrium between thiol (structure 5a ) and thione (structure 5b ) forms, Scheme 2. 33−35 Therefore, quinoxaline 5 is amenable to structure modification by simple chemoselective alkylation reactions at the sulfur and nitrogen atoms. Surprisingly, the reaction of 5 with acrylic acid derivatives, methyl acrylate, acrylamide, and acrylonitrile in the presence of triethylamine repeatedly afforded S-alkylated derivatives 6–8 in good yields, Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

Convenient Synthesis and Anticancer Activity of Methyl 2-[3-(3-Phenyl-quinoxalin-2-ylsulfanyl)propanamido]alkanoates and N-Alkyl 3-((3-Phenyl-quinoxalin-2-yl)sulfanyl)propanamides

et al. 2019

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A series of methyl 2-[3-(3-phenyl-quinoxalin-2-ylsulfanyl)propanamido]alkanoates and their corresponding hydrazides and N-alkyl 3-((3-phenylquinoxalin-2-yl)sulfanyl)propanamides were prepared on the basis of the chemoselective Michael reaction of acrylic acid with the parent substrate 3-phenylquinoxaline-2(1H)-thione. The parent thione was produced by a convenient novel thiation method from the corresponding 3-phenylquinoxalin-2(1H)-one. The chemical structures of the newly synthesized compounds were confirmed by elemental analyses, 1H and 13C NMR. The antiproliferative activity of the synthesized compounds was tested against human HCT-116 and MCF-7 cell lines. Out of 25 screened derivatives, 10 active compounds exhibited IC50’s in the range 1.9–7.52 μg/mL on the HCT-116, and 17 active compounds exhibited IC50’s in the range 2.3–6.62 μg/mL on the MCF-7 cell lines compared to the reference drug doxorubicin (IC50 3.23 μg/mL). The structure–activity relationship of the tested compounds was studied through their binding affinity to the human thymidylate synthase allosteric site in silico using molecular docking and proved the quinoxaline ring as a suitable scaffold carrying a peptidomimetic side chain in position 3.

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“…CPCC 200497, has shown moderate cytotoxicity against cancer cell line HepG2, [3] Caroverine has shown muscle relaxant activity, [4] and other derivatives have shown different pharmaceutical properties. Several quinoxalin-2-ones have been reported as antitumor agents, [5] antimicrobial compound, [6] angiotensin II receptor antagonist, [7] aldolase reductase inhibitor, [8] cannabinoid CB2 receptor agonist, [9] histamine-4 receptor antagonist, [10] epsteine-Barr virus inhibitor [11] among others. [12] Additionally, 3-arylquinoxalin-2-(1H)one derived polymers have been described as semiconductors having applications for material science.…”

Section: Introductionmentioning

confidence: 99%