Chemoselective synthesis of 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy]- and 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)quinoxaline derivatives

Fathalla, Walid

doi:10.1007/s10593-015-1661-1

Cited by 6 publications

(2 citation statements)

References 27 publications

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“…20 However a strong query still remains that is the development of simple, mild and efficient methods for preparation of quinazoline derivatives linked to amino acid residues by a spacer and the evaluation of their biological activities. In view of these facts and in continuation of our efforts in studing the chemoselective reactions of heterocyclic amides [21][22][23] and thioamides, 20,[24][25][26][27][28][29][30][31][32][33][34][35][36][37] we found interesting to synthesize a series of quinazoline derivatives linked to amino acids by a spacer. Here in we wish to report a novel synthesis of 3-arylquinazoline-2,4-dione and use this precursor in the synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Ismail¹,

Ali²,

Fathalla³

et al. 2017

Arkivoc

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A series of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate 10-13a-f has been developed on the basis of the N-chemoselective reaction of 3-substituted quinazoline-2,4-diones 3a-d with ethyl chloroacetate and azide coupling method with amino acid ester hydrochloride. The precursor quinazoline diones 3a-d chemoselective reactions were studied using DFT(B3LYP)/6-311G level of theory and were prepared by a new rearrangement method from the corresponding 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-2-ylthio) acetohydrazide 6.

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Section: Introductionmentioning

confidence: 99%

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Ismail¹,

Ali²,

Fathalla³

et al. 2017

Arkivoc

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“…Chemoselective reactions of heterocyclic amides with electrophiles were extensively investigated by our research group to afford either N-substituted, O-substituted, or a mixture of both. These results were used to structure and modify several heterocyclic systems and were supported by theoretical DFT calculations to predict the site of alkylation. − To find more promising quinoline derivatives for biological evaluation, we now report the preparation of N -alkyl-3-[2-oxoquinolin-1(2 H )-yl]propanamide and related compounds based on the chemoselective reaction of 2-quinolinone with methyl acrylate under Michael reaction conditions and investigate their activity as cytotoxic agents, highlighting the effective molecular target.…”

Section: Introductionmentioning

confidence: 90%

Synthesis of N-Alkyl-3-[2-oxoquinolin-1(2H)-yl]propanoic Acid Derivatives and Related Compounds: Cytotoxicity and EGFR Inhibition of Some Propanamide Derivatives

El Rayes,

Ali,

Fathalla

et al. 2024

ACS Omega

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A series of 20 new structure-modified quinolin-2-one derivatives were prepared for biological evaluation. This was successfully achieved based on chemoselective reactions of heterocyclic amides with acrylic acid derivatives, which gave 3-[2oxoquinolin-1-(2H)-yl] propanoic acid derivatives (N-substitution via a unique behavior). The ester was reacted with hydrazine to afford the corresponding hydrazide. Both the corresponding ester and hydrazide were used as building blocks to modify the quinolone structure and give N-hydroxyl propanamides, oxadiazoles, and thiosemicarbazides. The corresponding carboxylic acid and hydrazide were used to prepare several amides: N-alkyl-3-[2-oxoquinolin-1(2H)-yl]propanamides via azide and dicyclohexyl carbodiimide coupling methods. Among derivatives, compound 9e exhibited potent cytotoxicity against MCF-7 cells with an IC 50 value of 1.32 μM compared to doxorubicin with an IC 50 value of 1.21 μM. Additionally, it caused potent EGFR inhibition by 97% with an IC 50 value of 16.89 nM compared to Erlotinib with an IC 50 value of 29.8 nM. Finally, the binding mode of compound interactions toward EGFR was highlighted using a molecular docking study; compound 9e exhibited good binding affinity with a binding energy of −17.89 kcal/mol, and it formed H-bond interactions with Met 769 as the key amino acid of interaction. Accordingly, compound 9e may be developed as an EGFR-oriented chemotherapeutic antibreast cancer agent.

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ChemInform Abstract: Chemoselective Synthesis of 3,6,7‐Trisubstituted 2‐(2,3:5,6‐Di‐O‐isopropylidene‐β‐D‐mannofuranosyloxy)‐ and 2‐(2‐Acetamido‐3,4,6‐tri‐O‐acetyl‐2‐deoxy‐β‐D‐glucopyranosyloxy) quinoxaline Derivatives.

Fathalla

2015

ChemInform

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Chemoselective synthesis of 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy]- and 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)quinoxaline derivatives

Cited by 6 publications

References 27 publications

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Synthesis of N-Alkyl-3-[2-oxoquinolin-1(2H)-yl]propanoic Acid Derivatives and Related Compounds: Cytotoxicity and EGFR Inhibition of Some Propanamide Derivatives

ChemInform Abstract: Chemoselective Synthesis of 3,6,7‐Trisubstituted 2‐(2,3:5,6‐Di‐O‐isopropylidene‐β‐D‐mannofuranosyloxy)‐ and 2‐(2‐Acetamido‐3,4,6‐tri‐O‐acetyl‐2‐deoxy‐β‐D‐glucopyranosyloxy) quinoxaline Derivatives.

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