48 research outputs found
Novel catalyst-free synthesis of some 3-alkylaminoquinoxaline-2(1H)-thiones and 3-alkyloxyquinoxaline-2(1H)-thiones in ethanol
No full textSeventeen 3-alkylaminoquinoxaline-2(1H)-thiones and 3-alkyloxyquinoxaline-2(1H)-thiones were prepared by a novel thionation protocol from the readily available quinoxaline-2,3-dione in excellent overall yields. This protocol starts with the chlorination of dione using thionyl chloride to give 2,3-dichloroquinoxaline followed by the reaction with equimolar amounts of N-nucleophiles (primary amines and secondary amines) or O-nucleophiles (phenols and alcohols) to principally afford 2-alkanamino-3-chloroquinoxalines or 2-alkyloxy-3-chloroquinoxalines, respectively. The chloroquinoxalines reacted with the thionation reagent N-cyclohexyl dithiocarbamate cyclohexyl ammonium salt in ethanol under reflux to principally give the corresponding quinoxalin-2-yl cyclohexylcarbamodithioate that finally rearranges in situ to give the corresponding thiones in 76-93% overall yields. Our novel catalyst-free synthesis of some 3-alkylaminoquinoxaline-2(1H)-thiones and 3-alkyloxyquinoxaline-2(1H)-thiones in ethanol protocol has many advantages compared with traditional methods: excellent yields, one-pot reaction, simple experimental procedure, and commercial availability of the required reagents. In addition, this method could be generalized to involve a wide range of amines, phenols, and alcohols, and also during the reaction, we did not notice a bad odor. The structures of synthesized compounds are elucidated via different methods such as 1H NMR, 13C NMR, elemental analysis, and MS.</p
Synthesis of <i>N</i>-alkyl-3-[2-oxoquinolin-1(2<i>H</i>)-yl]propanoic acid derivatives and related compounds: cytotoxicity and EGFR inhibition of some propanamide derivatives
No full textA 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-[2-oxoquinolin-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 IC50 value of 1.32 μM compared to doxorubicin with an IC50 value of 1.21 μM. Additionally, it caused potent EGFR inhibition by 97% with an IC50 value of 16.89 nM compared to Erlotinib with an IC50 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.</p
Syntheses and reactions of methyl [3-(4-phenyl-thiazol-2-yl)-thioureido] alkanoates and related compounds
No full textChemInform 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.
No full textSynthesis of Heterocyclic Skeletons by the Reaction of N1-(2-Cyanophenyl)-benzimidoyl Chloride with Thioamides
No full textThe reaction of N-(2-cyanophenyl)benzimidoyl chloride with reagents containing a thioamide moiety, i.e. thioacetamide, benzylthiourea, symmetrical dialkyl- and diarylthioureas gave different cyclic products: 3,1-benzothiazine, 1,3,5-benzotriazocine and quinazoline. The reaction pathways of prepared compounds are discussed
Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate
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