Amine Adducts of β-Benzoylacrylic Acid and Its Methyl Ester. Hydrogenation Products

Cromwell, Norman H.; Cook, Kenneth E.

doi:10.1021/jo01103a022

Cited by 9 publications

(3 citation statements)

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“…1 H-NMR displayed a multiple peak at δ = 2.34–2.51 ppm characteristic to both diastereotopic (CH 2 ) protons at the b-carbon atom to the COOH group and singlet peaks at δ = 6.08 and 9.80 ppm for NH and primary NH 2 protons, respectively (exchangeable in D 2 O). The resulted structure came in agreement with several reported studies [57–62] indicated that β-aroylacrylic acids add amines to the more reactive [63] vinyl carbon (a-carbon to the COOH). Thus, the nucleophilic addition of the primary amino group attached to C-2(2) in 1, 3, 4-thiadiazole occurs predominantly at the a-carbon to afford the aza-Michael adduct 3.…”

Section: Methodssupporting

confidence: 90%

Synthesis and evaluation of novel thiazole moiety-containing compounds as antibreast cancer agents

2023

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Progesterone receptor (PR) agonists represent pivotal agents in trapping breast cancer cells through modulating the expression of estrogen receptor (ER). The present investigation aimed to test three novel thiadiazolecontaining compounds as antibreast cancer agents. Test compounds were synthesized and abbreviated as 2-{(5-amino-1, 3, 4-thiazole-2-yl) amino}-4-(4-chloro-3methylphenyl)-4-oxobutanoic acid (TAB), 4-(4-chloro-3methylphenyl)-4-oxo 2-[(5-sulfanyl-1, 3, 4-thiadiazol-2-yl)] sulfanyl-butanoic acid (TSB) and 4-(4-chloro-3methylphenyl)-4-oxo 2-[(5-sulfanyl-1, 3, 4-thiadiazol-2-yl)] sulphonyl-botanic acid (TSSB). Molecular docking of the test compounds with PR was simulated. The IC 50 of the test compounds against both Michigan cancer foundation-7 (MCF-7) and HepG2 was determined. Ehrlich solid tumor (EST) was grown in the right thigh of the mouse as a model of breast cancer in vivo. Hepatic and renal functions, besides hematological indicators, were tested. The expression of ER and ER genes in EST was determined using real-time PCR. Immunohistochemistry was carried out for the determination of Ki-67 and cyclindependent kinase 1 (CDK-1) in EST. Our results revealed that TAB, TSB and TSSB reduced Ehrlich tumor size by 48, 64 and 52%, respectively, compared to the EST control group. The docking scores achieved by TAB, TSB and TSSB with PR were −9.29, −9.41 and −9.24 kcal/mol, respectively. The most potent compound against MCF-7 was TSB, with an IC 50 of 3.9 g/ml. The administration of test compounds suppressed Ki-67 and CDK1, and the best effect was observed at TSB. Our findings suggest that test compounds are applicants to be antibreast cancer agents.

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Section: Methodssupporting

confidence: 90%

Synthesis and evaluation of novel thiazole moiety-containing compounds as antibreast cancer agents

2023

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“…A mixture of ethoxymethyleneamino-4H-pyran (6) (3.00 g, 8.70 mmol) and hydrazine hydrate 21 (0.30 mL, 8.70 mmol) or phenylhydrazine (0.85 mL, 8.70 mmol) in absolute ethanol (30 mL) was refluxed for (7h) .The reaction mixture was left to cool at room temperature then acidified with diluted HCl, the formed solid was filtered off, washed with cold water, dried and crystallized from the proper solvent to afford pyranopyrimidines (7) and/or (8).…”

Section: -(4-chloro-3-methylphenyl)-123a-trihydro-6-oxa-1279-tementioning

confidence: 99%

“…Particularly, the 5-amino-9-chloro-2-(2-furyl)-1,2,4-triazolo [1,5-c] quinazoline (1) (Figure 1) was found to be a highly potent adenosine antagonist, 1 Also pyran and fused 4H-pyran derivatives have attracted a great deal of interest owing to their antimicrobial activity, 3,4,5 inhibition of influenza, virus sialidases, 6 mutagenic activity as antiviral, 7 antiproliferation agents, 8 sex pheromones activity, 9,10 antitumor 11 and anti-inflammatory agent. 12 Moreover, pyran derivatives are well known for their antihistaminic activity.…”

Section: Introductionmentioning

confidence: 99%

Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis

El‐Hashash¹,

El‐Sawy²,

Eissa³

2009

Journal of the Korean Chemical Society

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ABSTRACT. The present work is devoted to study the interaction of β-aroylacrylic acid derivative (3) with malononitrile in (DMF) in the presence of piperidine and/or ammonium acetate, then using the formed compounds as starting materials for synthesizing fused and isolated heterocyclic systems. It has been established that the β-aroylacrylic acid (3) reacts with malononitrile in (DMF) in the presence of piperidine as a catalyst with the formation of 4H-pyran derivative (4). By changing the catalyst into ammonium acetate, pyridine derivative (5) has been obtained. Also the N-maleamic acid derivatives (19) and (27) have been synthesized via the interaction of (4) and (5) with maleic anhydride. The purpose of this step is to study the behavior of the formed maleamic acid derivatives -as analogies of β-aroylacrylic acids -towards different active methylene compounds under Michael addition reaction.

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Lactone, 18. Mitt. Synthese lactonverbrückter 1,1‐Diarylpropylamine

Lehmann

Gossen

1988

Archiv der Pharmazie

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durchAddition von Aminen an die &4roylaciylsauren 1-4 und anschlieDende Umsetzung von 5a-h mit Phenyllithium schlieljt die Lucke in der homologen Reihe lactonverbriickter Diarylalkylamine2-5).Synthesis of the 3~amino~5,5-diaryl~4,5~di~ydro~2~3N~~furanones 6a-h by addition of amines to the P-aroylacrylic acids 1-4 and treatment of 5a-h with phenyllithium closes the gap in the homologous series of y-lactonized diarylalkanamines2-s).uber die Darstellung y-lactonjsierter Diarylethyl-2), -b~t y l -~,~) und -pentylamine5) haben wir berichtet. Um fur pharmakologische Untersuchungen und die Diskussion von Struktur-Wirkungs-Beziehungen uber eine luckenlose homologe Reihe zu verfugen, sollten noch y-lactonisierte Diarylpropylamine zuganglich gemacht werden.Die friiher beschriebene Synthese von a-Amino-y-lactonen durch Aminolyse von a-Bromlactonen6) kann auf 6 nicht ubertragen werden, da bereits bei dem Versuch, y, y-Diphenylbutyrolacton zu bromieren, Elimination zum ungesattigten Lacton erfolgt6). Eine nachtragliche N-Alkylierung des N-unsubstituierten Analogons von 6a (R' = NH,) ist unzweckmaflig, da wir dieses Aminolacton nur in sehr geringer Ausbeute (5.9 %) erhielten' .). So priiften wir, ob uns die Umsetzung der a-Amino-y-ketosauren 5 rnit metalliertem Benzol zu 6 fuhren kann.

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Amine Adducts of β-Benzoylacrylic Acid and Its Methyl Ester. Hydrogenation Products

Cited by 9 publications

References 0 publications

Synthesis and evaluation of novel thiazole moiety-containing compounds as antibreast cancer agents

Synthesis and evaluation of novel thiazole moiety-containing compounds as antibreast cancer agents

Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis

Lactone, 18. Mitt. Synthese lactonverbrückter 1,1‐Diarylpropylamine

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