Heterocylen, 69.Mit.: Das Verhalten einiger <i>ortho</i>‐Hydroxyheterochalcone unter der Einwirkung von Hydrazinen. Heterocyclic Compounds, LXIX: Reaction of <i>o</i>‐Hydroxyheterochalcones with Hydrazines

Mager, Sorin; Zaharia, Valentin; Horn, M.; Simiti, I.

doi:10.1002/ardp.19923250917

Cited by 7 publications

(8 citation statements)

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“…In previous papers we described the preparation of some heterochalcones by condensation of thiazolcarbaldehydes and thiazolo [3,2-b] [1,2,4]triazolcarbaldehydes with a series of acetophenones [1][2][3][4]. Data related to the reaction of some α-substituted chalcones with nitrogen dinucleophiles, as well as the antifungal and antiprotozoar properties of these chalcones were already described [5,6].…”

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confidence: 99%

Heterocycles 21. Reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone

Zaharia¹,

Silvestru²,

Vérité³

et al. 2008

Rev. Chim.

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The condensation reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone was performed in basic catalysis, resulting in a mixture of 2,3-epoxy-1-phenyl-3-(2-phenyl-thiazol-4-yl)-propan-1-one (1), 1-phenyl-3-(2-phenyl-thiazol-4-yl)-propane-1,2-dione (2) and 2-phenyl-4,5-bis-(2-phenyl-thiazol-4-yl)-3-hydroxy-furane (4). The isolated solids were structurally investigated by spectroscopic methods, i.e. infrared spectroscopy, mass spectrometry and NMR. In solution the dicarbonylic derivative 2 undergoes a tautomeric process, resulting in the enol 2-hydroxy-1-phenyl-3-(2-phenyl-thiazol-4-yl)-prop-2-en-1-one 3. Compounds 3 and 4 were transformed in the corresponding acetyl derivatives 5 and 6, respectively, by reacting them with acetic anhydride. For the furane 4 the single crystal X-ray diffraction structure was determined.

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Heterocycles 21. Reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone

Zaharia¹,

Silvestru²,

Vérité³

et al. 2008

Rev. Chim.

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“…NMR data of compounds 8, 11 and 12 were consistent with those previously reported. [24,25] On the basis of the reported cytotoxicity effect for thiazole containing compounds, [17,26] the prepared 1-aryl-3-phenylthiazolylpropanoids were tested on a series of twenty cancer cells and one normal cell line.…”

Section: Resultsmentioning

confidence: 99%

“…The structures of these compounds were confirmed by using their spectroscopic and spectrometric data (Supporting information). Except for compounds 8 , 11 , and 12 , other compounds are newly described in the present work. NMR data of compounds 8 , 11 and 12 were consistent with those previously reported …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalized 1‐Aryl‐3‐phenylthiazolylpropanoids and Their Potential as Anticancer Agents

et al. 2020

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Natural products have inspired the development of multipletarget anticancer agents. To reach this goal, preparation of hybrid molecules was adopted as a recent approach to target and affect both sensitive and resistant cells. In the continuation of the search for potent anticancer agents, nine thiazole-based chalcones were prepared. Their cytotoxic activities were evaluated against twenty cancer cell lines and against the normal cell line AML12 hepatocytes. The key steps of these syntheses involved Hantzsch, Sommelet, and Claisen-Schmidt reactions. Julia-Colonna reaction was used to achieve the epoxidation of the double bond. The products were purified by chromatographic techniques and were characterized by spectroscopic methods. Cytotoxicity assays were performed by rezasurin reduction test. Compounds 4-10 showed promising cytotoxic activities. 4 and 7 were the most cytotoxic with IC 50 values lower than 1 μM against seven and two cancer cell lines, respectively. This study disclosed a new series of potential anticancer agents among which 4 and 7 deserve further investigation to develop drug for sensitive and multidrug resistant (MDR) cancer.

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“…Synthesis of thiazole chalcones and their use as intermediates for obtaining pyrazolines and pyrazoles [34] Figure 17. Synthesis of thiazole ortho-hydroxy chalcones and their cyclisation to hydroxychromones [41] In further studies, the reactivity of ortho-hydroxyheterochalcones derived from thiazole was studied in the condensation with different nitrogen-nucleophiles, such as hydrazine and phenylhydrazine and it was found that different cyclisation products are formed, depending on the nitrogen-nucleophile partner [42].…”

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confidence: 99%

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2022

FARMACIA

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The synthesis of the natural products analogues has performed a remarkable expansion in recent years, as natural structures have inspired researchers to develop new potential therapeutic agents with improved pharmacological and pharmacokinetic profiles. This review provides an overview on the synthesis, chemical behaviour and biological properties of some already synthesized heterocyclic chalcones bearing thiazole, indole and pyridine moieties. The attention is directed to the reactivity of the α,β-unsaturated ketone system which provides access to new heterocyclic compounds. The structures of chalcones and their cyclisation products that have shown encouraging in vitro antitumour and antifungal properties are highlighted. RezumatSinteza analogilor produșilor naturali a cunoscut o expansiune remarcabilă în ultima vreme, deoarece structurile naturale au inspirat cercetătorii să dezvolte noi potențiali agenți terapeutici cu profiluri farmacologice și farmacocinetice îmbunătățite. Acest studiu de literatură oferă o imagine de ansamblu asupra sintezei, comportamentului chimic și proprietăților biologice ale unor calcone heterociclice deja sintetizate care conțin în structura lor nucleele tiazol, indol și piridină. Atenția este îndreptată asupra reactivității sistemului carbonilic α,β-nesaturat, care oferă acces la noi structuri heterociclice. Sunt evidențiate structurile calconelor și ale produșilor lor de ciclizare, care au demonstrat proprietăți antitumorale și antifungice in vitro încurajatoare.

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Heterocylen, 69.Mit.: Das Verhalten einiger ortho‐Hydroxyheterochalcone unter der Einwirkung von Hydrazinen. Heterocyclic Compounds, LXIX: Reaction of o‐Hydroxyheterochalcones with Hydrazines

Cited by 7 publications

References 1 publication

Heterocycles 21. Reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone

Heterocycles 21. Reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone

Synthesis of Functionalized 1‐Aryl‐3‐phenylthiazolylpropanoids and Their Potential as Anticancer Agents

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