3-Hetarylisocoumarins in the synthesis of 1-functionalized 3-hetarylisoquinolines

Konovalenko, A.S.; Шаблыкин, О. В.; Броварец, В. С.; Shablykina, O. V.; Москвина, Виктория С.; Kozytskiy, Andriy V.

doi:10.1007/s10593-020-02769-3

Cited by 8 publications

(19 citation statements)

References 21 publications

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“…The derivatives marked with their NSC codes (Fig. 2) were chosen for the anticancer activity studies; their methods of synthesis and characteristics were given in [16].…”

Section: Compoundsmentioning

confidence: 99%

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The effect of heterocyclic substituent at C-3 position of 1-(4-methyl-piperazin-1-yl)isoquinolines on their anticancer activity

et al. 2022

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A comparative analysis of the anti-cancer activity of 1-(4-methylpiperazin-1-yl)isoquinolines with different heteroaromatic substituents in С-3 position: 2-methylthiazol-4-yl, 2-phenylthiazol-4-yl, 2-(pyridin-4-yl)thiazol-4-yl, imidazo[2,1-b]thiazol-6-yl, quinoxalin-2-yl, 6,7-dimethylquinoxalin-2-yl. Methods. Biological tests; statistic methods. Results. In vitro screening of the anticancer activity showed that the derivatives with 2-phenylthiazol-4-yl, quinoxaline-2-yl, 6,7-dimethylquinoxalin-2-yl substituents demonstrated the highest level of anticancer activity; however, they were inferior to 2-(pyridin-4-yl)thiazol-4-yl. The product with the 2-methylthiazol-4-yl residue almost did not demonstrated cytotoxicity. Comparative analysis showed no significant correlation with known drugs; hence these compounds have specific molecular targets. Conclusions. The resulting 1-amino-3-hetarylisoquinolines are a promising class of compounds for anticancer drug development. The level and direction of the activity significantly depend on the nature of heterocyclic substituents. K e y w o r d s: in vitro screening, anticancer activity, 1-amino-3-hetarylisoquinolines.

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“…The derivatives marked with their NSC codes (Fig. 2) were chosen for the anticancer activity studies; their methods of synthesis and characteristics were given in [16].…”

Section: Compoundsmentioning

confidence: 99%

“…Alternatively, to diversify the set of 1-amino-3-hetarylisoquinolines, we previously proposed [16] a synthetic sequence based on the use of bromoketone 8 and subsequent recyclization of isochromone to isoquinolone 10 (Scheme 2, Het -substituted thiazoles, quinoxalines, and imidazothiazole, X -O, NMe).…”

Section: Introductionmentioning

confidence: 99%

The effect of heterocyclic substituent at C-3 position of 1-(4-methyl-piperazin-1-yl)isoquinolines on their anticancer activity

et al. 2022

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“…The monobromo derivative 74 and the dibromo derivative 75 were used to construct the quinoxaline system. 21,47 It is noteworthy that the obtained 3-hetarylisocoumarins were subsequently used to synthesize new 1-amino-3-hetarylisoquinolines -potential anticancer agents. 47,48 Bromination of 3acetylisocoumarin 22 in acetic acid at 5 °С resulted in the formation of 3-(α-bromo)acetylisocoumarin (74).…”

Section: Scheme 25 Synthesis Of 2-amino-6-(isocoumarin-3-yl)-4-phenyl...mentioning

confidence: 99%

“…21,47 It is noteworthy that the obtained 3-hetarylisocoumarins were subsequently used to synthesize new 1-amino-3-hetarylisoquinolines -potential anticancer agents. 47,48 Bromination of 3acetylisocoumarin 22 in acetic acid at 5 °С resulted in the formation of 3-(α-bromo)acetylisocoumarin (74). 49 Its subsequent interaction with a methacrylic acid salt resulted in the formation of an ester; the authors studied the temperature decomposition parameters of the specified methacrylate polymer in detail.…”

Section: Scheme 25 Synthesis Of 2-amino-6-(isocoumarin-3-yl)-4-phenyl...mentioning

confidence: 99%

1H-isochromene-1-ones and isoquinoline-1(2H)-ones with carbonyl group in position 3: Features of synthetic approaches and transformation

Москвина¹,

Konovalenko²,

Shablykina³

et al. 2022

Arkivoc

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Oxygen-containing heterocyclic 1H-isochromen-1-ones are core structural components of various natural products and biologically active compounds. They are used as functional substrates in the synthesis of biologically active 1H-isochromen-1-ones and isoquinolin-1(2H)-ones exhibiting different biological properties and diverse applications. Synthetic approaches to these classes of heterocyclic compounds developed in parallel from the very beginning because one of the strategies for the synthesis of isoquinolin-1-one is the recyclization of the isochromen-1-one system by the action of primary amines. In this review, we comprehensively describe the synthesis of 1H-isochromen-1-ones and isoquinolin-1(2H)-ones with a carbonyl function in position 3, summarize their use as synthons in organic chemistry and highlight their biological activities.

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“…Recent achievements in this field include the synthesis of 2‐R‐5‐(acylamino)isoquinolin‐1(2 H )‐ones, which are modulators of the P2X7 receptor (Scheme 1a), [2] 2,3,6‐trisubstituted 1‐oxo‐1,2‐dihydroisoquinolines as potent CRTh2 antagonists (Scheme 1b), [3] new fluorinated and chlorinated indenoisoquinoline topoisomerase I poisons (Scheme 1c), [4] and a convenient approach to the synthesis of 1‐amino‐3‐hetarylisoquinolines with anticancer activity (Scheme 1d) [5,6] . One step involved in the synthesis of the latter was the recyclization of 3‐hetarylisocoumarins into the corresponding isoquinolin‐1‐ones [5–7] . These reactions are of significant interest as they offer more possibilities for further synthetic transformations.…”

Section: Introductionmentioning

confidence: 99%

Distinctive Features of 3‐Acetyl‐ and 3‐Benzoyl‐Isocoumarins’ Interaction with Active Primary Amines

Konovalenko,

Shablykin,

Shablykina

et al. 2023

ChemistrySelect

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Isoquinolones and isoquinolines are crucial natural and synthetic heterocyclic compounds exhibiting a range of biological activities. A less explored strategy for the recyclization of isocoumarins to isoquinolones involves the transformation of 1H‐isochromen‐1‐ones with a carbonyl group at position 3 using primary amines. This study presents a straightforward one‐pot protocol for the recyclization of 3‐acetyl‐ and 3‐benzoylisocoumarins into their corresponding isoquinolone derivatives using structurally diverse primary amines. This provides versatile and scalable routes for accessing a variety of 2‐R‐isoquinolin‐1(2H)‐ones. Interestingly, the acyl group also reacted with the hydroxyl group of 2‐aminoethanol, leading to the simultaneous formation of 3,4‐dihydro[1,4]oxazino[4,3‐b]isoquinolin‐6(1H)‐ones alongside lactone recyclization. Moreover, the recyclization process was accompanied by more complex alternative cyclizations, including an oxidative‐reductive stage. For instance, the recyclization of isocoumarins with benzylamine resulted in the formation of isochromeno[3,4‐c]pyrroles, whereas with glycine derivatives, 1,2‐dihydro‐6H‐pyrazino[1,2‐b]isoquinolin‐3,6(4H)‐diones were obtained.

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3-Hetarylisocoumarins in the synthesis of 1-functionalized 3-hetarylisoquinolines

Cited by 8 publications

References 21 publications

The effect of heterocyclic substituent at C-3 position of 1-(4-methyl-piperazin-1-yl)isoquinolines on their anticancer activity

The effect of heterocyclic substituent at C-3 position of 1-(4-methyl-piperazin-1-yl)isoquinolines on their anticancer activity

1H-isochromene-1-ones and isoquinoline-1(2H)-ones with carbonyl group in position 3: Features of synthetic approaches and transformation

Distinctive Features of 3‐Acetyl‐ and 3‐Benzoyl‐Isocoumarins’ Interaction with Active Primary Amines

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