Influenza Antiviral Activity of Br-Containing [2R,4R(S),4aR,7R,8aR]-4,7-Dimethyl-2-(Thiophen-2-YL)Octahydro-2H-Chromen-4-Ols Prepared from (–)-Isopulegol

Nazimova, E. V.; Штро, Анна А.; Anikin, Vadim; Patrusheva, Oksana S.; Ильина, И. В.; Корчагина, Д. В.; Zarubaev, Vladimir V.; Волчо, К. П.; Salakhutdinov, N. F.

doi:10.1007/s10600-017-1966-7

Cited by 17 publications

(17 citation statements)

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“…It is known that compounds with a chromene (benzopyran) scaffold have a broad spectrum of biological activity . A high pharmaceutical potential and low toxicity of these substances resulted in a considerable interest in the synthesis of new chromene derivatives . Recently, it has been shown, that in catalytic condensation of a natural allyl alcohol (−)‐isopulegol (I) with aldehydes, substituted octahydro‐2 H ‐chromen‐4‐ol (III) as 4 R ‐ and 4 S ‐diastereomers was formed along with a dehydration product IV (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

“…Recently, it has been shown, that in catalytic condensation of a natural allyl alcohol (−)‐isopulegol (I) with aldehydes, substituted octahydro‐2 H ‐chromen‐4‐ol (III) as 4 R ‐ and 4 S ‐diastereomers was formed along with a dehydration product IV (Scheme ). Different catalysts such as I 2 , p ‐toluenesulfonic acid, BF 3 ⋅Et 2 O, zeolites, clays were used in this reaction . A relatively high 4 R /4 S ratio (9.0) with overall yields of 70–88 % were observed in condensation of isopulegol (obtained by cyclization of R ‐citronellal) with aromatic aldehydes at −78 °C using scandium triflate .…”

Section: Methodsmentioning

confidence: 99%

“…Some synthesized octahydro‐2 H ‐chromen‐4‐ols on the basis of isopulegol display a pronounced physiological activity . Thus, 4 R ‐diastereomer obtained by the reaction of I with thiophene‐2‐carbaldehyde on K‐10 clay exhibited in vivo prolonged analgesic effect surpassing that of Diclofenac .…”

Section: Methodsmentioning

confidence: 99%

“…Thus, 4 R ‐diastereomer obtained by the reaction of I with thiophene‐2‐carbaldehyde on K‐10 clay exhibited in vivo prolonged analgesic effect surpassing that of Diclofenac . 4 R ‐isomers synthesized with 5‐bromo‐thiophene‐2‐carbaldehyde or acetone displayed a profound anti‐influenza activity, whereas only poor antiviral effect was showed by 4 S ‐diastereomers ,. Quite recently we have demonstrated that an increase in selectivity to thiophenyl‐substituted chromenol with illite clay as a catalyst was observed with an increase in the initial concentrations of reactants, the catalyst to reactants ratio, and a decrease in the reaction temperature .…”

Section: Methodsmentioning

confidence: 99%

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Acid‐modified Halloysite Nanotubes as a Stereoselective Catalyst for Synthesis of 2H‐Chromene Derivatives by the Reaction of Isopulegol with Aldehydes

et al. 2018

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Acid-modified halloysite nanotubes were used for the first time as a stereoselective catalyst for synthesis of oxygen-containing heterocycles applying of allyl alcohol (À)-isopulegol condensation with aldehydes to the octahydro-2H-chromenol (4R-and 4S-diastereomers) as an example. The catalysts were characterized by XRF, XRD, N 2 -adsorption, FTIR with pyridine and MAS NMR methods. A high ratio of 4R/4S diastereomers (7.6-14.5) under mild conditions in cyclohexane was considerably exceeding previously reported results. Unprecedented selectivity (79-83 %) to 4R isomer of thiophenyl-substituted chromenol exhibiting high analgesic activity was achieved. An increase in stereoselectivity with a decrease in the halloysite drying temperature and catalyst acidity clearly indicates formation of 4R diastereomer on the weak Brønsted sites. This work is an example that control of the stereoselectivity of acid-catalyzed organic reactions can be effectively carried out by varying water content on the aluminosilicate surface. Modified halloysite nanotubes can be considered as extremely promising catalysts for stereoselective synthesis of heterocyclic compounds.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Acid‐modified Halloysite Nanotubes as a Stereoselective Catalyst for Synthesis of 2H‐Chromene Derivatives by the Reaction of Isopulegol with Aldehydes

et al. 2018

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“…The cytotoxicity of the compounds against MDCK cells and antiviral activity of the compounds 3a–k against influenza virus A/Puerto Rico/8/34 (H1N1) in cell culture were studied by the technique described previously . Based on the results obtained, 50% cytotoxic concentration (CC 50 ), 50% inhibiting concentration (IC 50 ) were calculated for each compound.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel derivatives of 7,8‐dihydro‐6H‐imidazo[2,1‐b][1,3]benzothiazol‐5‐one and their virus‐inhibiting activity against influenza A virus

Galochkina

Bollikanda

Zarubaev

et al. 2018

Archiv der Pharmazie

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Influenza remains a highly pathogenic and hardly controlled human infection. The ability of selecting drug-resistant variants necessitates the search and development of novel anti-influenza drugs. Herein, we describe the synthesis and evaluation of a series of novel 2-substituted 7,8-dihydro-6H-imidazo[2,1-b][1,3]benzothiazol-5-ones 3a-k for their virus-inhibiting activity against influenza A virus. The new analogues 3a-k prepared in two steps from commercially available cyclohexane-1,3-diones were fully characterized by their NMR and mass spectral data. Among the new derivatives screened for cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells, three analogues 3i-k containing a thiophene unit were found to exhibit high virus-inhibiting activity (high SI values) and a favorable toxicity profile. The compound 3j (CC 50 : >1000 μM, SI = 77) with higher potency is the best anti-influenza hit analogue for further structural optimization and drug development. The most active compounds did not inhibit viral neuraminidase and possess therefore other targets and mechanisms of activity than the currently used neuraminidase inhibitors.

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Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

et al. 2020

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A range of heterogeneous -SO 3 H functionalized catalysts including carbon and halloysite nanotubes, commercial K10 clay, Amberlyst-15 etc. was investigated for the first time using as a model the Prins-Ritter reaction of (À )-isopulegol with benzaldehyde and acetonitrile producing 4-amido derivatives of octahydro-2H-chromenes (as (S)-and (R)-diastereomers). A strong effect of water addition prior the reaction on the overall selectivity and the ratio of isomers in the case of heterogeneous and homogeneous (p-toluenesulfonic acid) catalysis was found for the first time. The yield of the (R)-diastereomer sharply increased with increasing amount of added water, while the S-isomer prevailed with a minimum amount of added water. Experimental results and DFT calculations clearly indicate a kinetic control for R-amide formation. Typically synthesis of 4amidooctahydro-2H-chromenes requires subzero temperatures and toxic catalysts, which were avoided in the current work. Nevertheless, the yield of the desired products (up to 83 %) at 30°C after water addition exceeded the values reported previously. Thus, adding water is a simple and a very effective method for controlling both the yield and stereoselectivity of the Prins-Ritter reaction products under mild conditions.

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Influenza Antiviral Activity of Br-Containing [2R,4R(S),4aR,7R,8aR]-4,7-Dimethyl-2-(Thiophen-2-YL)Octahydro-2H-Chromen-4-Ols Prepared from (–)-Isopulegol

Cited by 17 publications

References 12 publications

Acid‐modified Halloysite Nanotubes as a Stereoselective Catalyst for Synthesis of 2H‐Chromene Derivatives by the Reaction of Isopulegol with Aldehydes

Acid‐modified Halloysite Nanotubes as a Stereoselective Catalyst for Synthesis of 2H‐Chromene Derivatives by the Reaction of Isopulegol with Aldehydes

Synthesis of novel derivatives of 7,8‐dihydro‐6H‐imidazo[2,1‐b][1,3]benzothiazol‐5‐one and their virus‐inhibiting activity against influenza A virus

Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

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Influenza Antiviral Activity of Br-Containing [2R,4R(S),4aR,7R,8aR]-4,7-Dimethyl-2-(Thiophen-2-YL)Octahydro-2H-Chromen-4-Ols Prepared from (–)-Isopulegol

Cited by 17 publications

References 12 publications

Acid‐modified Halloysite Nanotubes as a Stereoselective Catalyst for Synthesis of 2H‐Chromene Derivatives by the Reaction of Isopulegol with Aldehydes

Acid‐modified Halloysite Nanotubes as a Stereoselective Catalyst for Synthesis of 2H‐Chromene Derivatives by the Reaction of Isopulegol with Aldehydes

Synthesis of novel derivatives of 7,8‐dihydro‐6H‐imidazo[2,1‐b][1,3]benzothiazol‐5‐one and their virus‐inhibiting activity against influenza A virus

Stereoselectivity Inversion by Water Addition in the −SO3H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

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Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives