Synthesis and dopamine receptor binding affinity of 4H-thiochromenoapomorphines

Sipos, Attila; Tóth, Miklós; Mueller, Franziska K. U.; Lehmann, Jochen; Berényi, Sándor

doi:10.1007/s00706-008-0044-z

Cited by 15 publications

(18 citation statements)

References 21 publications

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“…1 H NMR (400 MHz, DMSO-d 6 ): d H = 2.22 (s, 3H), 5.04 (s, 1H), 6.77 (s, 2H), 6.89 (t, 1H, J = 7.2 Hz), 7.01 (t, 1H, J = 7.6 Hz), 7.07 (d, 2H, J = 7.6 Hz), 7.18-7.21 (m, 3H), 7.28 (d, 1H, J = 8.0 Hz), 11.43 (s, 1H). 13 C NMR (100 MHz, DMSO-d 6 ): d C = 151. 5, 142.1, 136.5, 135.6, 129.0, 127.2, 125.3, 121.2, 120.5, 120.0, 119.1, 117.3, 110.7, 107.8, 74.3, 40.2, 20.6.…”

Section: -Aminomentioning

confidence: 99%

“…1 H NMR (400 MHz, DMSO-d 6 ): d H = 5.13 (s, 1H), 6.88-6.92 (m, 3H), 7.03 (t, 1H, J = 7.6 Hz), 7.21 (d, 1H, J = 7.6 Hz), 7.29 (t, 3H, J = 7.2 Hz), 7.48 (d, 2H, J = 7.6 Hz), 11.50 (s, 1H). 13 C NMR (100 MHz, DMSO-d 6 ): d C = 151. 9, 144.5, 136.6, 131.4, 129.5, 125.2, 121.3, 120.7, 119.8, 119.7, 119.3, 117.2, 110.8, 107.1, 73.4 4, 149.6, 136.5, 126.5, 125.2, 124.6, 123.7, 121.3, 120.7, 119.9, 119.3, 117.3, 110.8, 107.8, 73.9, 35.5.…”

Section: -Aminomentioning

confidence: 99%

“…Thiopyran derivatives can act as modulators of the estrogen receptors 12 and are found to possess a high dopamine receptor binding affinity. 13 Indole subunits are frequently present in many biologically active natural products. 14 Thiopyranoindoleannulated heterocyclic compounds are important due to their biological activity.…”

Section: Introductionmentioning

confidence: 99%

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Green approach to highly functionalized thiopyrano derivatives via domino multi-component reaction in water

2012

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A green, operationally simple and highly efficient one pot three-component approach for the synthesis of thiopyrano[2,3-b]indole-3-carbonitrile, thiopyrano[2,3-b]thiochromene-3-carbonitrile and dihydrothiochromeno[2,3-b]thiochromene derivatives has been developed by the domino reaction of indoline-2-thione or 4-hydroxy-2H-thiochromene-2-thione with aldehyde and malononitrile or dimedone in water at 100 uC. The significant advantages of this protocol are highlighted by short reaction time, excellent yields and formation of three new bonds and a stereocenter in one operation from easily available starting materials.

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Section: -Aminomentioning

confidence: 99%

Section: -Aminomentioning

confidence: 99%

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Green approach to highly functionalized thiopyrano derivatives via domino multi-component reaction in water

2012

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“…RP 49356 is a K + channel opener [17]. Thiopyran derivatives are modulators of estrogen receptors, and possess a high dopamine receptor-binding affinity [21,22]. Pharmaceutically acceptable salts of tetrahydrothiopyranofused indoles are known for their psycho-analeptic and nootropic activities [19].…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis, biological evaluation, and docking study of new chromeno-annulated thiopyrano[2,3-c]pyrazoles

et al. 2016

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A one-pot synthesis of new chromeno-annulated thiopyrano[2,3-c]pyrazoles has been achieved through a domino-Knoevenagel-hetero-Diels-Alder reaction after combining various pyrazol-5-thiones with O-alkenyloxy/alkynyloxy-salicylaldehydes/naphthaldehydes in a Brønsted acidic ionic liquid, [Hmim]HSO[Formula: see text], methylimidazolium hydrogen sulphate, under microwave irradiation. The method is simple and in many cases the isolated products did not require further purification. The central pyranothiopyranyl cis-fusion was confirmed by 2D NMR NOESY and single-crystal X-ray analysis suggesting that the endo-E-Syn transition state would be the most favored pathway of the reaction. Many heterocycles of this new series were found active against six bacterial and two fungal strains. In addition, all the compounds possess good anti-oxidant activity with the ferric reducing anti-oxidant power value [Formula: see text]. All new structures were docked into active site of angiotensin I converting enzyme (ACE), assuming that the compounds possessed the anti-hypertensive activity potential on the basis of prediction of activity spectra of substances prediction results. Pyranyl ring oxygen in compound 9a forms two hydrogen bonds with HIS353 and HIS513 residues in the active site of the ACE having good G score ([Formula: see text]) of this compound, comparable to that of the reference drug captopril ([Formula: see text]).

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“…Thiopyran derivatives can act as modulators of the estrogen receptors 13 and are found to possess a high dopamine receptor binding affinity. 14 Thiopyrans are used as key units in medicinal chemistry and as versatile building blocks in organic synthesis. 15 For example, it has been reported that thiopyrans were widely used in the construction of analogues of natural products with various biological activities, such as tetrahydrodicranenone, 16 serricornin, 17 thromoboxanes, 18 and cyclopentanoids.…”

Section: Introductionmentioning

confidence: 99%

Novel one-pot Facile Synthesis of Thiopyranopyrazole Using [H mim]HSO4 Catalyst

Srivastava¹,

Singh²,

Singh³

2014

Croat. Chem. Acta

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An efficient and easy protocol has been developed for synthesis of thiopyranopyrazole by using [H mim]HSO 4 as recyclable catalyst under solvent-free condition at room temperature. This environmentally benign method has advantages, such as high yield of products, simple work-up procedure, and avoidance of the organic solvents, which will contribute in serving as a green process greatly. The catalyst was easily recovered and reused without any considerable loss of activity.

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Synthesis and dopamine receptor binding affinity of 4H-thiochromenoapomorphines

Cited by 15 publications

References 21 publications

Green approach to highly functionalized thiopyrano derivatives via domino multi-component reaction in water

Green approach to highly functionalized thiopyrano derivatives via domino multi-component reaction in water

One-pot synthesis, biological evaluation, and docking study of new chromeno-annulated thiopyrano[2,3-c]pyrazoles

Novel one-pot Facile Synthesis of Thiopyranopyrazole Using [H mim]HSO4 Catalyst

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