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Rapid access to oxazine fused furocoumarins and in vivo and in silico studies of theirs biological activity. / Lipeeva, Alla V.; Baev, Dmitry S.; Dolgikh, Margarita P. et al.

In: Medicinal Chemistry, Vol. 13, No. 7, 2017, p. 625-632.

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Lipeeva AV, Baev DS, Dolgikh MP, Tolstikova TG, Shults EE. Rapid access to oxazine fused furocoumarins and in vivo and in silico studies of theirs biological activity. Medicinal Chemistry. 2017;13(7):625-632. doi: 10.2174/1573406413666170601114527

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Lipeeva, Alla V. ; Baev, Dmitry S. ; Dolgikh, Margarita P. et al. / Rapid access to oxazine fused furocoumarins and in vivo and in silico studies of theirs biological activity. In: Medicinal Chemistry. 2017 ; Vol. 13, No. 7. pp. 625-632.

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@article{5559538d1d4f4999b453ba7a5ba71d75,
title = "Rapid access to oxazine fused furocoumarins and in vivo and in silico studies of theirs biological activity",
abstract = "Background: The synthesis of 1,2-oxazine-fused linear furocoumarins was performed involving the transition metal catalysis reaction of plant coumarin oreoselone derivatives. Objective and Method: The Pd-catalyzed desulfonative cross-coupling reactions of 2-(tosyl)oreoselone with terminal alkynes and the successive treatment of the obtained 2-(arylethynyl)furocoumarins with an excess of hydroxylamine gave the expected (Z,E)-3-(hydroxyimino)-2-(arylethynyl)furocoumarins with an (Z:E) ratio of about 1:0.5. The gold(III)-catalyzed cycloisomerization of furocoumarin {\ss},?-acetylenic (Z)-oximes led to a new group of heterocyclic compounds-chromeno[6',7':4,5]furo[3,2-c][1,2]oxazine. The (E)-isomer in this condition was transformed into (E)-3-(hydroxyimino)-2-(propan-2-ylidene) furocoumarin. Results: Pharmacological screening of the synthesized 1,2-oxazine-fused linear furocoumarins for anti-inflammatory and analgesic activity in vivo revealed that this compounds possessed high activity which was depend on the substitution in the aromatic ring of the oxazine unit. The results of experimental studies were found to be in accordance with that of the in silico docking results. Conclusion: The moderate toxicity of compounds (LD50 value was more than 2000 mg/kg) encouraged the further design of therapeutically relevant analogues based on this novel type of fused linear furocoumarins.",
keywords = "Analgesic activity, Anti-inflammatory activity, Furocoumarins, Gold catalysis, Molecular docking, Oximes, Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis, Catalytic Domain, Indomethacin/pharmacology, Furocoumarins/chemical synthesis, Oxazines/chemical synthesis, Cyclic Nucleotide Phosphodiesterases, Type 4/chemistry, Animals, Rolipram/pharmacology, Mice, Molecular Docking Simulation, Diclofenac/pharmacology, Drug Evaluation, Preclinical, Analgesics/chemical synthesis, gold catalysis, oximes, MEDICINAL CHEMISTRY, ISOXAZOLES, STREPTOMYCES, PLANT COUMARINS, DERIVATIVES, METABOLITES, GOLD CATALYSIS, anti-inflammatory activity, OXIMES, PEUCEDANIN, molecular docking, OREOSELONE, furocoumarins",
author = "Lipeeva, {Alla V.} and Baev, {Dmitry S.} and Dolgikh, {Margarita P.} and Tolstikova, {Tatijana G.} and Shults, {Elvira E.}",
note = "Copyright{\textcopyright} Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.",
year = "2017",
doi = "10.2174/1573406413666170601114527",
language = "English",
volume = "13",
pages = "625--632",
journal = "Medicinal Chemistry",
issn = "1573-4064",
publisher = "BENTHAM SCIENCE PUBL LTD",
number = "7",

}

RIS

TY - JOUR

T1 - Rapid access to oxazine fused furocoumarins and in vivo and in silico studies of theirs biological activity

AU - Lipeeva, Alla V.

AU - Baev, Dmitry S.

AU - Dolgikh, Margarita P.

AU - Tolstikova, Tatijana G.

AU - Shults, Elvira E.

N1 - Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

PY - 2017

Y1 - 2017

N2 - Background: The synthesis of 1,2-oxazine-fused linear furocoumarins was performed involving the transition metal catalysis reaction of plant coumarin oreoselone derivatives. Objective and Method: The Pd-catalyzed desulfonative cross-coupling reactions of 2-(tosyl)oreoselone with terminal alkynes and the successive treatment of the obtained 2-(arylethynyl)furocoumarins with an excess of hydroxylamine gave the expected (Z,E)-3-(hydroxyimino)-2-(arylethynyl)furocoumarins with an (Z:E) ratio of about 1:0.5. The gold(III)-catalyzed cycloisomerization of furocoumarin ß,?-acetylenic (Z)-oximes led to a new group of heterocyclic compounds-chromeno[6',7':4,5]furo[3,2-c][1,2]oxazine. The (E)-isomer in this condition was transformed into (E)-3-(hydroxyimino)-2-(propan-2-ylidene) furocoumarin. Results: Pharmacological screening of the synthesized 1,2-oxazine-fused linear furocoumarins for anti-inflammatory and analgesic activity in vivo revealed that this compounds possessed high activity which was depend on the substitution in the aromatic ring of the oxazine unit. The results of experimental studies were found to be in accordance with that of the in silico docking results. Conclusion: The moderate toxicity of compounds (LD50 value was more than 2000 mg/kg) encouraged the further design of therapeutically relevant analogues based on this novel type of fused linear furocoumarins.

AB - Background: The synthesis of 1,2-oxazine-fused linear furocoumarins was performed involving the transition metal catalysis reaction of plant coumarin oreoselone derivatives. Objective and Method: The Pd-catalyzed desulfonative cross-coupling reactions of 2-(tosyl)oreoselone with terminal alkynes and the successive treatment of the obtained 2-(arylethynyl)furocoumarins with an excess of hydroxylamine gave the expected (Z,E)-3-(hydroxyimino)-2-(arylethynyl)furocoumarins with an (Z:E) ratio of about 1:0.5. The gold(III)-catalyzed cycloisomerization of furocoumarin ß,?-acetylenic (Z)-oximes led to a new group of heterocyclic compounds-chromeno[6',7':4,5]furo[3,2-c][1,2]oxazine. The (E)-isomer in this condition was transformed into (E)-3-(hydroxyimino)-2-(propan-2-ylidene) furocoumarin. Results: Pharmacological screening of the synthesized 1,2-oxazine-fused linear furocoumarins for anti-inflammatory and analgesic activity in vivo revealed that this compounds possessed high activity which was depend on the substitution in the aromatic ring of the oxazine unit. The results of experimental studies were found to be in accordance with that of the in silico docking results. Conclusion: The moderate toxicity of compounds (LD50 value was more than 2000 mg/kg) encouraged the further design of therapeutically relevant analogues based on this novel type of fused linear furocoumarins.

KW - Analgesic activity

KW - Anti-inflammatory activity

KW - Furocoumarins

KW - Gold catalysis

KW - Molecular docking

KW - Oximes

KW - Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis

KW - Catalytic Domain

KW - Indomethacin/pharmacology

KW - Furocoumarins/chemical synthesis

KW - Oxazines/chemical synthesis

KW - Cyclic Nucleotide Phosphodiesterases, Type 4/chemistry

KW - Animals

KW - Rolipram/pharmacology

KW - Mice

KW - Molecular Docking Simulation

KW - Diclofenac/pharmacology

KW - Drug Evaluation, Preclinical

KW - Analgesics/chemical synthesis

KW - gold catalysis

KW - oximes

KW - MEDICINAL CHEMISTRY

KW - ISOXAZOLES

KW - STREPTOMYCES

KW - PLANT COUMARINS

KW - DERIVATIVES

KW - METABOLITES

KW - GOLD CATALYSIS

KW - anti-inflammatory activity

KW - OXIMES

KW - PEUCEDANIN

KW - molecular docking

KW - OREOSELONE

KW - furocoumarins

UR - http://www.scopus.com/inward/record.url?scp=85038129621&partnerID=8YFLogxK

U2 - 10.2174/1573406413666170601114527

DO - 10.2174/1573406413666170601114527

M3 - Article

C2 - 28571532

AN - SCOPUS:85038129621

VL - 13

SP - 625

EP - 632

JO - Medicinal Chemistry

JF - Medicinal Chemistry

SN - 1573-4064

IS - 7

ER -

ID: 9671272