Synthesis and Analgesic Activity Assessment of Furanolabdanoid Conjugates with Glucuronic Acid

Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri- O -acetyl-1-bromo- α -D-glucopyranuronate to form the 18- O - β -D-(glucuronopyranoside)-6′- O -methyl ester of 15,16-epoxylabda-8(9),13,14-triene. Reductive amination of methyl 16-formyl-15,16-epoxylabda-8(9),13,14-trienoate or this β -D-glucur...

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Published in:	Chemistry of natural compounds Vol. 56; no. 4; pp. 678 - 687
Main Authors:	Brusentseva, O. I., Kharitonov, Yu. V., Dolgikh, M. P., Tolstikova, T. G., Shul’ts, E. E.
Format:	Journal Article
Language:	English
Published:	New York Springer US 01-07-2020 Springer Springer Nature B.V
Subjects:	Alkynes Analgesics Chemical activity Cycloaddition Irritation Medicine Organic Chemistry Pharmacy Plant Sciences Trienes diterpenoids analgesic activity CuAAC reaction glycoconjugate azides glucuronic acid
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Abstract	Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri- O -acetyl-1-bromo- α -D-glucopyranuronate to form the 18- O - β -D-(glucuronopyranoside)-6′- O -methyl ester of 15,16-epoxylabda-8(9),13,14-triene. Reductive amination of methyl 16-formyl-15,16-epoxylabda-8(9),13,14-trienoate or this β -D-glucuronopyranoside of 16-formyl-15,16-epoxylabda-8(9),13,14-triene by propargylamine in the presence of NaBH 4 gave the corresponding 16-propargylaminomethyl-15,16-epoxylabda-8(9),13,14-trienes. Copper-catalyzed azide-alkyne cycloaddition of the new terpenoid alkynes and the propargylamide of phlomisoic acid with methyl 1-deoxy-2,3,4-tri- O -acetyl-1-azido- α -D-glucopyranuronate synthesized the corresponding labdanoid glucuronides and diglucuronide. Selective screening of the labdanoid triazolylglucuronides identified compounds with analgesic activity in chemical and thermal irritation tests.
AbstractList	Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri- O -acetyl-1-bromo- α -D-glucopyranuronate to form the 18- O - β -D-(glucuronopyranoside)-6′- O -methyl ester of 15,16-epoxylabda-8(9),13,14-triene. Reductive amination of methyl 16-formyl-15,16-epoxylabda-8(9),13,14-trienoate or this β -D-glucuronopyranoside of 16-formyl-15,16-epoxylabda-8(9),13,14-triene by propargylamine in the presence of NaBH 4 gave the corresponding 16-propargylaminomethyl-15,16-epoxylabda-8(9),13,14-trienes. Copper-catalyzed azide-alkyne cycloaddition of the new terpenoid alkynes and the propargylamide of phlomisoic acid with methyl 1-deoxy-2,3,4-tri- O -acetyl-1-azido- α -D-glucopyranuronate synthesized the corresponding labdanoid glucuronides and diglucuronide. Selective screening of the labdanoid triazolylglucuronides identified compounds with analgesic activity in chemical and thermal irritation tests. Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri-O-acetyl-1-bromo-[alpha]-D-glucopyranuronate to form the 18-O-[beta]-D-(glucuronopyranoside)-6'-O-methyl ester of 15,16-epoxylabda-8(9),13,14-triene. Reductive amination of methyl 16-formyl-15,16-epoxylabda-8(9),13,14-trienoate or this [beta]-D-glucuronopyranoside of 16-formyl-15,16-epoxylabda-8(9),13,14-triene by propargylamine in the presence of NaBH.sub.4 gave the corresponding 16-propargylaminomethyl-15,16-epoxylabda-8(9),13,14-trienes. Copper-catalyzed azide-alkyne cycloaddition of the new terpenoid alkynes and the propargylamide of phlomisoic acid with methyl 1-deoxy-2,3,4-tri-O-acetyl-1-azido-[alpha]-D-glucopyranuronate synthesized the corresponding labdanoid glucuronides and diglucuronide. Selective screening of the labdanoid triazolylglucuronides identified compounds with analgesic activity in chemical and thermal irritation tests. Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri-O-acetyl-1-bromo-α-D-glucopyranuronate to form the 18-O-β-D-(glucuronopyranoside)-6′-O-methyl ester of 15,16-epoxylabda-8(9),13,14-triene. Reductive amination of methyl 16-formyl-15,16-epoxylabda-8(9),13,14-trienoate or this β-D-glucuronopyranoside of 16-formyl-15,16-epoxylabda-8(9),13,14-triene by propargylamine in the presence of NaBH4 gave the corresponding 16-propargylaminomethyl-15,16-epoxylabda-8(9),13,14-trienes. Copper-catalyzed azide-alkyne cycloaddition of the new terpenoid alkynes and the propargylamide of phlomisoic acid with methyl 1-deoxy-2,3,4-tri-O-acetyl-1-azido-α-D-glucopyranuronate synthesized the corresponding labdanoid glucuronides and diglucuronide. Selective screening of the labdanoid triazolylglucuronides identified compounds with analgesic activity in chemical and thermal irritation tests.
Audience	Academic
Author	Dolgikh, M. P. Tolstikova, T. G. Kharitonov, Yu. V. Shul’ts, E. E. Brusentseva, O. I.
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Cites_doi	10.1016/j.tet.2006.03.094 10.1016/j.bmc.2008.05.009 10.1021/jf4046667 10.1007/s10600-014-0988-7 10.1016/S0031-9422(00)94777-0 10.1002/ffj.3195 10.1016/j.ejmech.2013.10.032 10.3390/molecules22050800 10.1021/ja209335z 10.1016/j.bmcl.2017.01.007 10.1134/S1070428017010092 10.1016/j.tetlet.2008.12.043 10.1002/cbdv.201500130 10.1007/s10600-014-0861-8 10.1016/0008-6215(94)00313-5 10.1016/j.carres.2009.01.019 10.1007/s10600-015-1385-6 10.1021/ja01617a047 10.1055/s-0030-1270781 10.1007/s10600-017-1915-5 10.1016/j.carres.2016.05.007 10.3390/molecules201119695 10.3390/molecules16053933 10.1002/slct.201600042 10.1039/B918846K 10.1134/S107042801012016X
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Snippet	Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri- O -acetyl-1-bromo- α -D-glucopyranuronate to form the 18- O - β -D-(glucuronopyranoside)-6′- O -methyl... Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri-O-acetyl-1-bromo-[alpha]-D-glucopyranuronate to form the 18-O-[beta]-D-(glucuronopyranoside)-6'-O-methyl... Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri-O-acetyl-1-bromo-α-D-glucopyranuronate to form the 18-O-β-D-(glucuronopyranoside)-6′-O-methyl ester of...
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SubjectTerms	Alkynes Analgesics Chemical activity Cycloaddition Irritation Medicine Organic Chemistry Pharmacy Plant Sciences Trienes
Title	Synthesis and Analgesic Activity Assessment of Furanolabdanoid Conjugates with Glucuronic Acid
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