An Expedient Synthesis of Functionalized Pyrazole-Based Aurone Analogs

被引：0

作者：

Myshko, Andrii ^{[1
]}

Mrug, Galyna ^{[1
]}

Kondratyuk, Kostyantyn ^{[1
]}

Demydchuk, Bohdan ^{[1
]}

Bondarenko, Svitlana ^{[2
]}

Frasinyuk, Mykhaylo ^{[1
]}

机构：

[1] Natl Acad Sci Ukraine, VP Kukhar Inst Bioorgan Chem & Petrochem, Dept Chem Bioact Nitrogen Heterocycl Bases, UA-02094 Kiev, Ukraine

[2] Natl Univ Food Technol, Dept Food Chem, UA-01601 Kiev, Ukraine

来源：

CHEMISTRYSELECT | 2023年 / 8卷 / 20期

关键词：

oxygen heterocycles; nitrogen heterocycles; fused-ring systems; ketones; enones; ATP-COMPETITIVE INHIBITORS; MAMMALIAN TARGET; ANTIBACTERIAL ACTIVITY; POTENT; 5-AMINOPYRAZOLES; 3-IODOCHROMONE; DERIVATIVES; CHROMONE; BEARING; BINDING;

D O I：

10.1002/slct.202300257

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The efficient methods for the synthesis of pyrazole-based aurones were developed. It was shown that reaction of benzofuran-3(2H)-ones with 1H-pyrazole-3(5)/4-carboxaldehydes or 4-[(dimethylamino)methylene]-2,4-dihydro-3H-pyrazol-3-ones led to formation of the 2-pyrazolylmethylene-1-benzofuran-3(2H)-ones or 2-[(3(5)-hydroxy-1H-pyrazol-4-yl)methylene]-1-benzofuran-3(2H)-ones respectively while the reaction of 2-[(dimethylamino)methylene]-1-benzofuran-3(2H)-ones with 1-methyl-5-aminopyrazoles led to formation of 2-[(5-amino-1-methyl-1H-pyrazol-4-yl)methylene]-1-benzofuran-3(2H)-ones and 1-methyl-1H-[1]benzofuro[3,2-b]pyrazolo[4,3-e]pyridines as minor products.

引用

页数：7

共 45 条

[1] Non-hinge-bindingpyrazolo[1,5-a]pyrimidines as potent B-Raf kinase inhibitors
Berger, Dan M.
Torres, Nancy
Dutia, Minu
Powell, Dennis
Ciszewski, Greg
Gopalsamy, Ariamala
Levin, Jeremy I.
Kim, Kyung-Hee
Xu, Weixin
Wilhelm, James
Hu, YongBo
Collins, Karen
Feldberg, Larry
Kim, Steven
Frommer, Eileen
Wojciechowicz, Donald
Mallon, Robert
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (23) : 6519 - 6523
[2] Blair L. M., 2017, ALKALOIDS CHEM BIOL, P85
[3] Chromone Alkaloids: Structural Features, Distribution in Nature, and Biological Activity
Bondarenko, S. P.
Frasinyuk, M. S.
[J]. CHEMISTRY OF NATURAL COMPOUNDS, 2019, 55 (02) : 201 - 234
[4] Observations from aminomethylation of 7-substituted 6-hydroxyaurones
Bondarenko, Svitlana P.
Frasinyuk, Mykhaylo S.
[J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (08) : 765 - 772
[5] Occurrences, biosynthesis and properties of aurones as high-end evolutionary products
Boucherle, Benjamin
Peuchmaur, Marine
Boumendjel, Ahcene
Haudecoeur, Romain
[J]. PHYTOCHEMISTRY, 2017, 142 : 92 - 111
[6] 4-hydroxy-6-methoxyaurones with high-affinity binding to cytosolic domain of P-glycoprotein
Boumendjel, A
Beney, C
Deka, N
Mariotte, AM
Lawson, MA
Trompier, D
Baubichon-Cortay, H
Di Pietro, A
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (06) : 854 - 856
[7] Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: Hit to lead studies
Bursavich, Matthew G.
Brooijmans, Natasja
Feldberg, Lawrence
Hollander, Irwin
Kim, Stephen
Lombardi, Sabrina
Park, Kaapjoo
Mallon, Robert
Gilbert, Adam M.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (08) : 2586 - 2590
[8] 3-Formylpyrazolo[1,5-a]pyrimidines as Key Intermediates for the Preparation of Functional Fluorophores
Castillo, Juan-Carlos
Tigreros, Alexis
Portilla, Jaime
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (18) : 10887 - 10897
[9] Catalytic System for Inhibition of Amination-Type Reaction and Palladium-Catalysed Direct Arylation using Non-Protected Pyrazole Derivatives
Derridj, Fazia
Roger, Julien
Djebbar, Safia
Doucet, Henri
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (04) : 747 - 750
[10] THE ADDITION OF AMINES TO 3-BROMOCHROMONE AND 6-BROMOFUROCHROMONE - AN UNEXPECTED RING CONTRACTION OF THE PYRONE RING
GAMMILL, RB
NASH, SA
MIZSAK, SA
[J]. TETRAHEDRON LETTERS, 1983, 24 (33) : 3435 - 3438

← 1 2 3 4 5 →