Synthesis and Anticancer Activity of 2-Aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-dione and 2-Aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones

被引：13

作者：

Chaban, T., I ^{[1
]}

Matiichuk, Y. E. ^{[1
]}

Horishny, V. Ya ^{[1
]}

Chaban, I. G. ^{[1
]}

Matiychuk, V. S. ^{[2
]}

机构：

[1] Danylo Halytsky Lviv Natl Med Univ, UA-79010 Lvov, Ukraine

[2] Ivan Franko Natl Univ Lviv, UA-79005 Lvov, Ukraine

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 56卷 / 05期

关键词：

organic synthesis; heterocyclization; tandem reactions; anticancer activity; ARYLATION PRODUCTS; TANDEM REACTIONS; TRANSFORMATIONS; HETEROCYCLES; DERIVATIVES; DOMINO;

D O I：

10.1134/S1070428020050139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of ethyl 1-aryl-4-(2-bromoacetyl)-5-methyl-1H-pyrazolocarboxylates withortho-hydroxybenzonitrile and 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile gave previously unknown 2-aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones and 2-aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones, respectively. It was found that this reaction occurred as a tandem process. The synthesized compounds were sceened for anticancer activity and exhibited moderate activity against the most part of malignant cancer cells.

引用

页码：813 / 818

页数：6

共 24 条

[1] Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity [J].

Ando, K ;

Tsuji, E ;

Ando, Y ;

Kuwata, N ;

Kunitomo, J ;

Yamashita, M ;

Ohta, S ;

Kohno, S ;

Ohishi, Y .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (04) :625-635

[2]

Boyd M.R., 1997, DRUG DEV PRECLINICAL, V2, P23, DOI DOI 10.1007/S12028-015-0160-7

[3] SOME PRACTICAL CONSIDERATIONS AND APPLICATIONS OF THE NATIONAL-CANCER-INSTITUTE IN-VITRO ANTICANCER DRUG DISCOVERY SCREEN [J].

BOYD, MR ;

PAULI, KD .

DRUG DEVELOPMENT RESEARCH, 1995, 34 (02) :91-109

[4] A convenient route to functionalized 3-amino-N-methylfuro[3,2-b]pyridine-2-carboxamides [J].

Breteche, Anne ;

Marchand, Pascal ;

Nourrisson, Marie-Renee ;

Hautefaye, Patrick ;

De Nanteuil, Guillaume ;

Duflos, Muriel .

TETRAHEDRON, 2011, 67 (26) :4767-4773

[5] RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].

BUNCE, RA .

TETRAHEDRON, 1995, 51 (48) :13103-13159

[6]

Chaban T, 2017, PHARMACIA, V64, P16

[7]

Chaban T. I., 2016, Der Pharma Chem, V8, P534

[8] SYNTHESIS OF SOME NOVEL THIAZOLO[4,5-b]PYRIDINES AND THEIR TUBERCULOSTATIC ACTIVITY EVALUATION [J].

Chaban, Taras ;

Klenina, Olena ;

Drapak, Iryna ;

Ogurtsov, Volodymyr ;

Chaban, Igor ;

Novikov, Volodymyr .

CHEMISTRY & CHEMICAL TECHNOLOGY, 2014, 8 (03) :287-292

[9] Synthesis, Anti-Inflammatory and Antioxidant Activities of Novel 3H-Thiazolo [4,5-b] Pyridines [J].

Chaban, Taras I. ;

Ogurtsov, Volodymyr V. ;

Matiychuk, Vasyl S. ;

Chaban, Ihor G. ;

Demchuk, Inna L. ;

Nektegayev, Ihor A. .

ACTA CHIMICA SLOVENICA, 2019, 66 (01) :103-111

[10] Synthesis of heterocycles from arylation products of unsaturated compounds: XVIII. 5-Arylfuran-2-carboxylic acids and their application in the synthesis of 1,2,4-thiadiazole, 1,3,4-oxadiazole, and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives [J].

Gorak, Yu. I. ;

Obushak, N. D. ;

Matiichuk, V. S. ;

Lytvyn, R. Z. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (04) :541-550

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