Microwave-assisted synthesis of 3-aminobenzo[b]-thiophene scaffolds for the preparation of kinase inhibitors

被引：20

作者：

Bagley, Mark C. ^{[1
]}

Dwyer, Jessica E. ^{[1
]}

Molina, Maria D. Beltran ^{[2
]}

Rand, Alexander W. ^{[1
]}

Rand, Hayley L. ^{[1
]}

Tomkinson, Nicholas C. O. ^{[2
]}

机构：

[1] Univ Sussex, Sch Life Sci, Dept Chem, Brighton BN1 9QJ, E Sussex, England

[2] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

BENZOTHIOPHENE INHIBITORS; BIOLOGICAL EVALUATION; THIONYL CHLORIDE; DERIVATIVES; P38; AGENTS; SERIES; MK2; FIBROBLASTS; SELECTIVITY;

D O I：

10.1039/c5ob00819k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Microwave irradiation of 2-halobenzonitriles and methyl thioglycolate in the presence of triethylamine in DMSO at 130 degrees C provides rapid access to 3-aminobenzo[b]thiophenes in 58-96% yield. This transformation has been applied in the synthesis of the thieno[2,3-b] pyridine core motif of LIMK1 inhibitors, the benzo[4,5]thieno[3,2-e][1,4]diazepin-5(2H)-one scaffold of MK2 inhibitors and a benzo[4,5] thieno[3,2-d]-pyrimidin-4-one inhibitor of the PIM kinases.

引用

页码：6814 / 6824

页数：11

共 77 条

[51] Synthesis and binding affinities of fluoroalkylated raloxifenes [J].

Lee, KC ;

Moon, BS ;

Lee, JH ;

Chung, KH ;

Katzenellenbogen, JA ;

Chi, DY .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (17) :3649-3658

[52] Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor [J].

Lu, P ;

Schrag, ML ;

Slaughter, DE ;

Raab, CE ;

Shou, MG ;

Rodrigues, AD .

DRUG METABOLISM AND DISPOSITION, 2003, 31 (11) :1352-1360

[53] SYNTHESIS OF CHIRAL HYDROXYLATED QUINOLIZIDINES VIA VINYLOGOUS BISCHLER-NAPIERALSKI NITRILIUM ION CYCLIZATIONS [J].

MARQUART, AL ;

PODLOGAR, BL ;

HUBER, EW ;

DEMETER, DA ;

PEET, NP ;

WEINTRAUB, HJR ;

ANGELASTRO, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :2092-2100

[54] THIONAPHTHEN DERIVATIVES .3. CHARACTERISATION OF SOME 5-SUBSTITUTED DERIVATIVES [J].

MARTINSMITH, M ;

REID, ST .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR) :938-944

[55] BROMINATION STUDIES WITH 5-HYDROXYBENZOTHIOPHENE [J].

MARTINSMITH, M ;

GATES, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (23) :6177-6180

[56] BENZOTHIOPHENE-4,5-QUINONES [J].

MARTINSMITH, M ;

GATES, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (20) :5351-5357

[57] SYNTHESIS AND INVITRO LTD4 ANTAGONIST ACTIVITY OF BICYCLIC AND MONOCYCLIC CYCLOPENTYLURETHANE AND CYCLOPENTYLACETAMIDE N-ARYLSULFONYL AMIDES [J].

MATASSA, VG ;

BROWN, FJ ;

BERNSTEIN, PR ;

SHAPIRO, HS ;

MADUSKUIE, TP ;

CRONK, LA ;

VACEK, EP ;

YEE, YK ;

SNYDER, DW ;

KRELL, RD ;

LERMAN, CL ;

MALONEY, JJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2621-2629

[58] Synthesis of new benzo[b]thieno fused ring systems via transition metal-mediated cyclisations [J].

Mbere, Johana M. ;

Bremner, John B. ;

Skelton, Brian W. ;

White, Allan H. .

TETRAHEDRON, 2011, 67 (36) :6895-6900

[59] Structure-activity studies for a novel series of tricyclic substituted hexahydrobenz[e]isoindole α1A adrenoceptor antagonists as potential agents for the symptomatic treatment of benign prostatic hyperplasia (BPH) [J].

Meyer, MD ;

Altenbach, RJ ;

Basha, FZ ;

Carroll, WA ;

Condon, S ;

Elmore, SW ;

Kerwin, JF ;

Sippy, KB ;

Tietje, K ;

Wendt, MD ;

Hancock, AA ;

Brune, ME ;

Buckner, SA ;

Drizin, I .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (08) :1586-1603

[60] Mice deficient for all PIM kinases display reduced body size and impaired responses to hematopoietic growth factors [J].

Mikkers, H ;

Nawijn, M ;

Allen, J ;

Brouwers, C ;

Verhoeven, E ;

Jonkers, J ;

Berns, A .

MOLECULAR AND CELLULAR BIOLOGY, 2004, 24 (13) :6104-6115

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