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

被引：19
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
收藏
页码：6814 / 6824
页数：11
相关论文
共 77 条
  • [51] Synthesis and binding affinities of fluoroalkylated raloxifenes
    Lee, KC
    Moon, BS
    Lee, JH
    Chung, KH
    Katzenellenbogen, JA
    Chi, DY
    [J]. 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
    Lu, P
    Schrag, ML
    Slaughter, DE
    Raab, CE
    Shou, MG
    Rodrigues, AD
    [J]. DRUG METABOLISM AND DISPOSITION, 2003, 31 (11) : 1352 - 1360
  • [53] SYNTHESIS OF CHIRAL HYDROXYLATED QUINOLIZIDINES VIA VINYLOGOUS BISCHLER-NAPIERALSKI NITRILIUM ION CYCLIZATIONS
    MARQUART, AL
    PODLOGAR, BL
    HUBER, EW
    DEMETER, DA
    PEET, NP
    WEINTRAUB, HJR
    ANGELASTRO, MR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) : 2092 - 2100
  • [54] THIONAPHTHEN DERIVATIVES .3. CHARACTERISATION OF SOME 5-SUBSTITUTED DERIVATIVES
    MARTINSMITH, M
    REID, ST
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR): : 938 - 944
  • [55] BROMINATION STUDIES WITH 5-HYDROXYBENZOTHIOPHENE
    MARTINSMITH, M
    GATES, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (23) : 6177 - 6180
  • [56] BENZOTHIOPHENE-4,5-QUINONES
    MARTINSMITH, M
    GATES, M
    [J]. 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
    MATASSA, VG
    BROWN, FJ
    BERNSTEIN, PR
    SHAPIRO, HS
    MADUSKUIE, TP
    CRONK, LA
    VACEK, EP
    YEE, YK
    SNYDER, DW
    KRELL, RD
    LERMAN, CL
    MALONEY, JJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) : 2621 - 2629
  • [58] Synthesis of new benzo[b]thieno fused ring systems via transition metal-mediated cyclisations
    Mbere, Johana M.
    Bremner, John B.
    Skelton, Brian W.
    White, Allan H.
    [J]. 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)
    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
    [J]. 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
    Mikkers, H
    Nawijn, M
    Allen, J
    Brouwers, C
    Verhoeven, E
    Jonkers, J
    Berns, A
    [J]. MOLECULAR AND CELLULAR BIOLOGY, 2004, 24 (13) : 6104 - 6115
12345678