Synthesis of novel 5H-pyrimido[5,4-b]indole-(1H,3H)2,4-diones as potential ligands for the cloned α1-adrenoceptor subtypes

被引：8
|
作者：
Romeo, G
Russo, F
De Blasi, A
机构：
[1] Univ Catania, Dipartimento Sci Farmaceut, I-95125 Catania, Italy
[2] Consorzio Mario Negri Sud, S Maria Imbaro CH, Pozzilli, Italy
[3] INM Neuromed, Pozzilli, Italy
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2001年 / 38卷 / 02期
关键词：
D O I：
10.1002/jhet.5570380213
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new series of 3-[omega-[4-(4-substituted phenyl)piperazin-1-yl]alkyl]-5H-pyrimido[5,4-b]indole-(1H,3H)-2,4-diones (3-10 and 12-13) were synthesized from the N-(2-chloroethyl)-N '-[3-(2-ethoxycarbonyl)indolyl] urea (1) or the N-(3-chloropropyl)-N '-[3-(2-ethoxycarbonyl)indolyl] urea (2) and a number of 1-(4-substituted-phenyl)piperazines. 3-[2-[4-(4-Aminophenyl)piperazin-1-yl]ethyl]-5H-pyrimido[5,4-b]indole-(1H,3H)2,4-dione (14) was obtained by reduction of the parent nitro compound 8. The obtained 5H-pyrimido[5,4-b]indole-(1H,3H)2,4-dione derivatives were tested towards cloned alpha (1A), alpha (1B) and alpha (1D)-adrenergic receptors subtypes in binding assays. Some compounds showed good affinity and selectivity for the alpha (1D)-adrenoceptor subtype.
引用
收藏
页码：391 / 395
页数：5
相关论文
共 50 条
  • [31] 1-Acetyl-4′,5′a-diphenyl-2′,2′a,5′,5′a-tetrahydrospiro[1H-indole-3,2′-oxeto[5,4-b]-oxazol]-2(3H)-one
    Li, XM
    Wang, L
    Xu, JH
    Zhang, SS
    Fun, HK
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O1883 - O1885
  • [32] Cu(I)-Catalyzed and Base-Promoted [5+2+1] Cascade Cyclization of 2-Nitrochalcones with Aliphatic Primary Amines to 5H-Pyrimido[5,4-b]indole Frameworks
    Wu, Qin
    Xu, Genrui
    Li, Weiqiang
    Wan, Juan
    Liu, Teng
    Huang, Chao
    ORGANIC LETTERS, 2022, 24 (22) : 3950 - 3954
  • [33] PYRIMIDO[5,4-B]INDOLE DERIVATIVES .1. A NEW CLASS OF POTENT AND SELECTIVE ALPHA-1 ADRENOCEPTOR LIGANDS
    RUSSO, F
    ROMEO, G
    GUCCIONE, S
    DEBLASI, A
    JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) : 1850 - 1854
  • [34] Nucleophile-Controlled Trapping of Gold Carbene by Nitriles and Water: Synthesis of 5H-Pyrimido[5,4-b]indoles and 2-Benzylidene-3-indolinones
    Zhu, Yun-Long
    Dong, Yi-Fan
    Wang, Si-Ru
    Li, You-Gui
    Wu, Xiang
    Ye, Long-Wu
    ORGANIC LETTERS, 2024, 26 (03) : 631 - 635
  • [35] Identification and characterization of 4-[4-(3-phenyl-2-propen-1-yl)-1-piperazinyl]-5H-pyrimido[5,4-b]indole derivatives as Salmonella biofilm inhibitors
    Robijns, Stijn Chris Arnold
    Pauw, Bart
    Loosen, Bram
    Marchand, Arnaud
    Chaltin, Patrick
    Keersmaecker, Sigrid C. J.
    Vanderleyden, Jos
    Steenackers, Hans P. L.
    FEMS IMMUNOLOGY AND MEDICAL MICROBIOLOGY, 2012, 65 (02): : 390 - 394
  • [36] 1-Acetyl-4′-ethyl-2a′-phenyl-2′,2a′,5′,5a′-tetrahydrospiro[1H-indole-3,2′-oxeto[5,4-b]oxazol]-2(3H)-one and 1-acetyl-4′,5a′-diphenyl-2′,2a′,5′,5a′-tetrahydrospiro[1H-indole-3,2′-oxeto[5,4-b]oxazol]-2(3H)-one
    Usman, A
    Fun, HK
    Wang, L
    Zhang, Y
    Xu, JH
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2003, 59 : O305 - O307
  • [37] SYNTHESIS AND SPECTROSCOPIC PROPERTIES OF 3-(2',4'-XYLYL)-1H,3H-QUINAZOLINE-2,4-DIONES
    VIGNE, C
    BUTI, M
    MONTGINOUL, C
    TORREILLES, E
    GIRAL, L
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (04) : 921 - 924
  • [38] SYNTHESIS OF SOME 7-SUBSTITUTED-2,4,8(1H,3H,7H)PYRIMIDO[5,4-D]PYRIMIDINETRIONES
    PENDERGAST, W
    HALL, WR
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (05) : 1411 - 1413
  • [39] SYNTHESIS AND PHARMACOLOGICAL EVALUTATION OF THIENO[2,3-D] PYRIMIDIN-2,4-DIONE AND 5H-PYRIMIDO [5,4-B]INDOL-2,4-DIONE DERIVATIVES
    SANTAGATI, NA
    CARUSO, A
    CUTULI, VMC
    CACCAMO, F
    FARMACO, 1995, 50 (10): : 689 - 695
  • [40] NEW SYNTHESIS OF PYRIMIDO[4,5-B]QUINOLINE-2,4(1H,3H)-DIONE (5-DEAZAALLOXAZINE) DERIVATIVES
    SENGA, K
    SHIMIZU, K
    NISHIGAKI, S
    YONEDA, F
    HETEROCYCLES, 1977, 6 (9-10) : 1361 - 1364
12345