New 3-[4-(3-substiluted phenyl)piperazin-1-yl]-1-(benzo[b]thiophen-3-yl)-propanol derivatives with dual action at 5-HT1A serotonin receptors and serotonin transporter as a new class of antidepressants

被引：0
|
作者：
Orús, L
Martínez, J
Pérez, S
Oficialdegui, AM
Del Castillo, JC
Mourelle, M
Lasheras, B
del Río, J
Monge, A
机构：
[1] Univ Navarra, Dept Med Chem, CIFA, E-31080 Pamplona, Spain
[2] Univ Navarra, Dept Pharmacol, CIFA, E-31080 Pamplona, Spain
[3] Vita Invest SA, Barcelona, Spain
来源：
PHARMAZIE | 2002年 / 57卷 / 08期
关键词：
D O I：
暂无
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
In this paper a series of new, 3-[4-(3-substituted phenylpiperazin-1-yl]-1-(benzo[b]thiophen-3-yl)propanol derivatives is presented as a new class of antidepressant drugs with dual activity at 5-HT1A serotonin receptors and serotonin transporter. The 5-HT1A receptor and 5-HT transporter binding affinities of hydroxylic compounds 4 a-e have been determined. The new compounds present nanomolar affinity for both activities, and 1-(benzo[b]thiophen-3-yl)-3-[4-(3-methoxyphenyl)piperazin-1-yl]propan-1-ol (4d) shows values (nM) of K-i = 86 for 5-HT1A receptors and K-i = 76 for the serotonin transporter, respectively.
引用
收藏
页码：515 / 518
页数：4
相关论文
共 50 条
  • [1] New 3-[4-(aryl)piperazin-1-yl]-1(benzo[b]thiophen-3-yl) propane derivatives with dual action at 5-HT1A serotonin receptors and serotonin transporter as a new class of antidepressants
    Martínez, J
    Pérez, S
    Oficialdegui, AM
    Heras, B
    Orús, L
    Villanueva, H
    Palop, JA
    Roca, J
    Mourelle, M
    Bosch, A
    Del Castillo, JC
    Lasheras, B
    Tordera, R
    del Río, J
    Monge, A
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (01) : 55 - 61
  • [2] New 3-[4-(aryl)piperazin-1-yl]-1-(benzo[b]thiophen-2-yl)propane derivatives with dual action at 5-HT1A serotonin receptors and serotonin transporter as a new class of antidepressants
    Orús, L
    Sáinz, Y
    Pérez, S
    Oficialdegui, AM
    Martinez, J
    Lasheras, B
    Del Río, J
    Monge, A
    PHARMAZIE, 2002, 57 (06): : 355 - 357
  • [3] New 3-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]-1-(5-substituted benzo[b]thiophen-3-yl)propanol derivatives with dual action at 5-HT1A serotonin receptors and serotonin transporter as a new class of antidepressants
    Silanes, SP
    Orús, L
    Oficialdegui, AM
    Esparza, JM
    Lasheras, B
    Del Río, J
    Monge, A
    PHARMAZIE, 2004, 59 (07): : 499 - 501
  • [4] New 1-aryl-3-(4-arylpiperazin-1-yl)propane derivatives, with dual action at 5-HT1A serotonin receptors and serotonin transporter, as a new class of antidepressants
    Martínez-Esparza, J
    Oficialdegui, AM
    Pérez-Silanes, S
    Heras, B
    Orús, L
    Palop, JA
    Lasheras, B
    Roca, J
    Mourelle, H
    Bosch, A
    Del Castillo, JC
    Tordera, R
    Del Río, J
    Monge, A
    JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (03) : 418 - 428
  • [5] New 3-(4-arylpiperazin-1-yl)-1-(benzo[b]thiophen-3-yl)-2-methylpropanol derivatives:: Synthesis and evaluation for dual 5-HT1A/SSRI activities
    Li, Ai Jun
    Zhang, Xiao Hua
    Zhou, Xue Qin
    Liu, Dong Zhi
    CHINESE CHEMICAL LETTERS, 2008, 19 (04) : 412 - 414
  • [6] New 3-(4-arylpiperazin-1-yl)-1-(benzo[b]thiophen-3-yl)-2-methylpropanol derivatives:Synthesis and evaluation for dual 5-HT1A/SSRI activities
    Ai Jun Li~(a
    Chinese Chemical Letters, 2008, (04) : 412 - 414
  • [7] Design, synthesis and biological evaluation of new 3-[(4-aryl)piperazin-1-yl]-1-arylpropane derivatives as potential antidepressants with a dual mode of action:: serotonin reuptake inhibition and 5-HT1A receptor antagonism
    Oficialdegui, AM
    Martinez, J
    Pérez, S
    Heras, B
    Irurzun, M
    Palop, JA
    Tordera, R
    Lasheras, B
    del Río, J
    Monge, A
    FARMACO, 2000, 55 (05): : 345 - 353
  • [8] Synthesis, Docking Studies and Biological Evaluation of Benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one Derivatives on 5-HT1A Serotonin Receptors
    Pessoa-Mahana, Hernan
    Recabarren-Gajardo, Gonzalo
    Fiedler Temer, Jenny
    Zapata-Torres, Gerald
    David Pessoa-Mahana, C.
    Saitz Barria, Claudio
    Araya-Maturana, Ramiro
    MOLECULES, 2012, 17 (02): : 1388 - 1407
  • [9] 4-(benzo[b]thiophen-3-yl)-1-methylpiperidine-4-carbonitrile
    Sonar, VN
    Parkin, S
    Crooks, PA
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O1533 - O1534
  • [10] 3-Chloro-6-{4-[3-(trifluoromethyl)-phenyl]piperazin-1-yl}pyridazine
    Arslan, Hakan
    Utku, Semra
    Hardcastle, Kenneth I.
    Gokce, Mehtap
    Lense, Sheri
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O532 - U4263
12345