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N-{2-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]ethyl}naphthalene-2-sulphonamide | 1365043-36-2

中文名称
——
中文别名
——
英文名称
N-{2-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]ethyl}naphthalene-2-sulphonamide
英文别名
N-(2-(4-(5-chloro-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethyl)naphthalene-2-sulfonamide;N-[2-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]ethyl]naphthalene-2-sulfonamide
N-{2-[4-(5-chloro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]ethyl}naphthalene-2-sulphonamide化学式
CAS
1365043-36-2
化学式
C25H24ClN3O2S
mdl
——
分子量
466.003
InChiKey
BXCDGOZRLHWEFT-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.8
  • 重原子数:
    32
  • 可旋转键数:
    6
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.2
  • 拓扑面积:
    73.6
  • 氢给体数:
    2
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    参考文献:
    名称:
    Novel 3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole-Based Multifunctional Ligands with Antipsychotic-Like, Mood-Modulating, and Procognitive Activity
    摘要:
    The most troublesome aspects of behavioral and psychological symptoms of dementia (BPSD) are nowadays addressed by antidepressant, anxiolytic, and antipsychotic drugs, often administered off-label. Considering their modest effectiveness in dementia patients, the increased risk of adverse events and cognitive decline, there is an unmet need for well tolerated and effective therapy of BPSD. We designed and synthesized multifunctional ligands characterized in vitro as high affinity partial agonists of D2R, antagonists of 5-HT6R, and blockers of SERT. Moreover, the molecules activated 5-HT1AR and blocked 5-HT7R while having no relevant affinity for off-target M1R and hERG channel. Compound 16 (N-{244-(5-chloro-1H-iridol-3-y1)-1,2,3,6-tetrahydropyridin-l-yllethy1}-3-methylbenzene-l-sulfonamide), exhibited a broad antipsychotic-, antidepressant-, and anxiolytic-like activity, not eliciting motor impairments in mice. Most importantly, 16 showed memory-enhancing properties and it ameliorated memory deficits induced by scopolamine. The molecule outperformed most important comparators in selected tests, indicating its potential in the treatment of both cognitive and noncognitive (behavioral and psychological) symptoms of dementia.
    DOI:
    10.1021/acs.jmedchem.7b00839
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文献信息

  • [EN] ARYLOSULFONAMIDES FOR THE TREATMENT OF CNS DISEASES<br/>[FR] ARYLSULFAMIDES POUR LE TRAITEMENT DE MALADIES DU SNC
    申请人:ADAMED SP ZOO
    公开号:WO2012035123A1
    公开(公告)日:2012-03-22
    Arylsulphonamide derivatives of formula (I) and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of disorders of the central nervous system.
    化学式(I)的芳基磺酰胺衍生物及其药用盐。这些化合物可能对中枢神经系统的治疗和/或预防具有用处。
  • ARYLOSULFONAMIDES FOR THE TREATMENT OF CNS DISEASES
    申请人:Kolaczkowski Marcin
    公开号:US20130172365A1
    公开(公告)日:2013-07-04
    Arylsulphonamide derivatives of formula (I) and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of disorders of the central nervous system.
    化学式(I)的芳基磺胺衍生物及其药用盐。这些化合物可能对中枢神经系统疾病的治疗和/或预防有用。
  • US8822517B2
    申请人:——
    公开号:US8822517B2
    公开(公告)日:2014-09-02
  • US9120767B2
    申请人:——
    公开号:US9120767B2
    公开(公告)日:2015-09-01
  • Novel 3-(1,2,3,6-Tetrahydropyridin-4-yl)-1<i>H</i>-indole-Based Multifunctional Ligands with Antipsychotic-Like, Mood-Modulating, and Procognitive Activity
    作者:Adam Bucki、Monika Marcinkowska、Joanna Śniecikowska、Krzysztof Więckowski、Maciej Pawłowski、Monika Głuch-Lutwin、Anna Gryboś、Agata Siwek、Karolina Pytka、Magdalena Jastrzębska-Więsek、Anna Partyka、Anna Wesołowska、Paweł Mierzejewski、Marcin Kołaczkowski
    DOI:10.1021/acs.jmedchem.7b00839
    日期:2017.9.14
    The most troublesome aspects of behavioral and psychological symptoms of dementia (BPSD) are nowadays addressed by antidepressant, anxiolytic, and antipsychotic drugs, often administered off-label. Considering their modest effectiveness in dementia patients, the increased risk of adverse events and cognitive decline, there is an unmet need for well tolerated and effective therapy of BPSD. We designed and synthesized multifunctional ligands characterized in vitro as high affinity partial agonists of D2R, antagonists of 5-HT6R, and blockers of SERT. Moreover, the molecules activated 5-HT1AR and blocked 5-HT7R while having no relevant affinity for off-target M1R and hERG channel. Compound 16 (N-244-(5-chloro-1H-iridol-3-y1)-1,2,3,6-tetrahydropyridin-l-yllethy1}-3-methylbenzene-l-sulfonamide), exhibited a broad antipsychotic-, antidepressant-, and anxiolytic-like activity, not eliciting motor impairments in mice. Most importantly, 16 showed memory-enhancing properties and it ameliorated memory deficits induced by scopolamine. The molecule outperformed most important comparators in selected tests, indicating its potential in the treatment of both cognitive and noncognitive (behavioral and psychological) symptoms of dementia.
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