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3-(p-toluenesulfonyl)-6,7,8,9-tetrahydro-3H-benzindol-8-one | 155591-01-8

中文名称
——
中文别名
——
英文名称
3-(p-toluenesulfonyl)-6,7,8,9-tetrahydro-3H-benzindol-8-one
英文别名
3-[(4-methylphenyl)sulfonyl]-6,7,8,9-tetrahydro-3H-benzo[e]indol-8-one;3-(toluene-4-sulfonyl)-6,9-dihydro-3H,7H-benzo[e]indol-8-one;3-(4-methylphenyl)sulfonyl-7,9-dihydro-6H-benzo[e]indol-8-one
3-(p-toluenesulfonyl)-6,7,8,9-tetrahydro-3H-benz<e>indol-8-one化学式
CAS
155591-01-8
化学式
C19H17NO3S
mdl
——
分子量
339.415
InChiKey
FRYGQOVSPWTENF-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

物化性质

  • 沸点:
    577.6±60.0 °C(Predicted)
  • 密度:
    1.34±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.3
  • 重原子数:
    24
  • 可旋转键数:
    2
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.21
  • 拓扑面积:
    64.5
  • 氢给体数:
    0
  • 氢受体数:
    3

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
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 2: Effect of 8-Amino Nitrogen Substitution on Serotonin Receptor Binding and Pharmacology
    摘要:
    A series of analogs of the potent and selective 5-HT1A agonist 8-(di-n-propylamino)-6,7,8,9-tetrahydro-3H-benz[e]indole-1-carbaldehyde (2b) (OSU191) was prepared in which the dipropylamino group was modified to bear a variety of substituents. These compounds were evaluated for both in vitro and in vivo effects, including the establishment of a receptor binding profile for these analogs at the 5-HT1A, dopamine D-2, dopamine D-3, 5-HT1D alpha, and 5-HT1D beta sites. Several of the analogs were evaluated for their biochemical effects in reserpinized rats, specifically with regard to in vivo changes in brain levels of 5-HTP and DOPA. Nearly all of the compounds prepared for this study were exceedingly potent at the 5-HT1A receptor, although most also displayed significant affinity for the dopamine D-2 receptor. A strong preference for the 5-HT1D alpha, over the 5-HT1D beta receptor was also apparent. An analog bearing a butylglutarimide side chain, S-7k, was extremely selective for the 5-HT1A receptor. Although this compound possessed a K-i of 0.6 nM, it elicited only modest changes in 5-HTP brain levels. However, this compound did not appear as an antagonist when tested in a cyclic-AMP-based intrinsic activity assay.
    DOI:
    10.1021/jm00012a022
  • 作为产物:
    参考文献:
    名称:
    (r)-和(s)-1-甲酰基-6,7,8,9-四氢-N,N-(二丙基)-3 H-苯并[ e ]吲哚-8-胺的合成:活性强且具有口服活性5-HT 1A受体激动剂
    摘要:
    的强有力的和口服活性的5-HT的高效合成1A激动剂,(- [R )- (+) -和(小号) - ( - ) - 1-甲酰基-6,7,8,9-四氢- N,N- -描述了二丙基-3 H-苯并[ e ]吲哚-8-胺1a和1b。从市售的1,5,6,7-四氢-4 H-吲哚-4-酮(5)以十二个步骤完成该合成。关键步骤包括将区域控制的1-(对甲苯磺酰基)吲哚-4-乙酰氯与乙烯的弗里德-克来夫斯酰化反应,以制得通用的合成子3-(对甲苯磺酰基)-6,7,8,9- tetrahydro-3 H -benz [e ]吲哚-8-一(10)。随后将该酮与手性α-甲基苄基胺在还原性胺化条件下偶联,得到非对映异构体的混合物。这些非对映异构体通过色谱法或衍生的盐酸盐的分步重结晶有效分离。纯非对映异构体的脱苄基作用后,进行烷基化和甲酰化反应,制得纯度> 99%的(R)-(+)-和(S)-(-)-对映体1a和1b。
    DOI:
    10.1002/jhet.5570310123
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文献信息

  • [EN] NOVEL TETRAYDROSPIRO{PIPERIDINE-2,7' -PYRROLO[3,2-b]PYRIDINE DERIVATIVES AND NOVEL INDOLE DERIVATIVES USEFUL IN THE TREATMENT OF 5-HT6 RECEPTOR -RELATED DISORDERS<br/>[FR] NOUVEAUX DERIVES TETRAHYDROSPIRO{PIPERIDINE-2,7'-PYRROLO[3,2-B]PYRIDINE ET NOUVEAUX DERIVES INDOLE UTILES POUR LE TRAITEMENT DES TROUBLES ASSOCIES AU RECEPTEUR 5-HT6
    申请人:BIOVITRUM AB
    公开号:WO2005037834A1
    公开(公告)日:2005-04-28
    The present invention relates to compounds of formula (I): Formula (I) wherein U, P, W1, W2, W3, v, Y, Z, Rm, and Rm’ are as described herein, to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds for the preparation of a medicament against 5-HT6 receptor-related disorders.
    本发明涉及式(I)的化合物:式(I)其中U、P、W1、W2、W3、v、Y、Z、Rm和Rm'如本文所述,以及包含这些化合物的药物组合物,用于其制备的方法,以及用于制备针对5-HT6受体相关疾病的药物的化合物的用途。
  • Sulfonyltetrahydro-3H-benzo(E)indole-8-amine compounds as 5-Hydroxytryptamine-6 ligands
    申请人:Cole Cecil Derek
    公开号:US20050101596A1
    公开(公告)日:2005-05-12
    The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of a CNS disorder related to or affected by the 5-HT6 receptor.
    本发明提供了一种I式化合物及其在治疗与5-HT6受体相关或受其影响的中枢神经系统疾病中的应用。
  • Novel tetraydrospiro(piperdine-2,7'- pyrrolo{3,2-b}pyridine derivatives and novel in-dole derivatives useful in the treatment of 5-ht6 receptor-related disorders
    申请人:Johansson Gary
    公开号:US20060148818A1
    公开(公告)日:2006-07-06
    The present invention relates to compounds of formula (I): Formula (I) wherein U, P, W 1 , W 2 , W 3 , v, Y, Z, R m , and R m′ are as described herein, to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds for the preparation of a medicament against 5-HT 6 receptor-related disorders.
    本发明涉及式(I)化合物:式(I)其中U、P、W1、W2、W3、v、Y、Z、Rm和Rm'如本文所述,以及包含该化合物的制药组合物、其制备过程,以及将该化合物用于制备用于治疗5-HT6受体相关疾病的药物的用途。
  • Sulfonyltetrahydro-3H-benzo(e)indole-8-amine compounds as 5-hydroxytryptamine-6 ligands
    申请人:Cole Cecil Derek
    公开号:US20080085925A1
    公开(公告)日:2008-04-10
    The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of a CNS disorder related to or affected by the 5-HT6 receptor.
    本发明提供了一种I式化合物及其在治疗与5-HT6受体相关或受其影响的中枢神经系统疾病中的应用。
  • NOVEL TETRAYDROSPIRO{PIPERIDINE-2,7'-PYRROLO [3,2]PYRIDINE} DERIVATIVES AND NOVEL INDOLE DERIVATIVES USEFUL IN THE TREATMENT OF 5-HT6 RECEPTOR -RELATED DISORDERS
    申请人:BIOVITRUM AB
    公开号:EP1675856A1
    公开(公告)日:2006-07-05
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