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4-Chloro-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine | 1368177-39-2

中文名称
——
中文别名
——
英文名称
4-Chloro-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine
英文别名
4-chloro-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine
4-Chloro-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine化学式
CAS
1368177-39-2
化学式
C7H7ClN2
mdl
——
分子量
154.599
InChiKey
XIIKLAXLTRPFPH-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):
    1.5
  • 重原子数:
    10
  • 可旋转键数:
    0
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.29
  • 拓扑面积:
    24.9
  • 氢给体数:
    1
  • 氢受体数:
    2

反应信息

  • 作为反应物:
    描述:
    4-Chloro-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 三乙胺 作用下, 以 二氯甲烷N,N-二甲基乙酰胺二甲胺 为溶剂, 反应 1.75h, 生成 4-cyano-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine
    参考文献:
    名称:
    1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators
    摘要:
    We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.
    DOI:
    10.1021/jm401625b
  • 作为产物:
    描述:
    4-氯-6-氮杂吲哚氢气 作用下, 以 乙醇 为溶剂, 70.0 ℃ 、344.75 kPa 条件下, 反应 24.0h, 以28%的产率得到4-Chloro-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine
    参考文献:
    名称:
    1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators
    摘要:
    We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.
    DOI:
    10.1021/jm401625b
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文献信息

  • 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators
    作者:Eugene L. Piatnitski Chekler、Rayomond Unwalla、Taukeer A. Khan、Raghuram S. Tangirala、Mark Johnson、Michael St. Andre、James T. Anderson、Thomas Kenney、Sue Chiparri、Chris McNally、Edward Kilbourne、Catherine Thompson、Sunil Nagpal、Gregory Weber、Scott Schelling、Jane Owens、Carl A. Morris、Dennis Powell、Patrick R. Verhoest、Adam M. Gilbert
    DOI:10.1021/jm401625b
    日期:2014.3.27
    We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.
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