(S)-(+)-4-[8-chloro-6-(1-piperazinyl)-1H-benzo[5,6]cyclohepta[1,2-b]pyridine-11-yl]-1-(methylsulfonyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并环庚烷吡啶
• 英文名称: (S)-(+)-4-[8-chloro-6-(1-piperazinyl)-1H-benzo[5,6]cyclohepta[1,2-b]pyridine-11-yl]-1-(methylsulfonyl)piperidine
• 英文别名: (11S)-8-Chloro-11-[1-(methylsulfonyl)piperidin-4-YL]-6-piperazin-1-YL-11H-benzo[5,6]cyclohepta[1,2-B]pyridine；(2S)-13-chloro-2-(1-methylsulfonylpiperidin-4-yl)-10-piperazin-1-yl-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene
• 化学式: C₂₄H₂₉ClN₄O₂S
• 分子量: 473.039
• InChiKey: ZMGCFGGMTCMSDP-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-bromo-8-chloro-11-(1-methanesulfonyl-piperidin-4-yl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridine 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-(+)-4-[8-chloro-6-(1-piperazinyl)-1H-benzo[5,6]cyclohepta[1,2-b]pyridine-11-yl]-1-(methylsulfonyl)piperidine
  参考文献：
  名称：

  Enhanced FTase activity achieved via piperazine interaction with catalytic zinc

  摘要：

  Benzocycloheptapyridine tricyclic compounds with piperazine or substituted piperidine moieties extending either from the 5- or 6-position of the tricyclic bridgehead exhibited enhanced FTase activity: this resulted from favorable binding of the ligand nitrogen with the catalytic zinc found in the FTase. A single isomer at C-11 with piperazine adduct extending from the 6-position, compound 24, exhibited excellent FTase activity with IC50 = 0.007 microM, soft agar IC50 = 72 nM, and Rat AUC(PO, 10 mpk) = 4.0 microM x h. X-ray of (-)-[8-chloro-6-(1-piperazinyl)-1H-benzo[5,6]]cyclohepta[1,2-b]pyridine-11-yl]-1-(methylsulfonyl)piperidine 24 bound to Ftase revealed favorable interaction between piperazine nitrogen and catalytic zinc atom.

  DOI：

  10.1016/j.bmcl.2005.10.090

文献信息

• IDENTIFICATION AND TARGETED MODULATION OF GENE SIGNALING NETWORKS
  申请人：CAMP4 THERAPEUTICS CORPORATION

  公开号：US20210254056A1

  公开（公告）日：2021-08-19

  The present invention provides methods and compositions for the evaluation, alteration and/or optimization of gene signaling. Methods and systems are also provided which exploit the information generated in the identification of new targets and non-canonical signaling pathways.
• Enhanced FTase activity achieved via piperazine interaction with catalytic zinc
  作者：F. George Njoroge、Bancha Vibulbhan、Patrick Pinto、Corey Strickland、W. Robert Bishop、Amin Nomeir、Vivyoor Girijavallabhan

  DOI：10.1016/j.bmcl.2005.10.090

  日期：2006.2

  Benzocycloheptapyridine tricyclic compounds with piperazine or substituted piperidine moieties extending either from the 5- or 6-position of the tricyclic bridgehead exhibited enhanced FTase activity: this resulted from favorable binding of the ligand nitrogen with the catalytic zinc found in the FTase. A single isomer at C-11 with piperazine adduct extending from the 6-position, compound 24, exhibited excellent FTase activity with IC50 = 0.007 microM, soft agar IC50 = 72 nM, and Rat AUC(PO, 10 mpk) = 4.0 microM x h. X-ray of (-)-[8-chloro-6-(1-piperazinyl)-1H-benzo[5,6]]cyclohepta[1,2-b]pyridine-11-yl]-1-(methylsulfonyl)piperidine 24 bound to Ftase revealed favorable interaction between piperazine nitrogen and catalytic zinc atom.