雄甾-1,4-二烯-3,17-二酮 | 2192-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 雄甾-1,4-二烯-3,17-二酮
• 英文名称: 4-fluoro-α-oxo-1H-indole-3-acetyl chloride
• 英文别名: 4-Fluor-3-chlorglyoxyloyl-indol；4-fluoro-2-(1H-indol-3-yl)-2-oxoacetyl chloride；2-(4-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride；(4-fluoro-1H-indol-3-yl)-oxo-acetyl chloride
• CAS: 2192-28-1
• 化学式: C₁₀H₅ClFNO₂
• 分子量: 225.607
• InChiKey: FKRRABHXUWVCEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  雄甾-1,4-二烯-3,17-二酮 在 氨 作用下， 以 1,4-二氧六环 为溶剂， 生成 4’-fluoro-2,3-dioxotryptamine
  参考文献：
  名称：

  Alpha-ethyltryptamines as dual dopamine–serotonin releasers

  摘要：

  The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were > 10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.062
• 作为产物：
  描述：

  4-氟吲哚 生成 雄甾-1,4-二烯-3,17-二酮
  参考文献：
  名称：

  Indole, azaindole and related heterocyclic pyrrolidine derivatives

  摘要：

  这项发明提供了具有药物和生物影响特性的化合物，它们的药物组合物和使用方法。具体来说，该发明涉及酰胺哌嗪衍生物。这些化合物具有独特的抗病毒活性，无论是单独使用还是与其他抗病毒药物、抗感染剂、免疫调节剂或HIV进入抑制剂结合使用。更具体地，本发明涉及HIV和艾滋病的治疗。

  公开号：

  US20030236277A1

文献信息

• [EN] DIKETO AZOLOPIPERIDINES AND AZOLOPIPERAZINES AS ANTI-HIV AGENTS<br/>[FR] DICÉTO-AZOLOPIPÉRIDINES ET AZOLOPIPÉRAZINES EN TANT QU'AGENTS ANTI-VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2009158394A1

  公开（公告）日：2009-12-30

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, diketo fused azolopiperidine and azolopiperazine derivatives that possess unique antiviral activity are provided. These compounds are useful the treatment of HIV and AIDS.

  具有药物和生物影响特性的化合物，其药物组合物和使用方法已经列出。具体来说，提供了具有独特抗病毒活性的二酮融合的咪唑哌啶和咪唑哌嗪衍生物。这些化合物对治疗艾滋病毒和艾滋病非常有用。
• Novel, potent and selective cyclin D1/CDK4 inhibitors: indolo[6,7-a]pyrrolo[3,4-c]carbazoles
  作者：Thomas A. Engler、Kelly Furness、Sushant Malhotra、Concha Sanchez-Martinez、Chuan Shih、Walter Xie、Guoxin Zhu、Xun Zhou、Scott Conner、Margaret M. Faul、Kevin A. Sullivan、Stanley P. Kolis、Harold B. Brooks、Bharvin Patel、Richard M. Schultz、Tammy B. DeHahn、Kashif Kirmani、Charles D. Spencer、Scott A. Watkins、Eileen L. Considine、Jack A. Dempsey、Catherine A. Ogg、Nancy B. Stamm、Bryan D. Anderson、Robert M. Campbell、Vasu Vasudevan、Michelle L. Lytle

  DOI：10.1016/s0960-894x(03)00461-x

  日期：2003.7

  The synthesis and CDK inhibitory properties of a series of indolo[6,7-a]pyrrolo[3,4-c]carbazoles is reported. In addition to their potent CDK activity, the compounds display antiproliferative activity against two human cancer cell lines. These inhibitors also effect strong G1 arrest in these cell lines and inhibit Rb phosphorylation at Ser780 consistent with inhibition of cyclin D1/CDK4.

  报道了一系列吲哚[6，7-a]吡咯并[3，4-c]咔唑的合成和CDK抑制性能。这些化合物除了具有强大的CDK活性外，还具有针对两种人类癌细胞系的抗增殖活性。这些抑制剂还影响这些细胞系中的强G1阻滞，并抑制Ser780处的Rb磷酸化，这与抑制细胞周期蛋白D1 / CDK4一致。
• Modification and structure–activity relationship of a small molecule HIV-1 inhibitor targeting the viral envelope glycoprotein gp120
  作者：Jingsong Wang、Nhut Le、Alonso Heredia、Haijing Song、Robert Redfield、Lai-Xi Wang

  DOI：10.1039/b415159c

  日期：——

  This paper describes selected modification and structure–activity relationship of the small molecule HIV-1 inhibitor, 4-benzoyl-1-[(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine (BMS-378806). The results revealed: i) that both the presence and configuration (R vs. S) of the 3-methyl group on the piperazine moiety are important for the antiviral activity, with the 3-(R)-methyl derivatives showing the highest activity; ii) that the electronegativity of the C-4 substituent on the indole or azaindole ring seems to be important for the activity, with a small, electron-donating group such as a fluoro or a methoxy group showing enhanced activity, while a nitro group diminishes the activity; iii) that the N-1 position of the indole ring is not eligible for modification without losing activity; and iv) that bulky groups around the C-4 position of the indole or azaindole ring diminish the activity, probably due to steric hindrance in the binding. We found that a synthetic bivalent compound with two BMS-378806 moieties being tethered by a spacer demonstrated about 5-fold enhanced activity in an nM range against HIV-1 infection than the corresponding monomeric inhibitor. But the polyacrylamide-based polyvalent compounds did not show inhibitory activity at up to 200 nM.

  本文描述了小分子HIV-1抑制剂4-benzoyl-1-[(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine (BMS-378806) 的部分修饰和结构-活性关系。结果表明：i) 在哌嗪部分3-甲基的存在及其构型（R与S）对抗病毒活性非常重要，其中3-(R)-甲基衍生物显示出最高的活性；ii) 吲哚或氮吲哚环C-4位的取代基电负性似乎对活性很重要，小的电子供体基团（如氟或甲氧基）显示出增强的活性，而硝基基团则降低活性；iii) 吲哚环的N-1位不适合修饰，否则会失去活性；iv) 在吲哚或氮吲哚环的C-4位附近体积较大的基团会降低活性，这可能是由于结合时的空间位阻。我们发现，一种合成的双价化合物，其具有两个BMS-378806基团通过连接子连接，在对抗HIV-1感染时的活性比对应的单体抑制剂提高了约5倍，活性范围达到纳摩尔级。但基于聚丙烯酰胺的多价化合物在高达200 nM时并未显示抑制活性。
• Piperazine amidines as antiviral agents
  申请人：Wang Tao

  公开号：US20070078141A1

  公开（公告）日：2007-04-05

  This disclosure provides compounds of Formula I as described herein having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the disclosure is concerned with indole and azaindole piperazine diamide derivatives that possess unique antiviral activity. More particularly, the present disclosure relates to compounds useful for the treatment of HIV and AIDS.

  本公开提供了具有药物和生物影响特性的Formula I化合物，其制药组合物和使用方法。具体而言，该公开涉及具有独特抗病毒活性的吲哚和氮杂吲哚哌嗪二酰胺衍生物。更具体地说，本公开涉及用于治疗HIV和艾滋病的化合物。
• 4-Squarylpiperazine Derivatives as Antiviral Agents
  申请人：Bachand Carol

  公开号：US20070249624A1

  公开（公告）日：2007-10-25

  This disclosure provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the disclosure is concerned with 4-squarylpiperazine derivatives that possess unique antiviral activity. More particularly, the present disclosure relates to compounds useful for the treatment of HIV and AIDS.

  本公开提供具有药物和生物影响特性的化合物，它们的药物组合物和使用方法。具体而言，该公开涉及具有独特抗病毒活性的4-四氢喹啉基哌嗪衍生物。更具体地说，本公开涉及用于治疗艾滋病毒和艾滋病的化合物。