2,3-dioxo-1,2,3,4-tetrahydropyrido[3,2-b]pyrazine-7-carbaldehyde | 874279-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶吡嗪类
• 英文名称: 2,3-dioxo-1,2,3,4-tetrahydropyrido[3,2-b]pyrazine-7-carbaldehyde
• 英文别名: 2,3-Dioxo-1,4-dihydropyrido[2,3-b]pyrazine-7-carbaldehyde
• CAS: 874279-22-8
• 化学式: C₈H₅N₃O₃
• 分子量: 191.146
• InChiKey: QQJNHFFSIURJJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-tert-butylphenyl)-4-(piperazin-1-yl)-1H-benzo[d]imidazole 、 2,3-dioxo-1,2,3,4-tetrahydropyrido[3,2-b]pyrazine-7-carbaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 以23%的产率得到7-({4-[2-(4-tert-butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)-1,4-dihydropyrido[2,3-b]pyrazine-3,4-dione
  参考文献：
  名称：

  Discovery of 6-({4-[2-(4-tert-Butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024): An Orally Active Antagonist of the Gonadotropin Releasing Hormone Receptor (GnRH-R)

  摘要：

  A potent, highly insoluble, GnRH antagonist with a 2-phenyl-4-piperazinylbenzimidazole template and a quinoxaline-2,3-dione pharmacophore was modified to maintain GnRH antagonist activity and improve in vitro pharmaceutical properties. Structural changes to the quinoxaline-2,3-dione portion of the molecule resulted in several structures with improved properties and culminated in the discovery of 6-((4-[2-(4-tertbutylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024). The compound was shown to have excellent pharmacokinetic parameters and lowered rat plasma LH levels after oral administration.

  DOI：

  10.1021/jm801572m
• 作为产物：
  描述：

  7-vinylpyrido[3,2-b]pyrazine-2,3(1H,4H)-dione 在 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 以40%的产率得到2,3-dioxo-1,2,3,4-tetrahydropyrido[3,2-b]pyrazine-7-carbaldehyde
  参考文献：
  名称：

  Discovery of 6-({4-[2-(4-tert-Butylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024): An Orally Active Antagonist of the Gonadotropin Releasing Hormone Receptor (GnRH-R)

  摘要：

  A potent, highly insoluble, GnRH antagonist with a 2-phenyl-4-piperazinylbenzimidazole template and a quinoxaline-2,3-dione pharmacophore was modified to maintain GnRH antagonist activity and improve in vitro pharmaceutical properties. Structural changes to the quinoxaline-2,3-dione portion of the molecule resulted in several structures with improved properties and culminated in the discovery of 6-((4-[2-(4-tertbutylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024). The compound was shown to have excellent pharmacokinetic parameters and lowered rat plasma LH levels after oral administration.

  DOI：

  10.1021/jm801572m

文献信息

• US7696210B2
  申请人：——

  公开号：US7696210B2

  公开（公告）日：2010-04-13
• Discovery of 6-({4-[2-(4-<i>tert</i>-Butylphenyl)-1<i>H</i>-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024): An Orally Active Antagonist of the Gonadotropin Releasing Hormone Receptor (GnRH-R)
  作者：Jeffrey C. Pelletier、Murty V. Chengalvala、Joshua E. Cottom、Irene B. Feingold、Daniel M. Green、Diane B. Hauze、Christine A. Huselton、James W. Jetter、Gregory S. Kopf、Joseph T. Lundquist、Ronald L. Magolda、Charles W. Mann、John F. Mehlmann、John F. Rogers、Linda K. Shanno、William R. Adams、Cesario O. Tio、Jay E. Wrobel

  DOI：10.1021/jm801572m

  日期：2009.4.9

  A potent, highly insoluble, GnRH antagonist with a 2-phenyl-4-piperazinylbenzimidazole template and a quinoxaline-2,3-dione pharmacophore was modified to maintain GnRH antagonist activity and improve in vitro pharmaceutical properties. Structural changes to the quinoxaline-2,3-dione portion of the molecule resulted in several structures with improved properties and culminated in the discovery of 6-((4-[2-(4-tertbutylphenyl)-1H-benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024). The compound was shown to have excellent pharmacokinetic parameters and lowered rat plasma LH levels after oral administration.