5-乙烯基吡啶-2,3-二胺 | 874279-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-乙烯基吡啶-2,3-二胺
• 英文名称: 2,3-diamino-5-vinylpyridine
• 英文别名: 5-Ethenylpyridine-2,3-diamine
• CAS: 874279-20-6
• 化学式: C₇H₉N₃
• mdl: MFCD13175995
• 分子量: 135.169
• InChiKey: SVCKZTXZIPRCHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-乙烯基吡啶-2,3-二胺 、 草酰基二咪唑 以 四氢呋喃 为溶剂， 反应 3.0h， 以79%的产率得到7-vinylpyrido[3,2-b]pyrazine-2,3(1H,4H)-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：

  2-amino-3-nitro-5-vinylpyridine 在 sodium tetrahydroborate 、 tin(II) chloride dihdyrate 作用下， 以 乙酸乙酯 、 叔丁醇 为溶剂， 反应 3.0h， 以82%的产率得到5-乙烯基吡啶-2,3-二胺
  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

• Gonadotropin releasing hormone receptor antagonists
  申请人：Garrick Michael Lloyd

  公开号：US20060019965A1

  公开（公告）日：2006-01-26

  The present invention relates to Gonadotropin Releasing Hormone (“GnRH”) (also known as Leutinizing Hormone Releasing Hormone) receptor antagonists.

  本发明涉及促性腺激素释放激素（“GnRH”）（也称为促黄体生成激素释放激素）受体拮抗剂。
• GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS
  申请人：Wyeth

  公开号：EP1758895A1

  公开（公告）日：2007-03-07
• US7696210B2
  申请人：——

  公开号：US7696210B2

  公开（公告）日：2010-04-13
• [EN] GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RÉCEPTEURS DE L'HORMONE DE LIBÉRATION DE GONADOTROPHINES
  申请人：WYETH CORP

  公开号：WO2006009734A1

  公开（公告）日：2006-01-26

  The present invention relates to Gonadotropin Releasing Hormone (“GnRH”) (also known as Leutinizing Hormone Releasing Hormone) receptor antagonists.
• 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.