2-amino-3-nitro-5-vinylpyridine | 874279-19-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-amino-3-nitro-5-vinylpyridine
• 英文别名: 3-nitro-5-vinylpyridin-2-amine；5-Ethenyl-3-nitropyridin-2-amine
• CAS: 874279-19-3
• 化学式: C₇H₇N₃O₂
• mdl: MFCD18802865
• 分子量: 165.151
• InChiKey: GULRPAWBTYLWTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 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：
  84.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  三丁基乙烯基锡 、 2-氨基-5-溴-3-硝基吡啶 在 四(三苯基膦)钯 、 lithium chloride 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以77%的产率得到2-amino-3-nitro-5-vinylpyridine
  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。
• Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium
  作者：Woen Susanto、Chi-Yuan Chu、Wei Jie Ang、Tzyy-Chao Chou、Lee-Chiang Lo、Yulin Lam

  DOI：10.1021/jo202482h

  日期：2012.3.16

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.
• 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.