ethyl cinnoline-6-carboxylate | 1562366-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl cinnoline-6-carboxylate
• CAS: 1562366-89-5
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: DQAOMKRPWXBXFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl cinnoline-6-carboxylate 、 (E)-2-碘三甲基硅基乙烯 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 zinc(II) chloride 、 三(2-呋喃基)膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以57%的产率得到(E)-ethyl 8-(2-(trimethylsilyl)vinyl)cinnoline-6-carboxylate
  参考文献：
  名称：

  TMP–Magnesium and TMP–Zinc Bases for the Regioselective Metalation of the Cinnoline Scaffold

  摘要：

  A regioselective functionalization of cinnolines in positions 3 and 8 using metalations has been developed. This involves either the use of a frustrated Lewis pair consisting of BF3 center dot Et2O and TMP2Mg center dot 2LiCl or the in situ generated base TMP2Zn center dot 2MgCl(2)center dot 2LiCl. Successive metalations allow the preparation of 3,8-disubstituted cinnolines. Various functionalizations by acylation, allylation, and cross-coupling reactions with aryl halides or alkenyl iodides were carried out successfully.

  DOI：

  10.1021/ol5001999

文献信息

• NOVEL CHEMICAL COMPOUNDS
  申请人：SmithKline Beecham Corporation

  公开号：EP1940812A2

  公开（公告）日：2008-07-09
• THIAZOLONES FOR USE AS PI3 KINASE INHIBITORS
  申请人：SmithKline Beecham Corporation

  公开号：EP1996191A2

  公开（公告）日：2008-12-03
• Novel Chemical Compounds
  申请人：Duffy Kevin J

  公开号：US20080261974A1

  公开（公告）日：2008-10-23

  This invention relates to newly identified compounds for inhibiting hYAK3 proteins and methods for treating diseases associated with the imbalance or inappropriate activity of hYAK3 proteins.
• [EN] NOVEL CHEMICAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2007038331A2

  公开（公告）日：2007-04-05

  (EN) This invention relates to newly identified compounds for inhibiting hYAK3 proteins and methods for treating diseases associated with the imbalance or inappropriate activity of hYAK3 proteins.(FR) L'invention concerne des composés nouvellement identifiés destinés à l'inhibition de protéines hYAK3 et des méthodes de traitement de maladies liées au déséquilibre ou à une activité inappropriée des protéines hYAK3.
• [EN] THIAZOLONES FOR USE AS PI3 KINASE INHIBITORS<br/>[FR] THIAZOLONES UTILISÉS EN TANT QU'INHIBITEURS DE P13-KINASES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2007103759A2

  公开（公告）日：2007-09-13

  [EN] Invented is a method of inhibiting the activity/function of PI3 kinases using substituted thiazolones. Also invented is a method of treating one or more disease states selected from: autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergy, asthma, pancreatitis, multiorgan failure, kidney diseases, platelet aggregation, cancer, sperm motility, transplantation rejection, graft rejection and lung injuries by the administration of substituted thiazolones.
  [FR] Cette invention concerne un procédé permettant d'inhiber l'activité/la fonction des P13-kinases au moyen de thizolones substitués. En outre, cette invention concerne une méthode permettant de traiter par administration des thiazolones substitués, un ou plusieurs états pathologiques parmi lesquels: les maladies autoimmunes, les maladies inflammatoires, les maladies cardiovasculaires, les maladies neurodégénératives, l'allergie, l'asthme, la pancréatite, la défaillance multiviscérale, les maladies rénales, l'agrégation plaquettaire, le cancer, la motilité du sperme, le rejet d'une transplantation, le rejet d'un greffon, et les lésions pulmonaires.