LY 293559 | 150010-68-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: LY 293559
• 英文别名: (3R,4aS,6S,8aS)-6-[2-(1H-tetrazol-5-yl)-ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid；(3R,4aS,6S,8aS)-6-(2-(1H-Tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid；(-)-LY-293559；LY293559；(3R,4aS,6S,8aS)-6-[2-(1H-tetrazol-5-yl)ethyl]decahydroxyisoquinoline-3-carboxylic acid；3-Isoquinolinecarboxylic acid, decahydro-6-(2-(1H-tetrazol-5-yl)ethyl)-, (3R,4aS,6S,8aS)-rel-；(3R,4aS,6S,8aS)-6-[2-(2H-tetrazol-5-yl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid
• CAS: 150010-68-7
• 化学式: C₁₃H₂₁N₅O₂
• 分子量: 279.342
• InChiKey: ZXFRFPSZAKNPQQ-ZRUFSTJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Ethyl (3S,4aR,6S,8aR)-6-(hydroxymethyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate 在 盐酸 、 甲醇 、 草酰氯 、 sodium hydride 、 magnesium 、 二甲基亚砜 、 三乙胺 、 三正丁基叠氮化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 LY 293559
  参考文献：
  名称：

  （3SR，4aRS，6RS，8aRS）-6- [2-（1H-四唑-5-基）乙基]十氢异喹啉-3-羧酸：一种结构新颖的，具有系统活性的竞争性AMPA受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm00066a016

文献信息

• Stereoselective Synthesis of 6-Substituted Decahydroisoquinoline-3-carboxylates: Intermediates for the Preparation of Conformationally Constrained Acidic Amino Acids
  作者：Paul L. Ornstein、Nancy K. Augenstein、M. Brian Arnold

  DOI：10.1021/jo00104a051

  日期：1994.12

  In this article we describe the stereoselective preparation of two 6-(hydroxymethyl) substituted decahydroisoquinoline-3-carboxylates, which are useful in the synthesis of a number of excitatory amino acid antagonists, e.g., (-)-1a (LY235959), (-)-2a (LY202157) and (-)-3a(LY293558). For example, the known ketone 4 was converted to either the (3SR,4aRS,6SR,8aRS)-alcohol 18 or the (3SR,4aRS,6RS,8aRS)-alcohol 21, the former via a stereoselective hydroboration reaction, the latter via a stereoselective enol ether hydrolysis followed by reduction. These C-6 epimeric alcohols were easily converted to a number of useful intermediates, e.g., aldehydes, bromides and iodides. If we used resolved ketone 4, then these intermediates could be obtained in optically active form. In either racemic or non-racemic form, these intermediates provided access to a number of diastereomerically pure amino acids that were difficult to obtain by earlier routes.
• GLUTAMATE RECEPTOR ANTAGONISTS AND METHODS OF USE
  申请人：The Johns Hopkins University

  公开号：EP2150248A2

  公开（公告）日：2010-02-10
• US8603980B2
  申请人：——

  公开号：US8603980B2

  公开（公告）日：2013-12-10
• [EN] GLUTAMATE RECEPTOR ANTAGONISTS AND METHODS OF USE<br/>[FR] ANTAGONISTES DE RÉCEPTEUR DE GLUTAMATE ET PROCÉDÉS D'UTILISATION
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2008088820A2

  公开（公告）日：2008-07-24

  [EN] The present invention relates to methods and compositions for modulating platelet activity by inhibiting or activating glutamate receptors. The invention further relates to preventing or treating thrombotic diseases.
  [FR] La présente invention concerne des procédés et des compositions pour moduler une activité de plaquette en inhibant ou en activant des récepteurs de glutamate. L'invention concerne en outre la prévention ou le traitement de maladies thrombotiques.
• (3SR,4aRS,6RS,8aRS)-6-[2-(1H-Tetrazol-5-yl)ethyl]decahydroisoquinoline-3-carboxylic acid: a structurally novel, systemically active, competitive AMPA receptor antagonist
  作者：Paul L. Ornstein、M. Brian Arnold、Nancy K. Augenstein、David Lodge、J. David Leander、Darryle D. Schoepp

  DOI：10.1021/jm00066a016

  日期：1993.7