ethyl 5-ethylpyridine-2-carboxylate 1-oxide | 1269028-76-3

• 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
• 英文名称: ethyl 5-ethylpyridine-2-carboxylate 1-oxide
• 英文别名: 5-ethylpyridine-2-carboxylate ethyl 1-oxide；Ethyl 5-ethyl-1-oxidopyridin-1-ium-2-carboxylate
• CAS: 1269028-76-3
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: RXIJZDMCGDIFBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-ethylpyridine-2-carboxylate 1-oxide 在 吡啶 、 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 palladium 10% on activated carbon 、 水 、 氢气 、 sodium ethanolate 、 caesium carbonate 、 N,N-二异丙基乙胺 、 silver carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 131.0h， 生成 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of hedgehog signaling inhibitor with novel core system

  摘要：

  As we previously reported, N-methylpyrrolo[3,2-c] pyridine derivatives 1 (TAK-441) was discovered as a clinical candidate of hedgehog (Hh) signaling inhibitor by modification of the upper part. We next focused on modification of the lower part including core skeletons to discover new Hh signaling inhibitors with novel core rings. Efforts to find novel chemotypes by using X-ray single crystal structure analysis led to some potent Hh signaling inhibitors (2c, 2d, 2e, 2f) with novel core ring systems, which had benzamide moiety at the 5-position as a key component for potent activity. The suppression of Gli1 expression with these new Hh signaling inhibitors were weaker than that of compound 1 (TAK-441) because of low pharmacokinetic property. We recognized again TAK-441 is a good compound as clinical candidate with good structural and pharmacokinetic advantages. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.036
• 作为产物：
  描述：

  5-Ethylpyridin-2-carbonsaeureethylester 在 m-chloroperoxybenzoic acid 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以83%的产率得到ethyl 5-ethylpyridine-2-carboxylate 1-oxide
  参考文献：
  名称：

  Synthesis and evaluation of hedgehog signaling inhibitor with novel core system

  摘要：

  As we previously reported, N-methylpyrrolo[3,2-c] pyridine derivatives 1 (TAK-441) was discovered as a clinical candidate of hedgehog (Hh) signaling inhibitor by modification of the upper part. We next focused on modification of the lower part including core skeletons to discover new Hh signaling inhibitors with novel core rings. Efforts to find novel chemotypes by using X-ray single crystal structure analysis led to some potent Hh signaling inhibitors (2c, 2d, 2e, 2f) with novel core ring systems, which had benzamide moiety at the 5-position as a key component for potent activity. The suppression of Gli1 expression with these new Hh signaling inhibitors were weaker than that of compound 1 (TAK-441) because of low pharmacokinetic property. We recognized again TAK-441 is a good compound as clinical candidate with good structural and pharmacokinetic advantages. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.036

文献信息

• SULFUR-CONTAINING HETEROCYCLIC DERIVATIVE HAVING BETA SECRETASE INHIBITORY ACTIVITY
  申请人：Shionogi & Co., Ltd.

  公开号：US20160108052A1

  公开（公告）日：2016-04-21

  The following compound is provided as an agent for treating a disease induced by production, secretion and/or deposition of amyloid β protein, for example, a compound represented by the formula (I): wherein ring A is an optionally substituted carbocyclic group or an optionally substituted heterocyclic group, R 1 is optionally substituted lower alkyl or the like, R 2a and R 2b are each independently hydrogen, optionally substituted lower alkyl or the like, R 3a and R 3c are each independently hydrogen, halogen, hydroxy, optionally substituted lower alkyl or the like, or a pharmaceutically acceptable salt thereof, or a solvate thereof.

  以下化合物作为治疗由淀粉样β蛋白的产生、分泌和/或沉积引起的疾病的药剂，例如由式(I)表示的化合物：其中环A是可选取代的碳环基或可选取代的杂环基，R1是可选取代的低碳基或类似物，R2a和R2b各自独立地是氢、可选取代的低碳基或类似物，R3a和R3b各自独立地是氢、卤素、羟基、可选取代的低碳基或类似物，或其药学上可接受的盐或溶剂。
• FUSED HETEROCYCLIC RING DERIVATIVE AND USE THEREOF
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2471789B9

  公开（公告）日：2015-03-25
• US8486965B2
  申请人：——

  公开号：US8486965B2

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  申请人：——

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  公开（公告）日：2014-01-28
• US9273053B2
  申请人：——

  公开号：US9273053B2

  公开（公告）日：2016-03-01