1-phenyl-4H-pyrrolo[3,2-b]pyridin-5-one | 514182-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-phenyl-4H-pyrrolo[3,2-b]pyridin-5-one
• CAS: 514182-83-3
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: ISHWWRIXAJRMRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-4H-pyrrolo[3,2-b]pyridin-5-one 在 N-甲基吗啉 、 吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate 、 palladium on activated charcoal 、 氢气 、 溴 、 锌 、 叔丁醇 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  Structure-based optimization of potent 4- and 6-azaindole-3-carboxamides as renin inhibitors

  摘要：

  The control of hypertension and associated cardiovascular risk factors is possible by selective inhibition of the aspartyl protease renin due to its unique position in the renin-angiotensin system. Starting from a previously disclosed series of potent and nonchiral indole-3-carboxamides, we further explored this motif by structure-based drug design guided by X-ray crystallography in combination with efficient parallel synthesis. This resulted in the discovery of 4- or 6-azaindole derivatives with remarkable potency for renin inhibition. The best compound from these series showed an IC(50) value of 1.3 nM. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.06.114
• 作为产物：
  描述：

  碘苯 、 1H-吡咯并[3,2-b]吡啶-5-醇 在 copper(l) iodide 、 8-羟基喹啉 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 1-phenyl-4H-pyrrolo[3,2-b]pyridin-5-one
  参考文献：
  名称：

  Structure-based optimization of potent 4- and 6-azaindole-3-carboxamides as renin inhibitors

  摘要：

  The control of hypertension and associated cardiovascular risk factors is possible by selective inhibition of the aspartyl protease renin due to its unique position in the renin-angiotensin system. Starting from a previously disclosed series of potent and nonchiral indole-3-carboxamides, we further explored this motif by structure-based drug design guided by X-ray crystallography in combination with efficient parallel synthesis. This resulted in the discovery of 4- or 6-azaindole derivatives with remarkable potency for renin inhibition. The best compound from these series showed an IC(50) value of 1.3 nM. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.06.114

文献信息

• Bicyclic oxopyridine and oxopyrimidine derivatives
  申请人：——

  公开号：US20040254200A1

  公开（公告）日：2004-12-16

  Compounds of formulae (1a) and (1b) are described: in which the dashed line represents an optional bond; A is a —N=atom or a —N(R b )—, —C(R b )═ or —C(R b )(R C )— group; R a , R b and R c is each independently a hydrogen atom or an optionally substituted C 1-6 alkyl group; X is an —O— or —S— atom or —NH— group or substituted N atom; each Y is independently a N atom or CH group or substituted C atom; n is zero or the integer 1; Alk 1 is an optionally substituted aliphatic or heteroaliphatic chain L 1 is a covalent bond or a linker atom or group; Cy 1 is a hydrogen atom or an optionally substituted cycloaliphatic, polycycloaliphatic, heterocycloaliphatic, polyheterocycloaliphatic, aromatic or heteroaromatic group; Ar is an optionally substituted aromatic or heteroaromatic group; and the salts, solvates, hydrates and N-oxides thereof; The compounds are potent inhibitors of p38 kinase and are use in the prophylaxis or treatment of p38 kinase mediated diseases or disorders, such as rheumatoid arthritis. 1

  描述了式（1a）和（1b）的化合物：其中虚线代表可选键；A是-N=原子或-N（Rb）-，-C（Rb）-或-C（Rb）（RC）-基团；Ra，Rb和Rc分别独立地是氢原子或可选地取代的C1-6烷基基团；X是-O-或-S-原子或-NH-基团或取代的N原子；每个Y独立地是N原子或CH基团或取代的C原子；n为零或整数1；Alk1是可选地取代的脂肪或杂脂肪链；L1是共价键或连接原子或基团；Cy1是氢原子或可选地取代的环脂肪，多环脂肪，杂环脂肪，多杂环脂肪，芳香或杂芳香基团；Ar是可选地取代的芳香或杂芳香基团；以及其盐，溶剂合物，水合物和N-氧化物。这些化合物是p38激酶的有效抑制剂，并用于预防或治疗p38激酶介导的疾病或障碍，如类风湿性关节炎。
• US7176215B2
  申请人：——

  公开号：US7176215B2

  公开（公告）日：2007-02-13
• Structure-based optimization of potent 4- and 6-azaindole-3-carboxamides as renin inhibitors
  作者：Bodo Scheiper、Hans Matter、Henning Steinhagen、Zsolt Böcskei、Valérie Fleury、Gary McCort

  DOI：10.1016/j.bmcl.2011.06.114

  日期：2011.9

  The control of hypertension and associated cardiovascular risk factors is possible by selective inhibition of the aspartyl protease renin due to its unique position in the renin-angiotensin system. Starting from a previously disclosed series of potent and nonchiral indole-3-carboxamides, we further explored this motif by structure-based drug design guided by X-ray crystallography in combination with efficient parallel synthesis. This resulted in the discovery of 4- or 6-azaindole derivatives with remarkable potency for renin inhibition. The best compound from these series showed an IC(50) value of 1.3 nM. (C) 2011 Published by Elsevier Ltd.