5-氰基-1H-吡咯-2-羧酸 | 854044-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 5-氰基-1H-吡咯-2-羧酸
• 中文别名: 5-氰基-1H-2-吡咯甲酸
• 英文名称: 5-carboxy-1H-pyrrole-2-carbonitrile
• 英文别名: 5-cyano-1H-pyrrole-2-carboxylic acid
• CAS: 854044-30-7
• 化学式: C₆H₄N₂O₂
• mdl: MFCD12923500
• 分子量: 136.11
• InChiKey: RCODEPXKMGSYIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 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：
  76.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-氰基-1H-吡咯-2-羧酸甲酯	5-cyano-1H-pyrrole-2-carboxylic acid methyl ester	937-19-9	C7H6N2O2	150.137
  5-氰基-1H-吡咯-2-甲酸乙酯	ethyl 5-cyano-1H-pyrrole-2-carboxylate	21635-99-4	C8H8N2O2	164.164

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-甲酰基-1H-吡咯-2-甲酸乙酯	ethyl 5-formyl-1H-pyrrole-2-carboxylate	7126-50-3	C8H9NO3	167.164

反应信息

• 作为反应物：
  描述：

  5-氰基-1H-吡咯-2-羧酸 在 sodium azide 、 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 N-(4-methylphenyl)-5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Dissecting the Complex Recognition Interfaces of Potent Tetrazole- and Pyrrole-Based Anion Binders

  摘要：

  Tetrazoles are potent anion binders. We report here a new family of tetrazole pyrrole amide hosts that arise when a tetrazole is incorporated as a new binding element alongside the well-known amidopyrrole anion-binding scaffold. In addition to reporting three new, modular synthetic routes that can be used to access these structures, we also report that the new hosts are highly potent binders of chloride. Along the way, we carried out studies of a pyrrole ester control compound that, surprisingly, bound anions almost as strongly as did the amide analogues. This led us to investigate further the relative importance of the amide NH in halide binding. We report that, despite the regular appearance of this dose amide NH-Cl contact in calculated and experimental X-ray structures, the amide NH in this family of anion hosts does solution.

  DOI：

  10.1021/jo400372c
• 作为产物：
  描述：

  2-吡咯甲酸甲酯 在 lithium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.0h， 生成 5-氰基-1H-吡咯-2-羧酸
  参考文献：
  名称：

  Dissecting the Complex Recognition Interfaces of Potent Tetrazole- and Pyrrole-Based Anion Binders

  摘要：

  Tetrazoles are potent anion binders. We report here a new family of tetrazole pyrrole amide hosts that arise when a tetrazole is incorporated as a new binding element alongside the well-known amidopyrrole anion-binding scaffold. In addition to reporting three new, modular synthetic routes that can be used to access these structures, we also report that the new hosts are highly potent binders of chloride. Along the way, we carried out studies of a pyrrole ester control compound that, surprisingly, bound anions almost as strongly as did the amide analogues. This led us to investigate further the relative importance of the amide NH in halide binding. We report that, despite the regular appearance of this dose amide NH-Cl contact in calculated and experimental X-ray structures, the amide NH in this family of anion hosts does solution.

  DOI：

  10.1021/jo400372c

文献信息

• C-fms kinase inhibitors
  申请人：Player R. Mark

  公开号：US20050131022A1

  公开（公告）日：2005-06-16

  The invention is directed to compounds of Formulae I: wherein A, R 1 , R 2 , R 3 , R 4 , X, and W are set forth in the specification, as well as solvates, hydrates, tautomers or pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase.

  该发明涉及以下式I的化合物：其中A、R1、R2、R3、R4、X和W如规范中所述，以及其溶剂合物、水合物、互变体或药学上可接受的盐，可以抑制蛋白酪氨酸激酶，尤其是c-fms激酶。
• c-fms kinase inhibitors
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US07427683B2

  公开（公告）日：2008-09-23

  The invention is directed to compounds of Formulae I: wherein A, R1, R2, R3, R4, X, and W are set forth in the specification, as well as solvates, hydrates, tautomers or pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase.

  该发明涉及式I的化合物：其中A，R1，R2，R3，R4，X和W在规范中列出，以及其溶剂化物，水合物，互变异构体或药学上可接受的盐，其抑制蛋白酪氨酸激酶，特别是c-fms激酶。
• [EN] PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AND RELATED USES<br/>[FR] DÉRIVÉS PYRROLIDINE-3-CARBOXAMIDE ET UTILISATIONS DE CES DERNIERS
  申请人：CHULALONGKORN UNIV

  公开号：WO2022087422A9

  公开（公告）日：2022-06-09
• C-FMS KINASE INHIBITORS
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1812425A2

  公开（公告）日：2007-08-01
• COMPOUNDS, COMPOSITIONS AND METHODS
  申请人：Denali Therapeutics Inc.

  公开号：US20170226127A1

  公开（公告）日：2017-08-10

  The present disclosure relates generally to compounds and compositions, and their use as kinase inhibitors.