5-(3-pyridinyl)-2-benzofurancarboxylic acid | 85624-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-(3-pyridinyl)-2-benzofurancarboxylic acid
• 英文别名: 5-(Pyridin-3-yl)benzofuran-2-carboxylic acid；5-pyridin-3-yl-1-benzofuran-2-carboxylic acid
• CAS: 85624-66-4
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: VVNDUQUSRWAKSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5-溴苯并呋喃)-2-羧酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 水 、 palladium diacetate 、 potassium carbonate 、 cesium fluoride 、 lithium hydroxide 、 三环己基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 5-(3-pyridinyl)-2-benzofurancarboxylic acid
  参考文献：
  名称：

  The discovery of novel benzofuran-2-carboxylic acids as potent Pim-1 inhibitors

  摘要：

  Novel benzofuran-2-carboxylic acids, exemplified by 29, 38 and 39, have been discovered as potent Pim-1 inhibitors using fragment based screening followed by X-ray structure guided medicinal chemistry optimization. The compounds demonstrate potent inhibition against Pim-1 and Pim-2 in enzyme assays. Compound 29 has been tested in the Ambit 442 kinase panel and demonstrates good selectivity for the Pim kinase family. X-ray structures of the inhibitor/Pim-1 binding complex reveal important salt-bridge and hydrogen bond interactions mediated by the compound's carboxylic acid and amino groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.030

文献信息

• Pyridinyl and imidazolyl derivatives of benzofurans and benzothiophenes
  申请人：THE UPJOHN COMPANY

  公开号：EP0069521A2

  公开（公告）日：1983-01-12

  Compounds of the formula wherein Z, is pyridinyl or imidazolyl; X, is -(CH2)n-, -0-, -S-, -SO-, -SO2. -CH2-O-, -0-CH2-, -CH2-NR3-, -NR3-CH2-. -CHOH- or -CO-; Y, is -O- or -S-; R2 is H. C1-3 alkyl, phenyl or optionally esterified carboxyl; R7 is H, CH2OH, optionally esterified carboxyl, CN, aminomethyl. aminocarbonyl, CHO or a ketone; either Rg and R12 are independently selected from hydrogen, hydroxy, C1-4 alkyl, fluorine, chlorine, bromine and methoxy, or R9 and R12 are attached to adjacent carbon atoms and together are -O-CH2-O-; = represents a single bond (in which case the compound may be in enantiomeric or racemic form) or a double bond; and m and n are 0,1, 2,3 or 4. These compounds can inhibit TXA2 synthetase.

  式中的化合物 其中 Z 是吡啶基或咪唑基； X 是-(CH2)n-、-0-、-S-、-SO-、-SO2.-CH2-O，-0-CH2-，-CH2-NR3-，-NR3-CH2-。-CHOH-或-CO-；Y 是-O-或-S-；R2 是 H、C1-3 烷基、苯基或任选酯化的羧基；R7 是 H、CH2OH、任选酯化的羧基、CN、氨甲基或者 Rg 和 R12 独立选自氢、羟基、C1-4 烷基、氟、氯、溴和甲氧基，或者 R9 和 R12 连接到相邻的碳原子上，并共同为 -O-CH2-O-； = 代表单键（在这种情况下，化合物可能是对映异构体或外消旋体）或双键；m 和 n 分别为 0、1、2、3 或 4。这些化合物可抑制 TXA2 合成酶。
• US4495357A
  申请人：——

  公开号：US4495357A

  公开（公告）日：1985-01-22
• The discovery of novel benzofuran-2-carboxylic acids as potent Pim-1 inhibitors
  作者：Yibin Xiang、Bradford Hirth、Gary Asmussen、Hans-Peter Biemann、Kimberly A. Bishop、Andrew Good、Maria Fitzgerald、Tatiana Gladysheva、Annuradha Jain、Katherine Jancsics、Jinyu Liu、Markus Metz、Andrew Papoulis、Renato Skerlj、J. David Stepp、Ronnie R. Wei

  DOI：10.1016/j.bmcl.2011.03.030

  日期：2011.5

  Novel benzofuran-2-carboxylic acids, exemplified by 29, 38 and 39, have been discovered as potent Pim-1 inhibitors using fragment based screening followed by X-ray structure guided medicinal chemistry optimization. The compounds demonstrate potent inhibition against Pim-1 and Pim-2 in enzyme assays. Compound 29 has been tested in the Ambit 442 kinase panel and demonstrates good selectivity for the Pim kinase family. X-ray structures of the inhibitor/Pim-1 binding complex reveal important salt-bridge and hydrogen bond interactions mediated by the compound's carboxylic acid and amino groups. (C) 2011 Elsevier Ltd. All rights reserved.