2,2'-bipyridine-5,6'-dicarboxylic acid | 1272666-47-3

• 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: 2,2'-bipyridine-5,6'-dicarboxylic acid
• 英文别名: 6-(5-Carboxypyridin-2-yl)pyridine-2-carboxylic acid
• CAS: 1272666-47-3
• 化学式: C₁₂H₈N₂O₄
• 分子量: 244.207
• InChiKey: DLLMWDJOFJHBEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  烟酸甲酯 在 tri-tert-butylphosphonium tetrafluoroborate 、 palladium diacetate 、 potassium carbonate 、 间氯过氧苯甲酸 、 potassium hydroxide 、 三氯化磷 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 48.0h， 生成 2,2'-bipyridine-5,6'-dicarboxylic acid
  参考文献：
  名称：

  Selective inhibition of prolyl 4-hydroxylases by bipyridinedicarboxylates

  摘要：

  Collagen is the most abundant protein in animals. A variety of indications are associated with the overproduction of collagen, including fibrotic diseases and cancer metastasis. The stability of collagen relies on the posttranslational modification of proline residues to form (2S,4R)-4-hydroxyproline. This modification is catalyzed by collagen prolyl 4-hydroxylases (CP4Hs), which are Fe(II)- and alpha-ketoglutarate (AKG)-dependent dioxygenases located in the lumen of the endoplasmic reticulum. Human CP4Hs are validated targets for treatment of both fibrotic diseases and metastatic breast cancer. Herein, we report on 2,2'-bipyridinedicarboxylates as inhibitors of a human CP4H. Although most 2,2'-bipyridinedicarboxylates are capable of inhibition via iron sequestration, the 4,5'-and 5,5'-dicarboxylates were found to be potent competitive inhibitors of CP4H, and the 5,5'-dicarboxylate was selective in its inhibitory activity. Our findings clarify a strategy for developing CP4H inhibitors of clinical utility. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.003

文献信息

• A simple and environmentally benign synthesis of polypyridine-polycarboxylic acids
  作者：Niamh R. Kelly、Sandrine Goetz、Chris S. Hawes、Paul E. Kruger

  DOI：10.1016/j.tetlet.2010.12.074

  日期：2011.3

  An oxidation method using dilute nitric acid solutions under solvothermal conditions has been developed to synthesise a series of polypyridine-polycarboxylic acids. It has been successfully applied to a range of methyl substituted polypyridines including symmetrical and asymmetrical 2,2'-bipyridines; 2,2':6',2 ''-terpyridines and; 2,2':6',2 '':6 '',2'''-tetra-pyridines and yields crystalline polypyridine-polycarboxylic acids in a single step. Simple product recovery through filtration yields a recyclable filtrate. More forcing conditions led to demethylation of the polypyridine ligand most probably via decarboxylation. This simple approach avoids potentially harmful metal-based oxidants and negates any issues associated with the disposal of their resultant (hazardous) waste. (C) 2010 Elsevier Ltd. All rights reserved.
• CYCLIC PEPTIDES MULTIMERS TARGETING ALPHA-4-BETA-7 INTEGRIN
  申请人：Zealand Pharma A/S

  公开号：US20210324007A1

  公开（公告）日：2021-10-21

  There is described herein, multimers comprising plurality of compounds covalently linked together, the compounds independently being of formula (I).
• US7666979B2
  申请人：——

  公开号：US7666979B2

  公开（公告）日：2010-02-23
• Selective inhibition of prolyl 4-hydroxylases by bipyridinedicarboxylates
  作者：James D. Vasta、Ronald T. Raines

  DOI：10.1016/j.bmc.2015.05.003

  日期：2015.7

  Collagen is the most abundant protein in animals. A variety of indications are associated with the overproduction of collagen, including fibrotic diseases and cancer metastasis. The stability of collagen relies on the posttranslational modification of proline residues to form (2S,4R)-4-hydroxyproline. This modification is catalyzed by collagen prolyl 4-hydroxylases (CP4Hs), which are Fe(II)- and alpha-ketoglutarate (AKG)-dependent dioxygenases located in the lumen of the endoplasmic reticulum. Human CP4Hs are validated targets for treatment of both fibrotic diseases and metastatic breast cancer. Herein, we report on 2,2'-bipyridinedicarboxylates as inhibitors of a human CP4H. Although most 2,2'-bipyridinedicarboxylates are capable of inhibition via iron sequestration, the 4,5'-and 5,5'-dicarboxylates were found to be potent competitive inhibitors of CP4H, and the 5,5'-dicarboxylate was selective in its inhibitory activity. Our findings clarify a strategy for developing CP4H inhibitors of clinical utility. (C) 2015 Elsevier Ltd. All rights reserved.