(5-phenylpyridin-2-yl)acetic acid | 897016-92-1

• 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: (5-phenylpyridin-2-yl)acetic acid
• 英文别名: 2-(5-phenylpyridin-2-yl)acetic acid
• CAS: 897016-92-1
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: GJUCYUUYZYZDBM-UHFFFAOYSA-N

物化性质

• 沸点：
  399.7±30.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-phenylpyridin-2-yl)acetic acid 在 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-hydroxy-(5-phenylpyridine-2-yl)acetamide
  参考文献：
  名称：

  Inhibition of 1-Deoxy-d-Xylulose-5-Phosphate Reductoisomerase by Lipophilic Phosphonates: SAR, QSAR, and Crystallographic Studies

  摘要：

  1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) is a novel target for developing new antibacterial (including antituberculosis) and antimalaria drugs. Forty-one lipophilic phosphonates, representing a new class of DXR inhibitors, were synthesized, among which 5-phenylpyridin-2-ylmethylphosphonic acid possesses the most activity against E. coli DXR (EcDXR) with a K-i of 420 nM. Structure-activity relationships (SAR) are discussed, which can be rationalized using our EcDXR:inhibitor structures, and a predictive quantitative SAR (QSAR) model is also developed. Since inhibition studies of DXR from Mycobacterium tuberculosis (MtDXR) have not been performed well, 48 EcDXR inhibitors with a broad chemical diversity were found, however, to generally exhibit considerably reduced activity against MtDXR. The crystal structure of a, MtDXR:inhibitor complex reveals the flexible loop containing the residues 198-208 has no strong interactions with the 3,4-dichlorophenyl group of the inhibitor, representing a structural basis for the reduced activity. Overall, these results provide implications in the future design and development of potent DXR inhibitors.

  DOI：

  10.1021/jm200363d
• 作为产物：
  描述：

  2-(5-溴吡啶-2-基)乙酸甲酯 在 甲醇 、 四(三苯基膦)钯 、 sodium carbonate 、 potassium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 生成 (5-phenylpyridin-2-yl)acetic acid
  参考文献：
  名称：

  Inhibition of 1-Deoxy-d-Xylulose-5-Phosphate Reductoisomerase by Lipophilic Phosphonates: SAR, QSAR, and Crystallographic Studies

  摘要：

  1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) is a novel target for developing new antibacterial (including antituberculosis) and antimalaria drugs. Forty-one lipophilic phosphonates, representing a new class of DXR inhibitors, were synthesized, among which 5-phenylpyridin-2-ylmethylphosphonic acid possesses the most activity against E. coli DXR (EcDXR) with a K-i of 420 nM. Structure-activity relationships (SAR) are discussed, which can be rationalized using our EcDXR:inhibitor structures, and a predictive quantitative SAR (QSAR) model is also developed. Since inhibition studies of DXR from Mycobacterium tuberculosis (MtDXR) have not been performed well, 48 EcDXR inhibitors with a broad chemical diversity were found, however, to generally exhibit considerably reduced activity against MtDXR. The crystal structure of a, MtDXR:inhibitor complex reveals the flexible loop containing the residues 198-208 has no strong interactions with the 3,4-dichlorophenyl group of the inhibitor, representing a structural basis for the reduced activity. Overall, these results provide implications in the future design and development of potent DXR inhibitors.

  DOI：

  10.1021/jm200363d

文献信息

• Compositions and methods of treating cell proliferation disorders
  申请人：Hangauer G. David

  公开号：US20060160800A1

  公开（公告）日：2006-07-20

  The invention relates to compounds and methods for treating cell proliferation disorders.

  这项发明涉及化合物和治疗细胞增殖紊乱的方法。
• [EN] NOVEL DXR INHIBITORS FOR ANTIMICROBIAL THERAPY<br/>[FR] NOUVEAUX INHIBITEURS DE DXR POUR THÉRAPIE ANTIMICROBIENNE
  申请人：BAYLOR COLLEGE MEDICINE

  公开号：WO2011046920A1

  公开（公告）日：2011-04-21

  The present invention generally concerns particular methods and compositions for antimicrobial therapy. In particuarl embodiments, the compositions target DXR. In specific embodiments, the compositions are electron-deficient heterocyclic rings.

  本发明一般涉及特定的抗微生物治疗方法和组合物。在特定实施例中，这些组合物以DXR为靶点。在具体实施例中，这些组合物是电子亏缺的杂环环。
• Biaryl compositions and methods for modulating a kinase cascade
  申请人：Hangauer G. David

  公开号：US20070015752A1

  公开（公告）日：2007-01-18

  The invention relates to compounds and methods for modulating one or more components of a kinase cascade.

  该发明涉及化合物和方法，用于调节激酶级联中的一个或多个组分。
• Compositions and Methods of Treating Cell Proliferation Disorders
  申请人：Hangauer, JR. David G.

  公开号：US20110065705A1

  公开（公告）日：2011-03-17

  The invention relates to compounds and methods for treating cell proliferation disorders.

  本发明涉及化合物和治疗细胞增殖紊乱的方法。
• Biaryl Compositions and Methods for Modulating a Kinase Cascade
  申请人：Hangauer, JR. David G.

  公开号：US20120270874A1

  公开（公告）日：2012-10-25

  The invention relates to compounds and methods for modulating one or more components of a kinase cascade. The invention relates to compounds of the formula I: or a pharmaceutically acceptable salt thereof. The compounds of the invention are useful for methods of protecting against or treating hearing loss, osteoporosis, cell proliferative disorders, obesity, diabetes, eye disease, stroke, atherosclerosis, neuropathic pain or hepatitis B.

  该发明涉及化合物和方法，用于调节激酶级联的一个或多个组分。该发明涉及公式I的化合物：或其药学上可接受的盐。该发明的化合物对于预防或治疗听力损失、骨质疏松症、细胞增殖性疾病、肥胖症、糖尿病、眼病、中风、动脉粥样硬化、神经病性疼痛或乙型肝炎的方法是有用的。