5-(2,5-二甲基-吡咯-1-基)-2-羟基-苯甲酸 | 313701-92-7

• 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-(2,5-二甲基-吡咯-1-基)-2-羟基-苯甲酸
• 英文名称: N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrrole
• 英文别名: LDN-0062564；A12；5-(2,5-Dimethyl-pyrrol-1-yl)-2-hydroxy-benzoic acid；5-(2,5-dimethylpyrrol-1-yl)-2-hydroxybenzoic acid
• CAS: 313701-92-7
• 化学式: C₁₃H₁₃NO₃
• mdl: MFCD01125266
• 分子量: 231.251
• InChiKey: LBDOGIZEEBHJSE-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  429.7±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  62.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5-(2,5-二甲基-吡咯-1-基)-2-羟基-苯甲酸 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 tert-butyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)-4′-formylbiphenyl-2-carboxylate
  参考文献：
  名称：

  An effective conjugation strategy for designing short peptide-based HIV-1 fusion inhibitors

  摘要：

  我们为设计基于短肽的HIV-1融合抑制剂提供了一种有效的共轭策略。

  DOI：

  10.1039/c6ob01334a
• 作为产物：
  描述：

  5-氨基水杨酸 、 2,5-己二酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 5-(2,5-二甲基-吡咯-1-基)-2-羟基-苯甲酸
  参考文献：
  名称：

  An effective conjugation strategy for designing short peptide-based HIV-1 fusion inhibitors

  摘要：

  我们为设计基于短肽的HIV-1融合抑制剂提供了一种有效的共轭策略。

  DOI：

  10.1039/c6ob01334a

文献信息

• Small molecule fusion inhibitors: Design, synthesis and biological evaluation of (Z)-3-(5-(3-benzyl-4-oxo-2-thioxothiazolidinylidene)methyl)-N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrroles and related derivatives targeting HIV-1 gp41
  作者：Xiao-Yang He、Lu Lu、Jiayin Qiu、Peng Zou、Fei Yu、Xing-Kai Jiang、Lin Li、Shibo Jiang、Shuwen Liu、Lan Xie

  DOI：10.1016/j.bmc.2013.04.046

  日期：2013.12

  By a scaffold elongation strategy, a series of (Z)-3-(5-(3-benzyl-4-oxo-2-thioxothiazolidinylidene)methyl)-N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrroles and related derivatives with a linear multi-aromatic-ring skeleton were designed, synthesized, and evaluated in HIV-1 gp41 and cellular assays. Among them, the most active compounds, 12e, 12g, and 12k with a one-carbon linker (n = 1) between the

  通过支架伸长策略，一系列的（Z）-3-（5-（3-苄基-4-氧代-2-硫代噻唑并亚吡啶基亚甲基）甲基）-N-（3-羧基-4-羟基）苯基-2,5设计，合成并在HIV-1 gp41和细胞分析中评估了具有线性多芳族环骨架的-二甲基吡咯和相关衍生物。其中，活性最高的化合物12e，12g和12k 在若丹宁（C）和苯基（D）环之间具有一个碳原子的连接基（n = 1），表现出非常有希望的抑制效能，IC 50值为1.8– 2.6μM和EC 50值分别针对MT-2细胞中gp41 6-HB的形成和HIV-1复制的0.3-1.5μM的值。此外，它们对T20敏感和耐药菌株几乎同样有效。相关的SAR研究和分子建模结果为进一步开发针对HIV-1 gp41的新型非肽小分子融合抑制剂提供了潜力。
• Design, Synthesis, and Biological Evaluation of <i>N</i>-Carboxyphenylpyrrole Derivatives as Potent HIV Fusion Inhibitors Targeting gp41
  作者：Kun Liu、Hong Lu、Ling Hou、Zhi Qi、Cátia Teixeira、Florent Barbault、Bo-Tao Fan、Shuwen Liu、Shibo Jiang、Lan Xie

  DOI：10.1021/jm800869t

  日期：2008.12.25

  On the basis of the structures of small-molecule hits targeting the HIV-1 gp41, N-(4-carboxy-3-hydi-oxy)plieiiyl-2,5-dimethylpyl-role (2, NB-2), and N-(3-carboxy-4-chloro)phenylpyrrole (A(1), NB-64), 42 N-carboxyphenylpyrrole derivatives in two categories (A and B series) were designed and synthesized. We found that I I compounds exhibited promising anti-HIV-1 activity at micromolar level and their antiviral activity was correlated with their inhibitory activity on gp41 six-helix bundle formation, suggesting that these compounds block HIV fusion and entry by disrupting gp41 core formation. The structure-activity relationship and molecular docking analysis revealed that the carboxyl group Could interact with either Arg579 or Lys574 to form salt bridges and two methyl groups on the pyrrole ring were favorable for interaction with the residues in gp41 pocket. The most active compound, N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrrole (A(12)), partially occupied the deep hydrophobic pocket, suggesting that enlarging the molecular size of A(12) could improve its binding affinity and anti-HIV-1 activity for further development as a small-molecule HIV fusion and entry inhibitor.
• Structure-based design, synthesis and biological evaluation of new N-carboxyphenylpyrrole derivatives as HIV fusion inhibitors targeting gp41
  作者：Yong Wang、Hong Lu、Qiang Zhu、Shibo Jiang、Yun Liao

  DOI：10.1016/j.bmcl.2009.10.139

  日期：2010.1

  A new series of N-carboxyphenylpyrrole ligands were designed using GeometryFit based on an X-ray crystal structure of gp41. The synthesized ligands showed significant inhibitory activities against HIV gp41 6-helix bundle formation, HIV-1 mediated cell-cell fusion and HIV-1 replication. (C) 2009 Elsevier Ltd. All rights reserved.
• INHIBITORS OF PYRUVATE KINASE AND METHODS OF TREATING DISEASE
  申请人：Beth Israel Deaconess Medical Center

  公开号：EP2054058B1

  公开（公告）日：2016-11-09
• EPH RECEPTOR LIGANDS AND METHODS OF USE
  申请人：Pasquale Elena B.

  公开号：US20100256214A1

  公开（公告）日：2010-10-07

  Disclosed are methods and compositions relating to binder, modulators and inhibitors of EphA4 and EphA2.