5-(3-甲氧基苯基)-3-吡啶羧酸 | 97000-30-1

• 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
• 中文名称: 5-(3-甲氧基苯基)-3-吡啶羧酸
• 中文别名: 5-(3-甲氧基苯基)烟酸
• 英文名称: 5-(3-methoxyphenyl)nicotinic acid
• 英文别名: 5-(3-methoxyphenyl)pyridine-3-carboxylic acid
• CAS: 97000-30-1
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: ZHXBRJDPUURFHR-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±35.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 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：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险标志：
  GHS07
• 危险性描述：
  H302
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-(3-甲氧基苯基)-3-吡啶羧酸 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-[5-(3-Methoxyphenyl)pyridine-3-carbonyl]-1,3-dihydroquinoxalin-2-one
  参考文献：
  名称：

  Discovery of a new chemical series of BRD4(1) inhibitors using protein-ligand docking and structure-guided design

  摘要：

  Bromodomains are key transcriptional regulators that are thought to be druggable epigenetic targets for cancer, inflammation, diabetes and cardiovascular therapeutics. Of particular importance is the first of two bromodomains in bromodomain containing 4 protein (BRD4(1)). Protein-ligand docking in BRD4(1) was used to purchase a small, focused screening set of compounds possessing a large variety of core structures. Within this set, a small number of weak hits each contained a dihydroquinoxalinone ring system. We purchased other analogs with this ring system and further validated the new hit series and obtained improvement in binding inhibition. Limited exploration by new analog synthesis showed that the binding inhibition in a FRET assay could be improved to the low mu M level making this new core a potential hit-to-lead series. Additionally, the predicted geometries of the initial hit and an improved analog were confirmed by X-ray co-crystallography with BRD4(1). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.107
• 作为产物：
  描述：

  氯化烟碱盐酸盐 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 potassium permanganate 、 四(三苯基膦)钯 、 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.5h， 生成 5-(3-甲氧基苯基)-3-吡啶羧酸
  参考文献：
  名称：

  Synthesis and dopamine autoreceptor activity of a 5-(methylmercapto)methyl-substituted derivative of(.+-.)-3-PPP [3-(3-hydroxyphenyl)-1-propylpiperidine]

  摘要：

  In an attempt to enhance the potency of the dopamine autoreceptor agonist 3-PPP, racemic cis-3-(3-hydroxyphenyl)-5-[(methylmercapto)methyl]-N-n-propylpiperidine has been prepared in a stereoselective synthesis. NMR studies of 3 show a diequatorial conformation for the 3- and 5-substituents, which gives compound 3 an intriguing overlap with the ergoline derivative pergolide. Pharmacological testing revealed that 3, which is a 5-(methylmercapto)methyl derivative of racemic 3-PPP does not show the anticipated potency increase as a dopamine autoreceptor agonist. In vitro (inhibition of tyrosine hydroxylation) 3 and 1 have similar potency, and the in vivo potency (inhibition of GBL accelerated dopamine synthesis) of 3 is inferior to that of 1.

  DOI：

  10.1021/jm00147a046

文献信息

• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES ET À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2013139697A1

  公开（公告）日：2013-09-26

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1 ) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义明确的大环环形系统由三个不同的分子部分构成：模板A、构象调制剂B和桥梁C。由该环系统I描述的大环可通过溶液中的并行合成或组合化学，或者在固相上制造。它们被设计用来与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，对酶的抑制活性或抗菌活性。特别是，这些大环显示对第1亚型内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃肽3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。