2-(5-ethyl-1H-pyrazol-3-yl)phenol | 1234512-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(5-ethyl-1H-pyrazol-3-yl)phenol
• 英文别名: 3(5)-(2-hydroxyphenyl)-5(3)-ethylpyrazole；5(3)-(2-hydroxyphenyl)-3(5)-ethylpyrazole；H2phpzEt；2-(3-ethyl-1H-pyrazol-5-yl)phenol
• CAS: 1234512-63-0
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: QKRZILVYNJQBCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴-2-氯-3-硝基吡啶 、 2-(5-ethyl-1H-pyrazol-3-yl)phenol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以84%的产率得到10-bromo-2-ethylbenzo[f]pyrazolo[1,5-d]pyrido[3,2-b][1,4]oxazepine
  参考文献：
  名称：

  New tetracyclic 1,4-oxazepines constructed via practically simple tandem condensation strategy from readily available synthons

  摘要：

  A streamlined synthetic methodology towards novel tetracyclic 1,4-oxazepines from readily available precursors is described. The compounds, designed as more soluble version of the earlier described, poorly soluble dibenzo[bf][1,4]oxazepines, were obtained in high yields and as a single regioisomer as a result of three tandem chemical events-nucleophilic aromatic substitution, Smiles rearrangement and denitrocyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.026
• 作为产物：
  描述：

  1-(2-羟基苯基)戊烷-1,3-二酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-(5-ethyl-1H-pyrazol-3-yl)phenol
  参考文献：
  名称：

  Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus

  摘要：

  Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.

  DOI：

  10.1021/acschembio.5b00934

文献信息

• METHODS FOR USE OF SMALL MOLECULE ACTIVATORS OF HEM-Y / PROTOPORPHYRINOGEN OXIDASE (PPO)
  申请人：Vanderbilt University

  公开号：US20160213780A1

  公开（公告）日：2016-07-28

  A method for treating a microbial infection involves administering an effective amount of a compound of the formula: wherein R 1 is H, alkyl, aryl, heteroaryl, R 2 is H, halogen, alkyl, aryl, heteroaryl, R 3 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 4 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 5 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 6 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 7 is H, hydroxyl, alkoxy, alkyl, aryl, heteroaryl, amino, amino sulfonyl, acetamide, R 8 is —CR 3 , O, S, wherein R 5 and R 6 , R 7 and R 6 , R 5 and R 4 , R 4 and R 3 can cyclize forming a 3-10 member ring comprising C, O, S, and/or N optionally substituted with one or more R 3 ; and administering light therapy, such as a photodynamic therapy (PDT) light source.

  一种治疗微生物感染的方法包括给予一定量的化合物，其化学式为：其中R1为H，烷基，芳基，杂环芳基，R2为H，卤素，烷基，芳基，杂环芳基，R3为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R4为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R5为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R6为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R7为H，羟基，烷氧基，烷基，芳基，杂环芳基，氨基，氨基磺酰基，乙酰胺基，R8为—CR3，O，S，其中R5和R6，R7和R6，R5和R4，R4和R3可以环化形成一个由C，O，S和/或N组成的3-10成员环，可选地取代一个或多个R3；并且给予光疗法，例如光动力疗法（PDT）光源。
• High nuclearity manganese(iii) compounds containing phenol-pyrazole ligands: the influence of the ligand on the core geometry
  作者：Marta Viciano-Chumillas、Graham de Ruiter、Stefania Tanase、Jan M. M. Smits、René de Gelder、Ilpo Mutikainen、Urho Turpeinen、L. Jos de Jongh、Jan Reedijk

  DOI：10.1039/b924776a

  日期：——

  Three high-nuclearity manganese(III) clusters have been synthesized and characterized: [Mn8(μ4-O)4(phpzH)8(thf)4] (1), [Mn8(μ4-O)4(phpzH)4(EtOH)4]·2EtOH (2), and [Mn6(μ3-O)4(μ3-Br)2(HphpzEt)6(phpzEt)] (3). Compounds 1 and 2 contain a [Mn8(μ4-O4)(phpzH)8] core in which antiferromagnetic interactions between the manganese(III) ions are found. Compound 3 is a hexanuclear manganese(III) cluster in which weak ferromagnetic interactions appear to be operative. The formation and the stability of the cluster cores in relation to the type of phenol-pyrazole ligand and the reaction conditions are discussed.

  合成并鉴定了三种高核度锰（III）团簇：[Mn8(μ4-O)4(phpzH)8(thf)4]（1）、[Mn8(μ4-O)4(phpzH)4(EtOH)4]-2EtOH（2）和[Mn6(μ3-O)4(μ3-Br)2(HphpzEt)6(phpzEt)]（3）。化合物 1 和 2 包含一个 [Mn8(μ4-O4)(phpzH)8]核，其中的锰（III）离子之间存在反铁磁相互作用。化合物 3 是一个六核锰(III)团簇，其中似乎存在弱铁磁相互作用。本文讨论了簇核的形成和稳定性与苯酚-吡唑配体类型和反应条件的关系。
• Dibenzo[b,f]pyrazolo[1,5-d][1,4]oxazepines: Facile Construction of a Rare Heterocyclic System via Tandem Aromatic Nucleophilic Substitution-Smiles Rearrangement-Denitrocyclization
  作者：Mikhail Krasavin、Alexander Sapegin、Stanislav Kalinin、Alexey Smirnov、Mikhail Dorogov

  DOI：10.1055/s-0031-1289789

  日期：2012.8

  Condensation of 2-(1H-pyrazol-5-yl)phenols with 1-chloro-2-nitrobenzenes under basic conditions in N,N-dimethylformamide results in a tandem, atom-economical, aromatic nucleophilic substitution-Smiles rearrangement-denitrocyclization process to provide pyrazolo-fused dibenzo[b,f][1,4]oxazepines as a single regioisomer.
• A dinuclear manganese(III) and a rare pentanuclear manganese(III) compound with a phenol–pyrazole ligand
  作者：Marta Viciano-Chumillas、Stefania Tanase、Ilpo Mutikainen、Urho Turpeinen、L. Jos de Jongh、Jan Reedijk

  DOI：10.1016/j.poly.2012.03.001

  日期：2012.5

  Reacting Mn(ClO4)(2).6H(2)O and H(2)phpzEt (H(2)phpzEt = 5(3)-(2-hydroxypheny1)-3(5)-ethylpyrazole) in methanol in the presence of sodium hydroxide yields the compound [Mn-2(HphpzEt)(4)(H2O)(2)](ClO4)(2) (1). The pentanuclear [Mn-5(mu(3)-O)(2)(HphpzEt)(3)(PhpzEt)(3)(OCH3)(HOCH3)(2)(O2CPh)] (2) is obtained when performing a similar reaction with Mn(O2CPh)(2).2H(2)O. Compound 1 consists of a symmetric dinuclear manganese(III) cationic unit, [Mn-2(HphpzEt)(4)(H2O2](2+) with two non-coordinated perchlorate anions. Compound 2 is a rare pentanuclear complex containing all the manganese ions in the oxidation state III and it also has mu(3)-oxido ligands. Temperature- and field-dependent magnetization studies indicate dominant antiferromagnetic interactions between the manganese(III) ions in both compounds. (C) 2012 Elsevier Ltd. All rights reserved.
• COMPOSITIONS AND METHODS FOR TREATING MICROBIAL INFECTIONS
  申请人：Vanderbilt University

  公开号：US20170246149A1

  公开（公告）日：2017-08-31

  Embodiments of the presently-disclosed subject matter include activators of HssRS that induce endogenous heme biosynthesis by perturbing central metabolism. These molecules are toxic to fermenting S. aureus, including clinically relevant small colony variants (SCVs). The utility of targeting fermenting bacteria is exemplified by the fact that this compound prevents the emergence of antibiotic resistance, enhances phagocyte killing, and reduces S. aureus pathogenesis. This small molecule is a powerful tool not only for studying bacterial heme biosynthesis and central metabolism, but also establishes targeting of fermentation as a viable antibacterial strategy.