2-n-Butanoyl-5-chlorophenol | 4133-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-n-Butanoyl-5-chlorophenol
• 英文别名: 1-(4-chloro-hydroxyphenol)butane-1-one；2-Butytryl-5-chlorphenol；2'-Hydroxy-4'-chlorbutyrophenon；4-Chlor-2-hydroxy-butyrophenon；1-(4-chloro-2-hydroxy-phenyl)-butan-1-one；1-(4-Chlor-2-hydroxy-phenyl)-butan-1-on；1-(4-Chloro-2-hydroxyphenyl)-1-butanone；1-(4-chloro-2-hydroxyphenyl)butan-1-one
• CAS: 4133-95-3
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: NJFFCTTYNCSFBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-n-Butanoyl-5-chlorophenol 在 四甲基乙二胺 、 potassium tert-butylate 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (5-chloro-2-(methylenebutyryl)phenoxy)acetate
  参考文献：
  名称：

  A New Lead for Nonpeptidic Active-Site-Directed Inhibitors of the Severe Acute Respiratory Syndrome Coronavirus Main Protease Discovered by a Combination of Screening and Docking Methods

  摘要：

  The coronavirus main protease, M-pro, is considered to be a major target for drugs suitable for combating coronavirus infections including severe acute respiratory syndrome (SARS). An HPLC-based screening of electrophilic compounds that was performed to identify potential M-pro inhibitors revealed etacrynic acid tert-butylamide (6a) as an effective nonpeptidic inhibitor. Docking studies suggested a binding mode in which the phenyl ring acts as a spacer bridging the inhibitor's activated double bond and its hydrophobic tert-butyl moiety. The latter is supposed to fit into the S4 pocket of the target protease. Furthermore, these studies revealed etacrynic acid amide (6b) as a promising lead for nonpeptidic active-site-directed M-pro inhibitors. In a fluorimetric enzyme assay using a novel fluorescence resonance energy transfer (FRET) pair labeled substrate, compound 6b showed a K-i value of 35.3 mu M. Since the novel lead compound does not target the S1', S1, and S2 subsites of the enzyme's substrate-binding pockets, there is room for improvement that underlines the lead character of compound 6b.

  DOI：

  10.1021/jm0501782
• 作为产物：
  描述：

  m-Chlorophenylbutyrat 在 三氯化铝 作用下， 生成 2-n-Butanoyl-5-chlorophenol
  参考文献：
  名称：

  Sen; Tiwari, Journal of the Indian Chemical Society, 1952, vol. 29, p. 419,421,423

  摘要：

  DOI：

文献信息

• [EN] METHOD FOR TREATING NEUROPATHIC PAIN<br/>[FR] PROCEDE DE TRAITEMENT DE DOULEURS NEVROPATHIQUES
  申请人：ELI LILLY AND COMPANY

  公开号：WO1999009979A1

  公开（公告）日：1999-03-04

  (EN) The present invention provides a method for treating neuropathic pain comprising administering an analgesic dosage of a compound of formula (I) to an animal in need of such treatment certain phenyl oxazoles or phenyl thiazoles.(FR) La présente invention concerne un procédé permettant de traiter les douleurs névropathiques. Ce procédé consiste à administrer à un animal devant être ainsi traité une dose analgésique d'un composé selon la formule (I) comprenant certains phényl oxazoles ou phényl thiazoles.

  本发明提供了一种治疗神经病痛的方法，包括向需要此类治疗的动物施用公式（I）化合物的镇痛剂剂量，其中该化合物包括某些苯基噁唑或苯基噻唑。
• PAWAR, R. A.;BORSE, A. P., J. INDIAN CHEM. SOC., 66,(1989) N, C. 203-205
  作者：PAWAR, R. A.、BORSE, A. P.

  DOI：——

  日期：——
• [EN] CYCLIC AND BICYCLIC DIAMINO HISTAMINE-3 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR D'HISTAMINE-3 DIAMINO CYCLIQUES ET BICYCLIQUES
  申请人：ABBOTT LAB

  公开号：WO2001066534A2

  公开（公告）日：2001-09-13

  Compounds of formula (I), compounds of formula (II), compounds of formula (III), and compounds of formula (IV), or pharmaceutically acceptable salts thereof are useful as H3 receptor antagonists. Processes to make the compounds and methods of treatment using the compounds are also disclosed.
• Pawar, R. A.; Gogte, V. N., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 10, p. 921 - 923
  作者：Pawar, R. A.、Gogte, V. N.

  DOI：——

  日期：——
• A New Lead for Nonpeptidic Active-Site-Directed Inhibitors of the Severe Acute Respiratory Syndrome Coronavirus Main Protease Discovered by a Combination of Screening and Docking Methods
  作者：Ulrich Kaeppler、Nikolaus Stiefl、Markus Schiller、Radim Vicik、Alexander Breuning、Werner Schmitz、Daniel Rupprecht、Carsten Schmuck、Knut Baumann、John Ziebuhr、Tanja Schirmeister

  DOI：10.1021/jm0501782

  日期：2005.11.1

  The coronavirus main protease, M-pro, is considered to be a major target for drugs suitable for combating coronavirus infections including severe acute respiratory syndrome (SARS). An HPLC-based screening of electrophilic compounds that was performed to identify potential M-pro inhibitors revealed etacrynic acid tert-butylamide (6a) as an effective nonpeptidic inhibitor. Docking studies suggested a binding mode in which the phenyl ring acts as a spacer bridging the inhibitor's activated double bond and its hydrophobic tert-butyl moiety. The latter is supposed to fit into the S4 pocket of the target protease. Furthermore, these studies revealed etacrynic acid amide (6b) as a promising lead for nonpeptidic active-site-directed M-pro inhibitors. In a fluorimetric enzyme assay using a novel fluorescence resonance energy transfer (FRET) pair labeled substrate, compound 6b showed a K-i value of 35.3 mu M. Since the novel lead compound does not target the S1', S1, and S2 subsites of the enzyme's substrate-binding pockets, there is room for improvement that underlines the lead character of compound 6b.