3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxaldehyde | 495417-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxaldehyde
• 英文别名: 3-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carbaldehyde
• CAS: 495417-39-5
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: QLOBYXLIBXPDMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxaldehyde 在 吡啶 、 selenium(IV) oxide 作用下， 反应 3.5h， 以90.3 mg的产率得到
  参考文献：
  名称：

  一种用作抗流感病毒的双羰基类似物

  摘要：

  本文阐述了一种结构通式为（I）的一类化合物，或其在药学上可接受的盐，其中异恶唑5元杂环为具有邻近‑Ar取代基或邻近‑Ar取代基的连接点5元异恶唑杂环；Ar为芳基或者杂芳基；R为‑CH或者‑N；n为链长0‑1个碳原子；X为‑F,‑Cl,‑Br,‑CF3,‑CF2H；Y为‑NO2，‑Cl,‑Br,‑CHO,‑CN；Z为‑CH或者‑N；W为‑CH或者‑N。本文还提供了制备式I化合物的方法，和式I化合物作为药物和在预防和抗流感病毒中的用途。

  公开号：

  CN107056762B
• 作为产物：
  描述：

  乙基3-(2-甲氧基苯基)-5-甲基-1,2-恶唑-4-羧酸酯 在 lithium aluminium tetrahydride 、 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxaldehyde
  参考文献：
  名称：

  Unique Structure−Activity Relationship for 4-Isoxazolyl-1,4-dihydropyridines

  摘要：

  A series of 4-isoxazolyl-1,4-dihydropyridines (IDs) were prepared and characterized, and their interaction with the calcium channel was studied by patch clamp analysis. The structure-ctivity relationship (SAR) that emerges is distinct from the 4-aryldihydropyridines (DHPs), and affinity increases dramatically at higher holding potentials. Thus, among the 3'-arylisoxazolyl analogues p-Br > p-C much greater than p-F, and p-Cl > m-Cl > o-Cl much greater than o-MeO. Four of the analogues were examined by single-crystal X-ray diffractometry, and all were found to adopt an O-exo conformation in the solid state. The calculated barrier to rotation, however, suggests that rotation about the juncture between the heterocyclic rings is plausible under physiological conditions. A variable-temperature NMR study confirmed the computation. With Striessnig's computational sequence homologation procedure, a working hypothesis was derived from the data that explains the unique SAR for IDs.

  DOI：

  10.1021/jm020354w

文献信息

• [EN] NOVEL PIPERAZINE ANALOGS AS BROAD-SPECTRUM INFLUENZA ANTIVIRALS<br/>[FR] NOUVEAUX ANALOGUES DE LA PIPÉRAZINE EN TANT QU'ANTIVIRAUX ANTIGRIPPAUX À LARGE SPECTRE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012033736A1

  公开（公告）日：2012-03-15

  A compound of Formula (I) is set forth, including pharmaceutically acceptable salts thereof, wherein Het is a 5 or 6-membered heterocycle with -N, -O, or -S adjacent to the -Ar substituent or adjacent to the point of attachment for the -Ar substituent; Ar is aryl or heteroaryl; R is -CH3, -CH2F, or -CH=CH2; W is -NO2, -Cl, -Br, -CHO, -CH=CH2, or -CN; X is -Cl, -CH3, or -CN; Y is -CH or -N; and Z is C1-C6 alkyl, C3-C6 cycloalkyl, substituted aryl, substituted heteroaryl, OR1, or NHR1, wherein R1 is selected from the group of H, aryl, heteroaryl, C1-C6 alkyl and C3-C6 cycloalkyl. This compound is useful in compositions for the prevention and treatment of influenza virus.

  根据公式（I），提供一种化合物，包括其药用可接受的盐，其中Het是一个带有-N，-O或-S的5或6元杂环，与-Ar取代基相邻或与-Ar取代基的连接点相邻；Ar是芳基或杂芳基；R是-CH3，-CH2F或-CH=CH2；W是-NO2，-Cl，-Br，-CHO，-CH=CH2或-CN；X是-Cl，-CH3或-CN；Y是-CH或-N；Z是C1-C6烷基，C3-C6环烷基，取代芳基，取代杂芳基，OR1或NHR1，其中R1选择自H，芳基，杂芳基，C1-C6烷基和C3-C6环烷基组。该化合物在预防和治疗流感病毒的组合物中有用。
• Unique Structure−Activity Relationship for 4-Isoxazolyl-1,4-dihydropyridines
  作者：Gerald W. Zamponi、Stephanie C. Stotz、Richard J. Staples、Tina M. Andro、Jared K. Nelson、Victoria Hulubei、Alex Blumenfeld、Nicholas R. Natale

  DOI：10.1021/jm020354w

  日期：2003.1.1

  A series of 4-isoxazolyl-1,4-dihydropyridines (IDs) were prepared and characterized, and their interaction with the calcium channel was studied by patch clamp analysis. The structure-ctivity relationship (SAR) that emerges is distinct from the 4-aryldihydropyridines (DHPs), and affinity increases dramatically at higher holding potentials. Thus, among the 3'-arylisoxazolyl analogues p-Br > p-C much greater than p-F, and p-Cl > m-Cl > o-Cl much greater than o-MeO. Four of the analogues were examined by single-crystal X-ray diffractometry, and all were found to adopt an O-exo conformation in the solid state. The calculated barrier to rotation, however, suggests that rotation about the juncture between the heterocyclic rings is plausible under physiological conditions. A variable-temperature NMR study confirmed the computation. With Striessnig's computational sequence homologation procedure, a working hypothesis was derived from the data that explains the unique SAR for IDs.
• 一种用作抗流感病毒的双羰基类似物
  申请人：四川百利药业有限责任公司

  公开号：CN107056762B

  公开（公告）日：2020-08-28

  本文阐述了一种结构通式为（I）的一类化合物，或其在药学上可接受的盐，其中异恶唑5元杂环为具有邻近‑Ar取代基或邻近‑Ar取代基的连接点5元异恶唑杂环；Ar为芳基或者杂芳基；R为‑CH或者‑N；n为链长0‑1个碳原子；X为‑F,‑Cl,‑Br,‑CF3,‑CF2H；Y为‑NO2，‑Cl,‑Br,‑CHO,‑CN；Z为‑CH或者‑N；W为‑CH或者‑N。本文还提供了制备式I化合物的方法，和式I化合物作为药物和在预防和抗流感病毒中的用途。