3-bromo-5-(hydroxynaphthalen-1-ylmethyl)-4-methoxy-5H-furan-2-one | 847248-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-bromo-5-(hydroxynaphthalen-1-ylmethyl)-4-methoxy-5H-furan-2-one
• 英文别名: 4-bromo-2-[hydroxy(naphthalen-1-yl)methyl]-3-methoxy-2H-furan-5-one
• CAS: 847248-59-3
• 化学式: C₁₆H₁₃BrO₄
• 分子量: 349.181
• InChiKey: SCHYXFRNJXXPEB-UHFFFAOYSA-N

物化性质

• 沸点：
  582.5±50.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-5-(hydroxynaphthalen-1-ylmethyl)-4-methoxy-5H-furan-2-one 在 potassium phosphate 、 四(三苯基膦)钯 、 TEA 、 甲基磺酰氯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.58h， 生成 3-(4-chlorophenyl)-4-methoxy-5-[(Z)-1-naphthylmethyl-idene]furan-2(5H)-one
  参考文献：
  名称：

  Pulvinones as bacterial cell wall biosynthesis inhibitors

  摘要：

  Pulvin ones were synthesized (> 180) in arrays and evaluated as inhibitors of early stage cell wall biosynthesis enzymes MurA-MurD. Several pulvinones inhibited Mur enzymes with IC50's in the 1-10 mu g/mL range and demonstrated antibacterial activity against Gram-positive bacteria including methicillin-resistant Staphyloccus aureus, vancomycin-resistant Enterococcus faecalis, and penicillin-resistant Streptococcus pneumoniae. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.021
• 作为产物：
  描述：

  4-甲氧基-呋喃酮 在 溴 、 lithium cyclohexylisopropylamide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 3-bromo-5-(hydroxynaphthalen-1-ylmethyl)-4-methoxy-5H-furan-2-one
  参考文献：
  名称：

  Pulvinones as bacterial cell wall biosynthesis inhibitors

  摘要：

  Pulvin ones were synthesized (> 180) in arrays and evaluated as inhibitors of early stage cell wall biosynthesis enzymes MurA-MurD. Several pulvinones inhibited Mur enzymes with IC50's in the 1-10 mu g/mL range and demonstrated antibacterial activity against Gram-positive bacteria including methicillin-resistant Staphyloccus aureus, vancomycin-resistant Enterococcus faecalis, and penicillin-resistant Streptococcus pneumoniae. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.021

文献信息

• 3-Aryl-4-Hydroxyfuranone compounds and the human and animal health use thereof
  申请人：Caufield Eugene Craig

  公开号：US20050054721A1

  公开（公告）日：2005-03-10

  The present invention provides a compound of formula I and the use thereof for the inhibition of bacterial cell wall biosynthesis and for the therapeutic treatment of bacterial infection or disease in a patient in need thereof. The present invention also provides the use of the formula I compound for the control of ecto- or endoparasites in homeothermic animals.

  本发明提供了一种I式化合物及其用于抑制细菌细胞壁生物合成并用于治疗患有细菌感染或疾病的患者的用途。本发明还提供了使用I式化合物用于控制恒温动物体内或体外寄生虫的方法。
• 3-ARYL-4-HYDROXYFURANONE COMPOUNDS AND THE HUMAN AND ANIMAL HEALTH USE THEREOF
  申请人：Caufield Craig Eugene

  公开号：US20090036439A1

  公开（公告）日：2009-02-05

  The present invention provides a compound of formula I and the use thereof for the inhibition of bacterial cell wall biosynthesis and for the therapeutic treatment of bacterial infection or disease in a patient in need thereof. The present invention also provides the use of the formula I compound for the control of ecto- or endoparasites in homeothermic animals.

  本发明提供了一种I式化合物及其用于抑制细菌细胞壁生物合成和治疗患有细菌感染或疾病的患者的用途。本发明还提供了使用I式化合物控制恒温动物的外寄生虫或内寄生虫的用途。
• 3-aryl-4-hydroxyfuranone compounds and the human and animal health use thereof
  申请人：Wyeth

  公开号：US07495027B2

  公开（公告）日：2009-02-24

  The present invention provides a compound of formula I and the use thereof for the inhibition of bacterial cell wall biosynthesis and for the therapeutic treatment of bacterial infection or disease in a patient in need thereof. The present invention also provides the use of the formula I compound for the control of ecto- or endoparasites in homeothermic animals

  本发明提供了一种I式化合物及其用于抑制细菌细胞壁生物合成和治疗需要治疗细菌感染或疾病的患者的用途。本发明还提供了使用I式化合物控制恒温动物体内或体外寄生虫的用途。
• 3-ARYL-4-HYDROXYFURANONE COMPOUNDS AND PHARMACEUTICAL AND VETERINARY COMPOSITIONS CONTAINING THEM
  申请人：Wyeth

  公开号：EP1654244A1

  公开（公告）日：2006-05-10
• US7495027B2
  申请人：——

  公开号：US7495027B2

  公开（公告）日：2009-02-24