8-hydroxy-2-methylnaphtho[2,3-b]furan-4,9-dione | 196613-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 8-hydroxy-2-methylnaphtho[2,3-b]furan-4,9-dione
• 英文别名: Naphtho[2,3-b]furan-4,9-dione, 8-hydroxy-2-methyl-；8-hydroxy-2-methylbenzo[f][1]benzofuran-4,9-dione
• CAS: 196613-60-2
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: XEAPSWYMKGIIEX-UHFFFAOYSA-N

物化性质

• 沸点：
  435.8±45.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,8-dihydroxynaphthalene-1,2-dione 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 2.5h， 生成 8-hydroxy-2-methylnaphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  Short-Step Synthesis of 1,3-Disubstituted Naphtho[2,3-c]furan-4,9-dione and Naphtho[2,3-b]furan-4,9-dione by the Friedel-Crafts Reaction

  摘要：

  1,3-Dialkylnaphtho[2,3-c] furan-4,9-diones were obtained by the Friedel-Crafts reaction of phthalic anhydride with 2,5-dialkylfurans. The reaction of phthalic anhydride with 2-acetyl-5-methylfuran, instead of 2,5-dialkylfurans, produced 2-methylnaphtho[2,3-b] furan-4,9-dione. The application of this method to the synthesis of 8-hydroxynaphtho [2, 3-b] furan-4, 9-dione [isodiodantunezone] is also described.

  DOI：

  10.3987/com-98-8172

文献信息

• Antimicrobial Activity of Novel Furanonaphthoquinone Analogs
  作者：Kumiko Nagata、Kei-Ichi Hirai、Junko Koyama、Yasunao Wada、Toshihide Tamura

  DOI：10.1128/aac.42.3.700

  日期：1998.3

  Analogs of furanonaphthoquinone (FNQ) from Tecoma ipe Mart had MICs ranging from 1.56 to 25 μg/ml against gram-positive bacteria. FNQ showed significantly lower MICs against methicillin-resistant Staphylococcus aureus than against methicillin-sensitive S. aureus . FNQ inhibited Helicobacter pylori with an MIC of 0.1 μg/ml. Fungi, including pathogenic species, were sensitive to FNQ with MICs similar to those of amphotericin B.

  从Tecoma ipe Mart中提取的呋喃萘醌（FNQ）类似物对革兰氏阳性细菌的最小抑菌浓度（MIC）范围为1.56至25 μg/ml。FNQ对甲氧西林耐药的金黄色葡萄球菌比对甲氧西林敏感的金黄色葡萄球菌的MIC显著降低。FNQ以0.1 μg/ml的MIC抑制幽门螺杆菌。真菌，包括致病菌种，对FNQ敏感，其MIC类似于两性霉素B。

• Anti-drug resistant strain agents and antichlamydia agents
  申请人：Japan Science and Technology Corporation

  公开号：US06395773B1

  公开（公告）日：2002-05-28

  In order to provide antibacterial agents for drug-resistant bacteria and anti-Chlamydia agents, the furanonaphthoquinone derivative represented by the following formula (1): wherein each R may be the same or different, representing any one of the following (a) to (e): (wherein R′ is a hydrogen atom, alkyl group, hydroxyalkyl group, or alkoxyalkyl group), or two mutually adjacent Rs may be bonded via an oxygen atom to form a heterocyclic ring is used as the effective component.

  为了提供对抗耐药细菌和抗沙眼衣原体的抗菌剂，使用以下式子（1）所代表的呋喃萘醌衍生物：其中每个R可以相同或不同，代表以下任意一种（a）至（e）中的任意一种：（其中R'是氢原子，烷基，羟基烷基或烷氧基烷基），或两个相邻的R可以通过氧原子结合形成杂环环。作为有效成分。
• ANTI-DRUG RESISTANT STRAIN AGENTS AND ANTICHLAMYDIA AGENTS
  申请人：Japan Science and Technology Corporation

  公开号：EP1134216A1

  公开（公告）日：2001-09-19

  In order to provide antibacterial agents for drug-resistant bacteria and anti-Chlamydia agents, the furanonaphthoquinone derivative represented by the following formula (1): wherein each R may be the same or different, representing any one of the following (a) to (e) :         - R'     (a)         -OR'     (b)         - SR'     (e) (wherein R' is a hydrogen atom, alkyl group, hydroxyalkyl group, or alkoxyalkyl group), or two mutually adjacent Rs may be bonded via an oxygen atom to form a heterocyclic ring is used as the effective component.

  为了提供抗耐药性细菌的抗菌剂和抗衣原体剂，由下式(1)代表的呋喃并萘醌衍生物： 其中每个 R 可以相同或不同，代表以下(a)至(e)中的任意一种： - R' (a) -OR'（b） - SR' (e) (其中 R' 为氢原子、烷基、羟基烷基或烷氧基烷基），或两个相邻的 R 可通过氧原子键合形成杂环作为有效成分。
• US6395773B1
  申请人：——

  公开号：US6395773B1

  公开（公告）日：2002-05-28