5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione | 123297-90-5

• 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: 5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione
• 英文别名: 5-hydroxy-2-(1-hydroxyethyl)benzo[f][1]benzofuran-4,9-dione
• CAS: 123297-90-5
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: XJGFVZBTNKODFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione 在 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到2-(1-bromoethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  来自Tabebuia avellanedae 成分的抗菌萘醌的构效关系研究

  摘要：

  在本研究中，基于我们之前的研究，合成了萘并[2,3 - b ]呋喃-4,9-二酮的衍生物并评估了它们的抗菌活性。对这些萘醌类化合物的筛选表明，含氟NQ008化合物对革兰氏阳性菌（包括耐甲氧西林金黄色葡萄球菌(MRSA)、革兰氏阴性菌和真菌）表现出强大而广泛的抗菌活性。最低杀菌浓度 (MBC) 与最低抑菌浓度 (MIC) 之比和时间-杀灭试验结果表明NQ008的作用方式是杀菌。此外，一项耐药性研究的结果表明，NQ008表现出有效的抗菌活性，并可能延缓细菌耐药性的发展。此外，NQ008对猪流感病毒和猫杯状病毒表现出初步的抗病毒活性。 全尺寸图像

  DOI：

  10.1248/cpb.c21-00208
• 作为产物：
  描述：

  2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione 在 sodium tetrahydroborate 、 盐酸 、 水 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 以74%的产率得到5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  ANTICANCER COMPOUND, INTERMEDIATE THEREFOR, AND PROCESSES FOR PRODUCING THESE

  摘要：

  公开号：

  EP1860103B1

文献信息

• Preparation of optically active 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4, 9-diones having anticancer activities
  申请人：Iida Akira

  公开号：US20080300415A1

  公开（公告）日：2008-12-04

  An object of the present invention is to provide a method for efficiently preparing (S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]-furan-4,9-dione useful as a medicine at a low cost and in large amounts. According to the present invention, the desired (S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione can be prepared with high efficiency at a low cost and in large amounts by asymmetrically reducing 2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione in the presence of an asymmetric ruthenium complex and a hydrogen donor.

  本
• NOVEL PREPARATION OF ANTICANCER-ACTIVE TRICYCLIC COMPOUNDS VIA ALKYNE COUPLING REACTION
  申请人：IIDA Akira

  公开号：US20120077986A1

  公开（公告）日：2012-03-29

  The present invention is directed to provide a novel preparation of anticancer-active tricyclic compounds via alkyne coupling reaction. The present invention provides a process for preparing a compound of formula (Ia) or (Ib): wherein R 1 is optionally substituted C 1-6 alkyl, etc.; W is O, S or NR 2 ; R 2 is hydrogen atom, etc., which comprises Step (a) in which a compound of formula (II): wherein R 1 is the same as defined above, and a compound of formula (III) or (IV): wherein R 2 is the same as defined above; R 3 is hydrogen atom, etc.; X is halogen atom, etc., are reacted in the presence of a base, a copper catalyst and a palladium catalyst in an aprotic polar solvent.

  本发明旨在通过炔烃偶联反应提供一种新型抗癌活性三环化合物的制备方法。本发明提供了一种制备式(Ia)或(Ib)的化合物的方法：其中R1为可选择的取代的C1-6烷基等；W为O、S或NR2；R2为氢原子等；其中包括步骤(a)，其中式(II)的化合物：其中R1与上述定义相同，和式(III)或(IV)的化合物：其中R2与上述定义相同；R3为氢原子等；X为卤原子等，在无水极性溶剂中，在碱、铜催化剂和钯催化剂的存在下反应。
• Concise Synthesis of Heterocycle-Fused Naphthoquinones by Employing Sonogashira Coupling and Tandem Addition-Elimination/Intramolecular Cyclization
  作者：Kazunori Ueda、Mitsuaki Yamashita、Koichi Sakaguchi、Harukuni Tokuda、Akira Iida

  DOI：10.1248/cpb.c13-00102

  日期：——

  A concise method for the synthesis of heterocycle-fused naphthoquinones such as naphtho[2,3-b]-furan-4,9-dione, 1H-benz[f]indole-4,9-dione, and naphtho[2,3-b]thiophene-4,9-dione was developed. This method employed Sonogashira coupling and tandem addition-elimination/intramolecular cyclization, and it enabled the preparation of versatile heterocycle-fused naphthoquinones from one substrate.

  开发了一种合成杂环融合萘醌类化合物（如萘并[2,3-b]-呋喃-4,9-二酮、1H-苯并[f]吲哚-4,9-二酮和萘并[2,3-b]噻吩-4,9-二酮）的简便方法。该方法采用了 Sonogashira 偶联和串联加成-消除/分子内环化技术，能够用一种底物制备多功能杂环融合萘醌。
• Lignans and naphthoquinones from Tabebuia incana
  作者：Alaíde Braga de Oliveira、Délio Soares Raslan、Geovane G. de Oliveira、José Guilherme S. Maia

  DOI：10.1016/0031-9422(91)80039-4

  日期：1993.11

  Abstract The trunkwood of Tabebuia incana afforded the lignans pawlownin and cycloolivil as the major constituents together with a cycloolivil acetonide, la

  摘要 Tabebuia incana 的树干木提供木脂素 pawlownin 和 cycloolivil 作为主要成分以及 cycloolivil acetonide, la
• Anticancer Compound, Intermediate Therefor, and Processes for Producing These
  申请人：Tokuda Harukuni

  公开号：US20090042977A1

  公开（公告）日：2009-02-12

  The present invention provides a method for easily and inexpensively preparing a racemate or an optically-active 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione in high yields, 2-acetyl-2,3-dihydro-5-hydroxynaphtho[2,3-b]furan-4,9-dione which is useful as an intermediate for preparing NFD, and an anticancer agent comprising 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione as an active ingredient. Said 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione is obtained in 4 or 5 steps by using comparatively inexpensive 5-hydroxynaphthalene-1,4-dione (also referred to as juglone) as a starting material.

  本发明提供了一种简单、廉价的方法，以高收率制备拉氨酸盐或光学活性的2-(1-羟乙基)-5-羟基萘[2,3-b]呋喃-4,9-二酮，以及用于制备NFD的中间体2-乙酰基-2,3-二氢-5-羟基萘[2,3-b]呋喃-4,9-二酮和包含2-(1-羟乙基)-5-羟基萘[2,3-b]呋喃-4,9-二酮作为活性成分的抗癌剂。所述2-(1-羟乙基)-5-羟基萘[2,3-b]呋喃-4,9-二酮通过使用相对廉价的5-羟基萘醌（也称核桃醌）作为起始材料，在4或5个步骤中获得。