2-acetyl-5-hydroxy-2,3-dihydronaphtho[2,3-b]-furan-4,9-dione

• 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: 2-acetyl-5-hydroxy-2,3-dihydronaphtho[2,3-b]-furan-4,9-dione
• 英文别名: 2-acetyl-2,3-dihydro-5-hydroxy-naphtho[2,3-b]furan-4,9-dione；2-Acetyl-2,3-dihydro-5-hydroxynaphtho[2,3-b]furan-4,9-dione；2-acetyl-5-hydroxy-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: DWMJEEGBCMSGAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetyl-5-hydroxy-2,3-dihydronaphtho[2,3-b]-furan-4,9-dione 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以51%的产率得到2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  一种来自塔贝布氏菌的化学预防性萘醌的立体选择性合成和细胞毒性。

  摘要：

  通过利用Noyori还原作为关键步骤，从巴西传统药物Tabebuia avellanedae中选择性合成1种生物活性萘醌之一。与丝裂霉素相比，化合物1对几种人类肿瘤细胞系显示出有效的细胞毒性，而对某些人类正常细胞系显示出较低的细胞毒性。另一方面，其对映体对肿瘤细胞系的活性不如1。

  DOI：

  10.1016/j.bmcl.2007.10.005
• 作为产物：
  描述：

  2-(dimethylamino)-5-hydroxynaphthalene-1,4-dione 在 盐酸 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 2-acetyl-5-hydroxy-2,3-dihydronaphtho[2,3-b]-furan-4,9-dione
  参考文献：
  名称：

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

  摘要：

  本

  公开号：

  US20080300415A1

文献信息

• Stereoselective synthesis and cytotoxicity of a cancer chemopreventive naphthoquinone from Tabebuia avellanedae
  作者：Mitsuaki Yamashita、Masafumi Kaneko、Akira Iida、Harukuni Tokuda、Katsumi Nishimura

  DOI：10.1016/j.bmcl.2007.10.005

  日期：2007.12

  Stereoselective synthesis of 1, one of biologically active naphthoquinones from a Brazilian traditional medicine Tabebuia avellanedae, was achieved by utilizing Noyori reduction as a key step. Compound 1 displayed potent cytotoxicity against several human tumor cell lines, whereas it showed lower cytotoxicity against some human normal cell lines compared with that of mitomycin. On the other hand, its

  通过利用Noyori还原作为关键步骤，从巴西传统药物Tabebuia avellanedae中选择性合成1种生物活性萘醌之一。与丝裂霉素相比，化合物1对几种人类肿瘤细胞系显示出有效的细胞毒性，而对某些人类正常细胞系显示出较低的细胞毒性。另一方面，其对映体对肿瘤细胞系的活性不如1。
• 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。
• Structure–Activity Relationship Studies of Antimicrobial Naphthoquinones Derived from Constituents of <i>Tabebuia avellanedae</i>
  作者：Mitsuaki Yamashita、Jun Sawano、Ryuji Umeda、Ayuka Tatsumi、Yuko Kumeda、Akira Iida

  DOI：10.1248/cpb.c21-00208

  日期：2021.7.1

  3-b]furan-4,9-diones were synthesized and their antimicrobial activities were evaluated. The screening of these naphthoquinones revealed that the fluorine-containing NQ008 compound exhibited potent and broad antimicrobial activities against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), Gram-negative bacteria, and fungi. The results of the ratio of the minimum bactericidal

  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
• [EN] NEW NAPHTHO[2,3-B]FURAN DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE NAPHTHO[2,3-B]FURANE
  申请人：BAN HITOSHI

  公开号：WO2018096401A1

  公开（公告）日：2018-05-31

  The present invention provides a compound useful as a novel antitumor agent targeting a CSC that is important in continuous proliferation of malignant tumor, metastasis and recurrence of cancer, and its resistance to an antitumor agent; a medicament comprising the compound as an active ingredient; a pharmaceutical composition; and an antitumor agent; as well as a method of treating cancer and/or a method of preventing cancer. The present invention provides compounds represented by formula (I) : or pharmaceutically acceptable salts thereof, wherein X is an oxygen atom or sulfur atom; R1 is a hydrogen atom, an alkyl group, or the like; R2 is a halogen atom or the like; R3 is a hydrogen atom, an alkyl group, or the like; m is 0, 1, 2, 3, or 4; and n is 1, 2, 3, or 4 (with the proviso that the sum of m and n is 1, 2, 3, or 4).

  本发明提供了一种化合物，作为一种新型抗肿瘤剂，针对在恶性肿瘤的持续增殖、转移和复发以及其对抗肿瘤药物的耐药性中起重要作用的CSC；一种以该化合物作为活性成分的药物；一种制药组合物；一种抗肿瘤剂；以及治疗癌症和/或预防癌症的方法。本发明提供了由式（I）表示的化合物或其药学上可接受的盐，其中X是氧原子或硫原子；R1是氢原子、烷基或类似物；R2是卤原子或类似物；R3是氢原子、烷基或类似物；m是0、1、2、3或4；n是1、2、3或4（前提是m和n的总和为1、2、3或4）。
• 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。