2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione | 87549-97-1

• 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-hydroxynaphtho[2,3-b]furan-4,9-dione
• 英文别名: 2-acetyl-5-hydroxynaphtho<2,3-b>furan-4,9-dione；2-acetyl-5-hydroxybenzo[f][1]benzofuran-4,9-dione
• CAS: 87549-97-1
• 化学式: C₁₄H₈O₅
• 分子量: 256.215
• InChiKey: RABXYJBFTPBKKL-UHFFFAOYSA-N

物化性质

• 熔点：
  >247 °C (decomp)
• 沸点：
  512.6±50.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-羟基对萘醌 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 、 甲苯 为溶剂， 反应 2.0h， 生成 2-acetyl-5-hydroxynaphtho[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。
• Synthesis and evaluation of bioactive naphthoquinones from the Brazilian medicinal plant, Tabebuia avellanedae
  作者：Mitsuaki Yamashita、Masafumi Kaneko、Harukuni Tokuda、Katsumi Nishimura、Yuko Kumeda、Akira Iida

  DOI：10.1016/j.bmc.2009.07.039

  日期：2009.9.1

  A series of naphthoquinones based on the naphtho[2,3-b]furan-4,9-dione skeleton such as (−)-5-hydroxy-2-(1′-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione (1) and its positional isomer, (−)-8-hydroxy-2-(1′-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione (2), which are secondary metabolites found in the inner bark of Tabebuia avellanedae, were stereoselectively synthesized and their biological activities were

  基于萘并[2,3 - b ]呋喃-4,9-二酮骨架的一系列萘醌，例如（-）-5-羟基-2-（1'-羟乙基）萘并[2,3- b ]呋喃-4，9-二酮（1）及其位置异构体（-）-8-羟基-2-（1'-羟乙基）萘并[2,3 - b ]呋喃-4,9-二酮（2），是在塔伯布烟草（Tabebuia avellanedae）内树皮中发现的次级代谢产物，是立体选择性合成的，并与相应的对映异构体的生物学活性一起进行了生物活性评估。化合物1表现出对几种人类肿瘤细胞系的有效抗增殖作用，但对某些人类正常细胞系的作用远低于丝裂霉素。另一方面，其对映异构体（R）-1对上述肿瘤细胞系的活性低于1。2对所有肿瘤细胞系的抗增殖作用显着降低。这些结果表明，在C-5处酚羟基的存在对于增加抗增殖作用非常重要。此外，1个也显示出比2个更高的化学预防活性，而1和2之间没有显着差异。抗菌活性。两种化合物均显示出适度的抗真菌和抗菌活性（
• CHEMICALLY ACTIVATED WATER-SOLUBLE PRODRUG
  申请人：SUMITOMO DAINIPPON PHARMA CO., LTD

  公开号：US20200207782A1

  公开（公告）日：2020-07-02

  The present invention addresses the problem of providing a novel chemically activated water-soluble prodrug. The present invention provides a compound represented by formula (1), or a pharmacologically acceptable salt thereof (in the formula, A represents A-0; X 1 and X 2 are the same as or different from each other and each independently represent a hydroxyl group or —O—C(═O)—Y—(C(R 1A ) (R 1B ))n-NH—R 2 , where X 1 and X 2 are not simultaneously hydroxyl groups, n is 2, 3, or 4, Y represents an oxygen atom or —NR 4 , R 1A and R 1B are the same as or different from each other and each independently represent a hydrogen atom, etc., and R 2 represents a hydrogen atom, etc.; and R a to R d are optionally present, are the same as or different from each other, and each independently represent a hydrogen atom, etc.).

  本发明解决了提供一种新型化学活化的水溶性前药的问题。本发明提供了由式（1）表示的化合物，或其药理学上可接受的盐（在该式中，A代表A-0；X1和X2彼此相同或不同，每个独立地代表一个羟基或—O—C(═O)—Y—(C(R1A)(R1B))n-NH—R2，其中X1和X2不同时是羟基，n为2、3或4，Y代表氧原子或—NR4，R1A和R1B彼此相同或不同，每个独立地代表氢原子等，R2代表氢原子等；以及Ra到Rd可选地存在，彼此相同或不同，每个独立地代表氢原子等）。
• 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。
• [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）。