8,9-dihydroxy-6H-benzofuro<3,2-c><1>benzopyran-6-one | 15236-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8,9-dihydroxy-6H-benzofuro<3,2-c><1>benzopyran-6-one
• 英文别名: 8,9-dihydroxybenzofuro<3,2-c>benzopyran-6(H)-one；3,4-dihydroxy-6H-benzofuro[3,2-c][1]benzopyron-6-one；8,9-dihydroxybenzo[4,5]furo[3,2-c]chromen-6-one；8,9-dihydroxy-6H-benzofuro[3,2-c]chromen-6-one；8,9-dihydroxycoumestone；11,12-Dihydroxycumestan；8,9-dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one；8,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one
• CAS: 15236-06-3
• 化学式: C₁₅H₈O₅
• 分子量: 268.226
• InChiKey: RPTGHFLVJUHWET-UHFFFAOYSA-N

物化性质

• 熔点：
  308-310 °C (decomp)
• 沸点：
  385.8±22.0 °C(Predicted)
• 密度：
  1.602±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8,9-dihydroxy-6H-benzofuro<3,2-c><1>benzopyran-6-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 14.0h， 生成 11-allyl-10-hydroxy-8-methyl-7,8-dihydrofuro<3',2':4,5>benzofuro<3,2-c>benzopyran-6(H)-one
  参考文献：
  名称：

  Soman, Shubhangi S.; Trivedi, K. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 11, p. 1075 - 1079

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸 在 吡啶 、 iron(III) chloride 、 silica gel 、 三溴化硼 、 potassium hydroxide 、 三氯氧磷 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 19.5h， 生成 8,9-dihydroxy-6H-benzofuro<3,2-c><1>benzopyran-6-one
  参考文献：
  名称：

  Coumestan Inhibits Radical-Induced Oxidation of DNA: Is Hydroxyl a Necessary Functional Group?

  摘要：

  Coumestan is a natural tetracycle with a C═C bond shared by a coumarin moiety and a benzofuran moiety. In addition to the function of the hydroxyl group on the antioxidant activity of coumestan, it is worth exploring the influence of the oxygen-abundant scaffold on the antioxidant activity as well. In this work, seven coumestans containing electron-withdrawing and electron-donating groups were synthesized to evaluate the abilities to trap 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(•+)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively, and to inhibit the oxidations of DNA mediated by (•)OH, Cu(2+)/glutathione (GSH), and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH), respectively. It was found that all of the coumestans used herein can quench the aforementioned radicals and can inhibit (•)OH-, Cu(2+)/GSH-, and AAPH-induced oxidations of DNA. In particular, substituent-free coumestan exhibits higher ability to quench DPPH and to inhibit AAPH-induced oxidation of DNA than Trolox. In addition, nonsubstituted coumestan shows a similar ability to inhibit (•)OH- and Cu(2+)/GSH-induced oxidations of DNA relative to that of Trolox. The antioxidant effectiveness of the coumestan can be attributed to the lactone in the coumarin moiety and, therefore, a hydroxyl group may not be a necessary functional group for coumestan to be an antioxidant.

  DOI：

  10.1021/jf500013v

文献信息

• 天然产物Hirtellanine B及其衍生物的制备方法 与在制备治疗肿瘤药物中的应用
  申请人：巴塞利亚药业（中国）有限公司

  公开号：CN103319497B

  公开（公告）日：2016-05-18

  本发明提供了天然产物Hirtellanine？B的制备方法，以2，4，6-三羟基苯乙酮为原料，通过制备化合物a、b、c、d、e、f、g等步骤，制得天然产物Hirtellanine？B。本发明人对Hirtellanine？B及其14个Hirtellanine？B衍生物进行了生物活性筛选，结果显示天然产物Hirtellanine？B能够抑制Jurkat细胞，Raji细胞以及K562细胞增殖。它们对肿瘤细胞均具有一定的抑制活性。本发明方法原料易得，反应收率高，操作合理，宜于工业化生产。本发明Hirtellanine？B及其衍生物可用于制备治疗肿瘤药物，有较大的临床应用价值。本发明天然产物Hirtellanine？B的制备方法反应式如下：
• Sirtuin Inhibiting Compounds
  申请人：Sinclair David A

  公开号：US20090137681A1

  公开（公告）日：2009-05-28

  Provided herein are compositions and methods for treating or preventing cancer and autoimmune diseases. Compositions comprise a sirtuin inhibitory compound that decreases the activity of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a cell or a molecule with a sirtuin inhibitory compound that decreases the activity of a sirtuin and thereby reduces the life span of a cell, kills the cell or renders it susceptible to certain cell stresses including radiation and chemotherapy. Other methods include treating pathogens expressing a sirtuin.

  本文提供了治疗或预防癌症和自身免疫疾病的组合物和方法。组合物包括抑制sirtuin的化合物，降低sirtuin的活性，如SIRT1或Sir2。示例方法包括将细胞或分子与抑制sirtuin的化合物接触，降低sirtuin的活性，从而缩短细胞的寿命，杀死细胞或使其对包括放射治疗和化疗在内的某些细胞应激变得敏感。其他方法包括治疗表达sirtuin的病原体。
• An efficient conversion of catechols into 6<i>H</i>-benzofuro[3,2-<i>c</i>][1]-benzopyran-6-one derivatives
  作者：Davood Nematollahi、Davood Habibi、Abdolhamid Alizadeh、Mahdi Hesari

  DOI：10.1002/jhet.5570420218

  日期：2005.3

  agent in aqueous solution. The results indicate that the quinones derived from catechols, participate in Michael addition reactions with 4-hydroxycoumarin to form the 6H-benzofuro[3,2-c][1]benzopyran-6-one derivatives.

  在水溶液中存在作为氧化剂的铁氰化钾的情况下，已经研究了原位生成的邻苯并醌与4-羟基香豆素作为亲核试剂的偶联。结果表明，衍生自邻苯二酚的醌参与与4-羟基香豆素的迈克尔加成反应，形成6 H-苯并呋喃[3,2- c ] [1]苯并吡喃-6-衍生物。
• A one-pot laccase-catalysed synthesis of coumestan derivatives and their anticancer activity
  作者：Tozama Qwebani-Ogunleye、Natasha I. Kolesnikova、Paul Steenkamp、Charles B. de Koning、Dean Brady、Kevin W. Wellington

  DOI：10.1016/j.bmc.2016.12.025

  日期：2017.2

  TK10 cancer cell-line. The total growth inhibition, based on the TGI values, of several of the compounds was better than that of etoposide against the melanoma UACC62 and the breast MCF7 cancer cell lines. Several compounds, based on the LC50 values, were also more lethal than etoposide against the same cancer cell lines. The SAR for the coumestans is similar against the melanoma UACC62 and breast

  购自Novozymes的商业漆酶Suberase®用于催化香豆素的合成。在某些情况下，产率类似于或优于通过其他酶，化学或电化学合成获得的产率。针对肾TK10，黑素瘤UACC62和乳腺癌MCF7癌细胞系筛选化合物，并确定GI 50，TGI和LC 50值。抗癌筛选显示，coumestans的细胞抑制作用对表现出有效活性（GI 50）的黑色素瘤UACC62和乳腺癌MCF7癌细胞系最有效 分别为5.35和7.96μM。获得了针对肾TK10癌细胞系的中等活性。基于TGI值，几种化合物对黑素瘤UACC62和乳腺癌MCF7癌细胞的总生长抑制作用优于依托泊苷。基于LC 50值，几种化合物对相同癌细胞系的杀伤力也比依托泊苷高。头皮动物的SAR与黑色素瘤UACC62和乳腺MCF7细胞系相似。对乳腺MCF7和黑色素瘤UACC62细胞系均具有有效活性的化合物在苯环（环A）和邻苯二酚环（环B）上均具有甲基。当甲氧基
• O-Heterocycles via Laccase-Catalyzed Domino Reactions with O₂as the Oxidant
  作者：Uwe Beifuss、Heiko Leutbecher、Jürgen Conrad、Iris Klaiber

  DOI：10.1055/s-2005-922748

  日期：——

  Laccase-catalyzed domino reactions of 4-hydroxy-6-­methyl-2H-pyran-2-one or substituted 4-hydroxy-2H-chromen-2-ones with catechols using molecular oxygen as an oxidant afford coumestans and related O-heterocycles with yields ranging from 51% to 99%.

  以分子氧为氧化剂，4-羟基-6-甲基-2H-吡喃-2-酮或取代的4-羟基-2H-色烯-2-酮与儿茶酚的拉卡酶催化多米诺反应，能得到耦梅斯坦和相关的O-杂环，其产率范围为51%到99%。

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