2-phenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione | 139386-43-9

• 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-phenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
• 英文别名: 2-Phenyl-2,3-dihydrobenzo[g][1]benzofuran-4,5-dione
• CAS: 139386-43-9
• 化学式: C₁₈H₁₂O₃
• 分子量: 276.291
• InChiKey: FWWUHHCGSZBPMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione 、 trans-1,2-Diaminocyclohexane 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以49%的产率得到2-phenyl-1,2,9,10,11,12-hexahydrobenzo[a]furo[2,3-c]phenazine
  参考文献：
  名称：

  Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives

  摘要：

  9- and 10-membered macrolactones bearing benzo and diazine rings were obtained by chemoselective ozonolysis of dihydrofuran and pyran 1,4-diazaphenathrene derivatives. This is the first example of preparation of macrolactones by chemoselective ozonolysis of an enol double bond shared by aromatic and heterocyclic rings. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.075
• 作为产物：
  描述：

  苯乙烯 、 2-羟基-1,4-萘醌 在 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以26%的产率得到2-phenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  萘醌衍生物作为潜在的抗结直肠癌药物的合成，抗增殖活性评估和3D-QSAR研究。

  摘要：

  大肠癌（CRC）是一种高发病率和高死亡率的疾病，是全世界癌症死亡的第四大最常见原因。萘醌由于其生物学和结构特性而成为有吸引力的化合物。在这项工作中，合成了36种萘醌衍生物，并评估了它们对HT-29细胞的活性。总体而言，在该系列的大多数成员中均观察到了高到中度的抗增殖活性，其中15种化合物被归类为有活性的（1.73

  DOI：

  10.3390/molecules23010186

文献信息

• Synthesis and Pharmacophore Modeling of Naphthoquinone Derivatives with Cytotoxic Activity in Human Promyelocytic Leukemia HL-60 Cell Line
  作者：Elisa Pérez-Sacau、Raquel G. Díaz-Peñate、Ana Estévez-Braun、Angel G. Ravelo、Jose M. García-Castellano、Leonardo Pardo、Mercedes Campillo

  DOI：10.1021/jm060849b

  日期：2007.2.1

  quantitative structure-activity relationship (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to explain the cytotoxic activity of a set of 51 natural and synthesized naphthoquinone derivatives tested in human promyelocytic leukemia HL-60 cell line. The computational models have facilitated the identification of structural elements of the ligands

  催化剂/ HypoGen药效团建模方法和三维定量结构-活性关系（3D-QSAR）/比较分子相似性指数分析（CoMSIA）方法已成功用于解释一组测试的51种天然和合成萘醌衍生物的细胞毒活性在人早幼粒细胞白血病HL-60细胞系中。计算模型促进了对抗肿瘤特性至关重要的配体结构元素的鉴定。高活性β-环-吡喃-1,2-萘醌[0.1 microM
• Ceric Ammonium Nitrate Mediated Cycloaddition of Hydroxyquinones with Alkenes for the One-Step Construction of Furoquinone Derivatives
  作者：Kazuhiro Kobayashi、Masako Mori、Tomokazu Uneda、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/cl.1996.451

  日期：1996.6

  A one-step formation of furoquinones, such as naphtho[2,3-b]furan-4,9-dione, naphtho[1,2-b]furan-4,5-dione, benzofuran-4,7-dione, and benzofuran-4,5-dione derivatives, by the ceric ammonium nitrate mediated [3+2] type cycloaddition of 2-hydroxy-1,4-naphthoquinones and 2-hydroxy-1,4-benzoquinones with alkenes or phenylacetylene is described.

  通过硝酸铈铵介导的 [3+2] 型环加成反应，将 2-羟基-1,4-萘醌和 2-羟基-1,4-苯醌与烯烃或苯基乙炔一步合成呋喃[2,3-b]并萘烷-4,9-二酮、呋喃[1,2-b]并萘烷-4,5-二酮、苯并呋喃-4,7-二酮和苯并呋喃-4,5-二酮衍生物的方法被报道。
• One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition
  作者：Kazuhiro Kobayashi、Tomokazu Uneda、Koujirou Tanaka、Masako Mori、Hideo Tanaka、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/bcsj.71.1691

  日期：1998.7

  The 3+2-type cycloaddition reaction of 2-hydroxy-1,4-naphthoquinones with various alkenes or phenylacetylene was mediated by ammonium cerium(IV) nitrate (CAN) to give the corresponding naphtho[2,3-b]furan-4,9-dione and naphtho[1,2-b]furan-4,5-dione derivatives. The reaction of 2-hydroxy-1,4-benzoquinones with alkenes in the presence of CAN similarly proceeded to give benzofuran-4,7-dione and benzofuran-4,5-dione derivatives. 3-Hydroxy-1H-phenalen-1-one also underwent the CAN-mediated cycloaddition with alkenes or phenylacetylene to give the corresponding 7H-phenaleno[1,2-b]furan-7-one derivatives.

  2-羟基-1,4-萘醌与各种烯烃或苯乙炔在硝酸铈铵（CAN）的催化下发生3+2型环加成反应，生成相应的萘并[2,3-b]呋喃-4,9-二酮和萘并[1,2-b]呋喃-4,5-二酮衍生物。2-羟基-1,4-苯醌与烯烃在CAN存在下同样发生反应，得到苯并呋喃-4,7-二酮和苯并呋喃-4,5-二酮衍生物。3-羟基-1H-菲兰烯-1-酮也能在CAN的催化下与烯烃或苯乙炔发生环加成反应，生成相应的7H-菲兰诺[1,2-b]呋喃-7-酮衍生物。
• Synthesis, Stability Studies, and Antifungal Evaluation of Substituted α- and β-2,3-Dihydrofuranaphthoquinones against Sporothrix brasiliensis and Sporothrix schenckii
  作者：Patricia Garcia Ferreira、Luana Pereira Borba-Santos、Leticia Noronha、Caroline Deckman Nicoletti、Marcella de Sá Haddad Queiroz、Fernando de Carvalho da Silva、Sônia Rozental、Débora Omena Futuro、Vitor Francisco Ferreira

  DOI：10.3390/molecules24050930

  日期：——

  standard antifungal itraconazole has been recommended as a first-line therapy. However, failure cases in human and feline treatment have been reported in recent years. This study aimed to synthesize several α- and β-2,3-dihydrofuranaphthoquinones and evaluate them against Sporothrix schenckii and Sporothrix brasiliensis-the main etiological agents of sporotrichosis in Brazil. The stability of these compounds

  孢子丝菌病是由孢子丝菌（Sporothrix spp。）引起的被忽略的真菌感染，其在世界范围内分布。标准抗真菌伊曲康唑已被推荐作为一线治疗药物。然而，近年来已经报道了人类和猫治疗失败的案例。这项研究旨在合成几种α-和β-2,3-二氢呋喃萘醌，并评估它们对巴西孢子虫病的主要病原体-申氏孢子虫和巴西孢子菌的抵抗力。还研究了这些化合物在不同储存条件下3个月的稳定性。在0、60和90天取出样品并通过1 H-NMR评估，并测试其体外抗真菌药敏性。此外，我们使用扫描电子显微镜评估了最有效和稳定的化合物引起的表面变化，并确定了与伊曲康唑合用时的效果。九种二氢呋喃萘醌具有良好的抗真菌活性和稳定性，MIC值为2⁻32µM。对于这两种物种，化合物6和10是体外活性最高的二氢呋喃萘醌。在真菌中，这些化合物诱导了酵母菌丝的转化以及菌丝和分生孢子结构的改变。化合物10还显示出与伊曲康唑对申氏链球菌的协同活性，ΣFIC指数值为0
• Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives
  作者：Elisa Pérez-Sacau、Jorge Soto-Delgado、Ana Estévez-Braun、Ángel G. Ravelo

  DOI：10.1016/j.tet.2004.10.075

  日期：2005.1

  9- and 10-membered macrolactones bearing benzo and diazine rings were obtained by chemoselective ozonolysis of dihydrofuran and pyran 1,4-diazaphenathrene derivatives. This is the first example of preparation of macrolactones by chemoselective ozonolysis of an enol double bond shared by aromatic and heterocyclic rings. (C) 2004 Elsevier Ltd. All rights reserved.