2H-3,4-dihydronaphtho<2,3-b>pyran-5,10-dione | 106261-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2H-3,4-dihydronaphtho<2,3-b>pyran-5,10-dione
• 英文别名: 3,4-dihydro-2H-benzo[g]chromene-5,10-quinone；3,4-Dihydro-2H-benzo[g]chromen-5,10-chinon；8,9-Benzo-7,10-dioxo-2-oxabicyclo<4.4.0>deca-1⁶,8⁹-dien；3,4-Dihydro-2H-naphtho[2,3-b]pyran-5,10-dione；3,4-dihydro-2H-benzo[g]chromene-5,10-dione
• CAS: 106261-85-2
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: QVXBGFZUJLBQNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-allyloxy-1,4-naphthoquinone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.5h， 生成 2H-3,4-dihydronaphtho<2,3-b>pyran-5,10-dione
  参考文献：
  名称：

  Naito, Toshihiko; Makita, Yoshihiko; Yazaki, Shiomi, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 4, p. 1505 - 1517

  摘要：

  DOI：

文献信息

• Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones
  作者：Ngampong Kongkathip、Boonsong Kongkathip、Pongpun Siripong、Chak Sangma、Suwaporn Luangkamin、Momad Niyomdecha、Suppachai Pattanapa、Suratsawadee Piyaviriyagul、Palangpon Kongsaeree

  DOI：10.1016/s0968-0896(03)00226-8

  日期：2003.7

  Rhinacanthone (1) and two 1,2-pyranonaphthoquinones (2,3) were synthesized and found to show very potent cytotoxicity against three cancer cell lines (KB, HeLa and HepG(2)) with IC(50) values of 0.92-9.63 microM, whereas the corresponding hydroxylated derivative 4 had reduced cytotoxicity (IC(50) values of 7.61-24.13 microM). Three 1,2-furanonaphthoquinone derivatives (5-7) were also synthesized with

  合成了Rhinacanthone（1）和两个1,2-吡喃并萘醌（2,3），发现它们对三种癌细胞系（KB，HeLa和HepG（2））具有很强的细胞毒性，IC（50）值为0.92-9.63 microM，而相应的羟基化衍生物4则降低了细胞毒性（IC（50）值为7.61-24.13 microM）。还合成了三种具有与1,2-吡喃萘甲醌相似的细胞毒性的1,2-呋喃萘甲醌衍生物（5-7）。与1,2-萘醌相比，合成了与吡喃环（8-10）和呋喃环（11-13）融合的六个1,4-萘醌衍生物，它们显示出较低的细胞毒性或对癌细胞系无活性。此外，化合物13对HeLa细胞系具有明显的细胞毒性（IC（50）值为9.25 microM），而对Vero细胞无毒性。
• Antitumor agents. 89. Psychorubrin, a new cytotoxic naphthoquinone from Psychotria rubra and its structure-activity relationships
  作者：Toshimitsu Hayashi、Forrest T. Smith、Kuo Hsiung Lee

  DOI：10.1021/jm00394a013

  日期：1987.11

  A new naphthoquinone, isolated from the alcoholic extract of Psychotria rubra, exhibited significant cytotoxicity in the KB cell assay (ED50 = 3.0 micrograms/mL). Spectral data was used to assign the structure of psychorubrin as 2. Naphthoquinone derivatives 6, 8, 13, and 14 were prepared and exhibited superior cytotoxic activity to that of psychorubrin. All were potential Michael acceptors whose conjugation

  从Psychotria rubra的酒精提取物中分离出的新萘醌在KB细胞测定中表现出显着的细胞毒性（ED50 = 3.0微克/ mL）。光谱数据被用于将精神尿蛋白的结构指定为2。制备了萘醌衍生物6、8、13和14，并表现出比精神尿蛋白更好的细胞毒活性。所有这些都是潜在的迈克尔受体，其结合已扩展。然而，当此类化合物中存在亲水性羟基时，观察到体外活性降低。
• Studies on the oxidative cyclization of 3-hydroxyalkyl-1,2,4-trialkoxynaphthalenes and synthetic application for the biologically active natural compound rhinacanthone
  作者：Tokutaro Ogata、Misae Doe、Aya Matsubara、Eri Torii、Chiaki Nishiura、Arisa Nishiuchi、Yusuke Kobayashi、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2013.11.025

  日期：2014.1

  The oxidative intramolecular cyclization of 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes was investigated. A series of 1,2-naphthoquinone fused cyclic ethers were synthesized directly from 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes by exposure to diammonium cerium (IV) nitrate. To understand the reaction mechanism, the intramolecular cyclization of 3-hydroxyalkyl-naphthoquinones that were formed as reaction intermediates was also examined. The results suggested that the reaction proceeds by a stepwise oxidation-cyclization mechanism. Using this methodology, five-step synthesis of rhinacanthone was achieved with high yield. (C) 2013 Elsevier Ltd. All rights reserved.
• Naphthoquinone Antimalarials. XXVI.¹ Thioether Naphthoquinones²
  作者：Carl M. Moser、Marvin Paulshock

  DOI：10.1021/ja01168a015

  日期：1950.12
• NAITO, TOSHIHIKO;MAKITA, YOSHIHIKO;YAZAKI, SHIOMI;KANEKO, CHIKARA, CHEM. AND PHARM. BULL., 1986, 34, N 4, 1505-1517
  作者：NAITO, TOSHIHIKO、MAKITA, YOSHIHIKO、YAZAKI, SHIOMI、KANEKO, CHIKARA

  DOI：——

  日期：——