(+/-)-3,4-dihydro-2-methyl-2H-naphtho<2,3-b>pyran-5,10-dione | 64418-77-5

• 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: (+/-)-3,4-dihydro-2-methyl-2H-naphtho<2,3-b>pyran-5,10-dione
• 英文别名: alpha-Norlapachone；2-methyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
• CAS: 64418-77-5
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: XMZISKRNPYGBKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (+/-)-3,4-dihydro-2-methyl-2H-naphtho<2,3-b>pyran-5,10-dione 在 sodium dithionate 、 氢氧化钾 、 ammonium cerium(IV) nitrate 、 potassium tert-butylate 、 四丁基溴化铵 、 氧气 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.5h， 生成 (+/-)-(4S)-3,4-dihydro-4-hydroxy-2-methyl-2H-naphtho<2,3-b>pyran-5,10-dione
  参考文献：
  名称：

  合成一些 Naphtho[2,3-b]pyran-5,10-quinones 作为生物评价的初步模型

  摘要：

  摘要 Naphtho[2,3-b]pyran-5,10-quinones 与已知抗生素 erythrostominone 5 相关，已合成并证明其生物活性是吡喃环以及 C-2 和 C 上的取代基的函数。 -4.

  DOI：

  10.1080/00397919808004524
• 作为产物：
  描述：

  2-氯-1,4-萘醌 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 46.0h， 生成 (+/-)-3,4-dihydro-2-methyl-2H-naphtho<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

• Studies on quinones. VIII. The application of michael adducts from 2-hydroxy-1,4-naphthoquinones for the preparation of dihydronaphthopyrandiones
  作者：R. Cassis、R. Tapia、J. Valderrama

  DOI：10.1002/jhet.5570190233

  日期：1982.3

  Dihydronaphthopyran-5,10-diones 7,13, 16 and their corresponding dihydronaphthopyran-5,6-diones 8, 14,17 have been obtained starting from Michael adducts of 2-hydroxy- and 2-hydroxy-7-methoxy-1,4-naph-thoquinone (1, 9). An efficient synthesis of hydroxyhydrolapachol (4) employing 2-hydroxy-3-(3-oxobutyl)-1,4-naphthoquinone (5) is described.

  从2-羟基-和2-羟基-7-甲氧基-1的迈克尔加合物开始获得二氢萘并吡喃-5,10-二酮7,13,16及其相应的二氢萘并吡喃-5,6-二酮8,14,17。 4-萘醌（1，9）。描述了使用2-羟基-3-（3-氧丁基）-1,4-萘醌（5）的羟基氢苯酚（4）的有效合成。
• Trypanosoma cruzi: Activities of lapachol and α- and β-lapachone derivatives against epimastigote and trypomastigote forms
  作者：Cristian Salas、Ricardo A. Tapia、Karina Ciudad、Verónica Armstrong、Myriam Orellana、Ulrike Kemmerling、Jorge Ferreira、Juan Diego Maya、Antonio Morello

  DOI：10.1016/j.bmc.2007.10.038

  日期：2008.1

  Derivatives of natural quinones with biological activities, such as lapachol, alpha- and beta-lapachones, have been synthesized and their trypanocidal activity evaluated in vitro in Trypanosoma cruzi cells. All tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar or higher activity as compared with current trypanocidal drugs, nifurtimox and benznidazole. The results presented here show that the anti-T Cruzi activity of the alpha-lapachone derivatives can be increased by the replacement of the benzene ring by a pyridine moiety. Free radical production and consequently oxidative stress through redox cycling or production of electrophilic metabolites are the potential biological mechanism of action for these synthetic quinones. (c) 2007 Elsevier Ltd. All rights reserved.
• THE ALKYLATION OF HYDROXYNAPHTHOQUINONE. III. A SYNTHESIS OF LAPACHOL
  作者：Louis F. Fieser

  DOI：10.1021/ja01402a030

  日期：1927.3
• 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：——
• The Synthesis of Some Naphtho[2,3-<i>b</i>]pyran-5,10-Quinones as Preliminary Models for Biological Evaluations
  作者：Robin G.F. Giles、Ivan R. Green、Victor I. Hugo、Joanne L. Ireland

  DOI：10.1080/00397919808004524

  日期：1998.12

  Abstract Naphtho[2,3-b]pyran-5,10-quinones related to the known antibiotic, erythrostominone 5, have been synthesized and demonstrate that biological activity is a function of the pyran ring as well as substituents at C-2 and C-4.

  摘要 Naphtho[2,3-b]pyran-5,10-quinones 与已知抗生素 erythrostominone 5 相关，已合成并证明其生物活性是吡喃环以及 C-2 和 C 上的取代基的函数。 -4.