tetrahydro-α-lapachone

• 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: tetrahydro-α-lapachone
• 英文别名: 2,2-dimethyl-3,4,6,7,8,9-hexahydro-2H-benzo[g]chromene-5,10-dione；2,2-Dimethyl-3,4,6,7,8,9-hexahydrobenzo[g]chromene-5,10-dione
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: TYJZNKZGWQQLFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  重氮甲烷 、 tetrahydro-α-lapachone 以 乙醚 、 乙醇 为溶剂， 反应 48.0h， 以70%的产率得到2,2-dimethyl-3,4,6,7,8,9-hexahydrospiro[benzo[g]chromene-10,2'-oxirane]-5(2H)-one
  参考文献：
  名称：

  New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms

  摘要：

  New oxirane derivatives were synthesized using six naphthoquinones as the starting materials. Our biological results showed that these oxiranes acted as trypanocidal agents against Trypanosoma cruzi with minimal cytotoxicity in the VERO cell line compared to naphthoquinones. In particular, oxirane derivative 14 showed low cytotoxicity in a mammalian cell line and exhibited better activity against epimastigote forms of T. cruzi than the current drug used to treat Chagas disease, benznidazole. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.027
• 作为产物：
  描述：

  去氢-ALPHA-拉杷醌 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以97%的产率得到tetrahydro-α-lapachone
  参考文献：
  名称：

  Efficient Synthesis of Biologically Interesting Dehydro‐α‐Lapachone and α‐Lapachone

  摘要：

  An efficient synthesis of biologically active dehydro-alpha-lapachone and alpha-lapachone has been carried out starting from 2-hydroxy-1,4-naphthoquinone by a tandem Knoevenagel-electrocyclic reaction.

  DOI：

  10.1081/scc-200043216

文献信息

• Ferreira, Vitor F.; Pinto, Antonio V.; Pinto, Maria C. R. F., Journal of Chemical Research, Miniprint, 1987, # 1, p. 182 - 191
  作者：Ferreira, Vitor F.、Pinto, Antonio V.、Pinto, Maria C. R. F.、Silva, Mauricio M.

  DOI：——

  日期：——
• FERREIRA, VITOR F.;PINTO, ANTONIO V.;PINTO, MARIA C. F. R.;SILVA, MAURICI+, J. CHEM. RES. SYNOP.,(1987) N 1, 26
  作者：FERREIRA, VITOR F.、PINTO, ANTONIO V.、PINTO, MARIA C. F. R.、SILVA, MAURICI+

  DOI：——

  日期：——
• FERREIRA, VITOR F.;PINTO, ANTONIO V.;PINTO, MARIA C. F. R.;SILVA, MAURICI+, AN. ACAD. BRAS. CIENC., 59,(1987) N 4, C. 329-333
  作者：FERREIRA, VITOR F.、PINTO, ANTONIO V.、PINTO, MARIA C. F. R.、SILVA, MAURICI+

  DOI：——

  日期：——
• Efficient Synthesis of Biologically Interesting Dehydro‐α‐Lapachone and α‐Lapachone
  作者：Yong Rok Lee、Won Kyong Lee

  DOI：10.1081/scc-200043216

  日期：2004.1

  An efficient synthesis of biologically active dehydro-alpha-lapachone and alpha-lapachone has been carried out starting from 2-hydroxy-1,4-naphthoquinone by a tandem Knoevenagel-electrocyclic reaction.
• New oxirane derivatives of 1,4-naphthoquinones and their evaluation against T. cruzi epimastigote forms
  作者：Paula F. Carneiro、Samara B. do Nascimento、Antonio V. Pinto、Maria do Carmo F.R. Pinto、Guilherme C. Lechuga、Dilvani O. Santos、Helvécio M. dos Santos Júnior、Jackson A.L.C. Resende、Saulo C. Bourguignon、Vitor F. Ferreira

  DOI：10.1016/j.bmc.2012.06.027

  日期：2012.8

  New oxirane derivatives were synthesized using six naphthoquinones as the starting materials. Our biological results showed that these oxiranes acted as trypanocidal agents against Trypanosoma cruzi with minimal cytotoxicity in the VERO cell line compared to naphthoquinones. In particular, oxirane derivative 14 showed low cytotoxicity in a mammalian cell line and exhibited better activity against epimastigote forms of T. cruzi than the current drug used to treat Chagas disease, benznidazole. (C) 2012 Elsevier Ltd. All rights reserved.