9-Methoxy-14-(2,2,5-trimethyl-1,3-dioxan-5-yl)-3-oxa-14-azatetracyclo[6.6.1.02,6.012,15]pentadeca-1(15),2(6),4,8,10,12-hexaen-7-one | 232953-23-0

• 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: 9-Methoxy-14-(2,2,5-trimethyl-1,3-dioxan-5-yl)-3-oxa-14-azatetracyclo[6.6.1.02,6.012,15]pentadeca-1(15),2(6),4,8,10,12-hexaen-7-one
• CAS: 232953-23-0
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: PNVCEIGFKMYYIM-UHFFFAOYSA-N

物化性质

• 沸点：
  563.8±50.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-Methoxy-14-(2,2,5-trimethyl-1,3-dioxan-5-yl)-3-oxa-14-azatetracyclo[6.6.1.02,6.012,15]pentadeca-1(15),2(6),4,8,10,12-hexaen-7-one 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以80%的产率得到1-(2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-5-methoxy-1H-9-oxa-1-aza-cyclopenta[d]acenaphthylen-6-one
  参考文献：
  名称：

  Synthesis of Furanonaphthoquinones with Hydroxyamino Side Chains

  摘要：

  Several furanonaphthoquinones have shown useful activity in a yeast assay for DNA-damaging agents and cytotoxicity in mammalian cell culture assays. These results, together with the planar aromatic character of the furanonaphthoquinones, suggested that they might be acting as DNA intercalators. In an attempt to improve this activity, various analogues containing a hydroxyamino side chain have been synthesized. The analogues were prepared by standard methods, but some unexpected reactions were observed nonetheless. Thus, 8-formyl-5-methoxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (24) showed an unusual reactivity toward reductive amination, with the reaction proceeding further to give one of two different cyclized products, depending on the amination reagent used. Bioassay results indicated that only simple furanonaphthoquines showed activity in a yeast assay for DNA-damaging agents; compounds with a substituted hydroxyamino side chain were uniformly inactive in this assay. Most of the compounds with a substituted hydroxyamino side chain on the furan ring did, however, show cytotoxicity, although none of them was any more active than the simple aldehyde 2-formyl-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (14). This evidence tends to suggest that the furanonaphthoquinones do not serve primarily as DNA intercalators, because if this were the case, they would have been expected to show an increased activity on conversion to their hydroxyamino side chain derivatives.

  DOI：

  10.1021/np9900019
• 作为产物：
  描述：

  (2,2,5-trimethyl-[1,3]-dioxan-5-yl)carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 magnesium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 9-Methoxy-14-(2,2,5-trimethyl-1,3-dioxan-5-yl)-3-oxa-14-azatetracyclo[6.6.1.02,6.012,15]pentadeca-1(15),2(6),4,8,10,12-hexaen-7-one
  参考文献：
  名称：

  Synthesis of Furanonaphthoquinones with Hydroxyamino Side Chains

  摘要：

  Several furanonaphthoquinones have shown useful activity in a yeast assay for DNA-damaging agents and cytotoxicity in mammalian cell culture assays. These results, together with the planar aromatic character of the furanonaphthoquinones, suggested that they might be acting as DNA intercalators. In an attempt to improve this activity, various analogues containing a hydroxyamino side chain have been synthesized. The analogues were prepared by standard methods, but some unexpected reactions were observed nonetheless. Thus, 8-formyl-5-methoxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (24) showed an unusual reactivity toward reductive amination, with the reaction proceeding further to give one of two different cyclized products, depending on the amination reagent used. Bioassay results indicated that only simple furanonaphthoquines showed activity in a yeast assay for DNA-damaging agents; compounds with a substituted hydroxyamino side chain were uniformly inactive in this assay. Most of the compounds with a substituted hydroxyamino side chain on the furan ring did, however, show cytotoxicity, although none of them was any more active than the simple aldehyde 2-formyl-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (14). This evidence tends to suggest that the furanonaphthoquinones do not serve primarily as DNA intercalators, because if this were the case, they would have been expected to show an increased activity on conversion to their hydroxyamino side chain derivatives.

  DOI：

  10.1021/np9900019

文献信息

• Synthesis of Furanonaphthoquinones with Hydroxyamino Side Chains
  作者：Chongming Wu、Randall K. Johnson、Michael R. Mattern、Jackson C. Wong、David G. I. Kingston

  DOI：10.1021/np9900019

  日期：1999.7.1

  Several furanonaphthoquinones have shown useful activity in a yeast assay for DNA-damaging agents and cytotoxicity in mammalian cell culture assays. These results, together with the planar aromatic character of the furanonaphthoquinones, suggested that they might be acting as DNA intercalators. In an attempt to improve this activity, various analogues containing a hydroxyamino side chain have been synthesized. The analogues were prepared by standard methods, but some unexpected reactions were observed nonetheless. Thus, 8-formyl-5-methoxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (24) showed an unusual reactivity toward reductive amination, with the reaction proceeding further to give one of two different cyclized products, depending on the amination reagent used. Bioassay results indicated that only simple furanonaphthoquines showed activity in a yeast assay for DNA-damaging agents; compounds with a substituted hydroxyamino side chain were uniformly inactive in this assay. Most of the compounds with a substituted hydroxyamino side chain on the furan ring did, however, show cytotoxicity, although none of them was any more active than the simple aldehyde 2-formyl-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (14). This evidence tends to suggest that the furanonaphthoquinones do not serve primarily as DNA intercalators, because if this were the case, they would have been expected to show an increased activity on conversion to their hydroxyamino side chain derivatives.