(5Z)-7-<(2-hydroxy-7-methoxy-5-methyl-1-naphthoyl)oxy>-1-thia-5-cyclodecene-3,8-diyne | 151985-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5Z)-7-<(2-hydroxy-7-methoxy-5-methyl-1-naphthoyl)oxy>-1-thia-5-cyclodecene-3,8-diyne
• 英文别名: [(6Z)-1-thiacyclodec-6-en-3,8-diyn-5-yl] 2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylate
• CAS: 151985-50-1
• 化学式: C₂₂H₁₈O₄S
• 分子量: 378.449
• InChiKey: JIYXLJSPZCZTCJ-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯甲基甲基醚 、 (5Z)-7-<(2-hydroxy-7-methoxy-5-methyl-1-naphthoyl)oxy>-1-thia-5-cyclodecene-3,8-diyne 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到(5Z)-7-<(7-methoxy-2-(methoxymethyl)-5-methyl-1-naphthoyl)oxy>-1-thia-5-cyclodecene-3,8-diyne
  参考文献：
  名称：

  包含新型烯二炔和天然存在的DNA插入物的杂合体的设计，合成和DNA裂解图谱

  摘要：

  所设计的杂种5 - 11含有该DNA可切割的烯二炔4和天然存在的DNA嵌入剂12 - 18有效下没有任何添加剂的碱性条件下切割DNA; 杂种5和11表现出最强的DNA切割能力，并具有相同的高嘌呤碱基（G> A）选择性，可用于其DNA切割过程。

  DOI：

  10.1039/c39930001525
• 作为产物：
  描述：

  (4Z)-1,9-bis<(tert-butyldiphenylsilyl)oxy>-6-<(tetrahydro-2-pyranyl)oxy>-4-nonene-2,7-diyne 在 甲醇 、 sodium sulfide 、 四溴化碳 、 三辛基膦 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (5Z)-7-<(2-hydroxy-7-methoxy-5-methyl-1-naphthoyl)oxy>-1-thia-5-cyclodecene-3,8-diyne
  参考文献：
  名称：

  Molecular Design, Chemical Synthesis, and Study of Novel Enediyne-Sulfide Systems Related to the Neocarzinostatin Chromophore

  摘要：

  The design and synthesis of the novel monocyclic enediyne-sulfide systems and their chemical and DNA cleavage properties are described. The parent enediyne-sulfide 6 possessing a hydroxy group at the allylic position was effectively synthesized via the cross-coupling of the cis-vinyl iodide 11 and the acetylene derivative 12 using a Pd(O)-Cu(I) catalyst and the cyclization reaction of the acyclic dibromide 20 employing sodium sulfide as the key steps. In addition, the esterifications of 6 using appropriate procedures provided a series of its simple derivatives 21-29 and the hybrids 38-44 containing naturally occurring intercalators, all of which are quite stable when handled at ambient temperature. The representative enediyne-sulfide 22 was smoothly aromatized by 1,8-diazabicyclo[5.4.0]undec-7-ene in cyclohexa-1,4-diene through radical pathways and by a hydroxy anion in dimethyl sulfoxide-Tris-HCl, pH 8.5 buffer through a polar pathway. Furthermore, it was clearly found that all enediyne-sulfides cleaved DNA under alkaline conditions without any additive and the hybrids 38 and 44, each of which has the aromatic moiety of the neocarzinostatin chromophore and manzamins, respectively, exhibited the strongest DNA cleaving abilities with the identical high purine base (G > A) selectivity.

  DOI：

  10.1021/ja00122a012

文献信息

• Design, synthesis and DNA cleaving profiles of hybrids containing the novel enediyne and naturally occurring DNA intercalates
  作者：Kazunobu Toshima、Kazumi Ohta、Aya Ohashi、Takatsugu Nakamura、Masaya Nakata、Shuichi Matsumura

  DOI：10.1039/c39930001525

  日期：——

  The designed hybrids 5–11 containing the DNA cleavable enediyne 4 and naturally occurring DNA intercalators 12–18cleave DNA effectively under alkaline conditions without any additive; the hybrids 5 and 11 exhibit the strongest DNA-cleaving abilities with the identical high purine base (G>A) selectivities for their DNA-cleavage profiles.

  所设计的杂种5 - 11含有该DNA可切割的烯二炔4和天然存在的DNA嵌入剂12 - 18有效下没有任何添加剂的碱性条件下切割DNA; 杂种5和11表现出最强的DNA切割能力，并具有相同的高嘌呤碱基（G> A）选择性，可用于其DNA切割过程。
• Molecular Design, Chemical Synthesis, and Study of Novel Enediyne-Sulfide Systems Related to the Neocarzinostatin Chromophore
  作者：Kazunobu Toshima、Kazumi Ohta、Aya Ohashi、Takatsugu Nakamura、Masaya Nakata、Kuniaki Tatsuta、Shuichi Matsumura

  DOI：10.1021/ja00122a012

  日期：1995.5

  The design and synthesis of the novel monocyclic enediyne-sulfide systems and their chemical and DNA cleavage properties are described. The parent enediyne-sulfide 6 possessing a hydroxy group at the allylic position was effectively synthesized via the cross-coupling of the cis-vinyl iodide 11 and the acetylene derivative 12 using a Pd(O)-Cu(I) catalyst and the cyclization reaction of the acyclic dibromide 20 employing sodium sulfide as the key steps. In addition, the esterifications of 6 using appropriate procedures provided a series of its simple derivatives 21-29 and the hybrids 38-44 containing naturally occurring intercalators, all of which are quite stable when handled at ambient temperature. The representative enediyne-sulfide 22 was smoothly aromatized by 1,8-diazabicyclo[5.4.0]undec-7-ene in cyclohexa-1,4-diene through radical pathways and by a hydroxy anion in dimethyl sulfoxide-Tris-HCl, pH 8.5 buffer through a polar pathway. Furthermore, it was clearly found that all enediyne-sulfides cleaved DNA under alkaline conditions without any additive and the hybrids 38 and 44, each of which has the aromatic moiety of the neocarzinostatin chromophore and manzamins, respectively, exhibited the strongest DNA cleaving abilities with the identical high purine base (G > A) selectivity.