(1R,7S,7aR)-4-methyl-1-naphthalen-1-yl-7-prop-1-en-2-yl-1,6,7,7a-tetrahydro-2-benzofuran | 1203706-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,7S,7aR)-4-methyl-1-naphthalen-1-yl-7-prop-1-en-2-yl-1,6,7,7a-tetrahydro-2-benzofuran
• CAS: 1203706-04-0
• 化学式: C₂₂H₂₂O
• 分子量: 302.416
• InChiKey: FHDKKCYPMOPVOP-YHYVQYDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.08h， 以33%的产率得到(1R,7S,7aR)-4-methyl-1-naphthalen-1-yl-7-prop-1-en-2-yl-1,6,7,7a-tetrahydro-2-benzofuran
  参考文献：
  名称：

  Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans

  摘要：

  Three structurally related sets of hydroisobenzofuran analogs of sclerophytin A were prepared in three or four steps from (S)-(+)-carvone via an aldol-cycloaldol sequence. The most potent members of each set of analogs exhibited IC50's of 1-3 mu M in growth inhibitory assays against KB3 cells. The NCI 60-cell line 5-dose assay for analog 6h revealed a GI(50) = 0.148 mu M and LC50 = 9.36 mu M for the RPMI-8226 leukemia cell line, and a GI(50) = 0.552 mu M and LC50 = 26.8 mu M for the HOP-92 non-small cell lung cancer cell line. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.079

文献信息

• Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans
  作者：T. David Bateman、Aarti L. Joshi、Kwangyul Moon、Elena N. Galitovskaya、Meenakshi Upreti、Timothy C. Chambers、Matthias C. McIntosh

  DOI：10.1016/j.bmcl.2009.10.079

  日期：2009.12

  Three structurally related sets of hydroisobenzofuran analogs of sclerophytin A were prepared in three or four steps from (S)-(+)-carvone via an aldol-cycloaldol sequence. The most potent members of each set of analogs exhibited IC50's of 1-3 mu M in growth inhibitory assays against KB3 cells. The NCI 60-cell line 5-dose assay for analog 6h revealed a GI(50) = 0.148 mu M and LC50 = 9.36 mu M for the RPMI-8226 leukemia cell line, and a GI(50) = 0.552 mu M and LC50 = 26.8 mu M for the HOP-92 non-small cell lung cancer cell line. (C) 2009 Elsevier Ltd. All rights reserved.