(6aS,12bR)-3-(benzyloxy)-6a-hydroxy-10,10-dimethyl-6,6a,7,12b-tetrahydro-[1,3]dioxolo[4',5':5,6]indeno[2,1-c]chromen-4-yl trifluoromethanesulfonate | 1360437-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6aS,12bR)-3-(benzyloxy)-6a-hydroxy-10,10-dimethyl-6,6a,7,12b-tetrahydro-[1,3]dioxolo[4',5':5,6]indeno[2,1-c]chromen-4-yl trifluoromethanesulfonate
• CAS: 1360437-06-4
• 化学式: C₂₇H₂₃F₃O₈S
• 分子量: 564.536
• InChiKey: VATZTEKEQXHGFF-BKMJKUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (6aS,12bR)-3-(benzyloxy)-6a-hydroxy-10,10-dimethyl-6,6a,7,12b-tetrahydro-[1,3]dioxolo[4',5':5,6]indeno[2,1-c]chromen-4-yl trifluoromethanesulfonate 在 盐酸 、 甲酸 、 三正丁胺 、 Pd₂Cl₂[PPh₃]2 、 palladium 10% on activated carbon 、 1,3-双(二苯基膦)丙烷 、 水 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 苏枋精
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy-hematoxylin derivatives as a novel class of anti-HIV-1 agents

  摘要：

  SAR studies for the exploration a novel class of anti-human immunodeficiency virus type 1 (HIV-1) agents based on the hematoxylin structure (1) are described. The systematic deoxygenations of 1 including asymmetric synthesis were conducted to obtain a compound showing high potencies for inhibiting the nuclear import and viral replication as anti-HIV-1 agent. Among all, C-3-deoxygenated analog 16 exhibited most promising biological activities as anti-HIV-1 agent such as lower cytotoxicity (16: 1; >80:40 mu M), stronger inhibition of nuclear import (0.5:1.3 mu M), and viral replication in HIV-1-infected TZM-bl cells (24.6:100 mu M), human peripheral blood mononuclear cells (PMBCs) (30.1 mu M: toxic). Different spectra of inhibitory activities against infected three healthy humans macrophages with high (donor A) and low (donor B and C) amounts of virus were also observed. Thus 16 showed 10-times stronger activity than 1 (16: 1; 0.1:<1.0 mu M) in the case of A, while 16 and 1 showed comparable activities in the cases of B and C (>0.01 and >0.001 mu M). The comparison of the inhibition of viral p24 antigen production was clearly indicated that compound 16 is at least twofold more potent anti-viral activity than 1. Thus, structures and actions of deoxy analogs particularly 16 could provide valuable information for the development of a novel class of anti-HIV-1 agents. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.06.066
• 作为产物：
  描述：

  (6aS,12bR)-10,10-dimethyl-7,12b-dihydro-[1,3]dioxolo[4',5':5,6]indeno[2,1-c]chromene-3,4,6a(6H)-triol 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (6aS,12bR)-3-(benzyloxy)-6a-hydroxy-10,10-dimethyl-6,6a,7,12b-tetrahydro-[1,3]dioxolo[4',5':5,6]indeno[2,1-c]chromen-4-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy-hematoxylin derivatives as a novel class of anti-HIV-1 agents

  摘要：

  SAR studies for the exploration a novel class of anti-human immunodeficiency virus type 1 (HIV-1) agents based on the hematoxylin structure (1) are described. The systematic deoxygenations of 1 including asymmetric synthesis were conducted to obtain a compound showing high potencies for inhibiting the nuclear import and viral replication as anti-HIV-1 agent. Among all, C-3-deoxygenated analog 16 exhibited most promising biological activities as anti-HIV-1 agent such as lower cytotoxicity (16: 1; >80:40 mu M), stronger inhibition of nuclear import (0.5:1.3 mu M), and viral replication in HIV-1-infected TZM-bl cells (24.6:100 mu M), human peripheral blood mononuclear cells (PMBCs) (30.1 mu M: toxic). Different spectra of inhibitory activities against infected three healthy humans macrophages with high (donor A) and low (donor B and C) amounts of virus were also observed. Thus 16 showed 10-times stronger activity than 1 (16: 1; 0.1:<1.0 mu M) in the case of A, while 16 and 1 showed comparable activities in the cases of B and C (>0.01 and >0.001 mu M). The comparison of the inhibition of viral p24 antigen production was clearly indicated that compound 16 is at least twofold more potent anti-viral activity than 1. Thus, structures and actions of deoxy analogs particularly 16 could provide valuable information for the development of a novel class of anti-HIV-1 agents. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.06.066