dimethyl 3-[4-benzyloxy-5-methoxy-2-(methoxymethoxy)phenyl]-1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate | 1225441-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 3-[4-benzyloxy-5-methoxy-2-(methoxymethoxy)phenyl]-1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate
• 英文别名: Dimethyl 1-[2-(3,4-dimethoxyphenyl)ethyl]-3-[5-methoxy-2-(methoxymethoxy)-4-phenylmethoxyphenyl]-4-(trifluoromethylsulfonyloxy)pyrrole-2,5-dicarboxylate
• CAS: 1225441-55-3
• 化学式: C₃₅H₃₆F₃NO₁₃S
• 分子量: 767.731
• InChiKey: OTUOAFKGEFSDJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  dimethyl 3-[4-benzyloxy-5-methoxy-2-(methoxymethoxy)phenyl]-1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate 在 喹啉 、 盐酸 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 三氯化硼 、 sodium carbonate 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 [双(三氟乙酰氧基)碘]苯 、 copper(II) oxide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 54.67h， 生成 3-hydroxy-14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6H-[1]benzopyrano[4',3':4,5]-pyrrolo[2,1-a]isoquinolin-6-one
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues

  摘要：

  Lamellarin a and six different types of lamellarin alpha 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 mu M concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin alpha and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 mu M). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.030
• 作为产物：
  描述：

  dimethyl 3,4-dihydroxy-1-[2-(3,4-dimethoxyphenyl)ethyl]pyrrole-2,5-dicarboxylate 在 吡啶 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 dimethyl 3-[4-benzyloxy-5-methoxy-2-(methoxymethoxy)phenyl]-1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues

  摘要：

  Lamellarin a and six different types of lamellarin alpha 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 mu M concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin alpha and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 mu M). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.030

文献信息

• Divergent Synthesis of Lamellarin α 13-Sulfate, 20-Sulfate, and 13,20-Disulfate
  作者：Masatomo Iwao、Tsutomu Fukuda、Sho Saeki、Takeshi Ohta

  DOI：10.3987/com-09-s(s)100

  日期：——

  A divergent synthesis of three sulfate derivatives of lamellarin alpha, namely, lamellarin alpha 13-sulfate (2), 20-sulfate (1), and 13,20-disulfate (4) has been achieved via a common intermediate (6) in which 13-OH and 20-OH of the lamellarin core are differentially protected by MOM and benzyl groups, respectively. Compound (6) in turn was prepared using sequential Suzuki-Miyaura coupling of 3,4-dihydroxypyrrole bistriflate (7) as a key reaction.
• Synthesis, structure–activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues
  作者：Haruka Kamiyama、Yoshinao Kubo、Hironori Sato、Naoki Yamamoto、Tsutomu Fukuda、Fumito Ishibashi、Masatomo Iwao

  DOI：10.1016/j.bmc.2011.10.030

  日期：2011.12

  Lamellarin a and six different types of lamellarin alpha 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 mu M concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin alpha and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 mu M). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. (C) 2011 Elsevier Ltd. All rights reserved.