1-tert-butyl 2-methyl 2-((2,3,6,7-tetramethoxyphenanthren-9-yl)methyl)pyrrolidine-1,2-dicarboxylate | 1613158-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-tert-butyl 2-methyl 2-((2,3,6,7-tetramethoxyphenanthren-9-yl)methyl)pyrrolidine-1,2-dicarboxylate
• CAS: 1613158-77-2
• 化学式: C₃₀H₃₇NO₈
• 分子量: 539.626
• InChiKey: UKWWVMRBSGRWOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 2-methyl 2-((2,3,6,7-tetramethoxyphenanthren-9-yl)methyl)pyrrolidine-1,2-dicarboxylate 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 22.0h， 生成 (2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-13a-yl)methanol
  参考文献：
  名称：

  Design, synthesis, antiviral activity, and SARs of 13a-substituted phenanthroindolizidine alkaloid derivatives

  摘要：

  On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of 13a-substituted phenanthroindolizidine alkaloid analogues (3a-16a, 3b, 4b, 6b, 7b, 10b, and 14b) were designed targeting tobacco mosaic virus (TMV) RNA, synthesized, and evaluated for their antiviral activity against TMV for the first time. The bioassay results showed that most of the synthesized compounds (such as 4a, 6a, 7a, 11a, 14a, 6b, and 14b) exhibited good to excellent antiviral activity against TMV both in vitro and in vivo. Especially, for inactivation effect and curative effect, compounds 4a, 6a, 7a, 11a, 14a, and 14b showed higher activity at both concentrations (500 mu g mL(-1) and 100 mu g mL(-1)) than commercial Ningnanmycin. Preliminary SARs showed that the substituted groups with hydrogen donor at 13a position were found to be favorable for keeping high antiviral activity. The present work demonstrates that 13a-substituted phenanthroindolizidines can be used as possible lead compounds for developing anti-TMV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.101
• 作为产物：
  描述：

  9-(bromomethyl)-2,3,6,7-tetramethoxyphenanthrene 、 Boc-L-脯氨酸甲酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以93%的产率得到1-tert-butyl 2-methyl 2-((2,3,6,7-tetramethoxyphenanthren-9-yl)methyl)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Design, synthesis, antiviral activity, and SARs of 13a-substituted phenanthroindolizidine alkaloid derivatives

  摘要：

  On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of 13a-substituted phenanthroindolizidine alkaloid analogues (3a-16a, 3b, 4b, 6b, 7b, 10b, and 14b) were designed targeting tobacco mosaic virus (TMV) RNA, synthesized, and evaluated for their antiviral activity against TMV for the first time. The bioassay results showed that most of the synthesized compounds (such as 4a, 6a, 7a, 11a, 14a, 6b, and 14b) exhibited good to excellent antiviral activity against TMV both in vitro and in vivo. Especially, for inactivation effect and curative effect, compounds 4a, 6a, 7a, 11a, 14a, and 14b showed higher activity at both concentrations (500 mu g mL(-1) and 100 mu g mL(-1)) than commercial Ningnanmycin. Preliminary SARs showed that the substituted groups with hydrogen donor at 13a position were found to be favorable for keeping high antiviral activity. The present work demonstrates that 13a-substituted phenanthroindolizidines can be used as possible lead compounds for developing anti-TMV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.101