1-(3-((((2R,3S,4R,5R)-5-(6-((3-chlorobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(isopropyl)amino)propyl)-3-(4-methoxyphenyl)urea

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 1-(3-((((2R,3S,4R,5R)-5-(6-((3-chlorobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(isopropyl)amino)propyl)-3-(4-methoxyphenyl)urea
• 英文别名: 1-[3-[[(2R,3S,4R,5R)-5-[6-[(3-chlorophenyl)methylamino]purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl-propan-2-ylamino]propyl]-3-(4-methoxyphenyl)urea
• 化学式: C₃₁H₃₉ClN₈O₅
• 分子量: 639.154
• InChiKey: ZLPLCSIRLROBTA-BQOYKFDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  159
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-氯苄胺 在 lithium aluminium tetrahydride 、 邻苯二甲酸亚胺 、 sodium cyanotrihydroborate 、 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 24.25h， 生成 1-(3-((((2R,3S,4R,5R)-5-(6-((3-chlorobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(isopropyl)amino)propyl)-3-(4-methoxyphenyl)urea
  参考文献：
  名称：

  Design, synthesis and in vitro anti-Zika virus evaluation of novel Sinefungin derivatives

  摘要：

  We report herein the design and synthesis of a series of novel Sinefungin (SIN) derivatives, based on the structures of SIN and its analogue EPZ004777. Our results reveal that target compounds 1ad-af, 1ba-bb and 1bf-bh show better activity (IC50 = 4.56-20.16 mu M) than EPZ004777 (IC50 = 35.19 mu M). Surprisingly, SIN was founded to be not as active (IC50 > 50 mu M) as we and other research groups predicted. Interestingly, the intermediates 9a-b and 11b display potent anti-ZIKV potency (IC50 = 6.33-29.98 mu M), and compound 9a also exhibits acceptable cytotoxicity (CC50 > 200 mu M), suggesting their promising potential to be leads for further development. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.057

文献信息

• Design, synthesis and in vitro anti-Zika virus evaluation of novel Sinefungin derivatives
  作者：Zeyu Tao、Ruiyuan Cao、Yunzheng Yan、Guocheng Huang、Kai Lv、Wei Li、Yunhe Geng、Lei Zhao、Apeng Wang、Qinghao He、Jingjing Yang、Shiyong Fan、Menghao Huang、Huiyuan Guo、Wu Zhong、Mingliang Liu

  DOI：10.1016/j.ejmech.2018.08.057

  日期：2018.9

  We report herein the design and synthesis of a series of novel Sinefungin (SIN) derivatives, based on the structures of SIN and its analogue EPZ004777. Our results reveal that target compounds 1ad-af, 1ba-bb and 1bf-bh show better activity (IC50 = 4.56-20.16 mu M) than EPZ004777 (IC50 = 35.19 mu M). Surprisingly, SIN was founded to be not as active (IC50 > 50 mu M) as we and other research groups predicted. Interestingly, the intermediates 9a-b and 11b display potent anti-ZIKV potency (IC50 = 6.33-29.98 mu M), and compound 9a also exhibits acceptable cytotoxicity (CC50 > 200 mu M), suggesting their promising potential to be leads for further development. (C) 2018 Elsevier Masson SAS. All rights reserved.