(6-Methoxy-6-pentyl-[1,2]dioxan-3-yl)-acetic acid pentafluorophenyl ester | 644989-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (6-Methoxy-6-pentyl-[1,2]dioxan-3-yl)-acetic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-Pentafluorophenyl) 2-(6-methoxy-6-pentyldioxan-3-yl)acetate；(2,3,4,5,6-pentafluorophenyl) 2-(6-methoxy-6-pentyldioxan-3-yl)acetate
• CAS: 644989-67-3
• 化学式: C₁₈H₂₁F₅O₅
• 分子量: 412.354
• InChiKey: FKUWFMMIZRROPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 、 (6-Methoxy-6-pentyl-[1,2]dioxan-3-yl)-acetic acid pentafluorophenyl ester 以 四氢呋喃 为溶剂， 反应 0.17h， 以100%的产率得到2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl)-N-[4-[{2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl)acetylamino}propyl]tetrahydropyrazin-1(2H)-yl]propylacetamide
  参考文献：
  名称：

  Structure–activity relationship of anti-malarial spongean peroxides having a 3-methoxy-1,2-dioxane structure

  摘要：

  In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl) acetate were synthesized and evaluated for anti-malarial activity. The tert-butyl ester analogue 14 showed stability in mouse serum and a high selectivity index against the malaria parasite, Plasmodium falciparum, and the citronellyl analogue 31 exhibited the strongest in vitro antimalarial activity among them, and the imidazole analogue 25 showed desirable in vivo anti-malarial activity against P. berghei infected mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.051
• 作为产物：
  描述：

  Methyl 2-(6-methoxy-6-pentyldioxan-3-yl)acetate 在 吡啶 、 esterase (from porcine liver) 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 phosphate buffer 为溶剂， 生成 (6-Methoxy-6-pentyl-[1,2]dioxan-3-yl)-acetic acid pentafluorophenyl ester
  参考文献：
  名称：

  New anti-malarial peroxides with In vivo potency derived from spongean metabolites

  摘要：

  The structure-activity relationship of the anti-malarial substance 3 having a 6-carbomethoxymethyl-3-methoxy-1,2-dioxane structure was studied. The ester portion of the peroxide 3, showing little in vivo efficacy in malaria-infected mice in spite of the potent in vitro activity, was hydrolyzed in serum to afford an inactive free acid 4. The amide analogues (8 and 9) robust to mouse serum were disclosed to exhibit in vivo anti-malarial potency. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.073

文献信息

• Structure–activity relationship of anti-malarial spongean peroxides having a 3-methoxy-1,2-dioxane structure
  作者：Motoyuki Kawanishi、Naoyuki Kotoku、Sawako Itagaki、Toshihiro Horii、Motomasa Kobayashi

  DOI：10.1016/j.bmc.2004.04.051

  日期：2004.10

  In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl) acetate were synthesized and evaluated for anti-malarial activity. The tert-butyl ester analogue 14 showed stability in mouse serum and a high selectivity index against the malaria parasite, Plasmodium falciparum, and the citronellyl analogue 31 exhibited the strongest in vitro antimalarial activity among them, and the imidazole analogue 25 showed desirable in vivo anti-malarial activity against P. berghei infected mice. (C) 2004 Elsevier Ltd. All rights reserved.
• New anti-malarial peroxides with In vivo potency derived from spongean metabolites
  作者：Nobutoshi Murakami、Motoyuki Kawanishi、Huq Mohammad Mostaqul、Jie Li、Sawako Itagaki、Toshihiro Horii、Motomasa Kobayashi

  DOI：10.1016/j.bmcl.2003.08.073

  日期：2003.11

  The structure-activity relationship of the anti-malarial substance 3 having a 6-carbomethoxymethyl-3-methoxy-1,2-dioxane structure was studied. The ester portion of the peroxide 3, showing little in vivo efficacy in malaria-infected mice in spite of the potent in vitro activity, was hydrolyzed in serum to afford an inactive free acid 4. The amide analogues (8 and 9) robust to mouse serum were disclosed to exhibit in vivo anti-malarial potency. (C) 2003 Elsevier Ltd. All rights reserved.