Methyl 2-(6-methoxy-6-pentyldioxan-3-yl)acetate | 644989-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: Methyl 2-(6-methoxy-6-pentyldioxan-3-yl)acetate
• CAS: 644989-64-0
• 化学式: C₁₃H₂₄O₅
• 分子量: 260.331
• InChiKey: JKKOPOHLRXSFFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-氧代壬-1-醛 在 双氧水 、 二乙胺 、 尿素 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 2-(6-methoxy-6-pentyldioxan-3-yl)acetate
  参考文献：
  名称：

  New readily accessible peroxides with High Anti-malarial Potency

  摘要：

  In an explorative study for new anti-malarial substances using the methyl esters (1 and 2) of peroxyplakoric acids A(3) and B-3 as scaffolds, 6-carbomethoxymethyl-3-methoxy-3-pentyl-1,2-dioxane, which has been readily synthesized from 6-keto-alpha,beta -unsaturated ester, was found to exhibit potent anti-malarial activity with high selective toxicity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00673-4

文献信息

• Synthesis of a bioprobe for elucidation of target molecule of spongean anti-malarial peroxides
  作者：Nobutoshi Murakami、Motoyuki Kawanishi、Sawako Itagaki、Toshihiro Horii、Motomasa Kobayashi

  DOI：10.1016/j.bmcl.2004.04.086

  日期：2004.7

  The reactants of an anti-malarial peroxide having a 6-carbomethoxymethyl-3-methoxy-1,2-dioxane moiety treated with FeSO4 were analyzed. For mechanistic study of the anti-malarial peroxide, two biotinylated probes to elucidate the target molecules were designed and synthesized. The two synthesized probes showed potent anti-malarial activity, and one of them was proved to form an irreversible binding with protein in a model experiment. (C) 2004 Elsevier Ltd. All rights reserved.
• New readily accessible peroxides with High Anti-malarial Potency
  作者：Nobutoshi Murakami、Motoyuki Kawanishi、Sawako Itagaki、Toshihiro Horii、Motomasa Kobayashi

  DOI：10.1016/s0960-894x(01)00673-4

  日期：2002.1

  In an explorative study for new anti-malarial substances using the methyl esters (1 and 2) of peroxyplakoric acids A(3) and B-3 as scaffolds, 6-carbomethoxymethyl-3-methoxy-3-pentyl-1,2-dioxane, which has been readily synthesized from 6-keto-alpha,beta -unsaturated ester, was found to exhibit potent anti-malarial activity with high selective toxicity. (C) 2001 Elsevier Science 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.