6,19-diaza-10,13,16-trioxa-7,20-dioxo-29,31-tetratetraconta-diynyl methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)onate | 1261156-70-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6,19-diaza-10,13,16-trioxa-7,20-dioxo-29,31-tetratetraconta-diynyl methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)onate
• 英文别名: 6,19-diaza-10,13,16-trioxa-7,20-dioxo-29,31-tetratetrakontadiynyl methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)onate；methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[5-[3-[2-[2-[2-(pentacosa-10,12-diynoylamino)ethoxy]ethoxy]ethoxy]propanoylamino]pentoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 1261156-70-0
• 化学式: C₅₉H₉₇N₃O₁₈
• 分子量: 1136.43
• InChiKey: PYUQKVVFVRQUTJ-LEKAVULCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  80
• 可旋转键数：
  52
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  265
• 氢给体数：
  3
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  6,19-diaza-10,13,16-trioxa-7,20-dioxo-29,31-tetratetraconta-diynyl methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)onate 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 29.0h， 生成 6,19-diaza-10,13,16-trioxa-7,20-dioxo-29,31-tetratetracontadiynyl-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosylonic acid
  参考文献：
  名称：

  Molecular Wipes: Application to Epidemic Keratoconjuctivitis

  摘要：

  Epidemic keratoconjunctivitis (EKC) is a severe disease of the eye, caused by members of the Adenoviridae (Ad) family, with symptoms such as keratitis, conjunctivitis, pain, edema, and reduced vision that may last for months or years. There are no vaccines or antiviral drugs available to prevent or treat EKC. It was found previously that EKC-causing Ads use sialic acid as a cellular receptor and demonstrated that soluble, sialic acid-containing molecules can prevent infection. In this study, multivalent sialic acid constructs based on 10,12-pentacosadiynoic acid (PDA) have been synthesized, and these constructs are shown to be efficient inhibitors of Ad binding (IC50 = 0.9 mu M) and Ad infectivity (IC50 = 0.7 mu M). The mechanism of action is to aggregate virus particles and thereby prevent them from binding to ocular cells. Such formulations may be used for topical treatment of adenovirus-caused EKC.

  DOI：

  10.1021/jm200545m
• 作为产物：
  描述：

  N-芴甲氧羰基-12-氨基-4,7,10-三氧杂十二酸 在 哌啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 6,19-diaza-10,13,16-trioxa-7,20-dioxo-29,31-tetratetraconta-diynyl methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)onate
  参考文献：
  名称：

  Molecular Wipes: Application to Epidemic Keratoconjuctivitis

  摘要：

  Epidemic keratoconjunctivitis (EKC) is a severe disease of the eye, caused by members of the Adenoviridae (Ad) family, with symptoms such as keratitis, conjunctivitis, pain, edema, and reduced vision that may last for months or years. There are no vaccines or antiviral drugs available to prevent or treat EKC. It was found previously that EKC-causing Ads use sialic acid as a cellular receptor and demonstrated that soluble, sialic acid-containing molecules can prevent infection. In this study, multivalent sialic acid constructs based on 10,12-pentacosadiynoic acid (PDA) have been synthesized, and these constructs are shown to be efficient inhibitors of Ad binding (IC50 = 0.9 mu M) and Ad infectivity (IC50 = 0.7 mu M). The mechanism of action is to aggregate virus particles and thereby prevent them from binding to ocular cells. Such formulations may be used for topical treatment of adenovirus-caused EKC.

  DOI：

  10.1021/jm200545m