methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(2'-thienyl)prop-2-ynyl]-D-glycero-D-talo-non-2-enonate | 947152-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(2'-thienyl)prop-2-ynyl]-D-glycero-D-talo-non-2-enonate
• 英文别名: methyl (2R,3R,4R)-3-acetamido-4-(3-thiophen-2-ylprop-2-ynoxy)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 947152-72-9
• 化学式: C₁₉H₂₃NO₈S
• 分子量: 425.46
• InChiKey: JDEDEQFWJXHFBQ-RTKZEXODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(2'-thienyl)prop-2-ynyl]-D-glycero-D-talo-non-2-enonate 在 甲醇 、 氢氧化钾 作用下， 以60%的产率得到5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(2'-thienyl)prop-2-ynyl]-D-glycero-D-talo-non-2-enonic acid
  参考文献：
  名称：

  Synthesis of 4-O-[3-(aryl)prop-2-ynyl]-Neu5Ac2en and its 4-epi-analogs modified at C-4 by Sonogashira coupling reaction

  摘要：

  To explore new inhibitors of the sialidase of human parainfluenza virus type 1 (hPIV-1), a series of novel Neu5Ac2en derivatives were synthesized. Thus, 8,9-O-isopropylidene-4-O-2-propynyl-Neu5Ac2en methyl ester 8 was subjected to a Sonogashira coupling reaction with a variety of heteroaryl halides to produce a series of 4-O-(3-heteroaryl-2-propynyl) compound 9. Treatment of 9 with 80% acetic acid followed by alkaline hydrolysis afforded deprotected Neu5Ac2en compounds. The 4-epi-analogs of this type of Neu5Ac2en were synthesized in a similar manner. Compound 5d showed the most potent inhibitory activity (IC50 1.2 mu M) against hPIV-1 sialidase. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.049
• 作为产物：
  描述：

  methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(prop-2-ynyl)-D-glycero-D-talo-non-2-enonate 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 溶剂黄146 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-[3-(2'-thienyl)prop-2-ynyl]-D-glycero-D-talo-non-2-enonate
  参考文献：
  名称：

  Synthesis of 4-O-[3-(aryl)prop-2-ynyl]-Neu5Ac2en and its 4-epi-analogs modified at C-4 by Sonogashira coupling reaction

  摘要：

  To explore new inhibitors of the sialidase of human parainfluenza virus type 1 (hPIV-1), a series of novel Neu5Ac2en derivatives were synthesized. Thus, 8,9-O-isopropylidene-4-O-2-propynyl-Neu5Ac2en methyl ester 8 was subjected to a Sonogashira coupling reaction with a variety of heteroaryl halides to produce a series of 4-O-(3-heteroaryl-2-propynyl) compound 9. Treatment of 9 with 80% acetic acid followed by alkaline hydrolysis afforded deprotected Neu5Ac2en compounds. The 4-epi-analogs of this type of Neu5Ac2en were synthesized in a similar manner. Compound 5d showed the most potent inhibitory activity (IC50 1.2 mu M) against hPIV-1 sialidase. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.049

文献信息

• Synthesis of 4-O-[3-(aryl)prop-2-ynyl]-Neu5Ac2en and its 4-epi-analogs modified at C-4 by Sonogashira coupling reaction
  作者：Kazuki Sato、Kiyoshi Ikeda、Takashi Suzuki、Shinya Aoyama、Naoyoshi Maki、Yasuo Suzuki、Masayuki Sato

  DOI：10.1016/j.tet.2007.05.049

  日期：2007.8

  To explore new inhibitors of the sialidase of human parainfluenza virus type 1 (hPIV-1), a series of novel Neu5Ac2en derivatives were synthesized. Thus, 8,9-O-isopropylidene-4-O-2-propynyl-Neu5Ac2en methyl ester 8 was subjected to a Sonogashira coupling reaction with a variety of heteroaryl halides to produce a series of 4-O-(3-heteroaryl-2-propynyl) compound 9. Treatment of 9 with 80% acetic acid followed by alkaline hydrolysis afforded deprotected Neu5Ac2en compounds. The 4-epi-analogs of this type of Neu5Ac2en were synthesized in a similar manner. Compound 5d showed the most potent inhibitory activity (IC50 1.2 mu M) against hPIV-1 sialidase. (C) 2007 Elsevier Ltd. All rights reserved.