3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-N-ethyl-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside | 1310380-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-N-ethyl-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside
• 英文别名: (2S,3S,6R)-N-ethyl-2-methyl-6-[3-(2-phenyl-1-benzothiophen-3-yl)prop-2-ynoxy]oxan-3-amine
• CAS: 1310380-55-2
• 化学式: C₂₅H₂₇NO₂S
• 分子量: 405.561
• InChiKey: CYCDOSSMVKUXNK-JKFKMHIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(2-phenyl-benzo[b]thiophene-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside 、 乙醛 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以85%的产率得到3-(2-phenyl-benzo[b]thiophen-3-yl)-prop-2-ynyl 4-N-ethyl-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside
  参考文献：
  名称：

  Reprint of “Effect of carbohydrate amino group modifications on the cytotoxicity of glycosylated 2-phenyl-benzo[b]thiophenes and 2-phenyl-benzo[b]furans” [Bioorg. Med. Chem. Lett. 21 (2011) 2591–2596]

  摘要：

  In previous studies, we have identified a family of benzo[b]furan and benzo[b]thiophene derivatives linked to amino sugars (1-6) that are cytotoxic to a range of cancer cell lines. We describe here an exploration of the effect of structural modification of the amino group on one of the carbohydrate residues (4-amino-2,3,4,6-tetradeoxy-alpha-L-threo-hexopyranoside) on in vitro cytotoxicity. It has been found that maintaining at least one basic functional group around the C-4 position in the carbohydrate moiety is crucial for cytotoxicity. Furthermore, it appears that modifications around the C-4 position are limited by suitable hydrophilic/hydrophobic and/or ionic interactions, as well as steric constraints. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(11)01095-x

文献信息

• Reprint of “Effect of carbohydrate amino group modifications on the cytotoxicity of glycosylated 2-phenyl-benzo[b]thiophenes and 2-phenyl-benzo[b]furans” [Bioorg. Med. Chem. Lett. 21 (2011) 2591–2596]
  作者：Wei Shi、Todd L. Lowary

  DOI：10.1016/s0960-894x(11)01095-x

  日期：2011.9

  In previous studies, we have identified a family of benzo[b]furan and benzo[b]thiophene derivatives linked to amino sugars (1-6) that are cytotoxic to a range of cancer cell lines. We describe here an exploration of the effect of structural modification of the amino group on one of the carbohydrate residues (4-amino-2,3,4,6-tetradeoxy-alpha-L-threo-hexopyranoside) on in vitro cytotoxicity. It has been found that maintaining at least one basic functional group around the C-4 position in the carbohydrate moiety is crucial for cytotoxicity. Furthermore, it appears that modifications around the C-4 position are limited by suitable hydrophilic/hydrophobic and/or ionic interactions, as well as steric constraints. (c) 2011 Elsevier Ltd. All rights reserved.