3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside | 1192234-92-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside
• 英文别名: (2S,3S,6R)-2-methyl-6-[3-(2-phenyl-1-benzofuran-3-yl)prop-2-ynoxy]oxan-3-amine
• CAS: 1192234-92-6
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: GTRTVNQZJWUBTR-XUEUYAKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside 、 丙酮 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以82%的产率得到3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-N-isopropyl-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/j.bmcl.2011.02.051
• 作为产物：
  描述：

  3-(2-phenylbenzo[b]furan-3-yl)prop-2-ynyl 2,3,6-trideoxy-α-L-erythro-hexopyranoside 在 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside
  参考文献：
  名称：

  Synthesis and antibacterial activity of aminosugar-functionalized intercalating agents

  摘要：

  A series of previously reported amino sugar-functionalized intercalating agents, 3-14, were evaluated in two antibacterial assays (paper disk diffusion and 96-well microdilution) against Bacillus atrophaeus, ATCC 9372 and Escherichia coli, ATCC 47076. Although none of the compounds were active against this E. coli strain, several showed activity against B. atrophaeus. In anticipation of the need for larger amounts of these compounds for future structure-activity relationship studies, improved routes to 11-14 were developed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.10.010

文献信息

• Synthesis and DNA-binding affinity studies of glycosylated intercalators designed as functional mimics of the anthracycline antibiotics
  作者：Wei Shi、Robert S. Coleman、Todd L. Lowary

  DOI：10.1039/b909153j

  日期：——

  ide) via a propargyl linker. The DNA binding affinity of these twelve compounds has been evaluated by using both direct and indirect fluorescence measurements. Compared to Dauno and Dox, the DNA binding affinity of these analogues is weaker. However, both aromatic and aminosugar motifs are critical to DNA binding, with more influence coming from the structural features of the aromatic portion.

  蒽环类抗生素，如道诺霉素（道诺） 和阿霉素（多克斯）是众所周知的临床使用的癌症化疗药物，除其他机制外，它们与 DNA 结合，从而引发一系列生物反应，导致细胞死亡。然而，蒽环类药物具有心脏毒性，耐药性发展迅速，限制了其临床应用。我们在这里报告了一类新型功能性蒽环类药物模拟物的合成和 DNA 结合亲和力，该模拟物由与碳水化合物连接的芳香部分组成 ( 1-12 )。在目标中，芳香核由 2-苯基苯并[ b ]呋喃-3-基组成，2-苯基苯并[ b ]噻吩-3-基,1-甲苯磺酰基-2-苯基吲哚-3-基，或与三个氨基糖之一结合的 2-苯基吲哚-3-基（道诺糖胺,阿考斯胺， 或者4-氨基-2,3,4,6-十四氧基-α- L-吡喃己糖苷）通过炔丙基连接体。这十二种化合物的 DNA 结合亲和力已通过直接和间接荧光测量进行了评估。相比道诺和多克斯，这些类似物的DNA结合亲和力较弱。然而，无论是芳香族还是氨基糖基序对于
• 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.
• Synthesis and antibacterial activity of aminosugar-functionalized intercalating agents
  作者：Wei Shi、Sandra L. Marcus、Todd L. Lowary

  DOI：10.1016/j.carres.2009.10.010

  日期：2010.1

  A series of previously reported amino sugar-functionalized intercalating agents, 3-14, were evaluated in two antibacterial assays (paper disk diffusion and 96-well microdilution) against Bacillus atrophaeus, ATCC 9372 and Escherichia coli, ATCC 47076. Although none of the compounds were active against this E. coli strain, several showed activity against B. atrophaeus. In anticipation of the need for larger amounts of these compounds for future structure-activity relationship studies, improved routes to 11-14 were developed. (C) 2009 Elsevier Ltd. All rights reserved.