Fmoc-Ala-OPfp ((9H-fluoren-9-yl-methoxy)carbonyl-L-alanine pentafluorophenyl ester) | 1310380-30-3

• 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: Fmoc-Ala-OPfp ((9H-fluoren-9-yl-methoxy)carbonyl-L-alanine pentafluorophenyl ester)
• CAS: 1310380-30-3
• 化学式: C₄₁H₃₈N₂O₆
• 分子量: 654.763
• InChiKey: YVLWFPMIZRZNFF-KVGMFJBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  49.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99.03
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Ala-OPfp ((9H-fluoren-9-yl-methoxy)carbonyl-L-alanine pentafluorophenyl ester) 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 以14 mg的产率得到3-(2-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-N-L-ala-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-phenyl-benzo[b]furan-3-yl)-prop-2-ynyl 4-amino-2,3,4,6-tetradeoxy-α-L-threo-hexopyranoside 、 N-芴甲氧羰基-L-丙氨酸五氟苯酯 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 Fmoc-Ala-OPfp ((9H-fluoren-9-yl-methoxy)carbonyl-L-alanine pentafluorophenyl ester)
  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