6-(4'-azido-4'-deoxy-2',3'-O-isoprpylidene-β-L-rhamnopyranosylamino)-4-(diethoxymethyl)amino-5-nitropyrimidine | 216483-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-(4'-azido-4'-deoxy-2',3'-O-isoprpylidene-β-L-rhamnopyranosylamino)-4-(diethoxymethyl)amino-5-nitropyrimidine
• 英文别名: 6-N-[(3aR,4S,6S,7S,7aR)-7-azido-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-4-N-(diethoxymethyl)-5-nitropyrimidine-4,6-diamine
• CAS: 216483-83-9
• 化学式: C₁₈H₂₈N₈O₇
• 分子量: 468.47
• InChiKey: XZVGRDJMASPOOL-VMCRYPJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-(4'-azido-4'-deoxy-2',3'-O-isoprpylidene-β-L-rhamnopyranosylamino)-4-(diethoxymethyl)amino-5-nitropyrimidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以53%的产率得到6-(4'-amino-4'-deoxy-2',3'-O-isopropylidene-β-L-rhamnopyranosylamino)-9H-purine
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin—is the mode of action by modification of N-linked glycoproteins?

  摘要：

  The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl alpha-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00240-2
• 作为产物：
  描述：

  4-azido-4-deoxy-α/β-L-rhamnopyranoside 在 camphor-10-sulfonic acid 、 氨 、 水 、 silica gel 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 6-(4'-azido-4'-deoxy-2',3'-O-isoprpylidene-β-L-rhamnopyranosylamino)-4-(diethoxymethyl)amino-5-nitropyrimidine
  参考文献：
  名称：

  A highly cytotoxic l-rhamnose analogue of the antitumour agent spicamycin

  摘要：

  鼠李糖霉素 2 是天然组合库 spicamycin 1 的鼠李糖类似物（含有腺嘌呤、一种碳水化合物、一种氨基酸和一种脂肪酸），由 L-鼠李糖制备而成，对人类骨髓瘤细胞具有很强的细胞毒性（IC50 = 120 nM）。

  DOI：

  10.1039/a805878d

文献信息

• A highly cytotoxic l-rhamnose analogue of the antitumour agent spicamycin
  作者：Angeles Martín、George W. J. Fleet、Terry D. Butters

  DOI：10.1039/a805878d

  日期：——

  Rhamnospicamycin 2, a rhamnose analogue (containing adenine, a carbohydrate, an amino acid and a fatty acid) of the naturally occurring combinatorial library spicamycin 1, is prepared from L-rhamnose and shown to be highly cytotoxic towards human myeloma cells (IC50 = 120 nM).

  鼠李糖霉素 2 是天然组合库 spicamycin 1 的鼠李糖类似物（含有腺嘌呤、一种碳水化合物、一种氨基酸和一种脂肪酸），由 L-鼠李糖制备而成，对人类骨髓瘤细胞具有很强的细胞毒性（IC50 = 120 nM）。
• Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin—is the mode of action by modification of N-linked glycoproteins?
  作者：Angeles Martı́n、Terry D Butters、George W.J Fleet

  DOI：10.1016/s0957-4166(99)00240-2

  日期：1999.6

  The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl alpha-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.