N-(1-(4-O-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucoppyranosyl)-1H-1,2,3-triazol-4-yl)methylcyclopamine | 1017894-38-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N-(1-(4-O-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucoppyranosyl)-1H-1,2,3-triazol-4-yl)methylcyclopamine
• 英文别名: N-(1-(4-O-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl)methylcyclopamine；[(2R,3R,4S,5R,6R)-6-[4-[[(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-yl]methyl]triazol-1-yl]-4,5-diacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1017894-38-0
• 化学式: C₆₈H₉₄N₄O₂₇
• 分子量: 1399.5
• InChiKey: VKWDKLOJCRFUAQ-NVFKSLBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  99
• 可旋转键数：
  30
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  373
• 氢给体数：
  1
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  N-(1-(4-O-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucoppyranosyl)-1H-1,2,3-triazol-4-yl)methylcyclopamine 在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以86%的产率得到N-(1-(4-O-(4-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl)methylcyclopamine
  参考文献：
  名称：

  Synthesis and anticancer activity studies of cyclopamine derivatives

  摘要：

  A diversity-oriented synthesis has been developed for facile construction of a library of carbohydrate-cyclopamine conjugates. The synthetic protocol is suitable for generating cyclopamine derivatives with various structural motifs for exploring the desired activity. From this initial library, we have observed one derivative that exhibits improved activity against lung cancer cell as compared to cyclopamine. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.017
• 作为产物：
  描述：

  N-propargylcyclopamine 、 per-O-acetylated β-cellotriosyl azide 在 copper diacetate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.47h， 以80%的产率得到N-(1-(4-O-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucoppyranosyl)-1H-1,2,3-triazol-4-yl)methylcyclopamine
  参考文献：
  名称：

  Synthesis and anticancer activity studies of cyclopamine derivatives

  摘要：

  A diversity-oriented synthesis has been developed for facile construction of a library of carbohydrate-cyclopamine conjugates. The synthetic protocol is suitable for generating cyclopamine derivatives with various structural motifs for exploring the desired activity. From this initial library, we have observed one derivative that exhibits improved activity against lung cancer cell as compared to cyclopamine. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.017

文献信息

• Synthesis and anticancer activity studies of cyclopamine derivatives
  作者：Jianjun Zhang、Massoud Garrossian、Dale Gardner、Arash Garrossian、Young-Tae Chang、Yun Kyung Kim、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmcl.2008.01.017

  日期：2008.2

  A diversity-oriented synthesis has been developed for facile construction of a library of carbohydrate-cyclopamine conjugates. The synthetic protocol is suitable for generating cyclopamine derivatives with various structural motifs for exploring the desired activity. From this initial library, we have observed one derivative that exhibits improved activity against lung cancer cell as compared to cyclopamine. (c) 2008 Elsevier Ltd. All rights reserved.