N-propargylcyclopamine | 1017893-81-0

• 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-propargylcyclopamine
• 英文别名: (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethyl-4'-prop-2-ynylspiro[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]-3-ol
• CAS: 1017893-81-0
• 化学式: C₃₀H₄₃NO₂
• 分子量: 449.677
• InChiKey: AZSQWJSYHPYWRM-ZGQYWXEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-propargylcyclopamine 、 2,3,4-Tri-O-acetyl-α/β-L-rhamnopyranosyl 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99%的产率得到N-(1-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-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：

  环巴胺 、 3-溴丙炔 在 碳酸氢钠 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 2.5h， 以94%的产率得到N-propargylcyclopamine
  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

• [EN] CARBOHYDRATE-CYCLOPAMINE CONJUGATES AS ANTICANCER AGENTS<br/>[FR] CONJUGUÉS GLUCIDE-CYCLOPAMINE EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：UNIV UTAH STATE

  公开号：WO2010080817A3

  公开（公告）日：2010-11-25
• Carbohydrate-Cyclopamine Conjugates as Anticancer Agents
  申请人：Chang Cheng-Wei T

  公开号：US20110275576A1

  公开（公告）日：2011-11-10

  Various anticancer compounds are disclosed, including a series of carbohydrate-cyclopamine conjugates. These compounds include pyranose, furanose, and mannitol conjugates, linked through a 1,2,3-triazine ring to the nitrogen of cyclopamine. Methods for preparing these compounds, pharmaceutical compositions containing these compounds, and their use as anticancer agents are also disclosed.