1-Allyl-terguride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-Allyl-terguride
• 英文别名: 1-allyl-6-methyl-8α-(diethylcarbamoylamino)ergoline；3-[(6aR,9S,10aR)-7-methyl-4-prop-2-enyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]-1,1-diethylurea
• 化学式: C₂₃H₃₂N₄O
• 分子量: 380.533
• InChiKey: MEBZFVRCLVWKFF-FBBABVLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Allyl-terguride 生成 3-[(6aR,9S,10aR)-5-bromo-7-methyl-4-prop-2-enyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]-1,1-diethylurea
  参考文献：
  名称：

  BENES, JAN;CERNY, ANTONIN;KREJCI, IVAN;REZABEK, KAREL

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴丙烯 、 R-(+)-特麦角脲 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以86%的产率得到1-Allyl-terguride
  参考文献：
  名称：

  Clustered ergot alkaloids modulate cell-mediated cytotoxicity

  摘要：

  Dimers of agroclavine (1) and terguride (2), as well as a series of terguride oligomers, for example trimers (5, 6), tetramer (7), hexamer (8) and functionalized tergurides for further complex clustering were synthesized. Terguride oligomers were screened for their direct cellular toxicity on lymphoma cell lines in vitro and for their immunomodulating activities, represented by the natural killer (NK) cell-mediated cytotoxicity, as the most sensitive screening marker during immune responses. Dimers linked via aromatic spacer showed a high toxicity (1 muM) to lymphoma cells. which was not detected in other derivatives. In vitro and ex vivo experiments performed on mouse spleen lymphocytes in the presence of terguride oligomers demonstrated an immunosuppressive effect of dimers with aromatic spacer (4c-d) and NK cell stimulatory effect of terguride hexamer (8,) and trimer with aliphatic spacer (5c). There is a considerable evidence that indolic part of molecule contributes to immunosuppressive action of terguride, which is potentiated in dimers carrying aromatic linker. This effect can be reversed by higher oligomerization of the respective alkaloids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00291-7

文献信息

• BENES, JAN;CERNY, ANTONIN;KREJCI, IVAN;REZABEK, KAREL
  作者：BENES, JAN、CERNY, ANTONIN、KREJCI, IVAN、REZABEK, KAREL

  DOI：——

  日期：——
• Clustered ergot alkaloids modulate cell-mediated cytotoxicity
  作者：Vladimı́r Křen、Anna Fišerová、Lenka Weignerová、Ivan Stibor、Petr Halada、Věra Přikrylová、Petr Sedmera、Miloslav Pospı́šil

  DOI：10.1016/s0968-0896(01)00291-7

  日期：2002.2

  Dimers of agroclavine (1) and terguride (2), as well as a series of terguride oligomers, for example trimers (5, 6), tetramer (7), hexamer (8) and functionalized tergurides for further complex clustering were synthesized. Terguride oligomers were screened for their direct cellular toxicity on lymphoma cell lines in vitro and for their immunomodulating activities, represented by the natural killer (NK) cell-mediated cytotoxicity, as the most sensitive screening marker during immune responses. Dimers linked via aromatic spacer showed a high toxicity (1 muM) to lymphoma cells. which was not detected in other derivatives. In vitro and ex vivo experiments performed on mouse spleen lymphocytes in the presence of terguride oligomers demonstrated an immunosuppressive effect of dimers with aromatic spacer (4c-d) and NK cell stimulatory effect of terguride hexamer (8,) and trimer with aliphatic spacer (5c). There is a considerable evidence that indolic part of molecule contributes to immunosuppressive action of terguride, which is potentiated in dimers carrying aromatic linker. This effect can be reversed by higher oligomerization of the respective alkaloids. (C) 2001 Elsevier Science Ltd. All rights reserved.