2-(cyclohexylcarbonyl)-10-hydroxy-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one | 1352568-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-(cyclohexylcarbonyl)-10-hydroxy-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
• 英文别名: 10-hydroxypraziquantel；2-(cyclohexanecarbonyl)-10-hydroxy-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one
• CAS: 1352568-78-5
• 化学式: C₁₉H₂₄N₂O₃
• 分子量: 328.411
• InChiKey: WEKXQEQCPLQSMD-UHFFFAOYSA-N

物化性质

• 沸点：
  593.0±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(cyclohexylcarbonyl)-10-hydroxy-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 2-(Cyclohexylcarbonyl)-10-(3-{[3-(phenylsulfonyl)furoxan-4-yl]oxy}propoxy)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
  参考文献：
  名称：

  含有NO供体呋喃酮和相关呋喃嗪的新型吡喹酮衍生物作为抗曼氏血吸虫活性剂

  摘要：

  通过将吡喹酮 (PZQ) 和呋喃酮部分组合在一个实体中，获得了一系列 NO 供体吡喹酮杂化化合物。通过在存在L-半胱氨酸的情况下将产物在 7.4 pH 缓冲溶液中温育后检测亚硝酸盐来评估呋喃酮衍生物的 NO 供体性质。为了控制目的，还合成了结构相关的呋喃嗪，缺乏 NO 释放能力。研究了所有产品抑制重组曼氏血吸虫硫氧还蛋白谷胱甘肽还原酶（TGR）的能力。与 PZQ 相比，评估了在产品存在下培养的成年曼氏血吸虫蠕虫的活动性和死亡。结果分析表明，一些产品同时具有PZQ和NO依赖性抗寄生虫特性。化合物6、7、18和24成为最有趣的平衡杂种，值得对 PZQ 抗性寄生虫进行进一步研究。

  DOI：

  10.1016/j.ejmech.2014.07.007
• 作为产物：
  描述：

  10-aminopraziquantel 在 sodium nitrite 作用下， 以50%的产率得到2-(cyclohexylcarbonyl)-10-hydroxy-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
  参考文献：
  名称：

  Praziquantel derivatives exhibit activity against both juvenile and adult Schistosoma japonicum

  摘要：

  A praziquantel analog 10-hydroxy praziquantel and eight praziquantel/peroxide conjugates were synthesized. The biological activity of these compounds was evaluated against juvenile and adult stages of Schistosoma japonicum. Unlike praziquantel, 10-hydroxy praziquantel exhibits activity against both juvenile and adult Schistosoma japonicumin. All hybrid compounds displayed modest to significant worm killing activity. The present study has important significance for the development of hybrid antischistosomal drugs. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.133

文献信息

• Praziquantel Derivatives with Antischistosomal Activity: Aromatic Ring Modification
  作者：Zhi-xia Wang、Jing-lei Chen、Chunhua Qiao

  DOI：10.1111/cbdd.12153

  日期：2013.8

  A series of aromatic ring-modified praziquantel derivatives were prepared and evaluated against juvenile and adult stage of Schistosoma japonicumin. Several analogs comparable in activity to the drug praziquantel have been identified based on in vitro and in vivo japonuicum schistosomes worm viability assay. Structure and activity relationship of these praziquantel aromatic ring-modified compounds

  制备了一系列芳香环修饰的吡喹酮衍生物，并针对日本血吸虫的少年期和成年期进行了评估。根据体外和体内的日本血吸虫血吸虫血吸虫蠕虫活力测定法，已鉴定出几种活性与药物吡喹酮相当的类似物。揭示了这些吡喹酮芳香环改性化合物的结构和活性关系。具体地，在吡喹酮的芳香环中引入了溴的化合物在体内显示出对吡喹酮的紧密的抗血吸虫病活性。
• CN116283976
  申请人：——

  公开号：——

  公开（公告）日：——
• Praziquantel derivatives exhibit activity against both juvenile and adult Schistosoma japonicum
  作者：Wen-wen Duan、Si-jie Qiu、Yue Zhao、Huan Sun、Chunhua Qiao、Chao-ming Xia

  DOI：10.1016/j.bmcl.2011.12.133

  日期：2012.2

  A praziquantel analog 10-hydroxy praziquantel and eight praziquantel/peroxide conjugates were synthesized. The biological activity of these compounds was evaluated against juvenile and adult stages of Schistosoma japonicum. Unlike praziquantel, 10-hydroxy praziquantel exhibits activity against both juvenile and adult Schistosoma japonicumin. All hybrid compounds displayed modest to significant worm killing activity. The present study has important significance for the development of hybrid antischistosomal drugs. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• New praziquantel derivatives containing NO-donor furoxans and related furazans as active agents against Schistosoma mansoni
  作者：Stefano Guglielmo、Daniela Cortese、Francesca Vottero、Barbara Rolando、Valerie P. Kommer、David L. Williams、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.ejmech.2014.07.007

  日期：2014.9

  praziquantel hybrid compounds was obtained by combining praziquantel (PZQ) and furoxan moieties in a single entity. NO-donor properties of the furoxan derivatives were evaluated by detecting nitrite after incubation of the products in 7.4 pH buffered solution in the presence of l-cysteine. Structurally-related furazans, devoid of NO release capacity, were also synthesized for control purposes. All

  通过将吡喹酮 (PZQ) 和呋喃酮部分组合在一个实体中，获得了一系列 NO 供体吡喹酮杂化化合物。通过在存在L-半胱氨酸的情况下将产物在 7.4 pH 缓冲溶液中温育后检测亚硝酸盐来评估呋喃酮衍生物的 NO 供体性质。为了控制目的，还合成了结构相关的呋喃嗪，缺乏 NO 释放能力。研究了所有产品抑制重组曼氏血吸虫硫氧还蛋白谷胱甘肽还原酶（TGR）的能力。与 PZQ 相比，评估了在产品存在下培养的成年曼氏血吸虫蠕虫的活动性和死亡。结果分析表明，一些产品同时具有PZQ和NO依赖性抗寄生虫特性。化合物6、7、18和24成为最有趣的平衡杂种，值得对 PZQ 抗性寄生虫进行进一步研究。