5'-[4-(2-hydroxybutan-2-yl)triazol-1-yl]spiro[1,3-dioxolane-2,3'-1H-indole]-2'-one | 1446908-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5'-[4-(2-hydroxybutan-2-yl)triazol-1-yl]spiro[1,3-dioxolane-2,3'-1H-indole]-2'-one
• CAS: 1446908-05-9
• 化学式: C₁₆H₁₈N₄O₄
• 分子量: 330.343
• InChiKey: ILDWDHLEFWVRDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  98.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5'-氨基螺[1,3-二氧戊环-2,3'-吲哚]-2'(1'H)-酮 在 盐酸 、 copper(ll) sulfate pentahydrate 、 溶剂黄146 、 sodium ascorbate 、 sodium nitrite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 5'-[4-(2-hydroxybutan-2-yl)triazol-1-yl]spiro[1,3-dioxolane-2,3'-1H-indole]-2'-one
  参考文献：
  名称：

  Synthesis of Novel Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

  摘要：

  DOI：

  10.5935/0103-5053.20130023

文献信息

• The Hypnotic, Anxiolytic, and Antinociceptive Profile of a Novel µ-Opioid Agonist
  作者：Guilherme Montes、Bianca da Silva、Bismarck Rezende、Roberto Sudo、Vitor Ferreira、Fernando de Carvalho da Silva、Angelo da Cunha Pinto、Bárbara da Silva、Gisele Zapata-Sudo

  DOI：10.3390/molecules22050800

  日期：——

  5′-4-Alkyl/aryl-1H-1,2,3-triazole derivatives PILAB 1–12 were synthesized and a pharmacological screening of these derivatives was performed to identify a possible effect on the Central Nervous System (CNS) and to explore the associated mechanisms of action. The mice received a peritoneal injection (100 µmol/kg) of each of the 12 PILAB derivatives 10 min prior to the injection of pentobarbital and the mean hypnosis times were recorded. The mean hypnosis time increased for the mice treated with PILAB 8, which was prevented when mice were administered CTOP, a µ-opioid antagonist. Locomotor and motor activities were not affected by PILAB 8. The anxiolytic effect of PILAB 8 was evaluated next in an elevated-plus maze apparatus. PILAB 8 and midazolam increased a percentage of entries and spent time in the open arms of the apparatus compared with the control group. Conversely, a decrease in the percentages of entries and time spent in the closed arms were observed. Pretreatment with naloxone, a non-specific opioid antagonist, prior to administration of PILAB 8 exhibited a reverted anxiolytic effect. PILAB 8 exhibited antinociceptive activity in the hot plate test, and reduced reactivity to formalin in the neurogenic and the inflammatory phases. These data suggest that PILAB 8 can activate µ-opioid receptors to provoke antinociceptive and anti-inflammatory effects in mice.

  5′-4-烷基/芳基-1H-1,2,3-三唑衍生物PILAB 1–12被合成，并对这些衍生物进行了药理学筛选，以识别对中枢神经系统（CNS）的可能影响并探索相关的机制。小鼠在接受戊巴比妥注射前10分钟，通过腹腔注射（100 µmol/kg）给予每种PILAB衍生物，并记录平均催眠时间。接受PILAB 8处理的小鼠的平均催眠时间增加，而在给予μ-阿片拮抗剂CTOP后，这种增加被阻止。PILAB 8对小鼠的 locomotor和运动活性没有影响。接着在高架十字迷宫装置中评估了PILAB 8的抗焦虑效应。与对照组相比，PILAB 8和咪达唑仑提高了进入和在开放臂中停留时间的百分比，同时减少了进入和在封闭臂中停留时间的百分比。在给予PILAB 8之前预处理非特异性阿片拮抗剂纳洛酮，显示出逆转的抗焦虑效应。PILAB 8在热板测试中表现出镇痛活性，并在神经源性和炎症阶段减少了福尔马林反应性。这些数据表明PILAB 8能够激活μ-阿片受体，从而在小鼠中引发镇痛和抗炎效应。
• Ultrasound-Assisted Synthesis of Isatin-Type 5'-(4-Alkyl/Aryl-1<i>H</i>-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions
  作者：Bianca N. M. Silva、Angelo C. Pinto、Fernando C. Silva、Vitor F. Ferreira、Bárbara V. Silva

  DOI：10.5935/0103-5053.20160121

  日期：——

  This short report describes the preparation of twelve isatin derivatives, 5'-(4-alkyl/aryl-1H-1,2,3-triazoles), using 5-azido-spiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one in the presence of various alkynes under acidic conditions and ultrasound irradiation. Compared with conventional methods, yields increased to 78-98%, and reaction times decreased to 5 min. Besides time and energy saving, there was no need for purification of the product by column chromatography on silica gel, generating less waste and spent solvent.
• Synthesis of Novel Isatin-Type 5'-(4-Alkyl/Aryl-1<i>H</i>-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions
  作者：Bianca N. M. Silva、Bárbara V. Silva、Fernando C. Silva、Daniel T. G. Gonzaga、Vitor F. Ferreira、Angelo C. Pinto

  DOI：10.5935/0103-5053.20130023

  日期：——