6-acetoxymethyl-3,3,8-trimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-yl acetate | 1289166-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-acetoxymethyl-3,3,8-trimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-yl acetate
• 英文别名: (9-acetoxy-3,3,8-trimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-6-yl)methyl acetate；9-acetoxy-6-acetoxymethyl-3,3,8-trimethyl-1,5-dihydro[1,3]-dioxepino[5,6-c]pyridine；6-Acetoxymethyl-3,3,8-trimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-yl acetate；(9-acetyloxy-3,3,8-trimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-6-yl)methyl acetate
• CAS: 1289166-95-5
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: BSGNYEWFQGHTLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-acetoxymethyl-3,3,8-trimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-yl acetate 在 sodium ethanolate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 57.0h， 生成 6,8-bis(hydroxymethyl)-3,3-dimethyl-1,5-dihydro[1,3]dioxepino[5,6-c]pyridin-9-ol
  参考文献：
  名称：

  Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of cyclic 2,4,5,6-tetrakis-(hydroxymethyl)pyridin-3-ol acetonides

  摘要：

  Synthetic approaches to three cyclic 2,4,5,6-tetrakis(hydroxymethyl) pyridin-3-ol acetonides were developed. Among seven possible mono- and diketals, six-membered cyclic ketal incorporating the hydroxymethyl group in the 4-position turned out to be the most thermodynamically favorable. The experimental data were consistent with the results of quantum-chemical calculations of the Gibbs energies of formation of different acetonides. The structure of the isolated compounds was studied by X-ray diffraction.

  DOI：

  10.1134/s107042801101012x
• 作为产物：
  描述：

  6-(hydroxymethyl)-3,3,8-trimethyl-1,5-dihydro-[1,3] dioxepino [5,6-c] pyridin-9-ol 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到6-acetoxymethyl-3,3,8-trimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-yl acetate
  参考文献：
  名称：

  Pyridoxine Derivative for Treatment of Epilepsy

  摘要：

  一种以吡哌酮为基础的化合物，化学式为1，表现出高水平的抗癫痫活性。在25、50和100 mg/kg的剂量下，化合物1在腹腔注射给癫痫模型的大鼠后，一个小时内完全抑制了大脑的癫痫电活动。大鼠的心肌抽搐癫痫模型显示，在腹腔注射25和100 mg/kg以及口服100和200 mg/kg的化合物1后，癫痫发作的强度和持续时间减少，并在某些情况下口服250 mg/kg的剂量下完全预防了癫痫发作。化合物1毒性低，大鼠的LD50参数在腹腔注射和口服分别超过2000和5000 mg/kg体重。这一技术方案提供了一种新的高效且安全的药物，用于治疗癫痫。

  公开号：

  US20200157051A1

文献信息

• Synthesis and Antimicrobial Activity of Adamantyl Substituted Pyridoxine Derivatives
  作者：Rail Khaziev、Nikita Shtyrlin、Roman Pavelyev、Raushan Nigmatullin、Raylya Gabbasova、Denis Grishaev、Anna Shtro、Anastasia Galochkina、Yulia Nikolaeva、Tatiana Vinogradova、Olga Manicheva、Marine Dogonadze、Oleg Gnezdilov、Evgenii Sokolovich、Petr Yablonskiy、Konstantin Balakin、Yurii Shtyrlin

  DOI：10.2174/1570180816666190911150705

  日期：2019.11.8

  amination of aldehydes and nucleophilic substitution of alkyl halides. According to a tentative mechanism, it proceeds via paraand ortho-pyridinone methides which readily react with nucleophiles. None of the synthesized dipharmacophore compounds showed activity against M. tuberculosis H37Rv strain. At the same time, three compounds demonstrated some antiviral activity against H3N2 (A/Aichi/2/68) influenza

  背景：金刚烷衍生物具有多种药理活性，例如抗病毒，抗癌，抗分枝杆菌，抗糖尿病，抗帕金森病等。药物化学家对金刚烷化合物的兴趣是由于其独特的空间结构，高亲脂性和碳笼刚性。结果，这些分子可以容易地穿透生物脂质膜，并且通常具有独特的靶标特异性活性谱。这项工作中研究的另一种药效团是吡ido醇（维生素B6）。吡rid醇作为许多酶的关键辅因子，在活细胞中起着非常重要的作用。另一方面，它的分子支架是一个有价值的结构平台，已导致开发了几种已发布的药物（吡rit醇，皮瑞沙醇，Cycltanine， 目的：本研究的目的是合成吡ido醇-金刚烷和吡ido醇环辛烷双药效团分子。潜在的想法是基于在其结构中具有金刚烷和吡ido醇部分的有希望的抗感染剂的多个实例，来评估这种双药效团的抗菌和抗病毒潜力。另一个特定的原因是探索吡ido醇药效团抑制微生物病原体对药物分子产生耐药性的潜力。 方法：在这项研究中，基于三种不同的环烷基
• Pyridoxine derivative for treatment of epilepsy
  申请人：AO “TATKHIMFARMPREPARATY”

  公开号：US10844018B2

  公开（公告）日：2020-11-24

  A pyridoxine-based compound of formula 1: exhibits a high level of antiepileptic activity. At doses of 25, 50 and 100 mg/kg, compound 1 completely suppresses the epileptic electrical activity of the brain within an hour after intraperitoneal administration to rats on the penicillin model of epilepsy. The rats' corazol model of epilepsy shows a decrease in intensity and duration of seizures with the administration of compound 1 at doses of 25 and 100 mg/kg intraperitoneally and 100 and 200 mg/kg orally, and the complete prevention of seizures in some cases at a dosage of 250 mg/kg with oral administration. Compound 1 is low toxic. The LD50 parameter in rats exceeds 2000 and 5000 mg/kg of body weight with intraperitoneal and oral administration respectively. The technical solution provides a new highly effective and safe drug for the treatment of epilepsy.

  式 1 的吡哆醇基化合物： 具有很高的抗癫痫活性。对青霉素癫痫模型大鼠腹腔给药，剂量为 25、50 和 100 毫克/千克时，化合物 1 可在一小时内完全抑制大脑的癫痫电活动。在大鼠 corazol 癫痫模型中，腹腔给药剂量为 25 和 100 毫克/千克，口服给药剂量为 100 和 200 毫克/千克时，癫痫发作的强度和持续时间都会减少；口服给药剂量为 250 毫克/千克时，在某些情况下可完全防止癫痫发作。化合物 1 毒性低。大鼠腹腔注射和口服的半数致死剂量参数分别超过 2000 毫克/千克体重和 5000 毫克/千克体重。该技术方案为治疗癫痫提供了一种高效安全的新药。
• Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of cyclic 2,4,5,6-tetrakis-(hydroxymethyl)pyridin-3-ol acetonides
  作者：N. V. Shtyrlin、A. B. Dobrynin、T. I. Madzhidov、M. V. Pugachev、L. P. Sysoeva、R. Z. Musin、I. A. Litvinov、E. N. Klimovitskii、Yu. G. Shtyrlin

  DOI：10.1134/s107042801101012x

  日期：2011.1

  Synthetic approaches to three cyclic 2,4,5,6-tetrakis(hydroxymethyl) pyridin-3-ol acetonides were developed. Among seven possible mono- and diketals, six-membered cyclic ketal incorporating the hydroxymethyl group in the 4-position turned out to be the most thermodynamically favorable. The experimental data were consistent with the results of quantum-chemical calculations of the Gibbs energies of formation of different acetonides. The structure of the isolated compounds was studied by X-ray diffraction.
• Pyridoxine Derivative for Treatment of Epilepsy
  申请人：AO "TATKHIMFARMPREPARATY"

  公开号：US20200157051A1

  公开（公告）日：2020-05-21

  A pyridoxine-based compound of formula 1: exhibits a high level of antiepileptic activity. At doses of 25, 50 and 100 mg/kg, compound 1 completely suppresses the epileptic electrical activity of the brain within an hour after intraperitoneal administration to rats on the penicillin model of epilepsy. The rats' corazol model of epilepsy shows a decrease in intensity and duration of seizures with the administration of compound 1 at doses of 25 and 100 mg/kg intraperitoneally and 100 and 200 mg/kg orally, and the complete prevention of seizures in some cases at a dosage of 250 mg/kg with oral administration. Compound 1 is low toxic. The LD 50 parameter in rats exceeds 2000 and 5000 mg/kg of body weight with intraperitoneal and oral administration respectively. The technical solution provides a new highly effective and safe drug for the treatment of epilepsy.

  一种以吡哌酮为基础的化合物，化学式为1，表现出高水平的抗癫痫活性。在25、50和100 mg/kg的剂量下，化合物1在腹腔注射给癫痫模型的大鼠后，一个小时内完全抑制了大脑的癫痫电活动。大鼠的心肌抽搐癫痫模型显示，在腹腔注射25和100 mg/kg以及口服100和200 mg/kg的化合物1后，癫痫发作的强度和持续时间减少，并在某些情况下口服250 mg/kg的剂量下完全预防了癫痫发作。化合物1毒性低，大鼠的LD50参数在腹腔注射和口服分别超过2000和5000 mg/kg体重。这一技术方案提供了一种新的高效且安全的药物，用于治疗癫痫。