4-propyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione | 64224-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-propyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione
• 英文别名: 4-propyl-5-pyrazin-2-yl-[1,2]dithiole-3-thione；4-Propyl-5-pyrazin-2-yldithiole-3-thione
• CAS: 64224-23-3
• 化学式: C₁₀H₁₀N₂S₃
• 分子量: 254.401
• InChiKey: KQWXHFALLBWSKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 4-propyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione 在 ammonium acetate 、 sodium thiomethoxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 以65%的产率得到6,8-bis(methylthio)-7-propyl-pyrrolo[1,2-a]pyrazine hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,2-dithiol-3-thiones and pyrrolo[1,2-a]pyrazines as novel hypoxia inducible factor-1 (HIF-1) inhibitor

  摘要：

  Hypoxia-inducible factor-1 (HIF-1) is a key transcription factor which is strongly associated with tumor survival, progression, and therapeutic resistance. Accordingly, it has been suggested that the inhibition of the HIF-1 pathway can suppress tumor, and it has become an important therapeutic target. In present study, oltipraz, its metabolite M2, and their derivatives were synthesized and evaluated as HIF-1 alpha inhibitors. Among the synthesized, benzyl-substituted pyrrolo[1,2-a]pyrazine 2g most potently inhibited HIF-1 alpha protein accumulation (81% at 10 mu M) and VEGF, GLUT-1 transcription (77% and 92% at 10 mu M, respectively). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.054
• 作为产物：
  描述：

  吡嗪-2-羧酸甲酯 在 tetraphosphorus decasulfide 、 sodium hydride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 9.0h， 生成 4-propyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,2-dithiol-3-thiones and pyrrolo[1,2-a]pyrazines as novel hypoxia inducible factor-1 (HIF-1) inhibitor

  摘要：

  Hypoxia-inducible factor-1 (HIF-1) is a key transcription factor which is strongly associated with tumor survival, progression, and therapeutic resistance. Accordingly, it has been suggested that the inhibition of the HIF-1 pathway can suppress tumor, and it has become an important therapeutic target. In present study, oltipraz, its metabolite M2, and their derivatives were synthesized and evaluated as HIF-1 alpha inhibitors. Among the synthesized, benzyl-substituted pyrrolo[1,2-a]pyrazine 2g most potently inhibited HIF-1 alpha protein accumulation (81% at 10 mu M) and VEGF, GLUT-1 transcription (77% and 92% at 10 mu M, respectively). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.04.054

文献信息

• 1,2-Dithiole derivatives
  申请人：Rhone-Poulenc Industries

  公开号：US04110450A1

  公开（公告）日：1978-08-29

  1,2-Dithiole derivatives of the formula: ##STR1## WHEREIN Het represents an aromatic heterocyclic radical with six atoms in the ring two of which are nitrogen atoms, the heterocyclic radical optionally carrying a single substituent selected from halogen, alkyl, alkoxy, mercapto, alkylthio, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino and 4-alkylpiperazin-1-yl and R represents halogen, alkyl (optionally substituted by alkoxycarbonyl), carboxy, alkoxycarbonyl, carbamoyl, N-alkylcarbamoyl or a group R.sub.1 --C(OH)-- in which R.sub.1 represents hydrogen or alkyl, the said alkyl, alkoxy and alkylthio radicals or alkyl or alkoxy moieties containing 1 to 4 carbon atoms except in the case of R.sub.1 which contains 1 to 3 carbon atoms when an alkyl radical, are new compounds useful in the treatment of bilharziasis.

  1,2-二硫代烯衍生物的结构式如下：##STR1## 其中Het代表一个芳香杂环基团，环中有六个原子，其中两个是氮原子，该杂环基团可以携带从卤素、烷基、烷氧基、巯基、烷硫基、二烷基氨基、吡咯烷-1-基、哌啶基、吗啉基和4-烷基哌嗪-1-基中选择的单个取代基，R代表卤素、烷基（可由烷氧羰基取代）、羧基、烷氧羰基、氨基甲酰基、N-烷基氨基甲酰基或一个R.sub.1--C(OH)--基团，其中R.sub.1代表氢或烷基，所述的烷基、烷氧基和烷硫基基团或含有1至4个碳原子的烷基或烷氧基基团，除了在R.sub.1是烷基时含有1至3个碳原子的情况下，这些化合物是治疗血吸虫病的新化合物。
• US4144339A
  申请人：——

  公开号：US4144339A

  公开（公告）日：1979-03-13
• US4110450A
  申请人：——

  公开号：US4110450A

  公开（公告）日：1978-08-29
• US4138487A
  申请人：——

  公开号：US4138487A

  公开（公告）日：1979-02-06
• Synthesis and biological evaluation of 1,2-dithiol-3-thiones and pyrrolo[1,2-a]pyrazines as novel hypoxia inducible factor-1 (HIF-1) inhibitor
  作者：Young Hun Lee、Jung Min Lee、Sang Geon Kim、Yong Sup Lee

  DOI：10.1016/j.bmc.2016.04.054

  日期：2016.6

  Hypoxia-inducible factor-1 (HIF-1) is a key transcription factor which is strongly associated with tumor survival, progression, and therapeutic resistance. Accordingly, it has been suggested that the inhibition of the HIF-1 pathway can suppress tumor, and it has become an important therapeutic target. In present study, oltipraz, its metabolite M2, and their derivatives were synthesized and evaluated as HIF-1 alpha inhibitors. Among the synthesized, benzyl-substituted pyrrolo[1,2-a]pyrazine 2g most potently inhibited HIF-1 alpha protein accumulation (81% at 10 mu M) and VEGF, GLUT-1 transcription (77% and 92% at 10 mu M, respectively). (C) 2016 Elsevier Ltd. All rights reserved.