(9CI)-5,6,6a,7,8,9-六氢吡啶并[3,2-e]吡咯并[1,2-a]吡嗪 | 91622-97-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (9CI)-5,6,6a,7,8,9-六氢吡啶并[3,2-e]吡咯并[1,2-a]吡嗪
• 英文名称: 5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine
• 英文别名: 2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-triene
• CAS: 91622-97-8
• 化学式: C₁₀H₁₃N₃
• 分子量: 175.233
• InChiKey: LYCIKPFEMILQSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9CI)-5,6,6a,7,8,9-六氢吡啶并[3,2-e]吡咯并[1,2-a]吡嗪 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 21.0h， 生成 5-<(2,6-dimethoxyphenyl)methyl>-6a,7,8,9-tetrahydropyrido<3,2-e>pyrrolo<1,2-a>pyrazine
  参考文献：
  名称：

  Tetrahydropyrrolo[1,2-a]quinoxalines and tetrahydropyrrolo[1,2-a]pyrido[3,2-a]pyrazines: vascular smooth muscle relaxants and antihypertensive agents

  摘要：

  A series of tetrahydropyrrolo[1,2-a]quinoxalines and tetrahydropyrrolo[1,2-a]pyrido[3,2-a]pyrazines were synthesized and tested for their ability to relax K+-depolarized aortic smooth muscle and antihypertensive activity. It was shown that compounds producing the most relaxation of aortic smooth muscle (5-[2,6-dimethoxyphenyl)methyl]-1,2,3,3a-tetrahydropyrrolo[1,2-a] quinoxalin-4(5H)-one and 5-[(2,6-dimethoxyphenyl)methyl]-5,6,6a,7,8,9-hexahydropyrrolo[1,2- a] pyrazine, 10 and 19, respectively) demonstrated the least hypotensive activity. Those compounds that were the most effective hypotensive agents (6a,7,8,9-tetrahydro-5-(phenylmethyl)pyrido[3,2-a]pyrrolo[1,2-a]++ +pyrazin- 6(5H)-one and 6a,7,8,9-tetrahydro-5-(4-pyridinylmethyl)pyrido[3,2-e]pyrrolo [1,2-a]pyrazin-6(5H)-one, 12 and 13, respectively) displayed little vascular smooth muscle relaxant activity.

  DOI：

  10.1021/jm00378a039
• 作为产物：
  描述：

  N-(3-nitro-2-pyridinyl)pyrrolidine-2-carboxylic acid 在 lithium aluminium tetrahydride 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 21.0h， 生成 (9CI)-5,6,6a,7,8,9-六氢吡啶并[3,2-e]吡咯并[1,2-a]吡嗪
  参考文献：
  名称：

  Tetrahydropyrrolo[1,2-a]quinoxalines and tetrahydropyrrolo[1,2-a]pyrido[3,2-a]pyrazines: vascular smooth muscle relaxants and antihypertensive agents

  摘要：

  A series of tetrahydropyrrolo[1,2-a]quinoxalines and tetrahydropyrrolo[1,2-a]pyrido[3,2-a]pyrazines were synthesized and tested for their ability to relax K+-depolarized aortic smooth muscle and antihypertensive activity. It was shown that compounds producing the most relaxation of aortic smooth muscle (5-[2,6-dimethoxyphenyl)methyl]-1,2,3,3a-tetrahydropyrrolo[1,2-a] quinoxalin-4(5H)-one and 5-[(2,6-dimethoxyphenyl)methyl]-5,6,6a,7,8,9-hexahydropyrrolo[1,2- a] pyrazine, 10 and 19, respectively) demonstrated the least hypotensive activity. Those compounds that were the most effective hypotensive agents (6a,7,8,9-tetrahydro-5-(phenylmethyl)pyrido[3,2-a]pyrrolo[1,2-a]++ +pyrazin- 6(5H)-one and 6a,7,8,9-tetrahydro-5-(4-pyridinylmethyl)pyrido[3,2-e]pyrrolo [1,2-a]pyrazin-6(5H)-one, 12 and 13, respectively) displayed little vascular smooth muscle relaxant activity.

  DOI：

  10.1021/jm00378a039

文献信息

• Synthesis of new tetrahydropyridopyrazine derivatives via continuous flow chemistry approach and their spectroscopic characterizations
  作者：Nilesh D. Parmar、Sanjay D. Hadiyal、Vimal H. Kapupara、Jaydeep N. Lalpara、Hitendra S. Joshi

  DOI：10.1002/jhet.4270

  日期：2021.7

  We report here the synthesis of different substituted tetrahydropyridopyrazine derivatives. This approach of synthesis has been designed in a way that in first simple chloro-amine coupling as an alternative of Buchwald coupling followed by heterogeneous hydrogenation of nitro to give amine and further cyclization of this amine with carboxylic acid was accomplished in a single process with the help

  我们在这里报告不同取代的四氢吡啶并吡嗪衍生物的合成。这种合成方法的设计方式是，首先用简单的氯胺偶联代替 Buchwald 偶联，然后将硝基多相氢化得到胺，然后用羧酸进一步环化该胺，这是在一个单一的过程中完成的连续流加氢反应器的帮助。该过程是通过电解水分子并使用预装的钯催化剂盒产生氢气（原位）。在进一步的步骤中，LAH 用于将内酰胺还原为作为四氢吡啶并吡嗪 (TPP) 支架的产物。使用取代的苯甲酰基和磺酰基衍生物获得最终加合物。
• Tetra- and hexa-hydropyrrolo(1,2-a)quinoxaline and azaquinoxaline
  申请人：American Home Products Corporation

  公开号：US04446323A1

  公开（公告）日：1984-05-01

  Tetra- and hexa-hydropyrrolo[1,2-a]quinoxaline and azaquinoxaline derivatives of the formula: ##STR1## in which X is O or H.sub.2 ; Y is CH or N; R is hydrogen, alkyl, dialkylaminoalkyl, arylalkyl, phenoxyalkyl, benzoyl, pyridylalkyl or variations thereof; and R.sup.1 is hydrogen, alkyl, alkoxy, nitro, halo, trifluoromethyl, amino, alkylamino or dialkylamino; or pharmaceutically acceptable salts thereof; are anti-hypertensive agents.

  公式为：##STR1## 其中X为O或H.sub.2; Y为CH或N; R为氢，烷基，二烷氨基烷基，芳基烷基，苯氧基烷基，苯甲酰基，吡啶基烷基或其变体；R.sup.1为氢，烷基，烷氧基，硝基，卤素，三氟甲基，氨基，烷基氨基或二烷基氨基；或其药学上可接受的盐；是一种抗高血压药物。
• ABOU-GHARBIA, MAGID;FREED, M. E.;MCCAULLY, R. J.;SILVER, P. J.;WENDT, R. +, J. MED. CHEM., 1984, 27, N 12, 1743-1746
  作者：ABOU-GHARBIA, MAGID、FREED, M. E.、MCCAULLY, R. J.、SILVER, P. J.、WENDT, R. +

  DOI：——

  日期：——
• US4446323A
  申请人：——

  公开号：US4446323A

  公开（公告）日：1984-05-01
• Tetrahydropyrrolo[1,2-a]quinoxalines and tetrahydropyrrolo[1,2-a]pyrido[3,2-a]pyrazines: vascular smooth muscle relaxants and antihypertensive agents
  作者：Magid Abou-Gharbia、Meier E. Freed、Ronald J. McCaully、Paul J. Silver、Robert L. Wendt

  DOI：10.1021/jm00378a039

  日期：1984.12

  A series of tetrahydropyrrolo[1,2-a]quinoxalines and tetrahydropyrrolo[1,2-a]pyrido[3,2-a]pyrazines were synthesized and tested for their ability to relax K+-depolarized aortic smooth muscle and antihypertensive activity. It was shown that compounds producing the most relaxation of aortic smooth muscle (5-[2,6-dimethoxyphenyl)methyl]-1,2,3,3a-tetrahydropyrrolo[1,2-a] quinoxalin-4(5H)-one and 5-[(2,6-dimethoxyphenyl)methyl]-5,6,6a,7,8,9-hexahydropyrrolo[1,2- a] pyrazine, 10 and 19, respectively) demonstrated the least hypotensive activity. Those compounds that were the most effective hypotensive agents (6a,7,8,9-tetrahydro-5-(phenylmethyl)pyrido[3,2-a]pyrrolo[1,2-a]++ +pyrazin- 6(5H)-one and 6a,7,8,9-tetrahydro-5-(4-pyridinylmethyl)pyrido[3,2-e]pyrrolo [1,2-a]pyrazin-6(5H)-one, 12 and 13, respectively) displayed little vascular smooth muscle relaxant activity.