(9CI)-6a,7,8,9-四氢吡啶并[3,2-e]吡咯并[1,2-a]吡嗪-6(5H)-酮 | 91622-91-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (9CI)-6a,7,8,9-四氢吡啶并[3,2-e]吡咯并[1,2-a]吡嗪-6(5H)-酮
• 中文别名: (9CI)-6A,7,8,9-四氢吡啶并[3,2-E]吡咯并[1,2-A]吡嗪-6(5H)
• 英文名称: 6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one
• 英文别名: 2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one
• CAS: 91622-91-2
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: PGPPFIDIJMNDBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9CI)-6a,7,8,9-四氢吡啶并[3,2-e]吡咯并[1,2-a]吡嗪-6(5H)-酮 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 39.0h， 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 铁粉 、 溶剂黄146 作用下， 反应 3.0h， 以56%的产率得到(9CI)-6a,7,8,9-四氢吡啶并[3,2-e]吡咯并[1,2-a]吡嗪-6(5H)-酮
  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。
• Synthesis of Kappa Opioid Antagonists Based On Pyrrolo[1,2-α]quinoxalinones Using an <i>N</i>-Arylation/Condensation/Oxidation Reaction Sequence
  作者：Sarah M. Scarry、Kimberly M. Lovell、Kevin J. Frankowski、Laura M. Bohn、Jeffrey Aubé

  DOI：10.1021/acs.joc.6b01350

  日期：2016.11.4

  family of nitrogen heterocycles is present in molecules of therapeutic relevance for diverse applications ranging from infectious diseases to neuroscience targets. Here, we describe a general synthetic sequence to afford pyrrolo[1,2-α]quinoxalinones from commercially available starting materials and their use in preparing potential kappa opioid receptor antagonists. The biological data obtained from the

  氮杂环基喹喔啉和喹喔啉酮家族存在于与治疗相关的分子中，可用于从传染病到神经科学靶标的多种应用。在这里，我们描述了一种一般的合成序列，可从商业上可获得的起始原料中得到吡咯并[1,2-α]喹喔啉酮及其在制备潜在的κ阿片受体拮抗剂中的用途。简要介绍和讨论了从后一组化合物获得的生物学数据。
• 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、二烷基氨基烷基、芳基烷基、苯氧基烷基、苯甲酰基、吡啶基烷基或其变化物；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；可用作降压剂。
• Poly (ADP-Ribose) Polymerase (PARP) Inhibitors
  申请人：Gangloff Anthony R.

  公开号：US20100190763A1

  公开（公告）日：2010-07-29

  Disclosed are compounds of the following formula: in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X, and t are defined in the specification. Also disclosed are pharmaceutical compositions, kits, and articles of manufacture, which contain the compounds, methods and intermediates useful for making the compounds, and methods of using the compounds to treat diseases, disorders, and conditions related to PARP activity.

  本发明涉及下列公式的化合物：其中R1、R2、R3、R4、R5、R6、R7、X和t在说明书中定义。还公开了含有这些化合物的制药组合物、试剂盒和制造物品，以及制备这些化合物的中间体和方法，以及使用这些化合物治疗与PARP活性相关的疾病、疾病和状况的方法。
• THERAPEUTIC BENEFIT OF SUBOPTIMALLY ADMINISTERED CHEMICAL COMPOUNDS
  申请人：BROWN Dennis M.

  公开号：US20160045502A1

  公开（公告）日：2016-02-18

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutic agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to mustard-based alkylating agents such as uracil mustard and analogs, derivatives, or prodrugs thereof, including 6-methyluracil mustard and 6-ethyluracil mustard.

  本发明描述了一种改善先前受到治疗性能不佳限制的治疗剂的治疗效果的方法和组合物，通过改善单药疗法的功效或减少副作用。这种方法和组合物特别适用于芥子碱基烷基化剂，例如尿嘧啶芥和其类似物、衍生物或前药，包括6-甲基尿嘧啶芥和6-乙基尿嘧啶芥。