5H,10H-imidazo<1,2-a>indeno<1,2-e>pyrazin-4-one | 156484-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]吡嗪-8-酮
• 英文名称: 5H,10H-imidazo<1,2-a>indeno<1,2-e>pyrazin-4-one
• 英文别名: 5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazine-4-one；5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one；10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one；5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one；2,5,8-triazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),3,5,10,12,14-hexaen-7-one
• CAS: 156484-30-9
• 化学式: C₁₃H₉N₃O
• 分子量: 223.234
• InChiKey: AQQPIVYLMVOXNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5H,10H-imidazo<1,2-a>indeno<1,2-e>pyrazin-4-one 在 sodium hydride 、 锌 、 亚硝酸异戊酯 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成 10-acetamido-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one
  参考文献：
  名称：

  8-Methylureido-10-amino-10-methyl-imidazo[1,2- a ]indeno[1,2- e ]pyrazine-4-ones: Highly In vivo Potent and Selective AMPA Receptor Antagonists

  摘要：

  Water soluble 8-methylureido-10-amino-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one 4 represents a novel class of highly potent and selective AMPA receptors antagonists with in vivo activity. The dextrorotatory isomer (+)-4 was found to display the highest affinity with an IC50 of 10 nM. It also exhibited very good anticonvulsant effects after ip, sc and iv administration in mice subjected to electrical convulsions (MES) and ip in audiogenic seizure-e in DBA/2 mice (ED50's less than or equal to 10 mg/kg). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00161-9
• 作为产物：
  描述：

  2-溴-1-茚满酮 以 咪唑 、 N-甲基乙酰胺 、 甲醇 为溶剂， 生成 5H,10H-imidazo<1,2-a>indeno<1,2-e>pyrazin-4-one
  参考文献：
  名称：

  Derivatives of 5H, 10H-imidazo\x9b1, 2-a!indeno\x9b1,2-e!pyrazin-4-one,

  摘要：

  具有以下式（I）的化合物，其中R和R.sub.1，相似或不同，代表氢或卤素原子或基团烷基，烷氧基，氨基，酰胺基，苯基脲基，--N.dbd.CH--N(R.sub.2)R.sub.3，硝基，咪唑基，苯基，SO.sub.3 H或氰基；R.sub.2和R.sub.3可以相同也可以不同，分别代表烷基基团；本发明还涉及这些化合物的盐，它们的制备，用于制备它们的中间体以及含有它们的药物。

  公开号：

  US05677306A1

文献信息

• Imidazo (1,2-A)-Indeno (1,2-E) pyrazin-4-one derivatives and
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05807859A1

  公开（公告）日：1998-09-15

  Pharmaceutical compositions containing, as the active principle, compounds of formula (I): ##STR1## wherein R, R.sub.1 and R.sub.2 are as defined in the description, or salts thereof, the novel compounds of formula (I), and the preparation thereof. The compounds of formula (I) have valuable pharmacological properties and are alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, this receptor also being known as the quisqualate receptor. Furthermore, the compounds of formula (I) are non-competitive N-methyl-D-aspartate (NDMA) receptor antagonists, and particularly NMDA receptor glycine modulation site ligands.

  含有作为活性原理的化合物的药物组合物，其化学式为(I)：##STR1##其中R、R.sub.1和R.sub.2如描述中所定义，或其盐，化学式(I)的新化合物及其制备方法。化学式(I)的化合物具有有价值的药理特性，是α-氨基-3-羟基-5-甲基-4-异恶唑丙酸（AMPA）受体拮抗剂，该受体也被称为喹氨酸受体。此外，化学式(I)的化合物是非竞争性N-甲基-D-天冬氨酸（NDMA）受体拮抗剂，特别是NMDA受体甘氨酸调节位点配体。
• Imidazo\x9b1,2-A! pyrazine-4-one, preparation thereof and drugs containing
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05753657A1

  公开（公告）日：1998-05-19

  Compounds of formula (1) ##STR1## wherein either R is C.dbd.R.sub.3, C(R.sub.4)R.sub.5 or CH--R.sub.6, R.sub.1 and R.sub.2 are hydrogen, halogen, alkyl, alkoxy, amino, acylamino, --NH--CO--NH--Ar, --N.dbd.CH--N(alk)alk', nitro, cyano, phenyl, imidazolyl or SO.sub.3 H, R.sub.3 is oxygen, NOH, NO-alk-COOK or CH--R.sub.7, R.sub.4 is alkyl, -alk-Het or alk-Ar, R.sub.5 is alkyl, -alk-Het or -alk-Ar, or C(R.sub.4)R.sub.5 is cycloalkyl, R.sub.6 is hydroxy, alkyl, NR.sub.8 R.sub.9, -alk-OH, -alk-NR.sub.8 R.sub.9, -alk-Ar or -alk-Het, R.sub.7 is hydroxy, alkyl, phenyl, -alk-Ar, -alk-Het, NR.sub.10 R.sub.11 or a heterocyclic ring, R.sub.8 and R.sub.9 are alkyl, or R.sub.8 is hydrogen and R.sub.9 is hydrogen or alkyl, --COR.sub.12, --CSR.sub.30 or --SO.sub.2 R.sub.13, R.sub.10 and R.sub.11 are alkyl or cycloalkyl, R.sub.12 is alkyl, cycloalkyl, phenyl, --COO-alk, --CH.sub.2 --COOX, --CH.sub.2 NH.sub.2, --NH-alk, --NH--Ar, --NH.sub.2 or --NH-Het, R.sub.13 is alkyl or phenyl, R.sub.30 is --NH-alk, --NH--Ar, --NH.sub.2 or --NH-Het, R.sub.13 is alkyl or phenyl, R.sub.30 is --NH-alk, --NH--Ar, --NH.sub.2 or --NH-Het; or R is a 2-imidazolylmethyl radical and each of R.sub.1 and R.sub.2 is a hydrogen atom. The compounds of formula (I) are .alpha.-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, said receptor also being known as the quisqualate receptor. Furthermore, the compounds of formula (I) are non-competitive N-methyl-D-aspartate (NMDA) receptor antagonists, and especially NMDA receptor gylcine modulation site ligands.

  式（1）的化合物##STR1##其中R为C.dbd.R.sub.3、C(R.sub.4)R.sub.5或CH--R.sub.6，R.sub.1和R.sub.2为氢、卤素、烷基、烷氧基、氨基、酰胺基、--NH--CO--NH--Ar、--N.dbd.CH--N(alk)alk'、硝基、氰基、苯基、咪唑基或SO.sub.3 H，R.sub.3为氧、NOH、NO-烷基-COOK或CH--R.sub.7，R.sub.4为烷基、-烷基-Het或烷基-Ar，R.sub.5为烷基、-烷基-Het或-烷基-Ar，或C(R.sub.4)R.sub.5为环烷基，R.sub.6为羟基、烷基、NR.sub.8 R.sub.9、-烷基-OH、-烷基-NR.sub.8 R.sub.9、-烷基-Ar或-烷基-Het，R.sub.7为羟基、烷基、苯基、-烷基-Ar、-烷基-Het、NR.sub.10 R.sub.11或杂环戒，R.sub.8和R.sub.9为烷基，或R.sub.8为氢且R.sub.9为氢或烷基，--COR.sub.12、--CSR.sub.30或--SO.sub.2 R.sub.13，R.sub.10和R.sub.11为烷基或环烷基，R.sub.12为烷基、环烷基、苯基、--COO-烷基、--CH.sub.2 --COOX、--CH.sub.2 NH.sub.2、--NH-烷基、--NH--Ar、--NH.sub.2或--NH-Het，R.sub.13为烷基或苯基，R.sub.30为--NH-烷基、--NH--Ar、--NH.sub.2或--NH-Het，R.sub.13为烷基或苯基，R.sub.30为--NH-烷基、--NH--Ar、--NH.sub.2或--NH-Het；或R为2-咪唑甲基基团，且R.sub.1和R.sub.2中的每一个为氢原子。式（I）的化合物是α-氨基-3-羟基-5-甲基-4-异恶唑丙酸（AMPA）受体拮抗剂，该受体也被称为喹恶唑酸受体。此外，式（I）的化合物是非竞争性N-甲基-D-天冬氨酸（NMDA）受体拮抗剂，特别是NMDA受体甘氨酸调节位点配体。
• Indeno\x9b1,2-E!pyrazine-4-ones, their preparation and the medicaments
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05789406A1

  公开（公告）日：1998-08-04

  The compounds of formula (I) ##STR1## wherein R, R.sub.1 and R.sub.2 are defined in the disclosure, and salts thereof. The compounds of formula (I) are non-competitive N-methyl-D-asparate (NMDA) receptor antagonists, particularly NMDA receptor glycine modulation site ligands, and are alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, this receptor is also known as the quisqualate receptor.

  式(I)的化合物##STR1##其中R、R.sub.1和R.sub.2在披露中有定义，并其盐。式(I)的化合物是非竞争性N-甲基-D-天冬氨酸(NMDA)受体拮抗剂，特别是NMDA受体甘氨酸调节位点配体，并且是α-氨基-3-羟基-5-甲基-4-异恶唑丙酸(AMPA)受体拮抗剂，这种受体也被称为喹氯酸受体。
• Amino-substituted tetracyclic compounds useful as anti-inflammatory agents and pharmaceutical compositions comprising same
  申请人：——

  公开号：US20020072523A1

  公开（公告）日：2002-06-13

  Compounds of formula (I), or pharmaceutically-acceptable salts thereof, are useful in treating inflammatory and immune diseases and disorders, 1 wherein X, Y 1 , Y 2 , and R 2 -R 4 are as defined in the specification.

  式(I)的化合物，或其药用盐，在治疗炎症和免疫性疾病和紊乱方面具有用途，其中X、Y1、Y2和R2-R4如规范中所定义。
• Spiro\x9bheterocycle-imidazo\x9b1,2-a!indeno\x9b1,2-e!pyrazine!-4'-ones,
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05777114A1

  公开（公告）日：1998-07-07

  Compounds of formula (I): ##STR1## wherein R.sub.3 and R.sub.4, taken together with the carbon atom to which they are attached, form (a) a 2- or 3-pyrrolidine ring, a 2- or 4-piperidine ring or a 2-azacycloheptane ring, said rings being optionally substituted at the nitrogen atom by an alkyl, --CHO, --COOR.sub.11, --CO--alk--COOR.sub.6, --CO--alk--NR.sub.6 R.sub.12, --CO--alk--CONR.sub.6 R.sub.8, --CO--COOR.sub.6, --CO--CH.sub.2 --O--CH.sub.2 --COOR.sub.6, --CO--CH.sub.2 --S--CH.sub.2 --COOR.sub.6, --CO--CH.dbd.CH--COOR.sub.6, CO--alk, --CO--Ar", --CO--alk--Ar", --CO--NH--Ar", --CO--NH--alk--Ar", --CO--Het, --CO--alk--Het, --CO--NH--Het, --CO--NH--alk--Het, --CO--NH.sub.2, --CO--NH--alk, --CO--N(alk)alk', --CS--NH.sub.2, --CS--NH--alk, --CS--NH--Ar", --CS--NH--Het, --alk--Het, --alk--NR.sub.6 R.sub.8, --alk--COOR.sub.6, --alk--CO--NR.sub.6 R.sub.8, --alk--Ar", --SO.sub.2 --alk or --SO.sub.2 --Ar radical, or a --CO-cycloalkyl radical where the cycloalkyl is optionally 2-substituted by a carboxyl radical; or (b) a 2-pyrrolidin-5-one ring. The compounds of formula (I) have useful pharmacological properties and are .alpha.-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists, said receptor also being known as the quisqualate receptor. Furthermore, the compounds of formula (I) are non-competitive N-methyl-D-aspartate (NMDA) receptor antagonists, and especially NMDA receptor glycine modulation site ligands.

  公式（I）的化合物：其中R.sub.3和R.sub.4，与它们连接的碳原子一起形成（a）2-或3-吡咯烷环，2-或4-哌啶环或2-氮杂环庚烷环，所述环在氮原子上可选择地被烷基，-CHO，-COOR.sub.11，-CO-alk-COOR.sub.6，-CO-alk-NR.sub.6 R.sub.12，-CO-alk-CONR.sub.6 R.sub.8，-CO-COOR.sub.6，-CO-CH.sub.2-O-CH.sub.2-COOR.sub.6，-CO-CH.sub.2-S-CH.sub.2-COOR.sub.6，-CO-CH.dbd.CH-COOR.sub.6，CO-alk，-CO-Ar"，-CO-alk-Ar"，-CO-NH-Ar"，-CO-NH-alk-Ar"，-CO-Het，-CO-alk-Het，-CO-NH-Het，-CO-NH-alk-Het，-CO-NH.sub.2，-CO-NH-alk，-CO-N(alk)alk'，-CS-NH.sub.2，-CS-NH-alk，-CS-NH-Ar"，-CS-NH-Het，-alk-Het，-alk-NR.sub.6 R.sub.8，-alk-COOR.sub.6，-alk-CO-NR.sub.6 R.sub.8，-alk-Ar"，-SO.sub.2-alk或-SO.sub.2-Ar基团，或一个--CO-环烷基基团，其中环烷基可选择地被一个羧基基团取代；或（b）2-吡咯烷-5-酮环。公式（I）的化合物具有有用的药理学性质，并且是α-氨基-3-羟基-5-甲基-4-异噁唑丙酸（AMPA）受体拮抗剂，该受体也被称为喹嗪酸受体。此外，公式（I）的化合物是非竞争性N-甲基-D-天门冬氨酸（NMDA）受体拮抗剂，特别是NMDA受体甘氨酸调节位点配体。