Imidazo[1,2-a]quinoline-2-carbaldehyde | 76577-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Imidazo[1,2-a]quinoline-2-carbaldehyde
• CAS: 76577-49-6
• 化学式: C₁₂H₈N₂O
• 分子量: 196.208
• InChiKey: BMECITFWYLFLGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Imidazo[1,2-a]quinoline-2-carbaldehyde 在 palladium on activated charcoal 盐酸 、 盐酸羟胺 、 氢气 、 sodium acetate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 8.0h， 生成 imidazo[1,2-a]quinoline-2-methanamine dihydrochloride
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009
• 作为产物：
  描述：

  imidazo[1,2-a]quinoline-2-methanol 在 manganese dioxide cellulose 、 氯仿 、 乙醚 、 needles 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以to obtain 3.4 g of imidazo-[1,2-a]-quinoline-2-carboxaldehyde in the form of needles melting at 184°-185° C.的产率得到Imidazo[1,2-a]quinoline-2-carbaldehyde
  参考文献：
  名称：

  Imidazoquinoxalines and pyrroloquinoxalines

  摘要：

  化合物的新颖结构式为##STR1## 其中A选自氮和.dbd.CH--的群组，G选自##STR2##的群组，Z选自1到5个碳原子的氢和烷基，或与Y一起形成碳氮或碳碳键，Z'选自氢和卤素的群组，Y为氢，或与Z一起形成碳氮或碳碳键，或与X一起为.dbd.O，X为氢，或与Y一起为.dbd.O，R选自羟甲基、甲酰基、四唑-5-基、N-(四唑-5-基)氨甲酰基、氨甲基和氨基甲酰基的群组，R.sub.1选自1到5个碳原子的卤素和烷氧基的群组，以及其无毒、药学上可接受的酸盐，具有抗过敏活性，并且可以制备这些化合物。

  公开号：

  US04333934A1

文献信息

• [EN] HETEROTRICYCLYL 6-ALKYLIDENE-PENEMS AS BetaEpsilonTauAlpha-LACTAMASE INHIBITORS<br/>[FR] DERIVES D'HETEROTRICYCLYL 6-ALKYLIDENE-PENEMES EN TANT QU'INHIBITEURS DE BETA-LACTAMASE
  申请人：WYETH CORP

  公开号：WO2003093280A1

  公开（公告）日：2003-11-13

  The present invention provides a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.

  本发明提供了一种I式化合物，药物组合物以及其用于治疗患有细菌感染或疾病的患者的用途。
• Tricyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors
  申请人：Mansour Suhayl Tarek

  公开号：US20060276446A1

  公开（公告）日：2006-12-07

  This invention relates to certain tricyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present invention when combined with β-lactam antibiotics will provide an effective treatment against life threatening bacterial infections. In accordance with the present invention there are provided compounds of formula I which are useful for treatment of bacterial infections having class-D enzymes associated therewith: wherein: One of A and B denotes hydrogen and the other an optionally substituted fused tricyclic heteroaryl group; and X is S or O.

  这项发明涉及某些三环6-烷基亚胺基青霉素，其作为类D酶的抑制剂。β-内酰胺酶水解β-内酰胺类抗生素，因此是细菌抗药性的主要原因。本发明的化合物与β-内酰胺类抗生素结合时，将提供一种有效治疗危及生命的细菌感染的方法。根据本发明，提供了以下公式I的化合物，其用于治疗与类D酶相关的细菌感染：其中：A和B中的一个表示氢，另一个表示可选择取代的融合三环杂芳基团；X为S或O。
• Process for preparing 6-alkylidene penem derivatives
  申请人：Wyeth

  公开号：US20040132708A1

  公开（公告）日：2004-07-08

  The present invention provides a process of making compounds of formula I, which are useful for the treatment of bacterial infection or disease. 1

  本发明提供了一种制备式I化合物的方法，该化合物对治疗细菌感染或疾病有用。
• [EN] PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES DE 6-ALKYLIDENE PENEM
  申请人：WYETH CORP

  公开号：WO2003093277A1

  公开（公告）日：2003-11-13

  The present invention provides a process of making compounds of Formula (I), which are useful for the treatment of bacterial infection or disease.

  本发明提供了一种制备化合物的方法，该化合物符合式（I），对于治疗细菌感染或疾病非常有用。
• Substituted imidazo 1,2-a-quinoxaline-4-(5H)ones, their compositions and
  申请人：Roussel Uclaf

  公开号：US04474784A1

  公开（公告）日：1984-10-02

  Novel compounds of the formula ##STR1## wherein A is selected from the group consisting of nitrogen and .dbd.CH--, G is selected from the group consisting of --0--, ##STR2## Z is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken with Y forms a carbon-nitrogen or carbon-carbon bond, Z' is selected from the group consisting of hydrogen and halogen, Y is hydrogen, or taken with Z is a carbon-nitrogen or carbon-carbon bond or taken with X is .dbd.0 and X is hydrogen or taken with Y is .dbd.0, R is selected from the group consisting of hydroxymethyl, formyl, tetrazol-5-yl, N-(tetrazol-5-yl) carbamoyl, aminomethyl and carbamoyl, R.sub.1 is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms and its non-toxic, pharmaceutically acceptable acid addition salts having anti-allergic activity and their preparation.

  该文描述的是一种新型化合物，化学式为##STR1## 其中A可选自氮和.dbd.CH--，G可选自--0--，##STR2##，Z可选自氢和1至5个碳原子的烷基，或与Y形成碳氮或碳碳键，Z'可选自氢和卤素，Y为氢，或与Z形成碳氮或碳碳键，或与X形成.dbd.0，X为氢，或与Y形成.dbd.0，R可选自羟甲基、甲酰基、四唑-5-基、N-(四唑-5-基)氨基甲酰基、氨甲基和氨基甲酰基，R.sub.1可选自氢、卤素和1至5个碳原子的烷氧基，以及其无毒、药学上可接受的酸盐，具有抗过敏活性，并提供了其制备方法。