5-amino-6-nitro-3,3-diethyl-indolin-2-one | 100510-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-amino-6-nitro-3,3-diethyl-indolin-2-one
• 英文别名: 5-amino-3,3-diethyl-6-nitroindolin-2-one；5-amino-3,3-diethyl-6-nitro-1H-indol-2-one
• CAS: 100510-93-8
• 化学式: C₁₂H₁₅N₃O₃
• 分子量: 249.269
• InChiKey: DEGHDGPZUTYKPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  267-272 °C
• 沸点：
  456.1±45.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-6-nitro-3,3-diethyl-indolin-2-one 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Nonsteroidal cardiotonics. 1. 2-Pyridyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-ones, a novel class of cardiotonic agents

  摘要：

  A series of substituted 2-pyridyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-ones 1-24 were synthesized and evaluated for positive inotropic activity. In rats, cats, and dogs most of these tricyclic heterocycles produced a dose-related increase in myocardial contractility with little effect on heart rate and blood pressure. The increase in contractility was not mediated via stimulation of beta-adrenergic receptors. Compound 1 (BM 14.478) was more potent than milrinone (25) and enoximone when administered intravenously to rats, cats, and dogs. After oral administration of 1 mg/kg, compound 1, milrinone, and pimobendan were equipotent. However, only 1 and pimobendan were still active after 6 h. The structural requirements necessary for optimal cardiotonic activity within this novel class of heterocycles were investigated.

  DOI：

  10.1021/jm00391a004
• 作为产物：
  描述：

  1-苄基-3H-吲哚-2-酮 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 硫酸 、 氨 、 氢气 、 硝酸 、 sodium 、 苄基三丁基溴化铵 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 9.5h， 生成 5-amino-6-nitro-3,3-diethyl-indolin-2-one
  参考文献：
  名称：

  Nonsteroidal cardiotonics. 1. 2-Pyridyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-ones, a novel class of cardiotonic agents

  摘要：

  A series of substituted 2-pyridyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-ones 1-24 were synthesized and evaluated for positive inotropic activity. In rats, cats, and dogs most of these tricyclic heterocycles produced a dose-related increase in myocardial contractility with little effect on heart rate and blood pressure. The increase in contractility was not mediated via stimulation of beta-adrenergic receptors. Compound 1 (BM 14.478) was more potent than milrinone (25) and enoximone when administered intravenously to rats, cats, and dogs. After oral administration of 1 mg/kg, compound 1, milrinone, and pimobendan were equipotent. However, only 1 and pimobendan were still active after 6 h. The structural requirements necessary for optimal cardiotonic activity within this novel class of heterocycles were investigated.

  DOI：

  10.1021/jm00391a004

文献信息

• Pyrrolobenzimidazoles for treating heart or circulatory diseases
  申请人：Boehringer Mannheim GmbH

  公开号：US04666923A1

  公开（公告）日：1987-05-19

  Pyrrolobenzimidazoles, processes for the preparation thereof and pharmaceutical compositions thereof for the treatment of coronary insufficiencies, cardiac failure, blood circulatory disturbances and occlusive diseases. The new pyrrolobenzimidazoles are of the formula ##STR1## wherein R.sub.1 is hydrogen, alkyl, alkenyl or cycloalkyl, R.sub.2 is hydrogen, alkyl, alkenyl, cyano or a substituted carbonyl or R.sub.1 and R.sub.2 together represent cycloalkylene or form alkylidene or cycloalkylidene, X is a valency bond, C.sub.1 -C.sub.4 alkylene or vinylene, T is oxygen or sulphur and Py is pyridyl or substituted pyridyl and including the tautomers thereof and the physiologically acceptable salts thereof.

  吡咯并咪唑类化合物，其制备方法以及用于治疗冠状动脉不足、心力衰竭、血液循环障碍和闭塞性疾病的药物组合物。新的吡咯并咪唑类化合物的结构式为##STR1##其中R.sub.1为氢、烷基、烯基或环烷基，R.sub.2为氢、烷基、烯基、氰基或取代的羰基，或R.sub.1和R.sub.2一起代表环烷基或形成烷基亚甲基或环烷基亚甲基，X为价键，C.sub.1-C.sub.4烷基或乙烯基，T为氧或硫，Py为吡啶基或取代的吡啶基，包括其互变异构体和生理上可接受的盐。
• Neue Pyrrolo-Benzimidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel sowie Zwischenprodukte
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0161632A2

  公开（公告）日：1985-11-21

  Neue Pyrrolo-Benzimidazole der Formel 1 in welcher R1 ein Wasserstoffatom, eine Alkyl-, Alkenyl- oder eine Cycloalkylgruppe bedeutet, R2 ein Wasserstoffatom, eine Alkyl-, Alkenyl- oder Cyangruppe, eine durch eine Hydroxy-, Alkyl-, Alkoxy-, Amino-, Alkylamino-, Dialkylamino- oder Hydrazinogruppe substituierte Carbonylgruppe bedeutet oder mit R1 zusammen eine Cycloalkylengruppe darstellt oder R1 und R2 zusammen eine Alkyliden- oder Cycloalkylidengruppe bilden, X einen Valenzstrich, eine C1-C4-Alkylengruppe oder die Vinylengruppe bedeutet, T gleich Sauerstoff oder Schwefel bedeutet, Py einen 2-, 3- oder 4-Pyridylrest darstellt, der gegebenenfalls am Ringheteroatom ein Sauerstoffatom trägt und/oder durch eine oder mehrere Alkyl-, Alkoxy-, Hydroxy-, Cyano- oder Nitrogruppen sowie durch Halogen substituiert sein kann, deren Tautomere und deren physiologisch verträgliche Salze, Verfahren zu ihrer Herstellung, Arzneimittel, die Verbindungen der Formel enthalten, zur Behandlung von Herz- und Kreislauferkrankungen sowie Verbindungen der Formel II a in der R1 und R2 die in Formel I angegebenen Bedeutungen naben, A und B eine Amino- oder Nitrogruppe oder die Gruppe bedeutet, mit der Maßgabe, daß A und B nur gleichzeitig NH2 bedeuten dürfen, als Zwischenprodukte zur Herstellung von Verbindungen der Formel I.

  公式 1 中的新型吡咯并苯并咪唑 中的 R1 代表氢原子、烷基、烯基或环烷基、 R2代表氢原子、烷基、烯基或氰基、被羟基、烷基、烷氧基、氨基、烷基氨基、二烷基氨基或肼基取代的羰基，或与R1一起代表环烯基，或R1和R2一起形成亚烷基或亚环烷基、 X 代表价键、C1-C4 亚烷基或亚乙烯基、 T 是氧或硫、 Py 代表 2-、3-或 4-吡啶基，其环状杂原子上可选择带有一个氧原子，和/或可被一个或多个烷基、烷氧基、羟基、氰基或硝基以及卤素取代。 其中 R1 和 R2 具有式 I 中给出的含义、 A 和 B 表示氨基或硝基或以下基团 但书 但 A 和 B 只能同时表示 NH2，作为制备式 I 化合物的中间体。
• MERTENS, A.;MULLER-BECKMANN, B.;KAMPE, W.;HOLCK, J. -P.;SAAL, W. VON DER, J. MED. CHEM., 30,(1987) N 8, 1279-1287
  作者：MERTENS, A.、MULLER-BECKMANN, B.、KAMPE, W.、HOLCK, J. -P.、SAAL, W. VON DER

  DOI：——

  日期：——
• US4963686A
  申请人：——

  公开号：US4963686A

  公开（公告）日：1990-10-16
• Nonsteroidal cardiotonics. 1. 2-Pyridyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-ones, a novel class of cardiotonic agents
  作者：A. Mertens、B. Mueller-Beckmann、W. Kampe、J. P. Hoelck、W. Von der Saal

  DOI：10.1021/jm00391a004

  日期：1987.8

  A series of substituted 2-pyridyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-ones 1-24 were synthesized and evaluated for positive inotropic activity. In rats, cats, and dogs most of these tricyclic heterocycles produced a dose-related increase in myocardial contractility with little effect on heart rate and blood pressure. The increase in contractility was not mediated via stimulation of beta-adrenergic receptors. Compound 1 (BM 14.478) was more potent than milrinone (25) and enoximone when administered intravenously to rats, cats, and dogs. After oral administration of 1 mg/kg, compound 1, milrinone, and pimobendan were equipotent. However, only 1 and pimobendan were still active after 6 h. The structural requirements necessary for optimal cardiotonic activity within this novel class of heterocycles were investigated.