1-methyl-7-nitro-3,4-dihydroisoquinoline | 29076-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 1-methyl-7-nitro-3,4-dihydroisoquinoline
• 英文别名: 1-Methyl-7-nitro-3,4-dihydroisochinolin
• CAS: 29076-94-6
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: ZLHIVVQRBMFUCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-7-nitro-3,4-dihydroisoquinoline 在 sodium borohydrid 、 sodium chloride 作用下， 以 甲醇 、 水 为溶剂， 以82%的产率得到1-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Tetrahydroisoquinoline derivative and medical preparation containing the

  摘要：

  本发明涉及一种由以下公式1表示的四氢异喹啉衍生物，该衍生物表现出对由纤维蛋白原引起的凝集作用的抑制作用，可有效用作抗血栓剂或抑制血小板凝集的药剂。本发明还涉及含有这种化合物的医药制剂。 在公式1中，B和G是一种可选择地用烷基或类似物取代的烷基；D是H，烷基或类似物；E是1,2,3,4-四氢异喹啉，可选择地用R.sub.1至R.sub.4取代，R.sub.1至R.sub.4结合在位置2的G上；R.sub.1至R.sub.4是烷基或类似物；L是羟基或类似物；A是由公式（2）表示的取代基，C是碳。 在公式2中，M和R.sub.5至R.sub.8是H，烷基或类似物。

  公开号：

  US05789595A1
• 作为产物：
  描述：

  N-(4-硝基苯乙基)乙酰胺 在 硫酸 、 三氯化铁 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-methyl-7-nitro-3,4-dihydroisoquinoline
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014

文献信息

• Amidine and isothiourea derivatives, compositions containing them and
  申请人：Astra Aktiebolag

  公开号：US05929085A1

  公开（公告）日：1999-07-27

  There are provided novel compounds of formula (I) ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification and optical isomers and racemates thereof and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy.

  提供了化合物的新颖化合物，其化学式为（I）##STR1## 其中X、R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5如规范中定义的那样，以及它们的光学异构体和拉克酸盐，以及其制备过程、含有它们的组合物以及它们在治疗中的应用。
• Anti-convulsant isoquinolyl-benzamide derivatives
  申请人：SmithKline Beecham, p.l.c.

  公开号：US06277861B1

  公开（公告）日：2001-08-21

  Compounds of formula (I) and pharmaceutically acceptable salts thereof, where R1 is hydrogen, C1-6alkyl (optionally substituted by hydroxy or C1-4alkoxy), C1-6alkenyl, C1-6alkynyl, C1-6alkylCO—, formyl, CF3CO— or C1-6alkylSO2—; R2 is hydrogen or up to three substituents selected from halogen, NO2, CN, N3, CF3O—, CF3S—, CF3CO—, trifluoromethyldiazirinyl, C 1-6?alkyl, C1-6alkenyl, C1-6alkynyl, C1-6perfluoroalkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl-, C1-6alkylO—, C1-6alkylCO—, C3-6cycloalkylO—, C3-6cycloalkylCO—, C3-6cycloalkyl-C1-4alkylO—, C3-6cycloalkyl-C1-4alkylCO—, phenyl, phenoxy, benzyloxy, benzoyl, phenyl-C1-4alkyl-, C1-6alkylS—, C1-6alkylSO2—, (C1-4alkyl)2NSO2—, (C1-4alkyl)NHSO2—, (C1-4alkyl)2NCO—, (C1-4alkyl)NHCO— or CONH2; or —NR5R6 where R5 is hydrogen or C1-4alkyl, and R6 is hydrogen, C1-4alkyl, formyl, —CO2C1-4alkyl or —COC1-4alkyl; or two R2 groups together form a carbocyclic ring that is saturated or unsaturated and unsubstituted or substituted by —OH or ═O; and the two R3 groups and the two R4 groups are each independently hydrogen or C1-6alkyl or the two R3 groups and/or the two R4 groups together form a C3-6spiroalkyl group provided that at least one R3 and R4 group is not hydrogen, are useful in the treatment and prophylaxis of epilepsy and other disorders.

  式(I)的化合物及其药学上可接受的盐，其中R1是氢、C1-6烷基（可选地被羟基或C1-4烷氧基取代）、C1-6烯基、C1-6炔基、C1-6烷基CO-、甲酰基、CF3CO-或C1-6烷基SO2-；R2是氢或最多三个取代基，所选自卤素、NO2、CN、N3、CF3O-、CF3S-、CF3CO-、三氟甲基重氮基、C1-6烷基、C1-6烯基、C1-6炔基、C1-6全氟烷基、C3-6环烷基、C3-6环烷基-C1-4烷基、C1-6烷氧基、C1-6烷基CO-、C3-6环烷基氧基、C3-6环烷基CO-、C3-6环烷基-C1-4烷氧基、C3-6环烷基-C1-4烷基CO-、苯基、苯氧基、苄氧基、苯甲酰基、苯基-C1-4烷基、C1-6烷基S-、C1-6烷基SO2-、（C1-4烷基）2NSO2-、（C1-4烷基）NHSO2-、（C1-4烷基）2NCO-、（C1-4烷基）NHCO-或CONH2；或-NR5R6，其中R5是氢或C1-4烷基，R6是氢、C1-4烷基、甲酰基、-CO2C1-4烷基或-COC1-4烷基；或两个R2基共同形成一个碳环，该碳环饱和或不饱和，未取代或被-OH或═O取代；两个R3基和两个R4基各自独立地是氢或C1-6烷基，或两个R3基和/或两个R4基共同形成一个C3-6螺环烷基，前提是至少一个R3和R4基不是氢，可用于治疗和预防癫痫和其他疾病。
• Amidine and isothiourea derivatives as inhibitors of nitric oxide
  申请人：Astra Aktiebolag

  公开号：US06140322A1

  公开（公告）日：2000-10-31

  There are provided novel compounds of formula (I) ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification and optical isomers and racemates thereof and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy.

  提供了式(I)的新化合物：##STR1## 其中X，R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5如规范中所定义，以及其光学异构体和外消旋体以及其药学上可接受的盐；以及它们的制备过程，含有它们的组合物以及它们在治疗中的用途。
• TETRAHYDROISOQUINOLINE DERIVATIVE AND MEDICINAL PREPARATION CONTAINING THE SAME
  申请人：TERUMO KABUSHIKI KAISHA

  公开号：EP0790247A1

  公开（公告）日：1997-08-20

  The present invention relates to a tetrahydroisoquinoline derivative represented by the following formula 1 exhibiting an inhibitory action for agglutination caused by fibrinogen, which may be effectively used as an antithrombotic agent or a platelet agglutination-inhibiting agent. The present invention also relates to a medical preparation containing such compound. In formula 1, B and G are an alkylene optionally substituted with an alkyl or the like; D is H, an alkyl, or the like; E is 1,2,3,4-tetrahydroisoquinoline optionally substituted with R1 to R4 which binds to G at position 2; R1 to R4 are an alkyl or the like; L is hydroxy or the like; and A is a substituent represented by formula (2), and C is carbon. In formula 2, M and R5 to R8 are H, an alkyl or the like.

  本发明涉及一种由下式 1 表示的四氢异喹啉衍生物，该衍生物对纤维蛋白原引起的凝集具有抑制作用，可有效用作抗血栓剂或血小板凝集抑制剂。本发明还涉及一种含有此类化合物的医疗制剂。 在式 1 中，B 和 G 是任选被烷基或类似物取代的亚烷基；D 是 H、烷基或类似物；E 是任选被 R1 至 R4 取代的 1，2，3，4-四氢异喹啉，它在第 2 位与 G 结合；R1 至 R4 是烷基或类似物；L 是羟基或类似物；A 是式 (2) 所代表的取代基，C 是碳。 在式 2 中，M 和 R5 至 R8 是 H、烷基或类似物。
• PREPARATION OF 1,7-DISUBSTITUTED-1,2,3,4-TETRAHYDROISOQUINOLINES
  作者：Jag P. Heer、John D. Harling、Mervyn Thompson

  DOI：10.1081/scc-120005939

  日期：2002.1

  A simple procedure for the preparation of 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines from 3,4-dihydroisoquinoline (2) is presented. This strategy overcomes the limitation of cyclisation approaches which generally require electron rich ring systems. A variety of 1-substituents has been incorporated using the appropriate organometallic or activated methylene nucleophile to prepare both electron rich (7a-f) and electron deficient 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines (16, 17).