2-amino-4,5-dimethoxyindan | 83598-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-amino-4,5-dimethoxyindan
• 英文别名: 4,5-dimethoxy-2-aminoindan；2-Amino-4,5-dimethyoxyindane；4,5-dimethoxy-2,3-dihydro-1H-inden-2-amine
• CAS: 83598-56-5
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: OVOZNCAEVHJDNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-4,5-dimethoxyindan 、 丙醛 在 sodium cyanoborohydride 作用下， 生成 4,5-dimethoxy-2-(di-n-propylamino)indan
  参考文献：
  名称：

  Conformationally restricted congeners of dopamine derived from 2-aminoindan

  摘要：

  Two series of N-substituted 2-aminoindan systems have been prepared: 4,5-dihydroxy-2-aminoindan (1) has a hydroxylation pattern analogous to the alpha conformer of dopamine, and 5,6-dihydroxy-2-aminoindan (2) has a hydroxylation pattern of the beta conformer of dopamine. All members of both series demonstrated only extremely weak binding to calf caudate homogenate. Certain N-alkylated 4,5-dihydroxyindans were violent emetics in the dog and were potent in blockade of the effect of stimulation of the cardioaccelerator nerve of the cat. In contrast, the 5,6-dihydroxy series displayed low or no activity/potency in these assays. Conformational analysis of the 2-aminoindan system is described and discussed.

  DOI：

  10.1021/jm00354a010
• 作为产物：
  描述：

  4,5-dimethoxy-2-oximino-1-indanone 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 2-amino-4,5-dimethoxyindan
  参考文献：
  名称：

  Conformationally restricted congeners of dopamine derived from 2-aminoindan

  摘要：

  Two series of N-substituted 2-aminoindan systems have been prepared: 4,5-dihydroxy-2-aminoindan (1) has a hydroxylation pattern analogous to the alpha conformer of dopamine, and 5,6-dihydroxy-2-aminoindan (2) has a hydroxylation pattern of the beta conformer of dopamine. All members of both series demonstrated only extremely weak binding to calf caudate homogenate. Certain N-alkylated 4,5-dihydroxyindans were violent emetics in the dog and were potent in blockade of the effect of stimulation of the cardioaccelerator nerve of the cat. In contrast, the 5,6-dihydroxy series displayed low or no activity/potency in these assays. Conformational analysis of the 2-aminoindan system is described and discussed.

  DOI：

  10.1021/jm00354a010

文献信息

• Aminocycloalkanobenzodioxoles as beta-3 selective adrenergic agents
  申请人：American Cyanamid Company

  公开号：US05594027A1

  公开（公告）日：1997-01-14

  The invention is antiobesity/antidiabetic/beta-3 agonists of the formula ##STR1## wherein the substituents R.sub.o, R.sub.1, R.sub.4, R.sub.4 ', R.sub.5, R.sub.6 or n are as defined in the specification.

  该发明是公式##STR1##的抗肥胖/抗糖尿病/beta-3激动剂，其中取代基R.sub.o，R.sub.1，R.sub.4，R.sub.4'，R.sub.5，R.sub.6或n如规范中所定义。
• Pyrazolo[3,4-b]Pyridine Compounds, and their Use as Phosphodiesterase Inhibitors
  申请人：ALLEN David George

  公开号：US20080175914A1

  公开（公告）日：2008-07-24

  The invention relates to a compound of formula (I) or a salt thereof: wherein: R 1 is C 1-4 alkyl, C 1-3 fluoroalkyl, —CH 2 CH 2 OH or —CH 2 CH 2 CO 2 C 1-2 alkyl; R 2 is a hydrogen atom (H), methyl or C 1 fluoroalkyl; R 3 is optionally substituted C 3-8 cycloalkyl or optionally substituted mono-unsaturated-C 5-7 cycloalkenyl or an optionally substituted heterocyclic group of sub-formula (aa), (bb) or (cc); in which n 1 and n 2 independently are 1 or 2; and in which Y is O, S, SO 2 , or NR 10 ; or R 3 is a bicyclic group (dd) or (ee): and wherein X is NR 4 R 5 or OR 5a . The compounds are phosphodiesterase (PDE) inhibitors, in particular PDE 4 inhibitors. Also provided is the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment and/or prophylaxis of an inflammatory and/or allergic disease in a mammal such as a human, for example chronic obstructive pulmonary disease (COPD), asthma, or allergic rhinitis.

  本发明涉及公式（I）的化合物或其盐： 其中： R1是C1-4烷基，C1-3氟烷基，-CH2CH2OH或-CH2CH2CO2C1-2烷基; R2是氢原子（H），甲基或C1氟烷基; R3是可选取代的C3-8环烷基或可选取代的单不饱和C5-7环烯基或亚公式（aa），（bb）或（cc）的可选取代的杂环基; 其中n1和n2独立地为1或2; Y是O，S，SO2或NR10; 或R3是双环基（dd）或（ee）： 其中X是NR4R5或OR5a。 该化合物是磷酸二酯酶（PDE）抑制剂，特别是PDE4抑制剂。本发明还提供了公式（I）的化合物或其药学上可接受的盐的用途，用于制造治疗和/或预防哺乳动物，如人类的炎症性和/或过敏性疾病的药物，例如慢性阻塞性肺疾病（COPD），哮喘或过敏性鼻炎。
• US5510376A
  申请人：——

  公开号：US5510376A

  公开（公告）日：1996-04-23
• US5594027A
  申请人：——

  公开号：US5594027A

  公开（公告）日：1997-01-14
• Conformationally restricted congeners of dopamine derived from 2-aminoindan
  作者：Joseph G. Cannon、Julio A. Perez、Ranbir K. Bhatnagar、John Paul Long、Fouad M. Sharabi

  DOI：10.1021/jm00354a010

  日期：1982.12

  Two series of N-substituted 2-aminoindan systems have been prepared: 4,5-dihydroxy-2-aminoindan (1) has a hydroxylation pattern analogous to the alpha conformer of dopamine, and 5,6-dihydroxy-2-aminoindan (2) has a hydroxylation pattern of the beta conformer of dopamine. All members of both series demonstrated only extremely weak binding to calf caudate homogenate. Certain N-alkylated 4,5-dihydroxyindans were violent emetics in the dog and were potent in blockade of the effect of stimulation of the cardioaccelerator nerve of the cat. In contrast, the 5,6-dihydroxy series displayed low or no activity/potency in these assays. Conformational analysis of the 2-aminoindan system is described and discussed.