2,3-二氢-5,6-二甲氧基-N,N-二丙基-1H-茚-2-胺 | 82668-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 2,3-二氢-5,6-二甲氧基-N,N-二丙基-1H-茚-2-胺
• 英文名称: 5,6-dimethoxy-2-(di-n-propylamino)indan
• 英文别名: 2,3-dihydro-5,6-dimethoxy-N, N-dipropyl-1H-inden-2-amine；JPC 211；1H-Inden-2-amine, 2,3-dihydro-5,6-dimethoxy-N,N-dipropyl-；5,6-dimethoxy-N,N-dipropyl-2,3-dihydro-1H-inden-2-amine
• CAS: 82668-33-5
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: UOLJKAPABHXFRE-UHFFFAOYSA-N

物化性质

• 熔点：
  210-214 °C
• 沸点：
  380.7±42.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(3,4-dimethoxy-phenyl)-propionyl chloride 在 10percent Pd/C 盐酸 、 三氯化铝 、 亚硝酸丁酯 、 硫酸 、 氢气 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 20.0~40.0 ℃ 、344.75 kPa 条件下， 反应 34.5h， 生成 2,3-二氢-5,6-二甲氧基-N,N-二丙基-1H-茚-2-胺
  参考文献：
  名称：

  Dopamine D₃ Receptor Antagonists. 1. Synthesis and Structure−Activity Relationships of 5,6-Dimethoxy-N-alkyl- and N-Alkylaryl-Substituted 2-Aminoindans

  摘要：

  5,6-Dimethoxy-2-(N-dipropyl)-aminoindan (3, PNU-99194A) was found to be a selective dopamine D-3 receptor antagonist with potential antipsychotic properties in animal models. To investigate the effects of nitrogen substitution on structure-activity relationships, a series of 5,6-dimethoxy-N-alkyl- and N-alkylaryl-substituted 2-aminoindans were synthesized and evaluated in vitro for binding affinity and metabolic stability. The results indicate that substitution at the amine nitrogen of the 2-aminoindans is fairly limited to the di-N-propyl group in order to achieve selective D-3 antagonists. Thus, combinations of various alkyl groups were generally inactive at the D-3 receptor. Although substitution with an N-alkylaryl or N-alkylheteroaryl group yields compounds with potent D-3 binding affinity, the D-2 affinity is also enhanced, resulting in a less than 4-fold preference for the D-3 receptor site, and no improvements in metabolic stability were noted. A large-scale synthesis of the D-3 antagonist 3 has been developed that has proven to be reproducible with few purification steps. The improvements include the use of 3,4-dimethoxybenzaldehyde as a low-cost starting material to provide the desired 5,6-dimethoxy-1-indanone 5c in good overall yield (65%) and the formation of a soluble silyl oxime 17 that was reduced efficiently with BH3. Me2S. The resulting amino alcohol was alkylated and then deoxygenated using a Lewis acid and Et3SiH to give the desired product 3 in good overall yield of (similar to 65%) from the indanone 5c.

  DOI：

  10.1021/jm010145w

文献信息

• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• 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.
• 2-AMINOINDANS AS SELECTIVE DOPAMINE D3 LIGANDS
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0712387B1

  公开（公告）日：1999-12-08
• BINGE BEHAVIOR REGULATORS
  申请人：GOLAN Ezekiel

  公开号：US20210330609A1

  公开（公告）日：2021-10-28

  Methods and compositions utilizing 2-aminoindan derivatives collectively represented by Formula I as described and defined in the specification for regulating binge behavior, particularly binge drinking, are disclosed.
• US8569481B2
  申请人：——

  公开号：US8569481B2

  公开（公告）日：2013-10-29