N-(2,3-dihydro-1H-inden-2-yl)-N-(prop-1-yl)amine | 82985-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-(2,3-dihydro-1H-inden-2-yl)-N-(prop-1-yl)amine
• 英文别名: 2-propylaminoindane oxalate；N-propyl-2,3-dihydro-1H-inden-2-amine；N-propyl-2,3-dihydro-1H-indan-2-amine；2-N-n-Propylaminoindan；2-(N-propyl)aminoindan；2-(propylamino)-indane
• CAS: 82985-09-9
• 化学式: C₁₂H₁₇N
• mdl: MFCD10686590
• 分子量: 175.274
• InChiKey: OYJSAKGCKMRLQO-UHFFFAOYSA-N

物化性质

• 熔点：
  173 °C
• 沸点：
  271.9±29.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N-(2,3-dihydro-1H-inden-2-yl)-N-(prop-1-yl)amine 在 10percent Pd/C 硫酸 、 硼烷 、 硝酸 、 甲酸铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 5-amino-2-(N,N-di-n-propylamino)indan
  参考文献：
  名称：

  Thiazoloindans and Thiazolobenzopyrans:  A Novel Class of Orally Active Central Dopamine (Partial) Agonists

  摘要：

  The 2-aminothiazole moiety has proven its value in medicinal chemistry as a stable and lipophilic bioisosteric replacement of a phenol group. This approach has provided dopamine (DA) agonists with good oral availability. To further explore its use in the development of DA agonists, we have combined the 2-aminothiazole moiety with 2-aminoindans and 3-aminobenzopyrans, which are known templates for DA agonists. In this study we have synthesized 6-amino-3-(N,N-di-n-propylamino)-3,4-dihydro-2H-thiazole[5,4-f]-[1]benzopyran (12) and 6-amino-2-(N,N-di-n-propylamino)thiazolo[4,5-f]indan (20) and several analogues (13, 17, and 21). The affinity of the thiazolobenzopyrans and thiazoloindans for DA receptors was evaluated, which revealed compound 20 to have high affinity for DA DQ receptors. In addition, the compounds were screened for their potential to inhibit lipid peroxidation, to determine their radical scavenging properties. Compounds 12, 20, and 21 were subjected to further pharmacological evaluation in a functional assay to determine intrinsic activity. Compound 20 was also studied with microdialysis (to determine effects on DA turnover in striatum) and in unilaterally 6-OH-DA lesioned rats (to determine their potential as DA agonists). These studies selected compound 20 (GMC 1111) as particularly interesting. Compound 20 caused a rotation activation in unilaterally B-OH-DA lesioned rats and an increase in DA turnover in rat striatum. This dual agonist/antagonist action is best accounted for by its partial agonism at striatal DA D-2 receptors. Interestingly, 20 displayed long-lasting activity and excellent oral availability in B-OH-DA lesioned rats, making this compound potentially useful for the treatment of Parkinson's disease.

  DOI：

  10.1021/jm000087z
• 作为产物：
  描述：

  2-氨基茚满盐酸盐 在 硼烷 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 为溶剂， 生成 N-(2,3-dihydro-1H-inden-2-yl)-N-(prop-1-yl)amine
  参考文献：
  名称：

  Thiazoloindans and Thiazolobenzopyrans:  A Novel Class of Orally Active Central Dopamine (Partial) Agonists

  摘要：

  The 2-aminothiazole moiety has proven its value in medicinal chemistry as a stable and lipophilic bioisosteric replacement of a phenol group. This approach has provided dopamine (DA) agonists with good oral availability. To further explore its use in the development of DA agonists, we have combined the 2-aminothiazole moiety with 2-aminoindans and 3-aminobenzopyrans, which are known templates for DA agonists. In this study we have synthesized 6-amino-3-(N,N-di-n-propylamino)-3,4-dihydro-2H-thiazole[5,4-f]-[1]benzopyran (12) and 6-amino-2-(N,N-di-n-propylamino)thiazolo[4,5-f]indan (20) and several analogues (13, 17, and 21). The affinity of the thiazolobenzopyrans and thiazoloindans for DA receptors was evaluated, which revealed compound 20 to have high affinity for DA DQ receptors. In addition, the compounds were screened for their potential to inhibit lipid peroxidation, to determine their radical scavenging properties. Compounds 12, 20, and 21 were subjected to further pharmacological evaluation in a functional assay to determine intrinsic activity. Compound 20 was also studied with microdialysis (to determine effects on DA turnover in striatum) and in unilaterally 6-OH-DA lesioned rats (to determine their potential as DA agonists). These studies selected compound 20 (GMC 1111) as particularly interesting. Compound 20 caused a rotation activation in unilaterally B-OH-DA lesioned rats and an increase in DA turnover in rat striatum. This dual agonist/antagonist action is best accounted for by its partial agonism at striatal DA D-2 receptors. Interestingly, 20 displayed long-lasting activity and excellent oral availability in B-OH-DA lesioned rats, making this compound potentially useful for the treatment of Parkinson's disease.

  DOI：

  10.1021/jm000087z

文献信息

• [EN] MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTORS AND USES THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE ET LEURS UTILISATIONS
  申请人：BIONOMICS LTD

  公开号：WO2018102885A1

  公开（公告）日：2018-06-14

  The present invention relates generally to chemical compounds and methods for their use and preparation in relation to the treatment of diseases, disorders or conditions which would benefit from the modulation of the alpha 7 nicotinic acetylcholine receptor (α7 nAChR). The invention thus also relates to the use of these compounds in methods of therapy and the manufacture of medicaments as well as compositions containing these compounds.

  本发明一般涉及化合物及其在治疗需要调节α7尼古丁乙酰胆碱受体（α7 nAChR）的疾病、紊乱或症状方面的使用和制备方法。因此，本发明还涉及这些化合物在治疗方法和药物制造以及含有这些化合物的组合物方面的使用。
• Indane derivatives for treating endotoxin shock and/or nephritis
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05543409A1

  公开（公告）日：1996-08-06

  Disclosed are indane compounds represented by the formula: ##STR1## wherein R.sup.1 is aryl, lower alkyl, cycloalkyl, halogeno-lower alkyl, lower alkenyl, phenyl-substituted lower alkenyl, monocyclic or bicyclic aromatic heterocyclic having N, O or S as a hetero atom, lower alkoxy, phenoxy, lower alkylamino, lower alkenylamino, phenylamino, lower alkyl substituted by monocyclic or bicyclic aromatic heterocyclic having N, O or S as a hetero atom, or lower alkenyloxy; R.sup.2 is H or lower alkyl; X is carbonyl or thiocarbonyl; Alk is single bonding arm or lower alkylene; and the dotted line is presence or absence of a double bond, for treating endotoxin shock and/or nephritis.

  揭示了由以下式表示的茚烷化合物：##STR1##其中R.sup.1为芳基、较低烷基、环烷基、卤代较低烷基、较低烯基、苯基取代的较低烯基、具有N、O或S作为杂原子的单环或双环芳香杂环、较低烷氧基、苯氧基、较低烷基氨基、较低烯基氨基、苯基氨基、被具有N、O或S作为杂原子的单环或双环芳香杂环取代的较低烷基，或较低烯氧基；R.sup.2为H或较低烷基；X为羰基或硫代羰基；Alk为单键臂或较低烷基烯；虚线表示双键的存在或不存在，用于治疗内毒素休克和/或肾炎。
• Synthesis of Bitopic Ligands as Potent Dopamine D ₂ Receptor Agonists
  作者：Mingcheng Qian、Kuo Zhou、Yi Wu、Zhijie Luo、Zhekai Xiao、Jingjing Sun、Siyu Zeng、Yi Yao、Shuai Zhao、Xin Chen

  DOI：10.1002/cmdc.202100681

  日期：2022.2.16

  Optimal spacer length: In this study, we synthesized twelve bitopic ligands as dopamine D2 receptor agonists. Interestingly, compound 11 b showed 21-fold higher potency than lead compound 2 and 17-fold higher subtype selectivity for D2R over D4R. Molecular modeling study exhibited that 11 b formed two H-bonds with amino acid Asp114, which contributes significantly to D2R functional activity.

  最佳间隔长度：在这项研究中，我们合成了十二个双位配体作为多巴胺 D 2受体激动剂。有趣的是，化合物11b的效力比先导化合物2高 21 倍，对 D 2 R 的亚型选择性比 D 4 R高 17 倍。分子模型研究表明，11 b与氨基酸 Asp114 形成了两个 H 键，这有助于D 2 R 功能活性显着。
• Derivatives of 4-(aminomethyl) piperidine, their preparation and their
  申请人：Synthelabo

  公开号：US05179108A1

  公开（公告）日：1993-01-12

  Compounds of general formula (I) ##STR1## in which n is 1 or 2; R represents a linear or branched C.sub.1 -C.sub.3 -alkyl group; and X represents at least one substituent chosen from hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -alkoxy, in the form of a free base or an acid addition salt thereof, and their therapeutic application.

  通式(I)的化合物 ##STR1##中，其中n为1或2；R代表直链或支链的C.sub.1 -C.sub.3 -烷基基团；X代表至少一个取自氢、卤素、C.sub.1 -C.sub.3 -烷基和C.sub.1 -C.sub.3 -烷氧基的取代基，以自由碱或其酸盐形式存在，并且它们的治疗应用。
• 2-aminothiazol-fused 2-aminoindans and 2-aminotetralins and their use
  申请人：——

  公开号：US06291494B1

  公开（公告）日：2001-09-18

  The invention relates to 2-aminothiazol-fused 2-aminoindans and 2-aminotetralins having general formula (1): wherein R1 and R2, which may be identical or different, are selected from the group consisting of a hydrogen atom, alkyl or haloalkyl groups of 1 to 7 carbon atoms, (alkyl)cycloalkyl groups of 3 to 7 carbon atoms, alkenyl or alkynyl groups of 3 to 6 carbon atoms, arylalkyl having 1 to 3 carbon atoms in the alkyl moiety, while the aryl nucleus may be substituted; and n and m are 1 or 2; and the enantiomers and the acid addition salts thereof, pharmaceutical compositions containing them and their use in the preparation of medicaments having an effect on the dopaminergic system of the central nervous system and/or the circulation.

  该发明涉及具有通式（1）的2-氨基噻唑融合的2-氨基茚和2-氨基四氢萘，其中R1和R2，可以相同也可以不同，选自包括氢原子、1到7个碳原子的烷基或卤代烷基基团、3到7个碳原子的（烷基）环烷基基团、3到6个碳原子的烯基或炔基基团、烷基中含有1到3个碳原子的芳基烷基，而芳基核可能被取代；n和m为1或2；以及其对映异构体和酸盐，含有它们的制剂和它们在制备对中枢神经系统和/或循环的多巴胺系统产生影响的药物中的用途。