(1S,2R)-顺-5-甲氧基-1-甲基-2-(N-丙胺)萘满盐酸盐 | 85379-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (1S,2R)-顺-5-甲氧基-1-甲基-2-(N-丙胺)萘满盐酸盐
• 英文名称: cis-5-methoxy-1-methyl-2-(n-propylamino)tetralin
• 英文别名: 5-Methoxy-1-methyl-2-(n-propylamino)tetralin；(1S,2R)-5-methoxy-1-methyl-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 85379-09-5
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: YGHLYBIUVOLKCV-SMDDNHRTSA-N

物化性质

• 沸点：
  345.3±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)
• 溶解度：
  在水中溶解度为 10 mM

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  (1S,2R)-顺-5-甲氧基-1-甲基-2-(N-丙胺)萘满盐酸盐 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 顺-(+)-5-甲氧基-1-甲基-2-(二正丙基氨基)萘满马来酸
  参考文献：
  名称：

  A short and efficient asymmetric synthesis of (1S,2R)-(+)-5-methoxy-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232)

  摘要：

  A general practical asymmetric synthesis of (1S,2R)-(+)-5-methoxyl-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232) was developed in a short and efficient method in high optical purity starting from commercially available 5-methoxy-1-tetralone. Asymmetric hydroboration of 5-methoxy-1-methyl-3,4-dihydronaphthalene with monoisopinocampheylborane followed by treatment with NaOH/H2O2 afforded key intermediate tetrahydronaphthol 4. Compound 4 was converted to the target molecule 1 using straightforward reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00333-x
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (1S,2S)-5-methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl ester 在 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,2R)-顺-5-甲氧基-1-甲基-2-(N-丙胺)萘满盐酸盐
  参考文献：
  名称：

  A short and efficient asymmetric synthesis of (1S,2R)-(+)-5-methoxy-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232)

  摘要：

  A general practical asymmetric synthesis of (1S,2R)-(+)-5-methoxyl-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232) was developed in a short and efficient method in high optical purity starting from commercially available 5-methoxy-1-tetralone. Asymmetric hydroboration of 5-methoxy-1-methyl-3,4-dihydronaphthalene with monoisopinocampheylborane followed by treatment with NaOH/H2O2 afforded key intermediate tetrahydronaphthol 4. Compound 4 was converted to the target molecule 1 using straightforward reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00333-x

文献信息

• Phenylethylamines and condensed rings variants as prodrugs of catecholamines, and their use
  申请人：——

  公开号：US20030087948A1

  公开（公告）日：2003-05-08

  Compounds of the general formula I 1 wherein rings B, C, D and E may be present or not and, when present, are combined with A as A+C, A+E, A+B+C, A+B+D, A+B+E, A+C+E, A+B+C+D or A+B+C+D+E, rings B, C and E being aliphatic whereas ring D may be aliphatic or aromatic/hetero-aromatic, and wherein X is —(CH 2 ) m —, in which m is an integer 1-3, to form a ring E or, when E is absent, a group R 1 bound to the nitrogen atom, wherein R 1 is selected from the group consisting of a hydrogen atom, alkyl or haloalkyl groups of 1 to 3 carbon atoms, cycloalkyl(alkyl) groups of 3 to 5 carbon atoms (i.e. including cyclopropyl, cyclopropylmethyl, cyclobutyl and cyclobutylmethyl) and wherein Y is —(CH 2 ) n —, in which n is an integer 1-3, to form a ring C or when C is absent, a group R 2 bound to the nitrogen atom, wherein R 2 is selected from the group consisting of a hydrogen atom, alkyl or haloalkyl groups of 1 to 7 carbon atoms, cycloalkyl(alkyl) groups of 3 to 7 carbon atoms, alkenyl or alkylnyl groups of 3 to 6 carbon atoms, arylalkyl, heteroarylalkyl having 1 to 3 carbon atoms in the alkyl moiety, whilst the aryl/heteroaryl nucleus may be substituted, provided that when rings B, C, D and E are absent NR 1 R 2 is different from dimethylamino, N-methyl-N-ethylamino, N-methyl-N-propynyl-amino, N-methyl-N-propylamino and N-hydroxipropyl-N-methylamino, and salts thereof with pharmaceutically acceptable acids or bases are disclosed as well as the use of such compounds for the manufacturing of pharmaceutical compositions for the treatment of Parkinson's disease, psychoses, Huntington's disease, impotence, renal failure, heart failure or hypertension, such pharmaceutical compositions and methods of treating Parkinson's disease and schizophrenia.

  通式I的化合物 其中环B、C、D和E可能存在也可能不存在，当存在时，与A结合为A+C、A+E、A+B+C、A+B+D、A+B+E、A+C+E、A+B+C+D或A+B+C+D+E，环B、C和E为脂肪环，而环D可以是脂肪环或芳香/杂环，其中X为—(CH 2 ) m —，其中m为1-3的整数，形成环E或者当E不存在时，与氮原子结合的基团R 1 ，其中R 1 选自氢原子、1至3个碳原子的烷基或卤代烷基基团、3至5个碳原子的环烷基(烷基)基团（即包括环丙基、环丙基甲基、环丁基和环丁基甲基），Y为—(CH 2 ) n —，其中n为1-3的整数，形成环C或者当C不存在时，与氮原子结合的基团R 2 ，其中R 2 选自氢原子、1至7个碳原子的烷基或卤代烷基基团、3至7个碳原子的环烷基(烷基)基团、3至6个碳原子的烯基或烷基基团、芳基烷基、杂环芳基烷基，其中烷基部分含有1至3个碳原子，而芳基/杂环芳基核可能被取代，前提是当环B、C、D和E不存在时，NR 1 R 2 与二甲氨基、N-甲基-N-乙基氨基、N-甲基-N-丙炔基氨基、N-甲基-N-丙基氨基和N-羟基丙基-N-甲基氨基不同，并且还披露了这些化合物与药学上可接受的酸或碱的盐以及用于制造治疗帕金森病、精神病、亨廷顿病、阳痿、肾衰竭、心力衰竭或高血压的药物组合物的用途，以及治疗帕金森病和精神分裂症的药物组合物和方法。
• 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。
• Resolved cis- and trans-2-amino-5-methoxy-1-methyltetralins: central dopamine receptor agonists and antagonists
  作者：Anette M. Johansson、Lars Erik Arvidsson、Uli Hacksell、J. Lars G. Nilsson、Kjell Svensson、Arvid Carlsson

  DOI：10.1021/jm00387a004

  日期：1987.4

  A series of 35 stereochemically well-defined C1-methyl-substituted derivatives of the potent dopamine (DA) receptor agonist 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) have been synthesized. The compounds were tested for central DA receptor agonistic and antagonistic activity, by use of biochemical and behavioral tests in rats. In addition, the compounds were tested for in vivo interactions with 5,6-dihydroxy-2-(di-n-propylamino)tetralin (DiPr-5,6-ADTN). On the basis of pharmacological activity profiles, the active compounds have been classified into four groups: classical pre- and postsynaptic DA receptor agonists, DA receptor agonists with preferential action at presynaptic receptors, pre- and postsynaptic DA receptor antagonists, and DA receptor antagonists with preferential action at presynaptic receptors. Results obtained indicate that both 2R and 2S enantiomers of C5-oxygenated 2-aminotetralins may be able to bind to DA receptors but that only 2S antipodes are able to activate the receptors. O-Methylation of the C5-oxygenated (1S,2R)-2-amino-1-methyltetralin derivatives tends to increase their DA receptor antagonistic activity, whereas decrease of the size of the N-substituent(s) from n-propyl to ethyl or methyl appears to increase their activity at postsynaptic DA receptors.
• C1-Methylated 5-hydroxy-2-(dipropylamino)tetralins: central dopamine-receptor stimulating activity
  作者：Uli Hacksell、Anette M. Johansson、Lars Erik Arvidsson、J. Lars G. Nilsson、Stephan Hjorth、Arvid Carlsson、Hakan Wikstroem、Domingo Sanchez、Per Lindberg

  DOI：10.1021/jm00374a012

  日期：1984.8

  C1-Methylated derivatives of the potent dopaminergic agonist 5-hydroxy-2-(di-n-propylamino)tetralin (6) have been synthesized and tested for central dopamine (DA) receptor stimulating activity, by using biochemical and behavioral tests in rats. Both cis- and trans-5-hydroxy-1-methyl-2-(di-n-propylamino) tetralin (4 and 3) may be classified as central DA-receptor agonists, albeit of lower potency than 6. The results obtained indicate that both 4 and 3 display DA-autoreceptor stimulation capacity. However, only one of the isomers, trans-3, is able to elicit clear-cut postsynaptic DA receptor agonist actions at larger doses. 5-Hydroxy-1,1-dimethyl-2-(n-propylamino) tetralin (5) was found to be inactive.
• Tetrahedron Asymmetry 1999, 10, 3281-3283
  作者：

  DOI：——

  日期：——