1,2,3,4-四氢-5,6-二甲氧基-2-氨基萘 | 21489-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 1,2,3,4-四氢-5,6-二甲氧基-2-氨基萘
• 英文名称: 5,6-dimethoxy-2-aminotetrahydronaphthalene
• 英文别名: 1,2,3,4-tetrahydro-5,6-dimethoxynaphthalene-2-amine；5,6-dimethoxy-2-amino-1,2,3,4-tetrahydronaphthalene；2-amino-5,6-dimethoxy-tetralin；2-Amino-5,6-Dimethoxy Tetralin；2-amino-5,6-dimethoxytetralin；1,2,3,4-Tetrahydro-2-amino-5,6-dimethoxy-naphthalin；1,2,3,4-Tetrahydro-5,6-dimethoxy-2-naphthylamine；5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 21489-50-9
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: BDHOUGWYKHSPIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢-5,6-二甲氧基-2-氨基萘 在 三溴化硼 、 potassium carbonate 、 一水合肼 、 copper(II) oxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 5,6-(methylenedioxy)-2-aminotetralin
  参考文献：
  名称：

  Nonneurotoxic tetralin and indan analogs of 3,4-(methylenedioxy)amphetamine (MDA)

  摘要：

  Four cyclic analogues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied. These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA.HCl (1.75 mg/kg) from saline. In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4- methylphenyl)-2-aminopropane (DOM) were also evaluated. None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats. Compounds 4a and 4b did not substitute in MDMA-trained rats. Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart. In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc. Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for [3H]paroxetine. By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity. These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.

  DOI：

  10.1021/jm00164a037
• 作为产物：
  描述：

  5,6-二甲氧基-1,2,3,4-四氢萘-2-酮 在 sodium hydroxide 作用下， 反应 2.0h， 生成 1,2,3,4-四氢-5,6-二甲氧基-2-氨基萘
  参考文献：
  名称：

  与α-甲基多巴有关的刚性氨基酸。

  摘要：

  DOI：

  10.1021/jm00251a029

文献信息

• Process for the manufacture of form I of nolomirole hydrochloride
  申请人：CHIESI FARMACEUTICI S.p.A.

  公开号：EP1384708A1

  公开（公告）日：2004-01-28

  A process for the preparation and isolation of the pharmaceutical chemical compound nolomirole hydrochloride in a highly purified crystalline Form I, as well as pharmaceutical preparations thereof for the treatment of patients suffering of cardiovascular diseases such as congestive heart failure and hypertension are described.

  本文描述了一种制备和分离药用化学物质nolomirole hydrochloride的过程，以高度纯化的结晶形式I，以及用于治疗心血管疾病（如充血性心力衰竭和高血压）患者的药物制剂。
• [EN] A PROCESS FOR THE PREPARATION OF 5,6-DIHYDROXY-2-AMINO-1,2,3,4-TETRAHYDRONAPHTHALENE DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES 5,6-DIHYDROXY-2-AMINO-1,2,3,4-TETRAHYDRONAPHTALENE
  申请人：CHIESI FARMACEUTICI S.P.A.

  公开号：WO1995029147A1

  公开（公告）日：1995-11-02

  (EN) A process, and variations thereof, for the preparation of 5,6-dihydroxy-2-amino-1,2,3,4-tetrahydronaphthalene derivatives of formula (I), wherein R1, R2, R3 can independently be hydrogen or lower alkyl.(FR) Procédé et ses variantes destinés à la préparation de dérivés 5,6-dihydroxy-2-amino-1,2,3,4-tétrahydronaphtalène de la formule (I) dans laquelle R1, R2 et R3 représentent indépendamment hydrogène ou alcoyle inférieur.

  一种用于制备式(I)的5,6-二羟基-2-氨基-1,2,3,4-四氢萘衍生物的方法及其变体，其中R1、R2、R3可以独立地是氢或较低的烷基。
• Phenylethylamine derivatives and pharmaceutical use
  申请人：Fisons plc

  公开号：US05013760A1

  公开（公告）日：1991-05-07

  Phenylethylamine derivatives of the formula ##STR1## wherein D.sub.1 represents a phenylethyl radical which is substituted with hydroxy and/or alkyl groups, R.sub.1 and R.sub.2 are hydrogen or alkyl, D.sub.2 represents hydrogen, an alkyl, or aryl group, and n is an integer from 3 to 5. These compounds are useful as pharmaceuticals, e.g., for treatment of cardiovascular conditions.

  公式为##STR1##的苯乙胺衍生物，其中D.sub.1代表苯乙基基团，该基团被羟基和/或烷基取代，R.sub.1和R.sub.2为氢或烷基，D.sub.2代表氢，烷基或芳基，n为3至5的整数。这些化合物可用作药物，例如用于治疗心血管疾病。
• An Alternative Synthesis of the Dopaminergic Drug 2-Amino-1,2,3,4-tetrahydronaphthalene-5,6-diol (5,6-ADTN)
  作者：Süleyman Göksu、Hasan Seçen、Yaşar Sütbeyaz

  DOI：10.1002/hlca.200690030

  日期：2006.2

  Racemic 2-amino-1,2,3,4-tetrahydronaphthalene-5,6-diol (5,6-ADTN; 4) was synthesized from 5,6-dimethoxynaphthalene-2-carboxylic acid (14) in four steps (60% overall yield; Scheme). The crucial steps of the synthesis are Birch reduction of 14 to the valuable synthon 15, Curtius reaction and carbamate formation (16), hydrogenolysis (17), and demethylation to the biologically active hydrobromide salt

  由5,6-二甲氧基萘-2-羧酸（14）分四个步骤（60 ）合成外消旋的2-氨基-1,2,3,4-四氢萘-5,6-二醇（5,6-ADTN; 4）％总产率；方案）。合成的关键步骤是桦木减少14到有价值的合成子15，库尔提斯反应和氨基甲酸酯形成（16），氢解（17），去甲基化和与生物活性氢溴酸盐18的4。
• Amine derivatives, processes for their production and pharmaceutical compositions containing them
  申请人：FISONS plc

  公开号：EP0072061A1

  公开（公告）日：1983-02-16

  There are described compounds of formula I, in which D, represents a group of formula II, where R, and R5, or H3 and R5 may form a chain -CH2CH2-, or R4 and R5 may form a chain -CH2-, or R3, R4 and R5 are each hydrogen, the remainder of R,, R3 and R4, which may be the same or different, being hydrogen, alkyl or phenyl, none, one or two of R6, R7, R8 and R, represent hydroxy and the remainder represent hydrogen, X represents a chain -(CH2)n-, optionally substituted by hydroxy, n is an integer from 1 to 7 inclusive, D2 represents hydrogen, alkyl, phenyl; alkyl substituted by one or more of hydroxy, pyridyl, phenyl; or alkyl substituted by phenyl which in turn is substituted by halogen, alkyl, amino, alkoxy or nitro, or D2 represents a group of formula III, where R2 and R12, or R,o and R12 may form a chain -CH2-CH2-, or R11 and R12 may form a chain -CH2-, or R10, R,, and R12 are each hydrogen, the remainder of R2, R10 and R11, which may be the same or different being hydrogen, alkyl or phenyl, none, one or two of R13, R14, R15 and R16 represent hydroxy, and the remainder represent hydrogen, or R2 and D2, together with the nitrogen atom to which they are attached, form a 5 or 6 membered heterocyclic ring, provided that when X is not substituted by hydroxy and i) when R3, R4 and R5 are hydrogen, R, and R2 are both hydrogen or lower alkyl, and two of R6, R7, R8 and R9 are hydroxy, D2 is not identical to D1, or ii) when R,, R3, R4, R5, R6, R7, R8 and R9 are hydrogen, R2 and D2 do not each represent lower alkyl, or do not together with the nitrogen atom to which they are attached, form a 5 or 6 membered heterocyclic ring, or iii) when R,, R4, R5, R6, R7, R8 and R9 are hydrogen, and R3 is alkyl, D2 is not identical to D1, or iv) when R, is phenyl, R3 and R5 together form the chain -CH2CH2-, R6, R7, R8 and R9 are hydrogen, n is 1, D2 and R2 do not each represent hydrogen or alkyl, or do not together form a heterocyclic ring, and pharmaceutically acceptable derivatives thereof. There are also described methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.

  所述化合物为式 I、 其中 D 代表式 II 的基团、 其中 R 和 R5，或 H3 和 R5 可形成链 -CH2CH2-，或 R4 和 R5 可形成链 -CH2CH2-，或 R3、R4 和 R5 各为氢，R、R3 和 R4 的其余部分（可相同或不同）为氢、烷基或苯基、 R6、R7、R8 和 R 的一个或两个不代表羟基，其余代表氢、 X 代表链-(CH2)n-，可选择被羟基取代、 n 是 1 到 7（包括 7）的整数、 D2 代表氢、烷基、苯基；被羟基、吡啶基、苯基中的一个或多个取代的烷基；或被苯基取代的烷基，而苯基又被卤素、烷基、氨基、烷氧基或硝基取代、 或 D2 代表式 III 的基团、 其中 R2 和 R12，或 R,o 和 R12 可形成链 -CH2-CH2-，或 R11 和 R12 可形成链 -CH2-，或 R10、R,, 和 R12 各为氢、 R2、R10 和 R11 的其余部分（可以相同或不同）为氢、烷基或苯基、 R13、R14、R15 和 R16 中没有一个或两个代表羟基，其余代表氢、 或 R2 和 D2 与它们所连接的氮原子一起形成一个 5 或 6 个成员的杂环、 但当 X 未被羟基取代且 i) 当 R3、R4 和 R5 为氢，R 和 R2 均为氢或低级烷基，且 R6、R7、R8 和 R9 中的两个为羟基时，D2 与 D1 不相同，或 ii) 当 R、R3、R4、R5、R6、R7、R8 和 R9 为氢，R2 和 D2 不各自代表低级烷基，或不与所连接的氮原子一起形成 5 或 6 位杂环时，或 iii) 当 R、R4、R5、R6、R7、R8 和 R9 为氢，且 R3 为烷基时，D2 与 D1 不完全相同，或 iv) 当 R 为苯基时，D2 与 D1 不完全相同。 当 R、R4、R5、R6、R7、R8 和 R9 为氢，且 R3 为烷基时，D2 与 D1 不相同，或 iv) 当 R、R4、R5、R6、R7、R8 和 R9 为氢，且 R3 为烷基时，D2 与 D1 不相同，或 及其药学上可接受的衍生物。 此外，还描述了制造这些化合物的方法和含有这些化合物的药物组合物，如心脏病组合物。