5,6-二甲氧基-2-氨基四氢化萘盐酸盐 | 21489-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 5,6-二甲氧基-2-氨基四氢化萘盐酸盐
• 英文名称: 1,2,3,4-tetrahydro-5,6-dimethoxynaphthalene-2-amine hydrochloride
• 英文别名: 2-amino-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene hydrochloride；1,2,3,4-Tetrahydro-5,6-dimethoxy-2-naphthalenamine hydrochloride；5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride
• CAS: 21489-75-8
• 化学式: C₁₂H₁₇NO₂*ClH
• 分子量: 243.733
• InChiKey: MDKVBKWGRHXAME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  16
• 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：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-二甲氧基-2-氨基四氢化萘盐酸盐 在 氢碘酸 、 乙酸酐 作用下， 生成 5,6-二羟基-2-氨基四氢萘
  参考文献：
  名称：

  Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists

  摘要：

  A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.

  DOI：

  10.1021/jm00238a008
• 作为产物：
  描述：

  5,6-dimethoxy-2-trifluoroacetylamino-tetralin 在 盐酸 、 sodium hydroxide 、 sodium borohydrid 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以90%的产率得到5,6-二甲氧基-2-氨基四氢化萘盐酸盐
  参考文献：
  名称：

  Process for the preparation of 2-amino-5,6-dimethoxy-tetralin

  摘要：

  一种制备2-氨基-5,6-二甲氧基四氢萘的方法被披露，这是制备药理活性化合物的有用中间体。

  公开号：

  US05221770A1

文献信息

• 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。
• 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。
• N-Aralkyl substitution of 2-amino-5,6- and -6,7-dihydroxy-1,2,3,4-tetrahydronaphthalenes. 1. Cardiac and pressor/depressor activities
  作者：Richard J. Gorczynski、William G. Anderson、David M. Stout

  DOI：10.1021/jm00139a013

  日期：1981.7

  Amino substitution o rigid forms of dopamine [2-amino-5,6-dihydroxy-1,2,3,4-tetrahydronaphthalene (A-5,6-DTN) and 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (A-6,7-DTN)] with aralkyl functionalities was carried out to investigate the role of such structural modifications upon cardiac inotropic/chronotropic and blood pressure activity. Derivatives of A-5,6-DTN were strong vasodepressor agents devoid action was associated with the dihydroxyphenyl-1-methylethyl derivative, which was also an inotropic selective compound. The amino substituent of dobutamine was ineffective in reducing peripheral vascular action when combined with the rigid forms of dopamine. It was also ineffective in imparting inotropic selectivity when combined with A-5,6-DTN. An analysis of these observations in light of existing structure-activity relationships of aminoaralkyl substitution of other catecholamine structure is presented.
• GORCZYNSKI, R. J.;ANDERSON, W. G.;STOUT, D. M., J. MED. CHEM., 1981, 24, N 7, 835-839
  作者：GORCZYNSKI, R. J.、ANDERSON, W. G.、STOUT, D. M.

  DOI：——

  日期：——
• CANNON J. G.; LEE T.; GOLDMAN H. D., J. MED. CHEM., 1977, 20, NO 9, 1111-
  作者：CANNON J. G.、 LEE T.、 GOLDMAN H. D.

  DOI：——

  日期：——