6-氨基-5,6,7,8-四氢-2,3-萘二醇 | 53463-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 6-氨基-5,6,7,8-四氢-2,3-萘二醇
• 中文别名: 2-氨基-6,7-二羟基四氢萘
• 英文名称: 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: 2-amino-6,7-dihydroxytetralin；6,7-dihydroxy-2-aminotetralin；6,7-ADTN；ADTN；1,2,3,4 tetrahydro 6,7 dihydroxy 2 naphthylamine；6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol
• CAS: 53463-78-8
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD09753386
• 分子量: 179.219
• InChiKey: ASXGAOFCKGHGMF-UHFFFAOYSA-N

物化性质

• 沸点：
  385.6±42.0 °C(Predicted)
• 密度：
  1.273

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  五氟丙酸酐 、 6-氨基-5,6,7,8-四氢-2,3-萘二醇 生成 2,2,3,3,3-Pentafluoro-propionic acid 7-(2,2,3,3,3-pentafluoro-propionylamino)-3-(2,2,3,3,3-pentafluoro-propionyloxy)-5,6,7,8-tetrahydro-naphthalen-2-yl ester
  参考文献：
  名称：

  Horn; Dijkstra; Feenstra, European Journal of Medicinal Chemistry, 1980, vol. 15, # 4, p. 387 - 392

  摘要：

  DOI：
• 作为产物：
  描述：

  6,7,-二甲氧基-1,2,3,4-四氢萘-2-胺盐酸盐 在 氢溴酸 作用下， 生成 6-氨基-5,6,7,8-四氢-2,3-萘二醇
  参考文献：
  名称：

  2-氨基四氢化萘的衍生物

  摘要：

  一些2-氨基-6,7-二甲氧基四氢萘已制备用于药理学测试。注意到与含苄基对位甲氧基的类似物相比，2-氨基-1-四氢萘酚和2-氨基-1-吲哚醇的反应性存在某些差异。

  DOI：

  10.1039/j39670000288

文献信息

• Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective MAO inhibitors
  申请人：——

  公开号：US20040010038A1

  公开（公告）日：2004-01-15

  The subject invention provides derivatives of propargylamino indan (PAI) and propargylamino tetralin that selectively inhibit monoamine oxidase (MAO) in the brain, having the structure: 1 wherein R 1 is OC(O)R 9 and R 2 is H, wherein R 9 is branched or unbranched C 1 to C 6 alkyl, aryl, or aralkyl, or R 1 is OC(O)R 4 and R 2 is OC(O)R 4 , wherein R 4 is branched or unbranched C 1 to C 6 alkyl, aryl, aralkyl or NR 5 R 6 , wherein R 5 and R 6 are each independently H, C 1 to C 8 alkyl, C 6 to C 12 aryl, C 6 to C 12 aralkyl or C 6 to C 12 cycloalkyl, each optionally substituted; wherein R 3 is H or C 1 to C 6 alkyl; wherein n is 0 or 1; and wherein m is 1 or 2, or a pharmaceutically acceptable salt thereof. Additionally, the subject invention provides methods of treating neurological disorders using these compounds, uses of these compounds for the manufacture of medicaments for treating neurological disorders and processes for synthesis of these compounds.

  本发明提供了独特的丙炔基氨基茚（PAI）和丙炔基氨基四氢萘的衍生物，能够选择性地抑制大脑中的单胺氧化酶（MAO），其结构如下： 其中R1为OC（O）R9，R2为H； 其中R9为支链或非支链的C1到C6烷基、芳基或芳基烷基，或者R1为OC（O）R4，R2为OC（O）R4； 其中R4为支链或非支链的C1到C6烷基、芳基、芳基烷基或NR5R6，其中R5和R6各自独立地为H、C1到C8烷基、C6到C12芳基、C6到C12芳基烷基或C6到C12环烷基，每种均可选择性地取代； 其中R3为H或C1到C6烷基； 其中n为0或1； 其中m为1或2； 或其药学上可接受的盐。此外，本发明还提供了使用这些化合物治疗神经系统疾病的方法，使用这些化合物制造治疗神经系统疾病的药物的用途以及这些化合物的合成过程。
• Pharmaceutical dopamine glycoconjugate compositions and methods of their preparation and use
  申请人：christian T. Samuel

  公开号：US20050250739A1

  公开（公告）日：2005-11-10

  Hydrophilic transportable N-linked glycosyl dopaminergic prodrug compounds according to FORMULA V and methods of their use, wherein, Ring 1 comprises an aryl or heteroaryl ring having 4 to 8 carbon atoms, among which atoms are counted “X” and “Y”; each of X and Y is optional; X, when present is either —C(R 1 ) 2 — or —C(R 1 ) 2 —; Y, when present, is either —CH 2 — or —CH 2 —CH 2 —; z, R 5 and R 5′ . are optional, and when present z, R 5 and R 5′ together form a lower alkyl or a substituted lower alkyl moiety; N is part of either an amine or an amide linkage; E is a saccharide which forms a linkage with N through a single bond from a carbon or oxygen atom thereof; R 1 and R 4 are selected form the group consisting of hydrogen, hydroxyl, halogen, halo-lower alkyl, alkoxyl, alkoxyl-lower alkyl, halo-alkoxy, thioamido, amidosulfonyl, alkoxylcarbonyl, carboxamide, aminocarbonyl, and alkylamino-carbonyl; R 2 and R 3 are hydroxyl; R 5 and R 6 , when present, are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carbonyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialkylamino-carbonyl; and, R 6 and R 6′ are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carboxyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialylamino-carbonyl, with the proviso that Ring 1 is capable of binding to any of: a dopaminergic receptor selected from the group consisting of a D1 receptor and a D5 receptor; a DAT transporter; a VMAT transporter; and, with the proviso that E is capable of binding to a GLUT transporter selected from the group consisting of a GLUT1 receptor and a GLUT3 receptor.

  根据FORMULA V，水亲性可运输的N-连接糖基的多巴胺前药化合物及其使用方法，其中，环1包括一个芳基或杂环芳基环，其中含有4至8个碳原子，其中原子被计为“X”和“Y”；X和Y各自是可选的；当存在X时，它是- C（R1）2-或-C（R1）2-；当存在Y时，它是-CH2-或-CH2-CH2-；z，R5和R5'是可选的，当存在z，R5和R5'时，它们共同形成较低的烷基或取代较低的烷基基团；N是氨基或酰胺连接的一部分；E是一个糖类，通过其碳或氧原子之一的单键与N形成连接；R1和R4从选组中选择，包括氢，羟基，卤素，卤代较低烷基，烷氧基，烷氧基较低烷基，卤代烷氧基，硫酰胺基，氨基磺酰基，烷氧羰基，羧酰胺，氨基羰基和烷基氨基羰基；R2和R3是羟基；当存在时，R5和R6从选组中选择，包括氢，羟基，烷氧基，羰基，烷氧基羰基，氨基羰基，烷基氨基羰基和二烷基氨基羰基；而R6和R6'从选组中选择，包括氢，羟基，烷氧基，羧基，烷氧基羰基，氨基羰基，烷基氨基羰基和二烷基氨基羰基，但前提是环1能够与以下任何一个结合：从选组中选择的多巴胺能感受器，包括D1受体和D5受体；DAT转运体；VMAT转运体；前提是E能够与以下从选组中选择的GLUT转运体结合：GLUT1受体和GLUT3受体。
• PHARMACEUTICAL DOPAMINE GLYCOCONJUGATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE
  申请人：Christian Samuel T.

  公开号：US20080194802A1

  公开（公告）日：2008-08-14

  Hydrophilic transportable N-linked glycosyl dopaminergic prodrug compounds according to FORMULA V and methods of their use, wherein, Ring 1 comprises an aryl or heteroaryl ring having 4 to 8 carbon atoms, among which atoms are counted “X” and “Y”; each of X and Y is optional; X, when present is either —C(R 1 ) 2 — or —C(R) 2 —; Y, when present, is either —CH 2 — or —CH 2 —CH 2 —; z, R 5 and R 5′ are optional, and when present z, R 5 and R 5′ together form a lower alkyl or a substituted lower alkyl moiety; N is part of either an amine or an amide linkage; E is a saccharide which forms a linkage with N through a single bond from a carbon or oxygen atom thereof; R 1 and R 4 are selected form the group consisting of hydrogen, hydroxyl, halogen, halo-lower alkyl, alkoxyl, alkoxyl-lower alkyl, halo-alkoxy, thioamido, amidosulfonyl, alkoxylcarbonyl, carboxamide, aminocarbonyl, and alkylamino-carbonyl; R 2 and R 3 are hydroxyl; R 5 and R 6 , when present, are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carbonyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialkylamino-carbonyl; and, R 6 and R 6′ are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carboxyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialylamino-carbonyl, with the proviso that Ring 1 is capable of binding to any of: a dopaminergic receptor selected from the group consisting of a D1 receptor and a D5 receptor; a DAT transporter; a VMAT transporter; and, with the proviso that E is capable of binding to a GLUT transporter selected from the group consisting of a GLUT1 receptor and a GLUT3 receptor.

  根据公式V及其使用方法，水亲和性可转运的N-连接糖基多巴胺前药化合物，其中，环1包括4至8个碳原子的芳基或杂芳基环，其中原子计算为“X”和“Y”；X和Y各自是可选的；当存在X时，它是—C（R1）2—或—C（R）2—；当存在Y时，它是—CH2—或—CH2—CH2—；z，R5和R5'是可选的，当存在时，z，R5和R5'共同形成较低的烷基或取代较低的烷基基团；N是胺或酰胺连接的一部分；E是一种糖，通过其碳或氧原子中的单键与N形成连接；R1和R4从氢、羟基、卤素、卤素较低烷基、烷氧基、烷氧基较低烷基、卤素烷氧基、硫酰胺、氨基磺酰、烷氧基羰基、羧酰胺、氨基羰基和烷基氨基羰基中选择；R2和R3是羟基；当存在R5和R6时，它们从氢、羟基、烷氧基、羰基、烷氧基羰基、氨基羰基、烷基氨基羰基和二烷基氨基羰基中选择；R6和R6'从氢、羟基、烷氧基、羧基、烷氧基羰基、氨基羰基、烷基氨基羰基和二烷基氨基羰基中选择，但环1能够与以下任意一种结合：D1受体和D5受体中选择的多巴胺能受体；DAT转运体；VMAT转运体；并且，E能够与GLUT1受体和GLUT3受体中选择的GLUT转运体结合。
• Pharmaceutical Dopamine Glycoconjugate Compositions and Methods of Their Preparation and Use
  申请人：Glycon LLC

  公开号：US20130203855A1

  公开（公告）日：2013-08-08

  Hydrophilic transportable N-linked glycosyl dopaminergic prodrug compounds and methods of their use.

  亲水性可转移的N-连接糖基多巴胺前药化合物及其使用方法。
• PROPARGYLAMINO INDAN DERIVATIVES AND PROPARGYLAMINO TETRALIN DERIVATIVES AS BRAIN-SELECTIVE MAO INHIBITORS
  申请人：Blaugrund Eran

  公开号：US20090131535A1

  公开（公告）日：2009-05-21

  The subject invention provides derivatives of propargylamino indan (PAI) and propargylamino tetralin that selectively inhibit monoamine oxidase (MAO) in the brain, having the structure: wherein R 1 is OC(O)R 9 and R 2 is H, wherein R 9 is branched or unbranched C 1 to C 6 alkyl, aryl, or aralkyl, or R 1 is OC(O)R 4 and R 2 is OC(O)R 4 , wherein R 4 is branched or unbranched C 1 to C 6 alkyl, aryl, aralkyl or NR 5 R 6 , wherein R 5 and R 6 are each independently H, C 1 to C 8 alkyl, C 6 to C 12 aryl, C 6 to C 12 aralkyl or C 6 to C 12 cycloalkyl, each optionally substituted; wherein R 3 is H or C 1 to C 6 alkyl; wherein n is 0 or 1; and wherein m is 1 or 2, or a pharmaceutically acceptable salt thereof. Additionally, the subject invention provides methods of treating neurological disorders using these compounds, uses of these compounds for the manufacture of medicaments for treating neurological disorders and processes for synthesis of these compounds.

  该发明提供了丙炔基氨基茚（PAI）和丙炔基氨基四氢萘的衍生物，其在大脑中选择性地抑制单胺氧化酶（MAO），具有以下结构： 其中R1为OC（O）R9，R2为H，其中R9为支链或非支链C1到C6烷基，芳基或芳基烷基；或R1为OC（O）R4，R2为OC（O）R4，其中R4为支链或非支链C1到C6烷基，芳基，芳基烷基或NR5R6，其中R5和R6各自独立地为H，C1到C8烷基，C6到C12芳基，C6到C12芳基烷基或C6到C12环烷基，每个可选择性地被取代；其中R3为H或C1到C6烷基；其中n为0或1；其中m为1或2；或其药学上可接受的盐。此外，该发明还提供了使用这些化合物治疗神经系统疾病的方法，使用这些化合物制造治疗神经系统疾病的药物的用途以及这些化合物的合成方法。