6-amino-1,2,3,4-tetrahydronaphthalen-1-ol | 503832-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-amino-1,2,3,4-tetrahydronaphthalen-1-ol
• 英文别名: 6-amino-1,2,3,4-tetrahydro-1-naphthalenol
• CAS: 503832-26-6
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: UOPYHMZDRXKRSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 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：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-amino-1,2,3,4-tetrahydronaphthalen-1-ol 、 5-氯吲哚-2-羧酸 在 1-羟基苯并三唑 、 1-<2-(N,N-Dimethylamino)ethyl>-3-ethylurea hydrochloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以30%的产率得到5-chloro-N-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Design, synthesis, and pharmacological evaluation of N-bicyclo-5-chloro-1H-indole-2-carboxamide derivatives as potent glycogen phosphorylase inhibitors

  摘要：

  As a result of the various N-bicyclo-5-chloro-1H-indole-2-carboxamide derivatives with a hydroxy moiety synthesized in an effort to discover novel glycogen phosphorylase (GP) inhibitors, 5-chloro-N-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2-carboxamide (5b) was found to have potent inhibitory activity. The introduction of fluorine atoms both at a position adjacent to the hydroxy group and in the central benzene moiety lead to the optically active derivative 5-chloro-N-[(5R)-1,3,6,6-tetrafluoro-5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl]-1H-indole-2-carboxamide(25e alpha, which was the most potent compound in this series (IC(50) = 0.020 mu M). This compound inhibited glucagon-induced glucose output in cultured primary hepatocytes with an IC(50) value of 0.69 mu M, and showed oral hypoglycemic activity in diabetic db/db mice at 10 mg/kg. Compound 25e alpha also had an excellent pharmacokinetic profile, with high oral bioavailability and a long plasma half-life, in male SD rats. The binding mode of 25e alpha to this molecule and the role of fluorine atoms in that binding were speculated in an enzyme docking study. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.021
• 作为产物：
  描述：

  6-硝基-Alpha-四氢萘酮 以 N-(6,7-dibutoxy-4-methyl-2-quinazolinyl)guanidine 为溶剂， 生成 6-amino-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Compounds for the treatment of pain

  摘要：

  这项发明提供了治疗疼痛、尿失禁和其他由NPFF受体介导的异常的方法，包括向受试者施用在NPFF1受体、NPFF2受体或同时在NPFF1和NPFF2受体上起作用的化学化合物的治疗有效量。

  公开号：

  US20030176314A1

文献信息

• Selective Catalytic Hydrogenation of Arenols by a Well-Defined Complex of Ruthenium and Phosphorus–Nitrogen PN³–Pincer Ligand Containing a Phenanthroline Backbone
  作者：Huaifeng Li、Yuan Wang、Zhiping Lai、Kuo-Wei Huang

  DOI：10.1021/acscatal.7b01316

  日期：2017.7.7

  Selective catalytic hydrogenation of aromatic compounds is extremely challenging using transition-metal catalysts. Hydrogenation of arenols to substituted tetrahydronaphthols or cyclohexanols has been reported only with heterogeneous catalysts. Herein, we demonstrate the selective hydrogenation of arenols to the corresponding tetrahydronaphthols or cyclohexanols catalyzed by a phenanthroline-based

  使用过渡金属催化剂对芳族化合物进行选择性催化加氢极具挑战性。仅使用非均相催化剂已经报道了将芳烃氢化为取代的四氢萘或环己醇。在本文中，我们证明了基于菲咯啉基的PN 3-钌钳催化剂将芳烃选择性氢化为相应的四氢萘或环己醇。
• Guanidines which are agonist/antagonist ligands for neuropeptide FF (NPFF) receptors
  申请人：——

  公开号：US20030139431A1

  公开（公告）日：2003-07-24

  This invention provides compounds having the structure: 1 wherein X=CH, C(CH 3 ) or N; each of R 1 , R 2 , R 3 , R 4 and R 5 is independently H, C 1 -C 10 straight chained or branched alkyl, C 2 -C 10 straight chained or branched alkenyl, C 2 -C 10 straight chained or branched alkynyl, C 3 -C 10 cycloalkyl, substituted or unsubstituted aryl, hydroxy, halogenated ether, nitro, amino, halogen, —CN, —C(═Z)R 6 , —C(═Z)OR 6 , —C(═Z)N(R 6 ) 2 , —N(R 6 )—C(═Z)R 6 , —N(R 6 )—C(═Z)N(R 6 ) 2 , —OC(═Z)R 6 , —C(═Z)OR 6 —OR 6 or —SR 6 ; wherein Z is O or S; and wherein R 6 is C 1 -C 10 straight chained or branched alkyl, aryl, (CH 2 ) n Q, C 2 -C 10 alkenyl, C 3 -C 10 cycloalkyl, C 5 -C 10 cycloalkenyl, wherein Q is OR 7 , SR 7 , N(R 7 ) 2 or aryl, wherein R 7 is H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, wherein R 2 and R 3 and the carbons to which they are attached form a fused aryl, heteroaryl, C 5 -C 10 cyclic alkyl or heterocyclic alkyl ring; or wherein R 3 and R 4 and the carbons to which they are attached form a fused aryl, heteroaryl, cyclic alkyl or heterocyclic alkyl ring; and wherein each alkyl, alkenyl, alkynyl and alkoxy group is optionally substituted with a substituent independently selected from R a , where R a is 1) hydroxy, 2) C 1 -C 10 alkoxy, 3) halogen, 4) nitro, 5) amino, 6) CF 3 , or 7) carboxy, and each cycloalkyl group is optionally substituted with a substituent independently selected from R b , where R b is 1) a group selected from R a , 2) C 1 -C 7 alkyl, 3) C 2 -C 7 alkenyl, 4) C 2 -C 7 alkynyl or 5) cyclic C 1 -C 10 alkyl, and each aryl is optionally substituted with R 1 . This invention also provides methods of treating pain, urge incontinence; as well as methods of preparing the compounds.

  这项发明提供了具有以下结构的化合物：其中 X==CH，C(CH3)或N；R1、R2、R3、R4和R5中的每一个独立地是H、C1-C10直链或支链烷基、C2-C10直链或支链烯基、C2-C10直链或支链炔基、C3-C10环烷基、取代或未取代芳基、羟基、卤代醚、硝基、氨基、卤素、—CN、—C(═Z)R6、—C(═Z)OR6、—C(═Z)N(R6)2、—N(R6)—C(═Z)R6、—N(R6)—C(═Z)N(R6)2、—OC(═Z)R6、—C(═Z)OR6—OR6或—SR6；其中 Z 是 O 或 S；且其中 R6 是 C1-C10直链或支链烷基、芳基、(CH2)nQ、C2-C10烯基、C3-C10环烷基、C5-C10环烯基，其中 Q 是OR7、SR7、N(R7)2或芳基，其中 R7 是H、烷基、烯基、炔基、环烷基、环烯基、芳基，其中 R2、R3和它们连接的碳形成融合芳基、杂芳基、C5-C10环烷基或杂环烷基环；或其中 R3、R4和它们连接的碳形成融合芳基、杂芳基、环烷基或杂环烷基环；以及每个烷基、烯基、炔基和烷氧基组分可以选择性地取代一个从 Ra 中独立选择的取代基，其中 Ra 是 1) 羟基，2) C1-C10烷氧基，3) 卤素，4) 硝基，5) 氨基，6) CF3，或 7) 羧基，每个环烷基组分可以选择性地取代一个从 Rb 中独立选择的取代基，其中 Rb 是 1) 从 Ra 中选择的一组，2) C1-C7烷基，3) C2-C7烯基，4) C2-C7炔基或 5) 环状 C1-C10 烷基，每个芳基可以选择性地取代为 R1。这项发明还提供了治疗疼痛、尿急失禁的方法；以及制备这些化合物的方法。
• NOVEL FUSED PYRIMIDINE DERIVATIVES FOR INHIBITION OF TYROSINE KINASE ACTIVITY
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2975042A1

  公开（公告）日：2016-01-20

  The present invention relates to a novel fused pyrimidine derivative having an inhibitory activity for tyrosine kinases, and a pharmaceutical composition for preventing or treating cancers, tumors, inflammatory diseases, autoimmune diseases, or immunologically mediated diseases comprising same as an active ingredient.

  本发明涉及一种对酪氨酸激酶具有抑制活性的新型融合嘧啶衍生物，以及一种用于预防或治疗癌症、肿瘤、炎症性疾病、自身免疫性疾病或免疫介导疾病的药物组合物，该药物组合物的有效成分包括嘧啶衍生物。
• [EN] COMPOUNDS FOR THE TREATMENT OF PAIN<br/>[FR] COMPOSES UTILES POUR LE TRAITEMENT DE LA DOULEUR
  申请人：SYNAPTIC PHARMA CORP

  公开号：WO2003026657A1

  公开（公告）日：2003-04-03

  This invention provides methods of treating pain, urinary incontinence and other abnormalities mediated by a NPFF receptor, which comprises administering to a subject a therapeutically effective amount of a chemical compound which acts at the NPFF1 receptor, the NPFF2 receptor, or at both the NPFF1 and NPFF2 receptors.
• [EN] QUINAZOLINO- AND QUINOLINO- GUANIDINES AS LIGANDS FOR THE NEUROP EPTIDE FF (NPFF) RECEPTORS<br/>[FR] QUINAZOLINO- ET QUINOLINO-GUANIDINES UTILISEES COMME LIGANDS POUR LES RECEPTEURS DU NEUROPEPTIDE FF (NPFF)
  申请人：SYNAPTIC PHARMA CORP

  公开号：WO2003026667A1

  公开（公告）日：2003-04-03

  This invention provides compounds having the structure formula (I); wherein X= CH, C(CH3) or N; each of R1, R2, R3, R4 and R5 is independently H, C1-C10 straight chained or branched alkyl, C2-C10 straight chained or branched alkenyl, C2-C10 straight chained or branched alkynyl, C3-C10 cycloalkyl, substituted or unsubstituted aryl, hydroxy, halogenated ether, nitro, amino, halogen, -CN, -C(=Z)R6, -C(=Z)OR6, -C(=Z)N(R6)2' -N(R6)-C(=Z)R6, -N(R6)-C(=Z)N(R)2, -OC(=Z)R6, -C(=Z)OR6 OR6 or SR6; wherein Z is O or S; and wherein R6 is C1-C10 straight chained or branched alkyl, aryl, (CH2)nQ, C2-C10 alkenyl, C3-C10 cycloalkyl, C3-C10 cycloalkyl, c5-c10 cycloalkenyl, wherein Q is OR7, SR7, N(R7)2 or aryl, wherein R7 is H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, wherein R2 and R3 and the carbons to which they are attached form a fused aryl, heteroaryl, C5-C10 cyclic alkyl or heterocyclic alkyl ring; or wherein R3 and R4 and the carbons to which they are attached form a fused aryl, heteroaryl, cyclic alkyl or heterocyclic alkyl ring; and wherein each alkyl, alkenyl, alkynyl and alkoxy group is optionally substituted with a substituent independently selected from Ra, where Ra is 1) hydroxy, 2) C1-C10 a1koxy, 3) halogen, 4) nitro, 5) amino, 6) CF3, or 7) carboxy, and each cycloa1kyl group is optionally substituted with a substituent independently selected from Rb, where Rb is 1) a group selected from Ra, 2) C1-C7 alkyl, 3) C2-C7 alkenyl, 4) C2-C7 alkynyl or 5) cyclic C1-C10 alkyl, and each aryl is optionally substituted with R1. This invention also provides methods of treating pain, urge incontinence; as well as methods of preparing the compounds.