4-(2-甲氧基苯基)哌啶-4-醇 | 81950-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-(2-甲氧基苯基)哌啶-4-醇
• 中文别名: 4-(2-甲氧苯基)哌啶-4-醇
• 英文名称: 4-(2-methoxyphenyl)piperidin-4-ol
• 英文别名: 4-Hydroxy-4-(2-methoxyphenyl)piperidine
• CAS: 81950-85-8
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD05237199
• 分子量: 207.272
• InChiKey: RQKOZXQKXHODOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-(2-甲氧基苯基)哌啶-4-醇 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-exo-6-(2-methoxyphenyl)-1-azabicyclo<3.3.1>nonan-4-(endo)-ol hydrochloride
  参考文献：
  名称：

  Intramolecular Cyclization with Oxocarbenium Ion. Synthesis of 1-Azabicyclo[3.3.1]nonene and [3.2.1]octene Derivatives

  摘要：

  Hydroxy- and aryl-substituted 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives have been synthesized by the intramolecular cationic cyclization of 4-aryl-1,2,5,6-tetrahydropyridines bearing an acetal moiety in the nitrogen substituent. Factors governing the stereoselectivity of the ring closure step have been disclosed. Two compounds were resolved into the enantiomers and the absolute configuration of one of them was deduced from CD investigations. Among the new compounds substances with valuable antiamnesic effect have been found.

  DOI：

  10.3987/com-94-6975
• 作为产物：
  描述：

  2-Methoxyphenylmagnesium bromide 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 25.5h， 生成 4-(2-甲氧基苯基)哌啶-4-醇
  参考文献：
  名称：

  Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT₃ Serotonin Receptors

  摘要：

  Arylpiperazines are nonselective agents that bind at 5-HT3 serotonin receptors with moderate to high affinity, whereas 1-phenylbiguanide is a low-affinity but more selective 5-HT3 agonist. In an attempt to enhance the affinity of the latter agent, and working with the assumption that similarities might exist between the binding of the two types of agents, we formulated structure-activity relationships for the binding of the arylpiperazines and then incorporated those substituents, leading to high affinity for the arylpiperazines, into 1-phenylbiguanide. A subsequent investigation examined the structure-activity relationships of the arylbiguanides and identified arylguanidines as a novel class of 5-HT3 ligands. Although curious similarities exist between the structure-activity relationships of the arylpiperazines, arylbiguanides, and arylguanidines, it cannot be concluded that all three series of compounds are binding in the same manner. Furthermore, upon investigating pairs of compounds in the three series, the arylpiperazines behaved as 5-HT3 antagonists (von Bezold-Jarisch assay) whereas the arylbiguanides and arylguanidines acted as 5-HT3 agonists.

  DOI：

  10.1021/jm9603936

文献信息

• Synthesis and biological evaluation of fluorescent GAT-ligands based on meso-substituted BODIPY dyes
  作者：Markus Daerr、Jörg Pabel、Georg Höfner、Peter Mayer、Klaus T. Wanner

  DOI：10.1007/s00044-019-02483-6

  日期：2020.2

  alkyl chain of three to five carbon atoms that originates from the meso-position of the BODIPY dye to the amino function of different cyclic amines. Screening of these fluorescent probes for their biological activity as GABA uptake inhibitors of mGAT1–mGAT4 revealed ligands with pIC50 values up to 5.35.

  BODIPY染料以其出色的光谱特性而闻名，因此在一系列基于荧光的分析技术中得到了广泛应用，可用于体外以及体内测量。首次，我们基于BODIPY染料作为荧光亚基，为SLC6家族转运蛋白mGAT1-mGAT4设计并合成了一系列荧光配体。在新颖的荧光化合物系列中，BODIPY染料亚基与3到5个碳原子的烷基链连接，该烷基链从BODIPY染料的内消旋位置衍生到不同环胺的氨基官能团。筛选这些荧光探针作为mGAT1–mGAT4的GABA吸收抑制剂的生物学活性，发现配体的pIC 50值高达5.35。
• Synthesis and biological evaluation of fluorescent GAT-ligands based on asymmetric substituted BODIPY dyes
  作者：Markus Daerr、Lars Allmendinger、Georg Höfner、Klaus T. Wanner

  DOI：10.1007/s00044-020-02521-8

  日期：2020.4

  development of fluorescent inhibitors addressing the GABA transporters mGAT1–mGAT4 as potential tool compounds in fluorescence based biological assays. The design of these fluorescent GAT inhibitors followed the structural motifs common for many GAT1–GAT4 inhibitors publicly known except that the lipophilic domain present in this compounds was replaced by a BODIPY moiety to serve as a fluorescent subunit

  本研究旨在开发针对GABA转运蛋白mGAT1-mGAT4的荧光抑制剂，将其作为基于荧光的生物学分析中潜在的工具化合物。这些荧光GAT抑制剂的设计遵循了许多广为人知的GAT1-GAT4抑制剂共有的结构基序，只是该化合物中存在的亲脂结构域被BODIPY部分取代，以充当荧光亚基。测试了以此方式获得的荧光化合物对四种鼠类GABA转运蛋白亚型mGAT1–mGAT4的抑制力和亚型选择性，以及它们对mGAT1的结合亲和力。所有BODIPY衍生物在GABA转运蛋白mGAT1–mGAT4上仅表现出低抑制力和亚型选择性，而对mGAT1的亲和力却很低。仍然，ķ我 〜5.0），并在MGAT2和mGAT4（抑制能力的pIC 50  〜5.0）。
• Benzofuran derivatives, pharmaceutical composition containing the same, and a process for the preparation of the active ingredient
  申请人：EGIS GYOGYSZERGYAR

  公开号：US20040186170A1

  公开（公告）日：2004-09-23

  The present invention is a piperazinylalkylbenzofuran derivative of the formula 1 wherein R 1 represents a C1-4 alkyl group, R 2 stands for a hydrogen atom, X means an oxygen atom, Y is a hydroxyl group, Z represents a hydrogen atom, Ar′ represents a diphenylmethyl group, a pyridyl group, a partially saturated 5-membered heterocyclic group or a phenyl group, n has a value of 0 or 1, and pharmaceutically suitable acid addition salts thereof.

  该发明涉及一种化合物，为一种哌嗪基烷基苯并呋喃衍生物，其化学式为1，其中R1代表一个C1-4烷基基团，R2代表一个氢原子，X代表一个氧原子，Y代表一个羟基，Z代表一个氢原子，Ar′代表一个二苯甲基基团、一个吡啶基、一个部分饱和的5-成员杂环基团或一个苯基，n的值为0或1，并且其药学上适宜的酸盐。
• [EN] NEW 1-AZABICYCLOALKANE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESS FOR PREPARING SAME
  申请人：GYÓGYSZERKUTATÓ INTÉZET KV.

  公开号：WO1992007854A1

  公开（公告）日：1992-05-14

  (EN) The invention relates to new 1-azabicycloalkane derivatives and their stereoisomers of general formula (I), wherein R1 représents a phenyl, substituted phenyl, naphthyl or thienyl group, wherein the phenyl group can be substituted by one or several halogen atom(s), methyl, methoxy, methylthio or trifluoromethyl group(s), R2 represents a hydrogen atom or a C2-5 aliphatic acyl group, R3 represents a hydrogen atom or a methyl group, n can be zero or one, the dotted line can optionally represent a further C-C bond and the wavy line means that the respective substituent can be bound to the carbon atom in either of the two steric positions, furthermore their pharmaceutically acceptable acid addition salts. Furthermore, the invention relates to a process for preparing the above compounds and pharmaceutical compositions containing the same. The compounds of general formula (I) have valuable therapeutic, mainly antiamnesic, activity.(FR) Nouveaux dérivés d'azabicycloalcane-1 et leurs stéréoisomères répondant à la formule générale (I), dans laquelle R1 représente un groupe phényle, phényle substitué, naphtyle ou thiényle, où le groupe phényle peut être substitué par un ou plusieurs atomes d'halogène ou groupes méthyle, méthoxy, méthylthio ou trifluorométhyle; R2 représente un atome d'hydrogène ou un groupe acyle aliphatique C2-5; R3 représente un atome d'hydrogène ou un groupe méthyle; n peut être 0 ou 1; la ligne pointillée peut éventuellement représenter une liaison C-C supplémentaire et la ligne ondulée signifie que le substituant respectif peut être lié à l'atome de carbon au niveau de l'une ou l'autre des deux positions stériques; ainsi que leurs sels d'addition acide pharmaceutiquement acceptables. On a également prévu un procédé de préparation des composés précités et des compositions pharmaceutiques les contenant. Les composés répondant à la formule générale (I) présentent une précieuse activité thérapeutique, principalement anti-amnésique.

  该发明涉及新的1-氮杂双环烷衍生物及其立体异构体，其通式为（I），其中R1代表苯基，取代苯基，萘基或噻吩基，其中苯基可以被一个或多个卤素原子，甲基，甲氧基，甲硫基或三氟甲基基团取代，R2代表氢原子或C2-5脂肪酰基团，R3代表氢原子或甲基，n可以为零或一，虚线可以选择性地表示进一步的C-C键，而波浪线表示相应的取代基可以与碳原子中的任一二立体位置结合，此外还包括其药学上可接受的酸加成盐。此外，该发明还涉及制备上述化合物和含有它们的药物组合物的方法。通式（I）的化合物具有有价值的治疗作用，主要是抗遗忘症作用。
• Compounds which are selective antagonists of the human NK.sub.3 receptor
  申请人：Sanofi

  公开号：US05741910A1

  公开（公告）日：1998-04-21

  A compound of formula: ##STR1## in which: Ar represents a pyrid-2-yl or a phenyl which is unsubstituted or substituted by a halogen, a methyl or a (C.sub.1 -C.sub.4)alkoxy; R.sub.1 represents a methyl group; R.sub.11 represents hydrogen; or R.sub.1 and R.sub.11 together represent a --(CH.sub.2).sub.3 -- group; R.sub.2 represents a hydroxyl; a (C.sub.1 -C.sub.7)alkoxy; a (C.sub.1 -C.sub.7)acyloxy; a cyano; an --NR.sub.6 R.sub.7 group; an --NR.sub.3 COR.sub.4 group; an --NR.sub.3 COOR.sub.8 group; an --NR.sub.3 SO.sub.2 R.sub.9 group; an --NR.sub.3 CONR.sub.10 R.sub.12 group; a (C.sub.1 -C.sub.7)acyl group; a (C.sub.1 -C.sub.7)alkoxycarbonyl; a --CONR.sub.10 R.sub.12 group; a --CH.sub.2 OH group; a (C.sub.1 -C.sub.7)alkoxymethyl; a (C.sub.1 -C.sub.7)acyloxymethyl; a (C.sub.1 -C.sub.7)alkylaminocarbonyloxymethyl; a --CH.sub.2 NR.sub.13 R.sub.14 group; a --CH.sub.2 NR.sub.3 COR.sub.4 group; a --CH.sub.2 NR.sub.3 COOR.sub.8 group; a --CH.sub.2 NR.sub.3 SO.sub.2 R.sub.9 group; a --CH.sub.2 NR.sub.3 CONR.sub.10 R.sub.12 group; or R.sub.2 constitutes a double bond between the carbon atom to which it is attached and the adjacent carbon atom of the piperidine ring; or Ar and R.sub.2, together with the carbon atom to which they are attached, constitute a group of formula: ##STR2## as NK.sub.3 antagonists.

  化合物的式子为：##STR1## 其中：Ar代表未取代或卤素、甲基或(C.sub.1-C.sub.4)烷氧基取代的吡啶-2-基或苯基；R.sub.1代表甲基基团；R.sub.11代表氢原子；或R.sub.1和R.sub.11一起代表--(CH.sub.2).sub.3--基团；R.sub.2代表羟基；(C.sub.1-C.sub.7)烷氧基；(C.sub.1-C.sub.7)酰氧基；氰基；--NR.sub.6 R.sub.7基团；--NR.sub.3 COR.sub.4基团；--NR.sub.3 COOR.sub.8基团；--NR.sub.3 SO.sub.2 R.sub.9基团；--NR.sub.3 CONR.sub.10 R.sub.12基团；(C.sub.1-C.sub.7)酰基；(C.sub.1-C.sub.7)烷氧羰基；--CONR.sub.10 R.sub.12基团；--CH.sub.2 OH基团；(C.sub.1-C.sub.7)烷氧甲基；(C.sub.1-C.sub.7)酰氧甲基；(C.sub.1-C.sub.7)烷基氨基羰氧甲基；--CH.sub.2 NR.sub.13 R.sub.14基团；--CH.sub.2 NR.sub.3 COR.sub.4基团；--CH.sub.2 NR.sub.3 COOR.sub.8基团；--CH.sub.2 NR.sub.3 SO.sub.2 R.sub.9基团；--CH.sub.2 NR.sub.3 CONR.sub.10 R.sub.12基团；或R.sub.2构成双键，连接它附着的碳原子和哌啶环相邻的碳原子；或Ar和R.sub.2与它们附着的碳原子一起构成式子：##STR2## 作为NK.sub.3受体拮抗剂。