α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride | 15471-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride
• 英文别名: 1-(3,4-dimethoxyphenyl)-2-aminoethanol hydrochloride；2-amino-1-(3,4-dimethoxyphenyl)ethanol hydrochloride；(+/-)-2-amino-1-(3,4-dimethoxy-phenyl)-ethanol; hydrochloride；2-amino-1-(3,4-dimethoxy-phenyl)-ethanol; hydrochloride；(+/-)-2-Amino-1-(3,4-dimethoxy-phenyl)-aethanol; Hydrochlorid；2-Amino-1-(3,4-dimethoxy-phenyl)-aethanol; Hydrochlorid；2-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochloride；2-amino-1-(3,4-dimethoxyphenyl)ethanol;hydrochloride
• CAS: 15471-89-3
• 化学式: C₁₀H₁₅NO₃*ClH
• mdl: MFCD00798887
• 分子量: 233.695
• InChiKey: DZOXFFYCHQDIOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.71
• 氢给体数：
  2.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride 在 盐酸 、 sodium carbonate 、 三氯氧磷 作用下， 以 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 4.58h， 生成 4'-羟基罂粟碱
  参考文献：
  名称：

  Synthesis and in vitro evaluation of new analogues as inhibitors for phosphodiesterase 10A

  摘要：

  A series of analogues were synthesized by optimizing the structure of papaverine. The in vitro PDE10A binding affinity (IC50) values for these new analogues were measured; for compounds that have IC50 value less than 60 nM for PDE10A, the binding affinities (IC50 value) for PDE3A and PDE3B were tested. Of these analogues, compounds 6a, 6b, 6n, 8b, 8c and 11 displayed relatively higher PDE10A potency with IC50 value in the range of 28-60 nM. The most potent compound 1-(4-(2-(2-fluoroethoxy)ethoxy)-3-methoxybenzyl)-6,7-dimethoxyisoquinoline (8c) has the IC50 value of 28 +/- 1.2 nM for PDE10A, 2200 +/- 437 nM for PDE3A and 2520 +/- 210 nM for PDE3B. Compared to papaverine, compound 8c displayed similar PDE10A potency but improved selectivity to PDE10A versus PDE3A and PDE3B. To identify high potent PDE10A inhibitor, further optimization of the structures of these analogues is necessary. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.072
• 作为产物：
  描述：

  2-(3,4-dimethoxyphenyl)-2-(trimethylsilyloxy)acetonitrile 生成 α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride
  参考文献：
  名称：

  Chem Pharm Bull 1991, 39, 2910-2914

  摘要：

  DOI：

文献信息

• 4-(3,4-Dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline Derivatives. II. Their Renal Vasodilation Activity and Structure-Activity Relationship.
  作者：Hideki ANAN、Akihiro TANAKA、Ryuji TSUZUKI、Masaki YOKOTA、Takeyuki YATSU、Takashi FUJIKURA

  DOI：10.1248/cpb.44.1865

  日期：——

  A series of 4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline derivatives showed potent DA1 agonistic activities. We investigated the structure-activity relationship of the racemic compounds of this series. 4-(3,4-Dihydroxyphenyl)-7-methanesulfonamido-1,2,3,4-tetrahydroiso quinoline (43) was identified as a potent renal vasodilator with activity almost equal to that of YM435 (1).

  一系列的4-（3,4-二羟基苯基）-1,2,3,4-四氢异喹啉衍生物显示出强大的DA1激动活性。我们研究了该系列外消旋化合物的构效关系。4-（3,4-二羟基苯基）-7-甲磺酰胺基-1,2,3,4-四氢异喹啉（43）被确定为有效的肾血管扩张药，其活性几乎与YM435（1）相等。
• Syntheses of Apogalanthamine Analogues as α-Adrenergic Blocking Agents. XII. : Syntheses and Stereochemistry of Methoxy and Methylenedioxy Derivatives of 8-Hydroxy-5, 6, 7, 8-tetrahydrodibenz-[c, e]azocines
  作者：Masaru KIHARA、Kuniyoshi OHNISHI、Suwanna VANGVERAVONG、Shigeru KOBAYASHI

  DOI：10.1248/cpb.37.870

  日期：1989.4.25

  8-tetrahydrodibenz[c, e]azocines 4b, c and their methoxy and methylenedioxy derivatives 7a-c and 8a-c were prepared by cyclization of O-protected 1-phenyl-2-aminoethanols 6b, c, 9a-c and 10a-c with zerovalent nickel, followed by hydrolysis of the resulting O-protected azocines 4d, e, 7d-f and 8d-f, respectively. The half-tub conformation of the tetrahydroazocine ring of these 8-hydroxydibenz[c, e]azocines and the

  通过O-保护的1-苯基-2-氨基乙醇的环化反应制备8-羟基-5、6、7、8-四氢二苯并[c，e]偶氮星4b，c及其甲氧基和亚甲基二氧基衍生物7a-c和8a-c。在图6b，c，9a-c和10a-c中用零价镍，然后分别水解所得的O-保护的偶氮碱4d，e，7d-f和8d-f。这些8-羟基二苯并[c，e]偶氮电影的四氢偶氮嗪环的半桶构象和8-羟基的准赤道构型由质子核磁共振谱支持。
• Specific dopamine D-1 and DA1 properties of 4-(mono- and -dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline and its tetrahydrothieno[2,3c]pyridine analog
  作者：Robert M. Riggs、David E. Nichols、Mark M. Foreman、Lewis L. Truex、Dana Glock、Jai D. Kohli

  DOI：10.1021/jm00391a029

  日期：1987.8

  relationships of dopamine agonists related to nomifensine. Two of the compounds, 4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline and 4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydrothieno[2,3-c]pyridine, have been reported in the patent literature. In stimulation of rat retinal adenylate cyclase, a measure of dopamine D-1 agonist activity, the tetrahydroisoquinoline was about equipotent to dopamine. The thienyl

  制备并检查标题化合物以进一步阐明与诺米芬有关的多巴胺激动剂的结构-活性关系。化合物中的两种，4-（3,4-二羟基苯基）-1,2,3,4-四氢异喹啉和4-（3,4-二羟基苯基）-1,2,3,4-四氢噻吩并[2,3-c专利文献中已经报道了]吡啶。在刺激大鼠视网膜腺苷酸环化酶（一种测量多巴胺D-1激动剂活性）的过程中，四氢异喹啉与多巴胺大约等价。噻吩基异戊二烯的功效几乎是其两倍。两种化合物都是犬肾动脉中有效的血管扩张剂，通过刺激DA1型外周多巴胺受体产生扩张作用。单羟基类似物4-（3-羟基苯基）-1,2,3,4-四氢异喹啉，在环化酶测定中仅具有轻微活性，而在犬肾动脉中则无活性。这些结果与早期研究的结果相结合，表明N-烷基化同时降低了多巴胺D-1和DA-1激动剂的效力，其活性以H大于甲基大于乙基大于丙基的顺序排列。结果还证明了该系列中邻苯二酚功能的必要性。
• Solid oral preparation containing a pyrrolidine derivative with a
  申请人：Eisai Co., Ltd.

  公开号：US05292521A1

  公开（公告）日：1994-03-08

  An oral solid preparation comprising an organic acid or its salt and a catechol compound. The catechol compound is, for example, a pyrrolidine derivative having a catechol group of the following general formula (I). It exhibits an improved absorbability in vivo. ##STR1##

  一种口服固体制剂，包括有机酸或其盐和儿茶酚化合物。儿茶酚化合物可以是例如具有以下一般式(I)的儿茶酚基团的吡咯烷衍生物。它在体内表现出改善的吸收性。
• Synthesis, resolution, absolute stereochemistry, and enantioselectivity of 3',4'-dihydroxynomifensine
  作者：Penelope A. Dandridge、Carl Kaiser、Martin Brenner、Dimitri Gaitanopoulos、Larry D. Davis、R. Lee Webb、James J. Foley、Henry M. Sarau

  DOI：10.1021/jm00367a006

  日期：1984.1

  enantiomers of 1a was determined by single-crystal X-ray diffractometric analysis. Examination of the isomers in several pharmacological test systems revealed a high degree of enantioselectivity. D-1 dopaminergic activity resides almost exclusively in the S enantiomer. The findings of the study have been employed to suggest an accessory binding site on the dopamine receptor(s) that differs from that advanced

  3'，4'-Dihydroxynomifensine，8-amino-1,2,3,4-tetrahydro-4-（3,4-dihydroxyphenyl）-2-methylisoquinoline ne（1a）是中央和周围多巴胺受体的激动剂系统。由于该多巴胺受体激动剂在位置4处具有不对称中心，因此其合成和拆分是作为确定这些试剂与受体相互作用方式的研究的一部分。3'，4'-二羟基nomenfensine的对映异构体特别受关注，因为它们提供了多巴胺受体当前概念模型的其他探针。最初准备1a的尝试效率低下或未成功；相反，获得了异构体化合物1,2,4,5-四氢-2-（3,4-二羟基苯基）-4-甲基-3H-1,4-苯并二氮杂（9）。因此，一条通往3'，4'的新路线 使用了-二羟基nomifensine。拆分得到的外消旋二甲氧基中间体1d。1d的异构体的甲氧基裂解得到1a的对映体。这些对映体或适当的衍生