A 70360 | 130465-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: A 70360
• 英文别名: [1S,3R]1-Aminomethyl-3,4-dihydro-5,6-dihydroxy-3-phenyl-1H-2-benzopyran hydrochloride；(1S,3R)-1-(aminomethyl)-3-phenyl-3,4-dihydro-1H-isochromene-5,6-diol;hydrochloride
• CAS: 130465-42-8
• 化学式: C₁₆H₁₇NO₃*ClH
• 分子量: 307.777
• InChiKey: PQPGUUQPTSMLKU-CTHHTMFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-<2',3'-(cyclohexylidenedioxy)phenyl>-1-phenylethanone 在 盐酸 、 lithium aluminium tetrahydride 、 叠氮化锂 、 三氟化硼乙醚 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 A 70360
  参考文献：
  名称：

  Synthesis and dopaminergic activity of 3-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans: characterization of an auxiliary binding region in the D1 receptor

  摘要：

  The synthesis and dopaminergic activity of a series of C3 and nitrogen-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans (isochromans) is described. The synthesis of the compounds was stereospecific for the 1,3 cis isomer, and the enantioselective synthesis of both enantiomers of one of the analogoues (20) was achieved. It was determined that all of the dopaminergic activity resides in the [1R,3S] isomer. Generally, substitution at the C3 position provided compounds with very high potency (< 10 nm EC50) and selectivity for the D1 receptor, with a wide range of intrinsic activities (60-160%). Analogues containing C3 substituents including aryl, arylalkyl, and cyclic and acyclic alkyl groups showed a marked enhancement of dopaminergic activity compared to the unsubstituted compound. As a class, the drugs were orally active in the rat rotation model with a very long duration of action.

  DOI：

  10.1021/jm00112a034

文献信息

• Dopamine agonists
  申请人：Abbott Laboratories

  公开号：US05591884A1

  公开（公告）日：1997-01-07

  Novel compounds having the formula ##STR1## and the pharmaceutically acceptable salts, esters and amides thereof, wherein A is --O--, --S-- or --CR.sup.2 R.sup.8 --; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, X and Y are specifically defined; and up to one combination of (a) R.sup.2 and R.sup.5, (b) R.sup.5 and R.sup.6, (c) R.sup.5 and R.sup.7, (d) R.sup.6 and R.sup.7, and (e) R.sup.7 and Y, taken together with the atoms to which they are attached, may form a ring, the compounds being useful for treating dopamine-related neurological, psychological and cardiovascular disorders as well as in the treatment of cognitive impairment, attention deficit disorder, and substance abuse and other addictive behavior disorders. Also disclosed are intermediates and processes useful in the preparation of the above compounds.

  具有以下结构式##STR1##及其药学上可接受的盐、酯和酰胺的新化合物，其中A为--O--，--S--或--CR.sup.2 R.sup.8 --；R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6、R.sup.7、R.sup.8、R.sup.9、R.sup.10、X和Y具体定义；并且最多可以有一种组合的(a) R.sup.2和R.sup.5，(b) R.sup.5和R.sup.6，(c) R.sup.5和R.sup.7，(d) R.sup.6和R.sup.7，以及(e) R.sup.7和Y，与它们附着的原子一起形成环，这些化合物可用于治疗多巴胺相关的神经、心理和心血管疾病，以及认知障碍、注意力缺陷障碍和物质滥用和其他成瘾行为障碍的治疗。还公开了制备上述化合物有用的中间体和过程。
• Method for post mortem diagnosis of Alzheimer's Disease (AD)
  申请人：Red Bull GmbH

  公开号：EP2806276A1

  公开（公告）日：2014-11-26

  Disclosed is a method for diagnosing Alzheimer's Disease (AD) post mortem, wherein the amount of at least one receptor complex, selected from the group consisting of nicotinic acetylcholine receptor complex 4, nicotinic acetylcholine receptor complex 7, dopamine receptor complex D1 and dopamine receptor complex D2, is measured in a brain sample of a patient and diagnosing AD, if the amount of the complex in the sample is increased compared to normal, non-AD levels.

  本发明公开了一种用于死后诊断阿尔茨海默病（AD）的方法，该方法测量患者脑样本中至少一种受体复合物的含量，这些受体复合物选自由烟碱乙酰胆碱受体复合物 4、烟碱乙酰胆碱受体复合物 7、多巴胺受体复合物 D1 和多巴胺受体复合物 D2 组成的组，如果样本中的复合物含量与正常非 AD 水平相比有所增加，则诊断为 AD。
• DENINNO, M. P.;SCHOENLEBER, R.;ASIN, K. E.;MACKENZIE, R.;KEBABIAN, J. W., J. MED. CHEM., 33,(1990) N1, C. 2948-2950
  作者：DENINNO, M. P.、SCHOENLEBER, R.、ASIN, K. E.、MACKENZIE, R.、KEBABIAN, J. W.

  DOI：——

  日期：——
• KILLING HUMAN LYMPHOMA AND LEUKEMIA CANCER CELLS AND TCR-ACTIVATED NORMAL HUMAN CELLS BY DOPAMINE D1R AGONISTS
  申请人：Mineuet Therapeutics Ltd.

  公开号：EP1917277A2

  公开（公告）日：2008-05-07
• EP1917277A4
  申请人：——

  公开号：EP1917277A4

  公开（公告）日：2009-08-05