2-hydroximino-7-methoxy-1-tetralone | 2471-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-hydroximino-7-methoxy-1-tetralone
• 英文别名: 2-Hydroxyimino-7-methoxy-tetralon-(1)；2-oximino-7-methoxy-3,4-dihydronaphthalen-1(2H)-one；2-hydroxyimino-7-methoxy-3,4-dihydronaphthalen-1-one
• CAS: 2471-80-9
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: HIFXMEIRDONUAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroximino-7-methoxy-1-tetralone 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.25h， 生成 N-[(1R,2R)-1,2,3,4-四氢-1-羟基-7-甲氧基-2-萘基]丙酰胺
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 potassium tert-butylate 、 亚硝酸异戊酯 作用下， 以 乙醚 、 正丁醇 为溶剂， 反应 4.0h， 生成 2-hydroximino-7-methoxy-1-tetralone
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014

文献信息

• Hexahydronaphth[1,2-b]-1,4-oxazines
  申请人：Merck & Co., Inc.

  公开号：US04420480A1

  公开（公告）日：1983-12-13

  Hexahydronaphth[1,2-b]-1,4-oxazines have dopaminergic activity and display .alpha..sub.2 -adrenergic receptor antagonism. They are useful in the treatment of parkinsonism, depression and hypertension. An important method of preparation is by ring closure of the appropriate 2-chloroacetamidotetrahydronaphthalen-1-ol and reduction of the resulting cyclic amide carbonyl group.

  六氢萘[1,2-b]-1,4-噁嗪具有多巴胺能活性，并表现出α2-肾上腺素能受体拮抗作用。它们在帕金森病、抑郁症和高血压的治疗中非常有用。一种重要的制备方法是通过环闭合适当的2-氯乙酰胺基四氢萘酚并还原所得的环状酰胺羰基团。
• Dopamine agonists and use thereof
  申请人：Nelson Research & Development Co.

  公开号：US04540691A1

  公开（公告）日：1985-09-10

  Compounds are disclosed having the formula: ##STR1## wherein: R.sub.1 is H, OH, --OCH.sub.3, --CH.sub.2 OH, --NH.sub.2, --NHMe, --NHEt, --NMe.sub.2, --NEt.sub.2, ##STR2## R.sub.2 is H, --CH.sub.3, or ##STR3## R.sub.3 is phenyl, benzyl, or 1-4 carbon alkyl; R.sub.4 is H, --CH.sub.3, --CH.sub.2 OH, --CH.sub.2 --CN, --CH.sub.2 --S--Me, CH.sub.2 --S--CN, or ##STR4## R.sub.5 is H, 1-4 carbon alkyl, alkenyl, or alkynyl, or aralkyl having a 1-4 carbon alkylene moiety; and A is --CH.sub.2 --or --CH.sub.2 CH.sub.2 --, and pharmaceutically-acceptable salts thereof. Pharmaceutical preparations using these compounds and a method for inducing a dopaminergic response by administering these compounds are also disclosed.

  本发明揭示了具有以下式子的化合物：##STR1## 其中：R.sub.1为H，OH，--OCH.sub.3，--CH.sub.2 OH，--NH.sub.2，--NHMe，--NHEt，--NMe.sub.2，--NEt.sub.2，##STR2## R.sub.2为H，--CH.sub.3或##STR3## R.sub.3为苯基，苄基或1-4碳烷基; R.sub.4为H，--CH.sub.3，--CH.sub.2 OH，--CH.sub.2 --CN，--CH.sub.2 --S--Me，CH.sub.2 --S--CN或##STR4## R.sub.5为H，1-4碳烷基，烯基或炔基，或具有1-4碳烷基亚烷基的芳基烷基; A为--CH.sub.2 --或--CH.sub.2 CH.sub.2 --，以及其药学上可接受的盐。还揭示了使用这些化合物的制药制剂以及通过给予这些化合物诱导多巴胺能反应的方法。
• Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists
  作者：James H. Jones、Paul S. Anderson、John J. Baldwin、Bradley V. Clineschmidt、David E. McClure、George F. Lundell、William C. Randall、Gregory E. Martin、Michael Williams

  DOI：10.1021/jm00378a014

  日期：1984.12

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.