2-dimethylaminomethyl-6-methoxy-3,4-dihydronaphthalen-1(2H)-one hydrochloride | 72604-99-0

• 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-dimethylaminomethyl-6-methoxy-3,4-dihydronaphthalen-1(2H)-one hydrochloride
• 英文别名: 2-(N,N-dimethylamino)methyl-6-methoxy-1-tetralone hydrochloride；2-dimethylaminomethyl-6-methoxy-1-tetralone hydrochloride；2-dimethylaminomethyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one; hydrochloride；2-Dimethylaminomethyl-6-methoxy-3,4-dihydro-2H-naphthalin-1-on; Hydrochlorid；2-[(dimethylamino)methyl]-6-methoxy-3,4-dihydro-2H-naphthalen-1-one;hydrochloride
• CAS: 72604-99-0
• 化学式: C₁₄H₁₉NO₂*ClH
• 分子量: 269.771
• InChiKey: IUWQUYVJBICQBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.41
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-dimethylaminomethyl-6-methoxy-3,4-dihydronaphthalen-1(2H)-one hydrochloride 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 5.83h， 生成 2-(6-甲氧基-1-氧代-1,2,3,4-四氢萘-2-基)乙酸
  参考文献：
  名称：

  Inotropic, vasodilator and low Km, cAMP-selective, cGMP-inhibited phosphodiesterase (PDE III) inhibitory activities of 4a-methyl-4,4a-dihydro-5H-indeno[1,2-c]pyridazin-3(2H)-ones and 4a-methyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-ones

  摘要：

  Novel 7-substituted-4,4a-dihydro-4a-methyl-5H-indenol[1,2-c]pyridazin-3[2H]-ones and 8-substituted-4a-methylbenzo[h]cinnolin-3[2H]-ones have been synthesized and their PDE III inhibitory, inotropic and vasodilator potencies compared with those of their normethyl analogues and their bicyclic 4,5-dihydro-6-phenylpyridazinone analogues. The structure-activity relationships of the tricyclic pyridazinones differ from those of bicyclic pyridazinones mainly in respect of the effect of introducing the methyl group into the pyridazinone ring. Whilst in the 4,5-dihydro-6-phenylpyridazin-3(2H)-ones, introduction of a 5-methyl group has been widely reported to lead to compounds of significantly greater potency, the novel tricyclic 4a-methylpyridazinones showed similar levels of inotropic, vasodilator and PDE III inhibitory potency to their normethyl analogues. Possible reasons for this difference in behaviour are discussed.

  DOI：

  10.1016/0223-5234(90)90196-a
• 作为产物：
  描述：

  盐酸二甲胺 、 6-甲氧基-1-萘满酮 在 聚合甲醛 、 乙醇 作用下， 生成 2-dimethylaminomethyl-6-methoxy-3,4-dihydronaphthalen-1(2H)-one hydrochloride
  参考文献：
  名称：

  Lee et al., Barell-Festschr. S. 264, 294, 303

  摘要：

  DOI：

文献信息

• Heterocyclen via Mannich-Kondensation, 6. Mitt. Synthese von 2-Amino-3-pyridyl-phenylketonen
  作者：Mónica Söllhuber-Kretzer、Reinhard Troschütz、Hermann J. Roth

  DOI：10.1002/ardp.19823150303

  日期：——

  Benzoylacetimidsäure‐ethylester (1a) und seine Derivate 1b, 1c sowie Benzoylacetamidin (2a) liegen in Lösung in der Enolform vor. Mit Keton‐Mannichbasen setzen sie sich zu 2‐Amino‐3‐pyridyl‐phenylketonen um.

  苯甲酰乙酰亚胺乙酯 (1a) 及其衍生物 1b、1c 和苯甲酰乙脒 (2a) 以烯醇形式存在于溶液中。它们与酮曼尼希碱反应生成 2-氨基-3-吡啶基-苯基酮。
• Indeno and naphth[1,2-D]azepines
  申请人：Ciba-Geigy Corporation

  公开号：US04173633A1

  公开（公告）日：1979-11-06

  Hydrogenated 1-aminoalkyl-indeno- or naphth[1,2-d]-azepines, e.g. those of the formula ##STR1## Am'=NH.sub.2, (alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, or benzyl)amino, its N-lower alkyl derivatives; alkyleneimino morpholino or piperazino; R.sub.o-3 =H, OH, alkyl, alkoxy, halo or CF.sub.3 ; R.sub.4,5 =H or alkyl; X=H.sub.2 or 0; m=1 or 2; q=0 or 1; and salts thereof are potassium-sparing diuretic agents.

  氢化的1-氨基烷基吲哚-或萘[1,2-d]-氮杂环庚烷，例如式子##STR1## 中的那些化合物，其中Am'=NH.sub.2，（烷基，烯基，炔基，羟基烷基，环烷基或苄基）氨基，其N-较低烷基衍生物；烷基亚氨基吗啉或哌嗪；R.sub.o-3=H，OH，烷基，烷氧基，卤素或CF.sub.3；R.sub.4,5=H或烷基；X=H.sub.2或0；m=1或2；q=0或1；及其盐是保钾利尿剂。
• Indeno and naphth[1,2-d]azepines
  申请人：Ciba-Geigy Corporation

  公开号：US04309345A1

  公开（公告）日：1982-01-05

  Hydrogenated 1-aminoalkyl indeno- or -naphth[1,2-d]azepines, e.g. those of the formula ##STR1## Am'=NH.sub.2, (alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, or benzyl)amino, its N-lower alkyl derivatives; alkyleneimino morpholino or piperazino R.sub.o-3 =H, OH, alkyl, alkoxy, halo or CF.sub.3 R.sub.4,5 =H or alkyl; X=H.sub.2 or 0 m=1 or 2; q=0 or 1 and salts thereof are potassium-sparing diuretic agents.

  氢化的1-氨基烷基吲哚或萘[1,2-d]氮杂环庚烷，例如公式##STR1##中的化合物 Am'=NH.sub.2，(烷基，烯基，炔基，羟基烷基，环烷基或苄基)氨基，其N-较低烷基衍生物; 烷基亚氨基吗啉或哌嗪 R.sub.o-3=H，OH，烷基，烷氧基，卤素或CF.sub.3 R.sub.4,5=H或烷基; X=H.sub.2或0 m=1或2; q=0或1及其盐为保钾利尿剂。
• Discovery, synthesis, and structure–activity relationship of 6-aminomethyl-7,8-dihydronaphthalenes as human melanin-concentrating hormone receptor 1 antagonists
  作者：Makoto Kamata、Toshiro Yamashita、Toshihiro Imaeda、Toshio Tanaka、Jun Terauchi、Maki Miyamoto、Taiichi Ora、Michiko Tawada、Satoshi Endo、Shiro Takekawa、Asano Asami、Nobuhiro Suzuki、Yasutaka Nagisa、Yoshihide Nakano、Kaoru Watanabe、Hitomi Ogino、Koki Kato、Kaneyoshi Kato、Yuji Ishihara

  DOI：10.1016/j.bmc.2011.07.038

  日期：2011.9

  Human melanin-concentrating hormone receptor 1 (hMCHR1) antagonists are promising targets for obesity treatment. We identified the tetrahydronaphthalene derivative 1a with modest binding affinity for hMCHR1 by screening an in-house G protein-coupled receptor (GPCR) ligand library. We synthesized a series of 6-aminomethyl-5,6,7,8-tetrahydronaphthalenes and evaluated their activity as hMCHR1 antagonists. Modification of the biphenylcarbonylamino group revealed that the biphenyl moiety played a crucial role in the interaction of the antagonist with the receptor. The stereoselective effect of the chiral center on binding affinity generated the novel 6-aminomethyl-7,8-dihydronaphthalene scaffold without a chiral center. Optimization of the amino group led to the identification of a potent antagonist 2s (4'-fluoro-N[6-(1-pyrrolidinylmethyl)-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide), which significantly inhibited the nocturnal food intake in rats after oral administration. Pharmacokinetic analysis confirmed that 2s had good oral bioavailability and brain penetrance. This antagonist appears to be a viable lead compound that can be used to develop a promising therapy for obesity. (C) 2011 Elsevier Ltd. All rights reserved.
• Collins, David J.; Fallon, Gary D.; Skene, Colin E., Australian Journal of Chemistry, 1994, vol. 47, # 4, p. 623 - 648
  作者：Collins, David J.、Fallon, Gary D.、Skene, Colin E.

  DOI：——

  日期：——