1-(2-tosyloxyethoxy)naphthalene | 60225-63-0

• 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: 1-(2-tosyloxyethoxy)naphthalene
• 英文别名: 2(-1-naphthyloxy)ethanol-p-toluenesulfonate；2-(naphthalen-1-yloxy)ethyl 4-toluenesulfonate；1-[1]naphthyloxy-2-(toluene-4-sulfonyloxy)-ethane；1-[1]Naphthyloxy-2-(toluol-4-sulfonyloxy)-aethan；2-Naphthalen-1-yloxyethyl 4-methylbenzenesulfonate
• CAS: 60225-63-0
• 化学式: C₁₉H₁₈O₄S
• 分子量: 342.416
• InChiKey: YVTIANZHIRAISR-UHFFFAOYSA-N

物化性质

• 熔点：
  98.7-99.2 °C(Solv: methanol (67-56-1))
• 沸点：
  532.7±33.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-tosyloxyethoxy)naphthalene 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以92%的产率得到1-(2-azidoethoxy)naphthalene
  参考文献：
  名称：

  Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

  摘要：

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.040
• 作为产物：
  描述：

  萘酚 在 吡啶 、 4-甲基苯磺酸吡啶 、 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 28.08h， 生成 1-(2-tosyloxyethoxy)naphthalene
  参考文献：
  名称：

  WC-9 的含氟类似物和结构相关类似物对抗两种细胞内寄生虫：克氏锥虫和弓形虫的活性

  摘要：

  两种专性细胞内寄生虫，克氏锥虫（恰加斯病的病原体）和弓形虫（弓形虫病的病原体），在感染后上调宿主细胞的甲羟戊酸途径，这表明该宿主途径可能是潜在的药物靶点。在这项工作中，设计、合成了许多结构与WC-9 （4-苯氧基苯氧基乙基硫氰酸酯）（一种已知的角鲨烯合酶抑制剂）相关的化合物，并评估了它们对组织培养细胞中克氏弓形虫和刚地弓形虫生长的影响。两种含氟衍生物，3-(3-氟苯氧基)-和3-(4-氟苯氧基)苯氧基乙基硫氰酸盐，针对T的速殖子表现出半最大有效浓度(EC 50 )值分别为1.6和4.9μm 。 .​​​​此外，2-[3-（苯氧基）苯氧基乙硫基]乙基-1,1-二膦酸酯是一种含有 3-苯氧基苯氧基和二膦酸酯基团的混合抑制剂，具有亚微摩尔水平的抗弓形虫增殖活性（EC 50 = 0.7 μ m ），这表明两个官能团的联合抑制作用。

  DOI：

  10.1002/cmdc.201600505

文献信息

• Multicyclic compounds for use as melanin concentrating hormone antagonists in the treatment of obesity and diabetes
  申请人：Ammenn Jochen

  公开号：US20050272718A1

  公开（公告）日：2005-12-08

  The present invention relates to a melanin concentrating hormone antagonist compound of formula I: (I); or a pharmaceutically acceptable salt, solvate, enantiomer or prodrug thereof useful in the treatment, prevention or amelioration of symptoms associated with obesity and related diseases.

  本发明涉及一种式 I 的黑色素浓缩激素拮抗剂化合物：(I)；或其药学上可接受的盐、溶液剂、对映体或原药，可用于治疗、预防或改善与肥胖及相关疾病有关的症状。
• 2-(1-Naphthyloxy)ethylamines with Enhanced Affinity for Human 5-HT_1D_β (h5-HT_1B) Serotonin Receptors
  作者：Abd M. Ismaiel、Malgorzata Dukat、Ho Law、Rajender Kamboj、Ermi Fan、David K. H. Lee、Lucia Mazzocco、Donna Buekschkens、Milt Teitler、Myles E. Pierson、Richard A. Glennon

  DOI：10.1021/jm970507t

  日期：1997.12.1

  Although the beta-adrenergic antagonist propranolol (1) binds at rodent 5-HT1B serotonin receptors, it displays low affinity (K-i > 10 000 nM) for its species homologue 5-HT1D beta (i.e., h5-HT1B) receptors. The structure of propranolol was systematically modified in an attempt to enhance its affinity for the latter population of receptors. Removal of the alkyl hydroxyl group, shortening of the O-alkyl chain from three to two methylene groups, and variation of the terminal amine substituent resulted in compounds, such as N-monomethyl-2-(1-naphthyloxy)ethylamine (11; K-i = 26 nM), that display significantly higher h5-HT1B affinity than propranolol. Compound 11 was shown to bind equally well at human 5-HT1D alpha (h5-HT1D) receptors (K-i = 34 nM) and was further demonstrated to possess h5-HT1B agonist character in an adenylate cyclase assay. It would appear that such (aryloxy)alkylamines may represent a novel class of 5-HT1D receptor agonists.
• Glennon; Dukat; Westkaemper, Molecular Pharmacology, 1996, vol. 49, # 1, p. 198 - 206
  作者：Glennon、Dukat、Westkaemper、Ismaiel、Izzarelli、Parker

  DOI：——

  日期：——
• MULTICYCLIC COMPOUNDS FOR USE AS MELANIN CONCENTRATING HORMONE ANTAGONISTS IN THE TREATMENT OF OBESITY AND DIABETES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1505968A1

  公开（公告）日：2005-02-16
• US7229987B2
  申请人：——

  公开号：US7229987B2

  公开（公告）日：2007-06-12