1-(2-methanesulfonyloxyethyl)-4-methylbenzene | 66865-86-9

• 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-methanesulfonyloxyethyl)-4-methylbenzene
• 英文别名: 2-(4-methylphenyl)ethanol methanesulfonate；p-methylphenethyl mesylate；2-(4-methylphenyl)ethyl methanesulfonate
• CAS: 66865-86-9
• 化学式: C₁₀H₁₄O₃S
• 分子量: 214.285
• InChiKey: BOPBEAWXJQPOSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  372.0±21.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methanesulfonyloxyethyl)-4-methylbenzene 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 1-[2-(4-methylphenyl)ethyl]piperidin-4-amine
  参考文献：
  名称：

  Structure–Activity Relationships and Molecular Modeling of Sphingosine Kinase Inhibitors

  摘要：

  The design, synthesis, and evaluation of the potency of new isoform-selective inhibitors of sphingosine kinases I and 2 (SK1 and SK2), the enzyme that catalyzes the phosphorylation of D-erythro-sphingosine to produce the key signaling lipid, sphingosine 1-phosphate, are described. Recently, we reported that 1-(4-octylphenethyl)piperidin-4-ol (RB-005) is a selective inhibitor of SK1. Here we report the synthesis of 43 new analogues of RB-005, in which the lipophilic tail, polar headgroup, and linker region were modified to extend the structure-activity relationship profile for this lead compound, which we explain using modeling studies with the recently published crystal structure of SKI. We provide a basis for the key residues targeted by our profiled series and provide further evidence for the ability to discriminate between the two isoforms using pharmacological intervention.

  DOI：

  10.1021/jm401399c
• 作为产物：
  描述：

  甲基磺酰氯 生成 1-(2-methanesulfonyloxyethyl)-4-methylbenzene
  参考文献：
  名称：

  SPATZ, D. M.;CROSS, T. B.

  摘要：

  DOI：

文献信息

• Synthesis and pharmacological studies of 4,4-disubstituted piperidines: a new class of compounds with potent analgesic properties
  作者：Bruno S. Huegi、Anton M. Ebnoether、Erwin Rissi、Fulvio Gadient、Daniel Hauser、Dietmar Roemer、Heinz H. Buescher、Trevor J. Petcher

  DOI：10.1021/jm00355a010

  日期：1983.1

  activity. Several of these analogues show analgesic potency comparable to morphine in the mouse writhing and tail-flick tests. A number of compounds exhibit high affinity for [3H]naloxone binding sites in rat brain membranes. Among the most potent derivatives are compounds 15 and 48. Although opiate-like, attempts to modify this activity with various substituents have failed to produce antagonistic properties

  已经合成了一系列的4，4-二取代的哌啶并评估了其止痛活性。这些类似物中的几种在小鼠扭动和甩尾试验中显示出与吗啡相当的镇痛效果。许多化合物对大鼠脑膜中的[3H]纳洛酮结合位点显示出高亲和力。在最有效的衍生物中是化合物15和48。尽管是鸦片样的，但尝试用各种取代基修饰该活性未能产生拮抗作用。这些类似物中的一些在豚鼠5-羟色胺毒性试验中和在小鼠中由DL-5-羟色氨酸诱导的头抽搐模型中也显示出明显的持久性5-羟色胺拮抗作用。
• Imidazo[2,1-b]benzazepine derivatives, compositions and method of use
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05468743A1

  公开（公告）日：1995-11-21

  The present invention is concerned with novel imidazo[2, 1-b][3]benzazepines of formula ##STR1## the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, wherein each of the dotted lines independently represents an optional bond; R.sup.1 represents hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkyloxy; R.sup.2 represents hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkyloxy; R.sup.3 represents hydrogen, C.sub.1-4 alkyl, ethenyl substituted with hydroxycarbonyl or C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkyl substituted with hydroxycarbonyl or C.sub.1-4 alkyloxycarbonyl, hydroxyC.sub.1-4 alkyl, formyl or hydroxycarbonyl; R.sup.4 represents hydrogen, C.sub.1-4 alkyl, hydroxyC.sub.1-4 alkyl, phenyl or halo; R.sup.5 represents hydrogen, C.sub.1-4 alkyl or halo; L represents hydrogen; C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted with one substituent selected from the group consisting of hydroxy, halo, C.sub.1-4 alkyloxy, hydroxycarbonyl, C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkyloxycarbonyl-C.sub.1-4 alkyloxy, hydroxycarbonylC.sub.1-4 alkyloxy, C.sub.1-4 alkyloxycarbonylamino, C.sub.1-4 alkylaminocarbonyl, C.sub.1-4 alkylaminocarbonylamino, C.sub.1-4 alkylaminothiocarbonylamino, aryl, aryloxy and arylcarbonyl; C.sub.1-6 alkyl substituted with both hydroxy and aryloxy; C.sub.3-6 alkenyl; C.sub.3-6 alkenyl substituted with aryl; or, L represents a radical of formula --Alk--Y--Het.sup.1 (a-1),--Alk--NH--CO--Het.sup.2 (a-2)or --Alk--Het.sup.3 (a-3); provided that 6,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine is ecxluded, which are useful antiallergic compounds. Compositions comprising said compounds, methods of using and processes for preparing the same.

  本发明涉及具有以下结构的新型咪唑[2,1-b][3]苯并蒽啉化合物：其中每个虚线独立地表示可选键；R.sup.1代表氢、卤素、C.sub.1-4烷基或C.sub.1-4烷氧基；R.sup.2代表氢、卤素、C.sub.1-4烷基或C.sub.1-4烷氧基；R.sup.3代表氢、C.sub.1-4烷基、乙烯基取代的羟基羰基或C.sub.1-4烷氧羰基、烷基取代的羟基羰基或C.sub.1-4烷氧羰基、羟基C.sub.1-4烷基、甲酰基或羟基羰基；R.sup.4代表氢、C.sub.1-4烷基、羟基C.sub.1-4烷基、苯基或卤素；R.sup.5代表氢、C.sub.1-4烷基或卤素；L代表氢；C.sub.1-6烷基；C.sub.1-6烷基取代一个取自羟基、卤素、C.sub.1-4烷氧基、羟基羰基、C.sub.1-4烷氧羰基、C.sub.1-4烷氧羰基-C.sub.1-4烷氧基、羟基羰基C.sub.1-4烷氧基、C.sub.1-4烷氧羰基氨基、C.sub.1-4烷基氨基羰基、C.sub.1-4烷基氨基羰基氨基、C.sub.1-4烷基氨基硫氨基、芳基、芳氧基和芳基羰基的取代基的C.sub.1-6烷基；同时取代羟基和芳氧基的C.sub.1-6烷基；C.sub.3-6烯基；取代芳基的C.sub.3-6烯基；或，L代表以下结构的基团：--Alk--Y--Het.sup.1 (a-1)，--Alk--NH--CO--Het.sup.2 (a-2)或--Alk--Het.sup.3 (a-3)；但排除6,11-二氢-11-(4-哌啶基亚)咪唑[2,1-b][3]苯并蒽啉。这些化合物是有用的抗过敏化合物。包括这些化合物的组合物、使用方法和制备方法。
• Combinatorial synthesis and biological evaluation of peptide-binding GPCR-targeted library
  作者：Ju Yeon Lee、Isak Im、Thomas R. Webb、Douglas McGrath、Mi-Ryoung Song、Yong-Chul Kim

  DOI：10.1016/j.bioorg.2009.04.001

  日期：2009.6

  discovery for peptide-binding GPCRs based on the natural ligands, beta-turn peptidomimetic compound library with benzodiazepine skeleton was constructed using solid and solution phase parallel synthesis with four different scaffolds containing Phe, Lys, Ser and Glu, respectively. The usefulness of 162 library compounds was evaluated by the cell based screening at melanocortin 4 receptor in CHO-k1 cells

  作为基于天然配体的结合肽GPCR的新发现药物的有效策略，采用固相和溶液相平行合成方法，分别用四种不同的含有Phe，Lys，Ser和Glu的支架，构建了具有苯并二氮杂骨架的β-转肽模拟化合物文库，分别。通过在CHO-k1细胞中的黑皮质素4受体进行基于细胞的筛选，评估了162种文库化合物的有用性，以发现对受体表现出激动作用的命中化合物。文库的筛选提供了三种命中的化合物，包括最有效的类似物（S）-3-苄基-7-（4-氟苄氧基）-4-（4-甲氧基苯乙基）-4,5-二氢-1 H-苯并[ e] ] [1,4] diazepin -2（3 H）-one，13aiE，其中EC 50被确定为13μM。
• 3-<1-alkylenearyl>-4-<1,2,3,6-tetrahydropyridinyl>-and
  申请人：Eli Lilly and Company

  公开号：US05521197A1

  公开（公告）日：1996-05-28

  This invention provides novel 5-HT.sub.1F agonists which are useful for the treatment of migraine and associated disorders having the following formula: ##STR1## wherein A, B, X, Y, Ar and n are defined in the specification.

  这项发明提供了一种新型的5-HT.sub.1F激动剂，可用于治疗偏头痛和相关疾病，其化学结构如下：##STR1##其中A、B、X、Y、Ar和n在说明书中有定义。
• MANUFACTURING METHOD OF 2-HYDROXY-5-PHENYLALKYLAMINOBENZOIC ACID DERIVATIVES AND THEIR SALTS
  申请人：Gwag Byoung Joo

  公开号：US20110028757A1

  公开（公告）日：2011-02-03

  The present invention provides an efficient method for mass-producing 2-hydroxy-5-(substituted)phenylalkylaminobenzoic acid derivative represented by the specific Chemical formula or its salt, particularly 2-hydroxy-5-[2-(4-trifluoromethylphenyl)ethylamino] benzoic acid or its salt.

  本发明提供了一种高效的方法，用于大规模生产特定化学式或其盐所代表的2-羟基-5-(取代)苯基烷基氨基苯甲酸衍生物，特别是2-羟基-5-[2-(4-三氟甲基苯基)乙基]氨基苯甲酸或其盐。