2-(4-dodecylphenyl)ethanol | 162358-86-3

• 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: 2-(4-dodecylphenyl)ethanol
• 英文别名: (p-Dodecylphenyl)methylcarbinol
• CAS: 162358-86-3
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: LDVYZGRGZMIMKW-UHFFFAOYSA-N

物化性质

• 沸点：
  347.1±10.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-dodecylphenyl)ethanol 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.0h， 生成
  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：

  4-溴苯乙醇 在 copper(l) iodide 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 2-(4-dodecylphenyl)ethanol
  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

文献信息

• Synthesis and Immunosuppressive Activity of 2-Substituted 2-Aminopropane-1,3-diols and 2-Aminoethanols
  作者：Masatoshi Kiuchi、Kunitomo Adachi、Toshiyuki Kohara、Masanori Minoguchi、Tokushi Hanano、Yoshiyuki Aoki、Tadashi Mishina、Masafumi Arita、Noriyoshi Nakao、Makio Ohtsuki、Yukio Hoshino、Koji Teshima、Kenji Chiba、Shigeo Sasaki、Tetsuro Fujita

  DOI：10.1021/jm000173z

  日期：2000.7.1

  allograft. A phenyl ring was introduced into the alkyl chain of the lead compound 3, which is an immunosuppressive agent structurally simplified from myriocin (1, ISP-I) via compound 2. The potency of the various compounds was dependent upon the position of the phenyl ring within the alkyl side chain. The most suitable length between the quaternary carbon atom and the phenyl ring was two carbon atoms

  合成了一系列2-取代的2-氨基丙烷-1,3-二醇，并评估了它们对大鼠皮肤同种异体移植细胞的淋巴细胞减少作用和免疫抑制作用。通过化合物2，苯环被引入到先导化合物3的烷基链中，该化合物是一种从十四烷（1，ISP-1）结构上简化的免疫抑制剂。各种化合物的效价取决于苯环的位置在烷基侧链内。季碳原子和苯环之间的最合适的长度是两个碳原子。连续合成2-取代的2-氨基乙醇，并用a淋巴结增加试验评估大鼠的T细胞减少作用和免疫抑制作用。季碳的绝对构型影响活性，化合物6的（pro-S）-羟甲基对于有效的免疫抑制活性至关重要。6的（原-R）-羟甲基的有利取代基是羟烷基（羟乙基和羟丙基）或低级烷基（甲基和乙基）。发现2-氨基-2- [2-（2-（4-辛基苯基）乙基]丙烷-1,3-二醇盐酸盐（6，FTY720）具有相当大的活​​性，并有望用作器官移植的免疫抑制药物。
• NOVEL POLYTHIOPHENE POLYANION COMPLEXES IN HOMOPOLAR ORGANIC SOLVENTS
  申请人：Loevenich Wilfried

  公开号：US20110168946A1

  公开（公告）日：2011-07-14

  The invention relates to novel polythiophene-polyanion complexes which are soluble or dispersible in nonpolar organic solvents, and to the use thereof.

  本发明涉及一种新型聚噻吩-聚阴离子复合物，其可溶于或分散于非极性有机溶剂中，并涉及其用途。
• Polythiophene polyanion complexes in homopolar organic solvents
  申请人：Loevenich Wilfried

  公开号：US08721929B2

  公开（公告）日：2014-05-13

  The invention relates to novel polythiophene-polyanion complexes which are soluble or dispersible in nonpolar organic solvents, and to the use thereof.

  本发明涉及一种新型聚噻吩-聚阴离子复合物，其可溶于或分散于非极性有机溶剂中，并且涉及其使用。
• 2-AMINO-1,3-PROPANEDIOL COMPOUND AND IMMUNOSUPPRESSANT
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0627406A1

  公开（公告）日：1994-12-07

  A 2-amino-1,3-propanediol compound represented by general formula (I) or a pharmaceutically acceptable salt thereof, and an immunosuppressant containing the same as the active ingredient. In said formula R represents optionally substituted linear or branched carbon chain, optionally substituted aryl or optionally substituted cycloalkyl; and R2, R3, R4 and R5, which may be the same or different from one another, represent each hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl. The compound is immunodepressant and useful as an inhibitor against rejection in organ or bone marrow transplantation, as a preventive or remedy for autoimmune diseases and so forth, or a reagent in the medical and pharmaceutical fields.

  一种由通式(I)代表的2-氨基-1,3-丙二醇化合物或其药学上可接受的盐，以及一种以其为活性成分的免疫抑制剂。在所述式中，R 代表任选取代的直链或支链碳链、任选取代的芳基或任选取代的环烷基；而 R2、R3、R4 和 R5（它们彼此可以相同或不同）分别代表氢、烷基、芳烷基、酰基或烷氧基羰基。该化合物具有免疫抑制作用，可作为器官移植或骨髓移植中的排斥抑制剂、自身免疫性疾病的预防或治疗药物等，也可作为医疗和制药领域的试剂。
• EP0627406B1
  申请人：——

  公开号：EP0627406B1

  公开（公告）日：1998-10-28