4-(4'-n-octylphenyl)butan-1-ol | 183129-84-2

• 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: 4-(4'-n-octylphenyl)butan-1-ol
• 英文别名: 4-(4-octylphenyl)butan-1-ol；Benzenebutanol, 4-octyl-
• CAS: 183129-84-2
• 化学式: C₁₈H₃₀O
• 分子量: 262.436
• InChiKey: ZJGQRVYTDBNPQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  386.2±21.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4-(4'-n-octylphenyl)butan-1-ol 在 titanium(IV) isopropylate 、 cerium(III) chloride 四氮唑 、 盐酸 、 sodium tetrahydroborate 、 molecular sieve 、 过氧化氢异丙苯 、 sodium acetate 、 D-(-)-酒石酸二异丙酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 S) FTY720磷酸酯
  参考文献：
  名称：

  Enantioselective synthesis of the phosphate esters of the immunosuppressive lipid FTY720

  摘要：

  The enantiomers of FTY720-phosphate (3) were synthesized via 2-methylene-4-(4-octylphenyl)butan-1-ol (7), 2,3-epoxy alcohol 8, and Delta(2)-oxazoline 10. These compounds have potential use in the treatment of autoimmune diseases and prevention of kidney transplant rejection. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.092
• 作为产物：
  描述：

  1-苯基辛烷 在 氢氧化钾 、 sodium tetrahydroborate 、 三氯化铝 、 三氟化硼乙醚 、 一水合肼 作用下， 以 乙二醇 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 4-(4'-n-octylphenyl)butan-1-ol
  参考文献：
  名称：

  Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system

  摘要：

  A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (+/-)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.

  DOI：

  10.1016/0223-5234(96)85877-6

文献信息

• Chiral Vinylphosphonate and Phosphonate Analogues of the Immunosuppressive Agent FTY720
  作者：Xuequan Lu、Chaode Sun、William J. Valentine、Shuyu E、Jianxiong Liu、Gabor Tigyi、Robert Bittman

  DOI：10.1021/jo900023u

  日期：2009.4.17

  The first enantioselective synthesis of chiral isosteric phosphonate analogues of FTY720 is described. One of these analogues, FTY720-(E)-vinylphosphonate (S)-5, but not its R enantiomer, elicited a potent antiapoptotic effect in intestinal epithelial cells, suggesting that it exerts its action via the enantioselective activation of a receptor. (S)-5 failed to activate the sphingosine 1-phosphate type

  描述了 FTY720 的手性等排膦酸酯类似物的第一个对映选择性合成。其中一个类似物 FTY720-( E )-乙烯基膦酸酯 ( S )- 5，而不是它的R对映异构体，在肠上皮细胞中引起有效的抗凋亡作用，表明它通过受体的对映选择性激活发挥作用。( S ) -5未能激活 1-磷酸鞘氨醇 1 型 (S1P 1 ) 受体。
• Structure–Activity Relationships and Molecular Modeling of Sphingosine Kinase Inhibitors
  作者：Dong Jae Baek、Neil MacRitchie、Nahoum G. Anthony、Simon P. Mackay、Susan Pyne、Nigel J. Pyne、Robert Bittman

  DOI：10.1021/jm401399c

  日期：2013.11.27

  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.
• Synthesis of fluorinated agonist of sphingosine-1-phosphate receptor 1
  作者：Lucie Aliouane、Sovy Chao、Leyre Brizuela、Emmanuel Pfund、Olivier Cuvillier、Ludovic Jean、Pierre-Yves Renard、Thierry Lequeux

  DOI：10.1016/j.bmc.2014.06.038

  日期：2014.9

  The bioactive metabolite sphingosine-1-phosphate (S1P), a product of sphingosine kinases (SphKs), mediates diverse biological processes such as cell differentiation, proliferation, survival and angiogenesis. A fluorinated analogue of S1P receptor agonist has been synthesized by utilizing a ring opening reaction of oxacycles by a lithiated difluoromethylphosphonate anion as the key reaction. In vitro activity of this S1P analogue is also reported.
• Synthesis, evaluation and molecular dynamics study of human toll-like receptor 2/6 specific monoacyl lipopeptides as candidate immunostimulants
  作者：Yueyue Zhu、Bo Liu、Zonglong Chen、Xianyang Wang、Yujie Wang、Wenhong Zhang、Sen Wang、Mingming Zhang、Yingxia Li

  DOI：10.1016/j.bioorg.2023.106823

  日期：2023.12
• [EN] SELECTIVE INHIBITORS AND ALLOSTERIC ACTIVATORS OF SPHINGOSINE KINASE<br/>[FR] INHIBITEURS SÉLECTIFS ET ACTIVATEURS ALLOSTÉRIQUES DE LA SPHINGOSINE KINASE
  申请人：UNIV CITY NEW YORK RES FOUND

  公开号：WO2014118556A2

  公开（公告）日：2014-08-07

  Sphingosine 1-phosphate (S1P) is involved in hyper-proliferative diseases, such as cancer and vascular remodeling in pulmonary arterial hypertension. Inhibitors of sphingosine kinase 1 and 2 (SK1 and SK2), which catalyze the synthesis of S1P, may be useful anti- proliferative agents. We have synthesized a series of sphingosine-based inhibitors of SK and SK2. Also provided in this invention are compounds that activate SK1 which can be used in diseases such as fibrosis, where intracellular S1P is anti-fibrotic.