1-[4-(4-苯基苯氧基)苯基]乙酮 | 35155-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[4-(4-苯基苯氧基)苯基]乙酮
• 中文别名: 4′-（4-苯基苯氧基）苯乙酮
• 英文名称: 4-(biphenyl-4'-yloxy)acetophenone
• 英文别名: 4-(biphenyl-4'-yloxy)-acetophenone；4-p-Acetylphenoxy-biphenyl；4'-(4-Phenylphenoxy)acetophenone；1-[4-(4-phenylphenoxy)phenyl]ethanone
• CAS: 35155-09-0
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: ONNQMNMXBCPHAF-UHFFFAOYSA-N

物化性质

• 熔点：
  122-125°C
• 沸点：
  444.3±38.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(4-苯基苯氧基)苯基]乙酮 在 叔丁基过氧化氢 、 乌洛托品 、 碘 、 碳酸氢钠 、 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 5-(5-(4-([1,1'-biphenyl]-4-yloxy)phenyl)oxazol-2-yl)-3-bromobenzene-1,2-diol
  参考文献：
  名称：

  Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) has been considered as a validated biological target for type 2 diabetes treatment, but past endeavors to develop inhibitors of PTP1B into drugs have been unsuccessful. Two challenging aspects are selective inhibition and cell permeability. A structure-based strategy was employed to develop uncharged bromophenols as a new series of PTP1B inhibitors. The most potent compound 22 (LXQ46) inhibited PTP1B with an IC50 value of 0.190 mu M, and showed remarkable selectivity over other protein tyrosine phosphatases (PTPs, 20-200 folds). In the SPR study, increasing concentrations of compound 22 led to concentration-dependent increases in binding responses, indicating that compound 22 could bind to the surface of PTP1B via noncovalent means. By treating insulin resistant C2C12 myotubes with compound 22, enhanced insulin and leptin signaling pathways were observed. Long-term oral administration of compound 22 reduced the blood glucose level of diabetic BKS db mice. The glucose tolerance tests (OGTT) and insulin tolerance tests (ITT) in BKS db mice showed that oral administration of compound 22 could increase insulin sensitivity. In addition, long-term oral administration of compound 22 could protect mice from obesity, which was not the result of toxicity. Our pharmacokinetics results from the rat-based assays showed that orally administered compound 22 was absorbed rapidly from the gastrointestinal tract, extensively distributed to the tissues, and rapidly eliminated from the body. All these results indicate that compound 22 could serve as a qualified agent to treat type II diabetes. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.01.057
• 作为产物：
  描述：

  对羟基联苯 、 4-氟苯乙酮 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 1-[4-(4-苯基苯氧基)苯基]乙酮
  参考文献：
  名称：

  6-(4′-Aryloxy-phenyl)vinyl-1,2,4-trioxanes: A new series of orally active peroxides effective against multidrug-resistant Plasmodium yoelii in Swiss mice

  摘要：

  A new series of 6-(4'-aryloxy-phenyl)vinyl-1,2,4-trioxanes 10a-d, 11a-d, and 12a-d have been synthesized and evaluated for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. Trioxanes 10b and 10c, the two most active compounds of the series, provided 100% protection to the infected mice at 48 mg/kg x 4 days. Clinically useful drug beta-arteether provided 100% and 20% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively, in this model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.045

文献信息

• Design, synthesis and biological evaluation of uncharged catechol derivatives as selective inhibitors of PTP1B
  作者：Xiang-Qian Li、Qi Xu、Jiao Luo、Li-Jun Wang、Bo Jiang、Ren-Shuai Zhang、Da-Yong Shi

  DOI：10.1016/j.ejmech.2017.05.007

  日期：2017.8

  obesity. However, the development of charged PTP1B inhibitors was restricted due to their low cell permeability and poor bioavailability. Based on active natural products, two series of uncharged catechol derivatives were identified as PTP1B inhibitors by targeting a secondary aryl phosphate-binding site as well as the catalytic site. The most potent inhibitor 22 showed an IC50 of 0.487 μM against PTP1B and

  蛋白质酪氨酸磷酸酶1B（PTP1B）是有效治疗T2DM和肥胖症的有希望且经过验证的治疗靶标。但是，带电的PTP1B抑制剂由于其低的细胞渗透性和较差的生物利用度而受到限制。基于活性天然产物，通过靶向磷酸二芳基酯结合位点和催化位点，鉴定了两个系列的不带电荷的邻苯二酚衍生物为PTP1B抑制剂。最有效的抑制剂22对PTP1B的IC 50为0.487μM，相对于TCPTP具有很强的选择性（27倍）。还进行了动力学研究，发现22种可作为竞争性PTP1B抑制剂。22例C2C12肌管的治疗显着增加了IRβ，Akt和IRS1的磷酸化水平。其作用谱与胰岛素产生的相似，表明其作为一种新的非胰岛素依赖性候选药物的潜力。
• [EN] SUBSTITUTED 4-ARYLOXY AND 4-ARYLSULFANYL-PHENYL-2-AMINOTHIAZOLES AS INHIBITORS OF CELL PROLIFERATION<br/>[FR] AMINOTHIAZOLES SUBSTITUES DE 4-ARYLOXY ET DE 4-ARYLSULFANYL-PHENYL-2 EN TANT QU'INHIBITEURS DE LA PROLIFERATION CELLULAIRE
  申请人：UNIV VIRGINIA

  公开号：WO2005044263A1

  公开（公告）日：2005-05-19

  The invention discloses compounds which are substituted 4-aryloxy and 4-arylsulfanyl-phenyl-2-aminothiazoles with anti-cancer activity. The invention futher discloses methods of preparing compounds of the invention. The invention also discloses methods of inhibiting cell proliferation and tumor growth in a subject by administering compounds of the invention to the subject.

  本发明揭示了一些具有抗癌活性的取代4-芳氧基和4-芳基硫醇基苯基-2-氨基噻唑的化合物。本发明还揭示了制备本发明化合物的方法。本发明还揭示了通过向受体内注射本发明化合物来抑制细胞增殖和肿瘤生长的方法。
• Substituted 4-aryloxy and 4-arylsulfanyl-phenyl-2-aminothiazoles as inhibitors of cell proliferation
  申请人：Gorczynski J. Michael

  公开号：US20070082934A1

  公开（公告）日：2007-04-12

  The invention discloses compounds which are substituted 4-aryloxy and 4-arylsulfanyl-phenyl-2-aminothiazoles with anti-cancer activity. The invention futher discloses methods of preparing compounds of the invention. The invention also discloses methods of inhibiting cell proliferation and tumor growth in a subject by administering compounds of the invention to the subject.

  本发明揭示了具有抗癌活性的取代4-芳氧基和4-芳基硫基苯基-2-氨基噻唑的化合物。本发明进一步揭示了制备本发明化合物的方法。本发明还揭示了通过将本发明化合物用于受试者来抑制细胞增殖和肿瘤生长的方法。
• Synthesis and evaluation of substituted 4-aryloxy- and 4-arylsulfanyl-phenyl-2-aminothiazoles as inhibitors of human breast cancer cell proliferation
  作者：Michael J. Gorczynski、Rachel M. Leal、Susan L. Mooberry、John H. Bushweller、Milton L. Brown

  DOI：10.1016/j.bmc.2003.12.003

  日期：2004.3

  Several substituted 4-aryloxy- and 4-arylsulfanyl-phenyl-2-aminothiazoles were synthesized and evaluated for cytotoxic activity against estrogen-positive, estrogen-negative, and adriamycin-resistant human breast cancer cell lines. 4-[4'-(3,4-Dichlorophenoxy)-phenyl]-thiazol-2-yl ammonium iodide demonstrated potent activity against both estrogen-positive and negative breast cancer cell lines with low micromolar (muM) GI(50) values. In addition, we have identified several 2-aminothiazoles that demonstrated selective potency for the adriamycin-resistant and estrogen-negative breast cancer cell lines. The results suggest that these 2-aminothiazoles represent lead compounds for evaluation in animal models of breast cancer. (C) 2003 Elsevier Ltd. All rights reserved.
• Baroni,E.E. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 2486 - 2489
  作者：Baroni,E.E. et al.

  DOI：——

  日期：——