4-(4-丙-2-基苯氧基)苯甲醛 | 61343-86-0

• 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: 4-(4-丙-2-基苯氧基)苯甲醛
• 英文名称: 4-(4-Isopropyl-phenoxy)-benzaldehyde
• 英文别名: 4-(4-Isopropylphenoxy)benzaldehyde；4-(4-propan-2-ylphenoxy)benzaldehyde
• CAS: 61343-86-0
• 化学式: C₁₆H₁₆O₂
• mdl: MFCD09705644
• 分子量: 240.302
• InChiKey: CCHLJWKIPGOLAP-UHFFFAOYSA-N

物化性质

• 沸点：
  350.4±35.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 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：

  4-(4-丙-2-基苯氧基)苯甲醛 在 间氯过氧苯甲酸 作用下， 生成 4-isopropyl-4'-hydroxydiphenyl ether
  参考文献：
  名称：

  5-Aryl thiazolidine-2,4-diones: discovery of PPAR dual α/γ agonists as antidiabetic agents

  摘要：

  A novel series of 5-aryl tliiazolidine-2,4-diones based dual PPARalpha/gamma agonists was identified. A number of highly potent and orally bioavailable analogues were synthesized. Efficacy study results of some of these analogues in the db/db mice model of type 2 diabetes showed them superior to rosiglitazone in correcting hyperglycemia and hypertriglyceridemia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00505-5
• 作为产物：
  描述：

  4-异丙基苯酚 、 对氟苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 4-(4-丙-2-基苯氧基)苯甲醛
  参考文献：
  名称：

  5-Aryl thiazolidine-2,4-diones: discovery of PPAR dual α/γ agonists as antidiabetic agents

  摘要：

  A novel series of 5-aryl tliiazolidine-2,4-diones based dual PPARalpha/gamma agonists was identified. A number of highly potent and orally bioavailable analogues were synthesized. Efficacy study results of some of these analogues in the db/db mice model of type 2 diabetes showed them superior to rosiglitazone in correcting hyperglycemia and hypertriglyceridemia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00505-5

文献信息

• A Novel Class of Inhibitors for Human and Rat Steroid 5.ALPHA.-Reductases: Synthesis and Biological Evaluation of Indoline and Aniline Derivatives. III.
  作者：Susumu IGARASHI、Hiroshi INAMI、Hiromu HARA、Hiroshi KOUTOKU、Hiroyuki ORITANI、Toshiyasu MASE

  DOI：10.1248/cpb.48.1689

  日期：——

  While searching for novel nonsteroidal inhibitors of human and rat prostatic 5α-reductases, we found a new series of indoline and aniline derivatives that showed potent inhibitory activities for both enzymes. Among them, 3-chloro-4-1-(4-phenoxybenzyl)indolin-5-yl]oxy}benzoic acid (2e, YM-36117) showed a more portent inhibitory activity for the human enzyme than ONO-3805 with an IC50 value of 5.3 nM and a reduced rat prostatic dihydrotestosterone (DHT) concentration by oral administration. The synthesis and the structure-activity relationships of these indoline and aniline derivatives are presented.

  在寻找新型人类和大鼠前列腺5α-还原酶的非甾体抑制剂时，我们发现了一系列新的吲哚啶和芳胺衍生物，这些化合物对这两种酶均表现出强效的抑制活性。其中，3-氯-4-1-(4-苯氧苄基)吲哚啶-5-基}氧基苯甲酸（2e，YM-36117）对人类酶的抑制活性比ONO-3805更强，IC50值为5.3 nM，并且通过口服给药降低了大鼠前列腺二氢睾酮（DHT）浓度。这些吲哚啶和芳胺衍生物的合成及其结构-活性关系进行了阐述。
• Investigation of stereoisomeric bisarylethenesulfonic acid esters for discovering potent and selective PTP1B inhibitors
  作者：Fangzhou Xie、Fengzhi Yang、Yaoyao Liang、Liang Li、Yu Xia、Faqin Jiang、Wenlu Liu、Yunyue Qi、Sharmin Reza Chowdhury、Dongsheng Xie、Lei Fu

  DOI：10.1016/j.ejmech.2018.12.032

  日期：2019.2

  work, a series of cis- and trans-pyrrolidine bisarylethenesulfonic acid esters were prepared and their PTP1B inhibitory potency, selectivity and membrane permeability were evaluated. These novel stereoisomeric molecules especially trans-isomers exhibited remarkable inhibitory activity, significant selectivity as well as good membrane permeability (e.g. compound 28a, IC50 = 120, 1940 and 2670 nM against

  由于蛋白质酪氨酸磷酸酶1B（PTP1B）在胰岛素信号传导和瘦素受体途径中的关键调节作用，因此已被认为是2型糖尿病（T2DM）和肥胖症的有希望的治疗靶标。在这项工作中，制备了一系列顺式和反式吡咯烷双芳基磺酸磺酸酯，并评估了其对PTP1B的抑制力，选择性和膜通透性。这些新颖的立体异构分子，特别是反式异构体，表现出显着的抑制活性，显着的选择性以及良好的膜渗透性（例如，化合物28a，IC 50  = 120、1940和2670 nM，分别针对PTP1B，TCPTP和SHP2，以及P app = 1.74×10 -6  cm / s）。分子模拟表明，通过与PTP1B的非催化位点建立更多的相互作用，反式-吡咯烷双芳基磺酸磺酸酯比其顺式异构体具有更强的结合亲和力。进一步的生物学活性研究表明，化合物28a可以增强胰岛素刺激的葡萄糖摄取和胰岛素介导的胰岛素受体β（IRβ）磷酸化，而没有明显的细胞毒性。
• 5-Aryl thiazolidine-2,4-diones: discovery of PPAR dual α/γ agonists as antidiabetic agents
  作者：Ranjit C. Desai、Wei Han、Edward J. Metzger、Jeffrey P. Bergman、Dominick F. Gratale、Karen L. MacNaul、Joel P. Berger、Thomas W. Doebber、Kwan Leung、David E. Moller、James V. Heck、Soumya P. Sahoo

  DOI：10.1016/s0960-894x(03)00505-5

  日期：2003.8

  A novel series of 5-aryl tliiazolidine-2,4-diones based dual PPARalpha/gamma agonists was identified. A number of highly potent and orally bioavailable analogues were synthesized. Efficacy study results of some of these analogues in the db/db mice model of type 2 diabetes showed them superior to rosiglitazone in correcting hyperglycemia and hypertriglyceridemia. (C) 2003 Elsevier Ltd. All rights reserved.