2-丙烯-1-酮,1-(4-氯苯基)-3-[4-(1-甲基乙基)苯基]- | 169802-85-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 2-丙烯-1-酮,1-(4-氯苯基)-3-[4-(1-甲基乙基)苯基]-
• 英文名称: 1-(4-chlorophenyl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one
• 英文别名: (E)-1-(4-chlorophenyl)-3-(4-isopropylphenyl)-2-propen-1-one；1-(4-chlorophenyl)-3-(4-propan-2-ylphenyl)prop-2-en-1-one
• CAS: 169802-85-1
• 化学式: C₁₈H₁₇ClO
• 分子量: 284.785
• InChiKey: RYGRDEVSSARKGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-丙烯-1-酮,1-(4-氯苯基)-3-[4-(1-甲基乙基)苯基]- 在 sodium tetrahydroborate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 cis-5-(4-chlorophenyl)-7-(4-isopropylphenyl)-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Triazolo-pyrimidine Derivatives as Novel Inhibitors of Hepatitis B Virus Surface Antigen (HBsAg) Secretion

  摘要：

  The high levels of hepatitis B virus (HBV) surface antigen (HBsAg)-bearing subviral particles in the serum of chronically infected individuals play an important role in suppressing HBV-specific immune response and are only mildly affected by the current small molecule therapies. Thus, a therapy that specifically reduces HBsAg serum levels could be used in combination therapy with nucleos(t)ide drugs or permit therapeutic vaccination for the treatment of HBV infection. Herein, we report the design, synthesis, and evaluation of novel triazolo-pyrimidine inhibitors (1, 3, and 4) of HBsAg cellular secretion, with activity against drug-resistant HBV variants. Extensive SAR led to substantial improvements in the EC50 of the parent compound, 5 (HBF-0259), with the best being 3c, with EC50 = 1.4 +/- 0.4 mu M, SI >= 36. The lead candidates, both la (PBHBV-001) and 3c (PBHBV-2-15), were well-tolerated in both normal and HBV-transgenic mice and exhibited acceptable pharmacokinetics and bioavailability in Sprague-Dawley rats.

  DOI：

  10.1021/jm200696v
• 作为产物：
  描述：

  对氯苯乙酮 、 4-异丙基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以89%的产率得到2-丙烯-1-酮,1-(4-氯苯基)-3-[4-(1-甲基乙基)苯基]-
  参考文献：
  名称：

  多功能（2）-1-（4-氯苯基）-3- [4-（丙-2-基）苯基] prop-2-en-1-one的生物活性吡唑啉衍生物

  摘要：

  通过使水合肼及其衍生物与（2）-1-（4-氯苯基）-3- [4-（丙-2-基）苯基] prop-2反应，合成了一系列新的具有生物活性的N-取代吡唑啉衍生物。 -en-1-one，其随后通过碱催化4-（丙-2-基）苯甲醛与4-氯苯乙酮的克莱森-施密特缩合反应。筛选所有合成的化合物2a-e，3a-d，4a，b和5a-c的体外抗菌，抗氧化剂，抗增殖特性，并评估化合物3b，4b的体内抗炎活性。对这些化合物与TREX1（PDB：3B60）的抗α-淀粉酶的对接研究进行了预测，以预测它们的相互作用。一些测试化合物显示出显着的抗菌，抗氧化剂，抗增殖，抗炎活性和分子结合。

  DOI：

  10.2174/1570180813666160519151723

文献信息

• Chemoselective Reduction of α,β-Unsaturated Carbonyl Compounds via a CS₂/<i>t-</i>BuOK System: Dimethyl Sulfoxide as a Hydrogen Source
  作者：Saideh Rajai-Daryasarei、Mir Sadra Hosseini、Saeed Balalaie

  DOI：10.1021/acs.joc.3c00903

  日期：2023.8.4

  A novel and practical approach to access saturated ketones from unsaturated ketone derivatives via a CS2/t-BuOK system in dimethyl sulfoxide (DMSO) is reported. The in situ generation of xanthate salt through the reaction of carbon disulfide and potassium tert-butoxide is essential to this transformation. Deuterium-labeling experiments demonstrated that DMSO can act as a hydrogen donor.

  报道了一种通过二甲基亚砜 (DMSO) 中的CS 2 / t- BuOK 系统从不饱和酮衍生物中获取饱和酮的新颖且实用的方法。通过二硫化碳和叔丁醇钾的反应原位生成黄原盐对于这种转变至关重要。氘标记实验表明 DMSO 可以充当氢供体。
• Biologically Potent Pyrazoline Derivatives from Versatile (2)-1-(4- Chlorophenyl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one
  作者：Vinutha Salian、Badiadka Narayana、Balladka Sarojini、Enumadisetty Sindhupriya、Leelavathi Madhu、Shama Rao

  DOI：10.2174/1570180813666160519151723

  日期：2016.12.21

  with (2)-1-(4-chlorophenyl)-3-[4-(propan-2- yl)phenyl]prop-2-en-1-one, which in turn prepared by the base catalysed Claisen-Schmidt condensation reaction of 4-(propan-2-yl)benzaldehyde and 4-chloroacetophenone. All the synthesized compounds, 2a-e, 3a-d, 4a,b and 5a-c were screened for their in vitro antibacterial, antioxidant, antiproliferative properties and compounds 3b, 4b were evaluated for in

  通过使水合肼及其衍生物与（2）-1-（4-氯苯基）-3- [4-（丙-2-基）苯基] prop-2反应，合成了一系列新的具有生物活性的N-取代吡唑啉衍生物。 -en-1-one，其随后通过碱催化4-（丙-2-基）苯甲醛与4-氯苯乙酮的克莱森-施密特缩合反应。筛选所有合成的化合物2a-e，3a-d，4a，b和5a-c的体外抗菌，抗氧化剂，抗增殖特性，并评估化合物3b，4b的体内抗炎活性。对这些化合物与TREX1（PDB：3B60）的抗α-淀粉酶的对接研究进行了预测，以预测它们的相互作用。一些测试化合物显示出显着的抗菌，抗氧化剂，抗增殖，抗炎活性和分子结合。
• Design, Synthesis, and Biological Evaluation of Triazolo-pyrimidine Derivatives as Novel Inhibitors of Hepatitis B Virus Surface Antigen (HBsAg) Secretion
  作者：Wenquan Yu、Cally Goddard、Elizabeth Clearfield、Courtney Mills、Tong Xiao、Haitao Guo、John D. Morrey、Neil E. Motter、Kang Zhao、Timothy M. Block、Andrea Cuconati、Xiaodong Xu

  DOI：10.1021/jm200696v

  日期：2011.8.25

  The high levels of hepatitis B virus (HBV) surface antigen (HBsAg)-bearing subviral particles in the serum of chronically infected individuals play an important role in suppressing HBV-specific immune response and are only mildly affected by the current small molecule therapies. Thus, a therapy that specifically reduces HBsAg serum levels could be used in combination therapy with nucleos(t)ide drugs or permit therapeutic vaccination for the treatment of HBV infection. Herein, we report the design, synthesis, and evaluation of novel triazolo-pyrimidine inhibitors (1, 3, and 4) of HBsAg cellular secretion, with activity against drug-resistant HBV variants. Extensive SAR led to substantial improvements in the EC50 of the parent compound, 5 (HBF-0259), with the best being 3c, with EC50 = 1.4 +/- 0.4 mu M, SI >= 36. The lead candidates, both la (PBHBV-001) and 3c (PBHBV-2-15), were well-tolerated in both normal and HBV-transgenic mice and exhibited acceptable pharmacokinetics and bioavailability in Sprague-Dawley rats.