3,5-bis((E)-3-bromobenzylidene)-1-methylpiperidin-4-one | 1401079-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,5-bis((E)-3-bromobenzylidene)-1-methylpiperidin-4-one
• 英文别名: (3E,5E)-3,5-bis[(3-bromophenyl)methylidene]-1-methylpiperidin-4-one
• CAS: 1401079-50-2
• 化学式: C₂₀H₁₇Br₂NO
• 分子量: 447.169
• InChiKey: KHBXHLSTIOLHQI-GONBZBRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-bis((E)-3-bromobenzylidene)-1-methylpiperidin-4-one 、 苄脒盐酸盐 在 amino functionalized mesoporous silica decorated with iron oxide nanoparticles 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以92%的产率得到(E)-8-(3-bromobenzylidene)-4-(3-bromophenyl)-5,6,7,8-tetrahydro-6-methyl-2-phenylpyrido[4,3-d]pyrimidine
  参考文献：
  名称：

  Amino functionalized mesoporous silica decorated with iron oxide nanoparticles as a magnetically recoverable nanoreactor for the synthesis of a new series of 2,4-diphenylpyrido[4,3-d]pyrimidines

  摘要：

  (Fe2O3)–MCM-41–nPrNH2作为一种可磁性回收的纳米反应器，通过在干燥甲苯中回流(Fe2O3)–MCM-41与3-氨丙基三乙氧基硅烷的反应制备而成。含有10 wt%负载的氧化铁纳米颗粒的催化剂被发现是一种高效的纳米催化剂，在无溶剂条件下合成新型2,4-二苯基吡啶并[4,3-d]嘧啶，产率高到接近定量。通过使用外部磁铁，催化剂可以被回收并多次重复使用，而没有效率损失。制备的催化剂通过透射电子显微镜(TEM)、傅里叶变换红外光谱(FT-IR)、X射线粉末衍射(XRD)和氮气物理吸附测量进行了表征。

  DOI：

  10.1039/c4ra00038b
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 间溴苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3,5-bis((E)-3-bromobenzylidene)-1-methylpiperidin-4-one
  参考文献：
  名称：

  Amino functionalized mesoporous silica decorated with iron oxide nanoparticles as a magnetically recoverable nanoreactor for the synthesis of a new series of 2,4-diphenylpyrido[4,3-d]pyrimidines

  摘要：

  (Fe2O3)–MCM-41–nPrNH2作为一种可磁性回收的纳米反应器，通过在干燥甲苯中回流(Fe2O3)–MCM-41与3-氨丙基三乙氧基硅烷的反应制备而成。含有10 wt%负载的氧化铁纳米颗粒的催化剂被发现是一种高效的纳米催化剂，在无溶剂条件下合成新型2,4-二苯基吡啶并[4,3-d]嘧啶，产率高到接近定量。通过使用外部磁铁，催化剂可以被回收并多次重复使用，而没有效率损失。制备的催化剂通过透射电子显微镜(TEM)、傅里叶变换红外光谱(FT-IR)、X射线粉末衍射(XRD)和氮气物理吸附测量进行了表征。

  DOI：

  10.1039/c4ra00038b

文献信息

• [EN] METHOD FOR THE PROGNOSIS AND/OR TREATMENT OF ACUTE PROMYELOCYTIC LEUKEMIA<br/>[FR] MÉTHODE DE PRONOSTIC ET/OU DE TRAITEMENT DE LA LEUCÉMIE PROMYÉLOCYTAIRE AIGUË
  申请人：EPI-C S R L

  公开号：WO2017198870A1

  公开（公告）日：2017-11-23

  The present invention relates to a method for the diagnostic of low overall survival acute promyelocytic leukemia and/or of predicting and/or monitoring the response and/or the efficacy of a therapy for acute promyelocytic leukemia or to identify a subject to be treated with an inhibitor of HAT and/or an inhibitor of EZH2 comprising determining the acetylation or methylation status of specific relevant regions and relative kit and microarray. The invention also refers to histone acetyl transferase (HAT) inhibitor for use in the treatment of a solid or hematopoietic tumor.

  本发明涉及一种用于诊断低总生存急性早幼粒细胞白血病和/或预测和/或监测急性早幼粒细胞白血病治疗的反应和/或疗效或确定应使用HAT抑制剂和/或EZH2抑制剂治疗的受试者的方法，包括确定特定相关区域的乙酰化或甲基化状态和相关试剂盒和微阵列。该发明还涉及组蛋白乙酰转移酶（HAT）抑制剂用于治疗实体或造血肿瘤。
• [EN] INHIBITORS OF THE WNT/BETA-CATENIN PATHWAY<br/>[FR] INHIBITEURS DE LA VOIE WNT/BÊTA-CATÉNINE
  申请人：UNIV CALIFORNIA

  公开号：WO2019152536A1

  公开（公告）日：2019-08-08

  The present disclosure relates to compounds that are capable of modulating the WNT/Beta-Catenin pathway. The disclosure further relates to methods of treating colorectal cancer and other WNT/Beta-Catenin mediated cancers.

  本披露涉及能够调节WNT/Beta-Catenin通路的化合物。此外，该披露还涉及治疗结直肠癌和其他WNT/Beta-Catenin介导的癌症的方法。
• A Facile Stereoselective Domino Approach for the Construction of Novel Bis(spiropiperidone)–Tetrahydrothiophene Hybrid Heterocycles
  作者：Subbu Perumal、Chelliah Bharkavi、Sundaravel Kumar

  DOI：10.1055/s-0034-1380722

  日期：——

  A library of novel bis-spiropiperidone–tetrahydrothiophene hybrid heterocycles have been synthesized via pseudo-three-component domino reaction of (3 E ,5 E )-3,5-bis(arylidene)-1-methyl/benzyl piperidin-4-ones and 1,4-dithiane-2,5-diol in the presence of triethylamine. This transformation presumably proceeds via two annulations each involving the generation of 2-mercaptoacetaldehyde from 1,4-dithiane-2

  通过 (3 E ,5 E )-3,5-双(亚芳基)-1-甲基/苄基哌啶-4-酮的假三组分多米诺反应合成了新型双螺哌啶酮-四氢噻吩杂环化合物库和 1,4-二噻烷-2,5-二醇在三乙胺的存在下。这种转化大概是通过两个环化进行的，每个环化都涉及从 1,4-二噻烷-2,5-二醇-迈克尔加成-分子内醛醇序列生成 2-巯基乙醛，这导致在一锅操作中产生四个新键。该协议的优点是原子经济性高、立体选择性高、反应时间短、操作简单。
• Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
  作者：Lorraine M. Deck、Lucy A. Hunsaker、Thomas A. Vander Jagt、Lisa J. Whalen、Robert E. Royer、David L. Vander Jagt

  DOI：10.1016/j.ejmech.2017.11.048

  日期：2018.1

  Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability, to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues. (C) 2017 Published by Elsevier Masson SAS.
• Synthesis, cytotoxicity, and structure–activity insight of NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidones
  作者：Matthew Gregory、Armaan Dandavati、Megan Lee、Samuel Tzou、Mia Savagian、Kimberly A. Brien、Vijay Satam、Pravin Patil、Moses Lee

  DOI：10.1007/s00044-013-0557-9

  日期：2013.11

  Twenty-one NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidone analogs of curcumin, 12 of which are novel, were synthesized and evaluated for their cytotoxicity against B16 (murine melanoma) and L1210 (murine lymphoma) cells grown in culture. These curcumin analogs are related to a known anticancer STAT3 inhibitor 3,5-bis-(4-fluorobenzyl)-4-piperidone (3). The compounds showed remarkable cytotoxicity, especially against B16 cells. The dimethoxy substituted analogs 4e and 4f and dihydroxy analog 4i emerged as the most active compounds with IC50 values in the range of 0.2-2.3 mu M. 4e, f, and i were about 10-times more cytotoxic against both cell lines than 3. Analysis of the results demonstrates that the position of the hydroxyl group is crucial for cytotoxicity. Amino-containing analogs are generally less active than their halogenated and oxygen-containing analogs, and N-substitution in the 4-piperidone moiety adds value to the cytotoxicity of the compounds.