4-(2-bromoacetyl)benzaldehyde | 951656-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-bromoacetyl)benzaldehyde
• 英文别名: α-bromo-4-formylacetophenone；4-(bromoacetyl)benzaldehyde
• CAS: 951656-07-8
• 化学式: C₉H₇BrO₂
• 分子量: 227.057
• InChiKey: NGRCWWOAGMFRNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-bromoacetyl)benzaldehyde 在 sodium hydroxide 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 trans-3-[4-(benzofuran-2-carbonyl)phenyl]acrylic acid
  参考文献：
  名称：

  2-Aroylindoles and 2-Aroylbenzofurans with N-Hydroxyacrylamide Substructures as a Novel Series of Rationally Designed Histone Deacetylase Inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors are considered to be drugs for targeted cancer therapy and second-generation HDIs are currently being tested in clinical trials. Here, we report on the synthesis and biological evaluation of a novel HDAC inhibitor scaffold with the hydroxamate Zn2+ complexing headgroup, selected from the 2-aroylindol motif. Inhibition of nuclear extract HDAC and recombinant HDAC I as well as induction of histone H3K(9+14) hyperacetylation mediated by E-N-hydroxy-(2-aroylindole)acrylamides or E-Nhydroxy-(2-aroylbenzofuran)acrylamides were studied. Moreover, the cytotoxic activity, the effects on the cell cycle, and historic H3S(10) phosphorylation of selected compounds were determined. By use of a panel of 24 different human tumor cell lines, mean IC50 values of the most potent analogues 6c and 7b were 0.75 and 0.65 mu M, respectively. The novel compounds were shown to be no substrates of the P-glycoprotein drug transporter. Comparable to N-1-hydroxy-N-8-phenyloctanediamide "2 (SAHA)", cells in the S phase of the cell cycle are depleted, with partial arrest in G1 and G2/M and finally induction of massive apoptosis.

  DOI：

  10.1021/jm0703136
• 作为产物：
  描述：

  1-[4-(1,3-二氧杂烷-2-基)苯基]乙酮 在 对甲苯磺酸 、 copper(I) bromide 作用下， 以 水 、 丙酮 、 氯仿 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 4-(2-bromoacetyl)benzaldehyde
  参考文献：
  名称：

  [EN] FUSED IMIDAZOLES FOR CANCER TREATMENT
  [FR] IMIDAZOLES FUSIONNÉS POUR LE TRAITEMENT DU CANCER

  摘要：

  式(I)的化合物，其互变异构体或立体异构体，或其盐，其中环B和与其融合的咪唑，R4、R6和R7的含义如描述和权利要求中所述，是Pi3K/Akt途径的有效抑制剂。

  公开号：

  WO2009021990A1

文献信息

• FUSED BICYCLIC IMIDAZOLES
  申请人：HOLDER Swen

  公开号：US20090156604A1

  公开（公告）日：2009-06-18

  Compounds of formula (I) a tautomer or stereoisomer thereof, or a salt thereof, wherein ring B and the imidazole to which it is fused, R4, R6 and R7 have the meanings as given in the description and the claims, are effective inhibitors of the Pi3K/Akt pathway.

  式(I)的化合物或其互变异构体或立体异构体，或其盐，其中环B和其融合的咪唑环，R4，R6和R7的含义如描述和权利要求中所述，是Pi3K/Akt途径的有效抑制剂。
• Catalyst-Free Synthesis of Quinoxalines
  作者：Dongming Lu、Qinjie Xiang、Lihong Zhou、Qingle Zeng

  DOI：10.14233/ajchem.2015.18680

  日期：——

  Quinoxalines are a class of important heterocycles, so to explore a facile and practical new synthetic method is always demanded. We have developed a new catalyst-free domino synthesis of quinoxalines from phenacyl halides and 1,2-diaminoarenes. Phenacyl chlorides with lower activities are first used in synthesis of quinoxalines and afford up to 97 % yield with our protocol. Our process with sodium bicarbonate as deacid reagent is catalyst-free, simple, greener and practical.

  喹喔啉类化合物是一类重要的杂环化合物，因此一直需要探索一种简便实用的新合成方法。我们开发了一种无催化剂多米诺合成喹喔啉类化合物的新方法。在合成喹喔啉类化合物时，首先使用活性较低的苯酰基氯，在我们的方案下，产率可达 97%。我们采用碳酸氢钠作为脱酸试剂的工艺无需催化剂，简单、环保且实用。
• [EN] IMIDAZOPYRIDINE AND RELATED ANALOGS AS SIRTUIN MODULATORS<br/>[FR] IMIDAZOPYRIDINE ET ANALOGUES LIÉS EN TANT QUE MODULATEURS DE LA SIRTUINE
  申请人：SIRTRIS PHARMACEUTICALS INC

  公开号：WO2009146358A1

  公开（公告）日：2009-12-03

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了新颖的调节sirtuin的化合物及其使用方法。这些调节sirtuin的化合物可用于增加细胞的寿命，并用于治疗和/或预防各种疾病和紊乱，包括与老化或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块紊乱、炎症、癌症、潮红以及需要增加线粒体活性的疾病或紊乱相关的疾病或紊乱。还提供了包含sirtuin调节化合物与另一种治疗剂组合的组合物。
• [EN] BICYCLIC COMPOUNDS, COMPOSITIONS AND MEDICINAL APPLICATIONS THEREOF<br/>[FR] COMPOSÉS BICYCLIQUES, COMPOSITIONS ET APPLICATIONS MÉDICINALES DE CEUX-CI
  申请人：ADVINUS THERAPEUTICS LTD

  公开号：WO2013157021A1

  公开（公告）日：2013-10-24

  The present disclosure relates to a class of substituted bicyclic compounds of formula (I), their tautomers, polymorphs, stereoisomers, prodrugs, solvates, hydrates, N-oxides, co-crystals, pharmaceutically acceptable salts and pharmaceutical compositions containing them. The disclosure also relates to the process of preparation of compounds of Formula (I). These compounds are useful in the treatment, prevention, prophylaxis, management, or adjunct treatment of all medical conditions related to inhibition of Bruton's tyrosine kinase (Btk), such as inflammatory and/or autoimmune disorder, cell proliferation, rheumatoid arthritis, psoriasis, psoriatic arthritis, transplant rejection, graft-versus-host disease, multiple sclerosis, inflammatory bowel disease, allergic diseases, asthma, type 1 diabetes, myasthenia gravis, hematopoetic disfunction, B-cell malignancies, systemic lupus, erythematosus or other disorders.

  本公开涉及一类式（I）的取代双环化合物，它们的互变异构体、多晶形态、立体异构体、前药、溶剂化物、水合物、N-氧化物、共晶体、药学上可接受的盐和含有它们的制药组合物。本公开还涉及制备式（I）化合物的方法。这些化合物在治疗、预防、预防、管理或辅助治疗与布鲁顿酪氨酸激酶（Btk）抑制有关的所有医疗状况方面有用，例如炎症和/或自身免疫性疾病、细胞增殖、类风湿性关节炎、银屑病、银屑病性关节炎、移植排斥、移植物抗宿主病、多发性硬化症、炎症性肠病、过敏性疾病、哮喘、1型糖尿病、重症肌无力、造血功能障碍、B细胞恶性肿瘤、系统性红斑狼疮或其他疾病。
• 苯基三嗪化合物的制备方法及苯基吡啶化合 物的制备方法
  申请人：中国科学院长春应用化学研究所

  公开号：CN108586369B

  公开（公告）日：2021-08-17

  本发明涉及化合物的合成技术领域，尤其涉及一种苯基三嗪化合物的制备方法及苯基吡啶化合物的制备方法，本发明将具有式(I)所示结构的化合物、具有式(Ⅱ)所示结构的化合物、有机质子酸、铵盐和第一有机溶剂进行亲核加成反应和成环反应，制得具有式(Ⅲ)所示结构的苯基三嗪化合物，反应中无需使用贵金属催化剂，反应收率和纯度均较高。然后将上述方法制备的具有式(Ⅲ)所示结构的苯基三嗪化合物、降冰片二烯和第二有机溶剂进行逆Diels‑Alder反应，得到具有式(Ⅵ)所示结构的苯基吡啶化合物，反应中无需使用贵金属催化剂，反应收率和纯度均较高。另外，本发明提供的制备方法路线简洁，过程可控性好，成本较低，易于工业化生产。