1-(5-溴-2-羟基-3-碘苯基)乙酮 | 28467-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(5-溴-2-羟基-3-碘苯基)乙酮
• 英文名称: 5'-bromo-2'-hydroxy-3'-iodoacetophenone
• 英文别名: 1-(5-Bromo-2-hydroxy-3-iodophenyl)ethan-1-one；1-(5-bromo-2-hydroxy-3-iodophenyl)ethanone
• CAS: 28467-11-0
• 化学式: C₈H₆BrIO₂
• 分子量: 340.943
• InChiKey: SCFSMEJOAUYGGK-UHFFFAOYSA-N

物化性质

• 熔点：
  116°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-溴-2-羟基-3-碘苯基)乙酮 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 3-(2'-hydroxy-3'-iodo-5'-bromophenyl)-5-(3,4-methylenedioxyphenyl)-1-acetylpyrazoline
  参考文献：
  名称：

  Karamunge, Khushal G.; Sayyed, Mudassar A.; Vibhute, Archana Y., Journal of the Indian Chemical Society, 2011, vol. 88, # 3, p. 443 - 450

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 N-碘代丁二酰亚胺 、 溶剂黄146 作用下， 反应 3.5h， 生成 1-(5-溴-2-羟基-3-碘苯基)乙酮
  参考文献：
  名称：

  苯并呋喃添加的4-氨基喹唑啉杂化物作为表皮生长因子受体酪氨酸激酶抑制剂：合成，生物学评估和分子对接研究。

  摘要：

  制备了一系列附加有2-芳基苯并[b]呋喃的4-氨基喹唑啉杂化物，并评估了其对人肺癌（A549），大肠腺癌（Caco-2），肝细胞癌（C3A）和宫颈癌（ HeLa）细胞系。化合物10d和10j对C3A和Caco-2细胞系表现出明显的细胞毒性，并诱导了这些细胞系的凋亡。同样，化合物10d和10e对吉非替尼具有明显的表皮生长因子受体酪氨酸激酶磷酸化抑制作用（IC50值分别为29.3 nM和31.1 nM）。化合物10分子对接至EGFR-TK活性位点表明，它们与吉非替尼一样与EGFR区域结合。[公式：见文字]。

  DOI：

  10.1080/14756366.2018.1510919

文献信息

• A Practical Iodination of Aromatic Compounds by Using Iodine and Iodic Acid
  作者：Avinash T. Shinde、Sainath B. Zangade、Shivaji B. Chavan、Archana Y. Vibhute、Yogesh S. Nalwar、Yeshwant B. Vibhute

  DOI：10.1080/00397910903457332

  日期：2010.11.3

  This article describes simple and efficient method for the iodination of different aromatic amines, hydroxy aromatic aldehydes, hydroxy acetophenones and phenols using iodine and iodic acid in ethanol as a solvent. Notable advantages include mild reaction condition, no need of catalyst, short reaction time, simple practical procedure, giving excellent yield of the product.

  本文介绍了使用碘和碘酸在乙醇中作为溶剂对不同芳香胺、羟基芳香醛、羟基苯乙酮和苯酚进行碘化的简单有效方法。显着的优点是反应条件温和，无需催化剂，反应时间短，操作简单，产品收率高。
• Synthesis, Evaluation for Cytotoxicity and Molecular Docking Studies of Benzo[c]furan-Chalcones for Potential to Inhibit Tubulin Polymerization and/or EGFR-Tyrosine Kinase Phosphorylation
  作者：Malose Mphahlele、Marole Maluleka、Nishal Parbhoo、Sibusiso Malindisa

  DOI：10.3390/ijms19092552

  日期：——

  A series of 2-arylbenzo[c]furan-chalcone hybrids 3a–y have been synthesized and evaluated for antiproliferative effects against the human breast cancer (MCF-7) cell line and for its potential to induce apoptosis and also to inhibit tubulin polymerization and/or epidermal growth factor receptor-tyrosine kinase (EGFR-TK) phosphorylation. Most of these compounds exhibited moderate to significant antigrowth effects in vitro against the MCF-7 cell line when compared to the reference standard actinomycin D. The capabilities of the most cytotoxic benzofuran-chalcone hybrids 3b and 3i, to induce apoptosis, have been evaluated by Annexin V-Cy3 SYTOX staining and caspase-3 activation. The experimental and molecular docking results suggest that the title compounds have the potential to exhibit inhibitory effects against tubulin polymerization and epidermal growth factor receptor tyrosine kinase (EGFR-TK) phosphorylation. The modeled structures of representative compounds displayed hydrophobic interactions as well as hydrogen and/or halogen bonding with the protein residues. These interactions are probably responsible for the observed increased binding affinity for the two receptors and their significant antigrowth effect against the MCF-7 cell line.

  一系列2-芳基苯并[c]呋喃-香豆素杂合物3a-y已合成并评估其对人类乳腺癌（MCF-7）细胞系的抗增殖效果，以及其诱导凋亡的潜力，还有抑制微管聚合和/或表皮生长因子受体酪氨酸激酶（EGFR-TK）磷酸化的能力。与参考标准阿霉素D相比，大多数这些化合物在体外对MCF-7细胞系表现出中等到显著的抗生长效果。最具细胞毒性的苯并呋喃-香豆素杂合物3b和3i的诱导凋亡能力已通过Annexin V-Cy3 SYTOX染色和caspase-3激活评估。实验和分子对接结果表明，这些化合物具有潜力对微管聚合和表皮生长因子受体酪氨酸激酶（EGFR-TK）磷酸化展现出抑制作用。代表性化合物的模拟结构显示出与蛋白质残基的疏水相互作用以及氢键和/或卤素键。这些相互作用可能是导致这两个受体的结合亲和力增加以及对MCF-7细胞系的显著抗生长效果的原因。
• A simple and efficient method for solvent-free iodination of hydroxylated aromatic aldehydes and ketones using iodine and iodic acid by grinding method
  作者：Archana Vibhute、Shyam Mokle、Khushal Karamunge、Vasant Gurav、Yeshwant Vibhute

  DOI：10.1016/j.cclet.2010.04.008

  日期：2010.8

  Green, mild and efficient iodination of hydroxylated aromatic aldehydes and ketones using iodine and iodic acid in the solid-state by grinding under solvent-free conditions at room temperature. This method provides several advantages such as environmentally friendly, short reaction times, high yields, non-hazardous and simple work-up procedure.

  通过在室温下在无溶剂条件下研磨，使用固态的碘和碘酸对羟基化的芳族醛和酮进行绿色，温和且有效的碘化。该方法具有许多优点，例如环境友好，反应时间短，产率高，无害且后处理程序简单。
• Pyridinium Iodochloride: An Efficient Reagent for Iodination of Hydroxylated Aromatic Ketones and Aldehydes
  作者：Sandeep V. Khansole、Shyam S. Mokle、Mudassar A. Sayyed、Yeshwant B. Vibhute

  DOI：10.1002/jccs.200800130

  日期：2008.8

  Direct iodination of several reactive aromatic compounds like hydroxy substituted acetophenones and aldehydes with pyridinium iodochloride (PyICI) proceeded smoothly to afford the corresponding aromatic iodides in good to excellent yield. Pyridinium iodochloride has been found to be an efficient solid iodinating reagent with no hazardous effect and it can be handled safely.

  用碘氯化吡啶鎓 (PyICI) 对几种反应性芳族化合物（如羟基取代的苯乙酮和醛）进行直接碘化反应顺利进行，以良好至优异的收率得到相应的芳族碘化物。碘氯化吡啶鎓已被发现是一种有效的固体碘化试剂，没有有害影响，并且可以安全处理。
• [EN] PHOSPHOINOSITIDE 3 KINASE BETA INHIBITORS AND COMPOSITIONS AND METHODS THEREOF<br/>[FR] INHIBITEURS DE LA PHOSPHOINOSITIDE 3 KINASE BÊTA ET COMPOSITIONS ET PROCÉDÉS ASSOCIÉS
  申请人：GEODE THERAPEUTICS INC

  公开号：WO2022164812A1

  公开（公告）日：2022-08-04

  The invention provides novel phosphoinositide 3 kinase beta- selective inhibitors and pharmaceutical compositions thereof, as well as methods of their preparation and use, in therapy of various diseases and conditions, such as solid tunors.

  该发明提供了一种新型的磷脂酰肌醇3激酶β选择性抑制剂及其制备和应用方法，用于治疗各种疾病和病况，例如实体肿瘤。同时还提供了相关的制药组合物。