7-溴-2-(甲硫基)苯并[d]恶唑 | 1013642-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 7-溴-2-(甲硫基)苯并[d]恶唑
• 英文名称: 7-bromo-2-(methylthio)benzo[d]oxazole
• 英文别名: 7-Bromo-2-(methylthio)benzo[d]oxazole；7-bromo-2-methylsulfanyl-1,3-benzoxazole
• CAS: 1013642-98-2
• 化学式: C₈H₆BrNOS
• 分子量: 244.112
• InChiKey: XDPAKUGGKFDPSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-溴-2-(甲硫基)苯并[d]恶唑 在 potassium acetate 、 间氯过氧苯甲酸 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 三环己基膦 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3,4,5-trimethoxyphenyl)benzo[d]oxazol-2-amine
  参考文献：
  名称：

  2-Amino-7-substituted benzoxazole analogs as potent RSK2 inhibitors

  摘要：

  2-Amino-7-substituted benzoxazole analogs were identified by HTS as inhibitors of RSK2. Molecular modeling and medicinal chemistry techniques were employed to explore the SAR for this series with a focus of improving in vitro and target modulation potency and physicochemical properties. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.058
• 作为产物：
  描述：

  2-溴-6-硝基苯酚 在 tin(II) chloride dihdyrate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 7-溴-2-(甲硫基)苯并[d]恶唑
  参考文献：
  名称：

  Design, synthesis, and evaluation of the anticancer activity of 2-amino-aryl-7-aryl-benzoxazole compounds

  摘要：

  A series of 2‐amino‐aryl‐7‐aryl‐benzoxazole derivatives have been designed, synthesized, and evaluated as anticancer agents. Fourteen of the compounds exhibited cytotoxic effects toward human A549 lung cancer cells. We found 12l was the most potent with an EC50 of 0.4 μm, equivalent to the anticancer drug doxorubicin, but had low selectivity following cross screening in monkey kidney Vero cells. Eight of the most potent or most selective compounds were further profiled in additional cell lines (MCF7, NCI‐H187, and KB) to better understand their cytotoxic activity. Only compound 12l had a measurable EC50 in a single cell line (3.3 μm in the KB cell line). Taken together, this data suggest the series as a whole display specific cytotoxicity toward A549 cells. Cheminformatics searches pointed to JAK2 as a possible target. A subset of compounds assayed at this target showed IC50s ranging from 10 to 0.08 μm; however, no clear correlation between JAK2 potency and A549 cytotoxicity was observed.

  DOI：

  10.1111/cbdd.13025

文献信息

• General Entry into <i>o</i> -,<i>o′</i> -Heteroatom-Linked <i>N</i> -(Hetero)aryl-Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition
  作者：Miguel Garzón、Elsa M. Arce、Raju Jannapu Reddy、Paul W. Davies

  DOI：10.1002/adsc.201700249

  日期：2017.6.6

  general redox‐neutral approach into the o‐,o′‐heteroatom‐linked N‐(hetero)aryl‐imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench‐stable N‐(heteroaryl)‐pyridinium‐N‐aminides by formal gold‐catalysed [3+2]‐dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance

  已开发出一种将杂芳烃的邻，邻杂原子连接的N-（杂）芳基-咪唑家族的氧化还原中性方法。新型的杂原子取代的碳酰亚胺基亚硝基化合物可以通过稳定的，稳定的N-（杂芳基）-吡啶鎓-N-胺类化合物，通过正式的金催化的[3 + 2]-偶极环加成酰胺类有效地实现。广泛的结构多样性和官能团耐受性允许快速进入各种功能化的支架，如制备8个不同的杂芳族核心所示。
• Benzoxazoles and Oxazolopyridines Being Useful as Janus Kinases Inhibitors
  申请人：Gerspacher Marc

  公开号：US20100009978A1

  公开（公告）日：2010-01-14

  The invention relates to 2,7-disubstituted benzoxazole and 2,4-disubstituted oxazolo[5,4-c]pyridine compounds of the formula I given below, as well as salts thereof, processes for the preparation thereof, the application thereof in a process for the treatment of the human or animal body, these compounds for use in the treatment (including prophylaxis) of the animal, especially human, body (especially with regard to a proliferative disease), the use thereof—alone or in combination with one or more other pharmaceutically active compounds—for the treatment especially of a protein tyrosine kinase mediated disease (such as a tumor disease) or for the manufacture of a pharmaceutical preparation for use in the treatment of such a disease, a method for the treatment of such a disease and a pharmaceutical preparation for the treatment of a disease as mentioned. The compounds are of the formula I, wherein the symbols are as defined in the description. The compounds inhibit, for example, JAK2 and JAK3.

  本发明涉及以下式I所示的2,7-二取代苯并噁唑和2,4-二取代噁唑并[5,4-c]吡啶化合物及其盐，以及其制备方法、在人或动物体内治疗过程中的应用，这些化合物用于动物（特别是人体）的治疗（包括预防），特别是与增殖性疾病有关的治疗，其使用 - 单独或与一个或多个其他药理活性化合物结合使用 - 用于治疗特别是蛋白酪氨酸激酶介导的疾病（如肿瘤疾病）或制造用于治疗此类疾病的制药制剂，以及用于治疗此类疾病的方法和制药制剂。这些化合物的式I如描述中所定义的符号。这些化合物可以抑制例如JAK2和JAK3。
• Benzoxazoles and oxazolopyridines being useful as janus kinases inhibitors
  申请人：Gerspacher Marc

  公开号：US08629168B2

  公开（公告）日：2014-01-14

  The invention relates to 2,7-disubstituted benzoxazole and 2,4-disubstituted oxazolo[5,4-c]pyridine compounds of the formula I given below, as well as salts thereof, processes for the preparation thereof, the application thereof in a process for the treatment of the human or animal body, these compounds for use in the treatment (including prophylaxis) of the animal, especially human, body (especially with regard to a proliferative disease), the use thereof—alone or in combination with one or more other pharmaceutically active compounds—for the treatment especially of a protein tyrosine kinase mediated disease (such as a tumor disease) or for the manufacture of a pharmaceutical preparation for use in the treatment of such a disease, a method for the treatment of such a disease and a pharmaceutical preparation for the treatment of a disease as mentioned. The compounds are of the formula I, wherein the symbols are as defined in the description. The compounds inhibit, for example, JAK2 and JAK3.

  本发明涉及以下公式I所示的2,7-二取代苯并噁唑和2,4-二取代噁唑并[5,4-c]吡啶化合物及其盐，其制备方法，其在治疗人或动物体的过程中的应用，这些化合物用于治疗（包括预防）动物，特别是人体（特别是涉及增生性疾病的治疗），其用途 - 单独或与一种或多种其他药物活性化合物结合使用 - 用于治疗特别是蛋白酪氨酸激酶介导的疾病（例如肿瘤疾病）或用于制造用于治疗此类疾病的制药制剂，以及用于治疗所述疾病的方法和用于治疗所述疾病的制药制剂。这些化合物的公式I如描述中定义的符号所示。这些化合物抑制例如JAK2和JAK3。
• 2-Amino-aryl-7-aryl-benzoxazoles as potent, selective and orally available JAK2 inhibitors
  作者：Marc Gerspacher、Pascal Furet、Carole Pissot-Soldermann、Christoph Gaul、Philipp Holzer、Eric Vangrevelinghe、Marc Lang、Dirk Erdmann、Thomas Radimerski、Catherine H. Regnier、Patrick Chene、Alain De Pover、Francesco Hofmann、Fabienne Baffert、Thomas Buhl、Reiner Aichholz、Francesca Blasco、Ralf Endres、Jörg Trappe、Peter Drueckes

  DOI：10.1016/j.bmcl.2010.01.069

  日期：2010.3

  A series of novel benzoxazole derivatives has been designed and shown to exhibit attractive JAK2 inhibitory profiles in biochemical and cellular assays, capable of delivering compounds with favorable PK properties in rats. Synthesis and structure-activity relationship data are also provided. (C) 2010 Elsevier Ltd. All rights reserved.
• BENZOXAZOLES AND OXAZOLOPYRIDINES BEING USEFUL AS JANUS KINASES INHIBITORS
  申请人：NOVARTIS AG

  公开号：EP2066647A1

  公开（公告）日：2009-06-10