(2-氨基-5-溴苯基)(吡啶-4-基)甲酮 | 1694-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2-氨基-5-溴苯基)(吡啶-4-基)甲酮
• 英文名称: 4-(5-Brom-2-amino-benzoyl)-pyridin
• 英文别名: (2-amino-5-bromophenyl)-4-pyridinylmethanone；(2-Amino-5-bromophenyl)(pyridin-4-yl)methanone；(2-amino-5-bromophenyl)-pyridin-4-ylmethanone
• CAS: 1694-60-6
• 化学式: C₁₂H₉BrN₂O
• 分子量: 277.12
• InChiKey: SXRCAIZTOFMUJU-UHFFFAOYSA-N

物化性质

• 熔点：
  213-214 °C
• 沸点：
  452.6±40.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  (2-氨基-5-溴苯基)(吡啶-4-基)甲酮 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 3.83h， 生成 N-(5-(2-amino-4-(pyridin-4-yl)quinazolin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide
  参考文献：
  名称：

  Discovery of a Novel Series of Thienopyrimidine as Highly Potent and Selective PI3K Inhibitors

  摘要：

  Inhibition of the phosphoinositide 3-kinase (PI3K)/AKT/mammalian target of rapamycin (mTOR) signaling pathway provides a promising new approach for cancer therapy. Through a rational design, a novel series of thienopyrimidine was discovered as highly potent and selective PI3K inhibitors. These thienopyrimidine derivatives were demonstrated to bear nanomolar PI3K alpha inhibitory potency with over 100-fold selectivity against mTOR kinase. The lead compounds 6g and 6k showed good developability profiles in cell-based proliferation and ADME assays. In this communication, their design, synthesis, structure activity relationship, selectivity, and some developability properties are described.

  DOI：

  10.1021/ml5005014
• 作为产物：
  描述：

  4-氰基吡啶 、 4-溴苯胺 在 三氯化硼 、 aluminum (III) chloride 、 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 以63 %的产率得到(2-氨基-5-溴苯基)(吡啶-4-基)甲酮
  参考文献：
  名称：

  4-氰基吡啶与苯胺类和酮类通过 Sugasawa 和 Friedlander 反应合成 4-吡啶基喹啉

  摘要：

  首先，在Sugasawa条件下，将对位苯胺与腈邻位酰化合成了2-氨基芳酮，收率高达90.1%。然后，通过Friedlander反应与α-亚甲基酮合成了4-吡啶基喹啉衍生物，收率高达81.9%。五种 2-氨基芳香酮和十八种取代的喹啉的结构通过 MS、1H NMR 和 13C NMR 进行了表征。通过单晶X射线衍射进一步证实了结构，与预期结构一致。分析晶体结构，发现化合物4j和4q分别为单斜晶系，空间群为P21/n。化合物2c、2d、2e和4n分别为P-1空间群的三斜晶系​​结晶。其中化合物4n在三斜空间群P-1中结晶，在不对称单元中有两个结晶学上独立但化学等价的分子。发现这两个独立的分子相对于核心（喹啉）双环系统具有不同的氯、甲基、吡啶基和乙酰基取向。这项工作为制备 4-吡啶基喹啉衍生物提供了一种简单、直接的合成方案。

  DOI：

  10.2174/1570178620666230214100138

文献信息

• Aryl sulfonamides
  申请人：Ungashe Solomon

  公开号：US20060111351A1

  公开（公告）日：2006-05-25

  Compounds are provided that act as potent antagonists of the CCR9 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR9. The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR9-mediated diseases, and as controls in assays for the identification of CCR9 antagonists.

  提供了作为CCR9受体的有效拮抗剂的化合物，并在动物炎症测试中进一步确认了其效果，这是CCR9的标志性疾病状态之一。这些化合物通常是芳基磺酰胺衍生物，可用于制备药物组合物，治疗CCR9介导的疾病的方法，并作为CCR9拮抗剂鉴定的检测中的对照。
• Aryl Sulfonamides
  申请人：Ugashe Solomon

  公开号：US20090118307A1

  公开（公告）日：2009-05-07

  Compounds are provided that act as potent antagonists of the CCR9 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR9. The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR9-mediated diseases, and as controls in assays for the identification of CCR9 antagonists.

  提供了一些化合物，它们作为CCR9受体的有效拮抗剂，并且已经在动物炎症测试中得到了进一步的确认，这是CCR9的标志性疾病状态之一。这些化合物通常是芳基磺酰胺衍生物，可用于制药组合物、CCR9介导疾病的治疗方法，以及用于鉴定CCR9拮抗剂的测定中的对照。
• QUINAZOLINE DERIVATIVES AS P13 KINASE INHIBITORS
  申请人：ADAMS Nicholas D.

  公开号：US20090018131A1

  公开（公告）日：2009-01-15

  Invented is a method of inhibiting the activity/function of PI3 kinases using quinazoline derivatives. Also invented is a method of treating one or more disease states selected from: autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergy, asthma, pancreatitis, multiorgan failure, kidney diseases, platelet aggregation, cancer, sperm motility, transplantation rejection, graft rejection and lung injuries by the administration of quinazoline derivatives.

  本发明涉及使用喹唑啉衍生物来抑制PI3激酶的活性/功能的方法。本发明还涉及使用喹唑啉衍生物治疗以下一种或多种疾病状态的方法：自身免疫性疾病、炎症性疾病、心血管疾病、神经退行性疾病、过敏、哮喘、胰腺炎、多器官衰竭、肾脏疾病、血小板聚集、癌症、精子运动能力、移植排斥、移植物排斥和肺部损伤。通过给予喹唑啉衍生物进行治疗。
• ARYL SULFONAMIDES
  申请人：Ugashe Solomon

  公开号：US20090270616A1

  公开（公告）日：2009-10-29

  Compounds are provided that act as potent antagonists of the CCR9 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR9. The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR9-mediated diseases, and as controls in assays for the identification of CCR9 antagonists.

  提供了一些化合物，它们作为CCR9受体的有效拮抗剂，并且已经在动物炎症测试中进一步确认，这是CCR9的标志性疾病状态之一。这些化合物通常是芳基磺酰胺衍生物，可用于制药组合物、治疗CCR9介导的疾病的方法以及作为对CCR9拮抗剂鉴定试验的控制。
• Structure–Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin
  作者：Hajer Abdelkafi、Aurélien Michau、Valérie Pons、Flora Ngadjeua、Alexandra Clerget、Lilia Ait Ouarab、David-Alexandre Buisson、David Montoir、Lucie Caramelle、Daniel Gillet、Julien Barbier、Jean-Christophe Cintrat

  DOI：10.1021/acs.jmedchem.0c00298

  日期：2020.8.13

  High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.