(5-acetylthiophene-3-yl)boronic acid | 942190-74-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-acetylthiophene-3-yl)boronic acid
• 英文别名: (5-Acetylthiophen-3-YL)boronic acid
• CAS: 942190-74-1
• 化学式: C₆H₇BO₃S
• mdl: MFCD08701784
• 分子量: 169.997
• InChiKey: ABXWZNDYRCDJSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-4-(4-溴苯基)噻唑 、 (5-acetylthiophene-3-yl)boronic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 0.5h， 以73%的产率得到1-(4-(4-(2-aminothiazol-4-yl)phenyl)thiophen-2-yl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Thiazol-2yl-amine Derivatives as Potential Anticancer Agents

  摘要：

  背景：慢性髓性白血病（CML）是一种骨髓增生性肿瘤，可发生于任何年龄段，但常见于成人，约占成人白血病的20%，且在全球范围内所有类型的白血病中，CML可能占到15%。因此，CML的治疗仍然是癌症治疗学中的一个重大挑战。 方法：我们合成了一系列新型2-氨基-4-(4-取代苯基)噻唑衍生物，并通过台盼蓝和MTT试验评估了它们的抗白血病活性。从中识别出4-(4'-苯氧基联苯-4-基)噻唑-2-胺（化合物3m）作为潜在的抗癌药物，并进一步研究了3m对CML细胞（K562细胞）的影响，包括流式细胞术分析、Annexin V-FITC-碘化丙啶染色、线粒体膜电位检测（JC-1染色）以及DNA片段化实验。 结果：MTT和台盼蓝染色排除法测试结果显示3m具有潜在的抗癌活性。流式细胞分析显示，K562细胞在亚G1期的积累呈时间-剂量依赖性增加。Annexin V-FITC-PI染色表明，用3m处理后，凋亡细胞的比例上升。此外，3m还能剂量依赖性地诱导K562细胞的DNA片段化和破坏线粒体膜电位。同时，通过活-死细胞试验和共聚焦显微镜研究再次证实了3m的促凋亡效应。 结论：本研究表明，化合物3m具有成为治疗CML的有前景候选药物的潜力。

  DOI：

  10.2174/1570178614666170907122026

文献信息

• Novel [4 + 2]-Benzannulation To Access Substituted Benzenes and Polycyclic Aromatic and Benzene-Fused Heteroaromatic Compounds
  作者：Chada Raji Reddy、Uredi Dilipkumar、Motatipally Damoder Reddy

  DOI：10.1021/ol501683v

  日期：2014.7.18

  been developed for the synthesis of aromatic and heteroaromatic compounds through tandem allylic substitution/hydroarylative cycloisomerization process. This method provides a facile and general route to substituted benzenes, naphthalenes, other polycyclic aromatics, and various benzene-fused heteroaromatic compounds such as benzofuran, benzothiophene, indole, and carbazoles.

  已开发出一种常见的[4 + 2]苯乙醛的Morita–Baylis–Hillman乙酸酯与硼酸苯甲酸酯化方法，用于通过串联烯丙基取代/加氢芳基环异构化过程合成芳族和杂芳族化合物。此方法为取代的苯，萘，其他多环芳烃和各种苯稠合的杂芳族化合物（如苯并呋喃，苯并噻吩，吲哚和咔唑）提供了简便而通用的途径。
• Pyrrolo[2,3-b]pyridine derivatives as potent Bruton’s tyrosine kinase inhibitors
  作者：Xinge Zhao、Wei Huang、Yazhou Wang、Minhang Xin、Qiu Jin、Jianfeng Cai、Feng Tang、Yong Zhao、Hua Xiang

  DOI：10.1016/j.bmc.2015.06.023

  日期：2015.8

  A series of pyrrolo[2,3-b]pyridine-based derivatives were designed as potent Bruton's tyrosine kinase (BTK) inhibitors by using a scaffold-hopping strategy. Structure-activity relationship studies identified five compounds (3n, 3p, 3q, 3r, and 3s) with IC50 of less than 10 nM in BTK enzyme assay and five compounds (3m, 3n, 3o, 3p, and 3t) with IC50 of less than 20 nM in Ramos cell assay. As one of the most potent inhibitors, compound 3p exhibited superior activity to that of compound 1 (RN486) and pyrrolo[ 2,3-d]pyrimidine derivative 2 in both BTK enzymatic (IC50 = 6.0 nM) and cellular inhibition (IC50 = 14 nM) assays. In addition, 3p displayed favorable overall pharmacokinetic profiles compared with 1 and 2. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Novel Thiazol-2yl-amine Derivatives as Potential Anticancer Agents
  作者：Chaithanya Somu、Mahesh Hegde、Kothanahally S. Sharath Kumar、Ananda Hanumappa、Mrinal Srivastava、Kachigere B. Harsha、Chakrabhavi D. Mohan、Kavya Ananthaswamy、Basappa、Sathees C. Raghavan、Kanchugarakoppal S. Rangappa

  DOI：10.2174/1570178614666170907122026

  日期：2018.3.9

  Background: Chronic myelogenous leukemia (CML) is a myeloproliferative neoplasm that can occur in any age group but often seen in adults and contributing for about 20% of adult leukemias and it may contribute up to 15% of all types of leukemias threatening the globe. Therefore, treatment of CML remains as a major challenge in cancer therapeutics. Methods: We synthesized a library of novel 2-amino-4-(4-substituted phenyl) thiazole derivatives and evaluated their anti-leukemic activity by trypan blue and MTT assay. 4-(4'-phenoxybiphenyl-4-yl) thiazol- 2-amine (compound 3m) was identified as a lead anticancer agent and further, the effect of 3m on CML cells (K562) was investigated by flow cytometry, annexin V-FITC-propidium iodide staining, measuring the mitochondrial membrane potential (JC-1 staining) and DNA fragmentation assay. Results: MTT and trypan blue dye exclusion assay results presented 3m as the lead anticancer agent. Flow cytometric analysis revealed the accumulation of K562 cells in subG1phase in a time- and dosedependent manner. Annexin-V-FITC-PI staining demonstrated the increase in percentage of apoptotic cells on treatment with 3m. Furthermore, 3m also induced DNA fragmentation and disrupted mitochondrial membrane potential in K562 cells in dose-dependent manner. In addition, apoptosis inducing effect of 3m was reconfirmed by live-dead assay and confocal microscopic studies. Conclusion: The present study suggests that compound 3m has the potential to be a promising candidate for the treatment of CML.

  背景：慢性髓性白血病（CML）是一种骨髓增生性肿瘤，可发生于任何年龄段，但常见于成人，约占成人白血病的20%，且在全球范围内所有类型的白血病中，CML可能占到15%。因此，CML的治疗仍然是癌症治疗学中的一个重大挑战。 方法：我们合成了一系列新型2-氨基-4-(4-取代苯基)噻唑衍生物，并通过台盼蓝和MTT试验评估了它们的抗白血病活性。从中识别出4-(4'-苯氧基联苯-4-基)噻唑-2-胺（化合物3m）作为潜在的抗癌药物，并进一步研究了3m对CML细胞（K562细胞）的影响，包括流式细胞术分析、Annexin V-FITC-碘化丙啶染色、线粒体膜电位检测（JC-1染色）以及DNA片段化实验。 结果：MTT和台盼蓝染色排除法测试结果显示3m具有潜在的抗癌活性。流式细胞分析显示，K562细胞在亚G1期的积累呈时间-剂量依赖性增加。Annexin V-FITC-PI染色表明，用3m处理后，凋亡细胞的比例上升。此外，3m还能剂量依赖性地诱导K562细胞的DNA片段化和破坏线粒体膜电位。同时，通过活-死细胞试验和共聚焦显微镜研究再次证实了3m的促凋亡效应。 结论：本研究表明，化合物3m具有成为治疗CML的有前景候选药物的潜力。