4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-amine
• 英文别名: 4-Tert-butyl-5-[(2,4-dichlorophenyl)methyl]-1,3-thiazol-2-amine
• 化学式: C₁₄H₁₆Cl₂N₂S
• 分子量: 315.266
• InChiKey: IFFZRWHIDPHZIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-amine 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  N-(4-烷基-5-苄基噻唑-2-基)氨基烷酰胺及 其制备方法与应用

  摘要：

  本发明涉及化学结构式Ⅰ所示的N‑(4‑烷基‑5‑苄基噻唑‑2‑基)氨基烷酰胺或其盐；式中R选自：C1～C2烷基、C3～C4直链或C3～C4支链烷基；Y1、Y3选自：氢、甲基、乙基、羟基、甲氧基、乙氧基、氟、氯、溴或碘；Y2、Y4选自：氢、甲基、乙基；n选自：1～9；盐选自：盐酸盐、氢溴酸盐、硫酸盐、硝酸盐、磷酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐、苹果酸盐、乳酸盐、琥珀酸盐、马来酸盐或富马酸盐。N‑(4‑烷基‑5‑苄基噻唑‑2‑基)氨基烷酰胺或其盐在制备抗癌药物中的应用。

  公开号：

  CN106699682B
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 氢气 、 sodium hydroxide 、 copper(ll) bromide 作用下， 以 乙醇 为溶剂， 60.0~80.0 ℃ 、3.0 MPa 条件下， 反应 16.0h， 生成 4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-amine
  参考文献：
  名称：

  Design, synthesis and neuraminidase inhibitory activity of N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)benzamides

  摘要：

  A series of N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)benzamides were synthesized and the structures were characterized by H-1 NMR, MS and elemental analyses. The crystal structures of compounds F5 and F16 were determined by single-crystal X-ray diffraction. The neuraminidase inhibitory activities of compounds F1-F32 were evaluated in vitro at the concentration of 40 mu g/mL. The results indicated that compounds F8, F26 and F32 exhibited most potent inhibitory activity against NA. Molecular docking was performed by LeDock to further explain the structure-activity relationship of compound F26. The docking modeling showed that compound F26 was in good combination with oseltamivir binding sites of NA and could be a potential NA inhibitor agent.

  DOI：

  10.1007/s00044-015-1487-5

文献信息

• Synthesis and antitumor activity of novel N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)-2-(piperazin-1-yl)acetamides
  作者：Zhilin Wu、Na Ding、Yuting Tang、Jiao Ye、Junmei Peng、Aixi Hu

  DOI：10.1007/s11164-017-2915-6

  日期：2017.8

  A series of novel N-(5-benzyl-4-(tert-butyl) thiazol-2-yl)-2-(piperazin-1-yl)acetamides were designed, synthesized and evaluated for their antitumor activities in vitro. The structures of the synthesized compounds were characterized by 1H NMR, 13C NMR and elemental analysis. In general, compounds 5a, 5c and 6a showed potent antiproliferative activity against HeLa (human cervical cancer) and A549 (human lung cancer) cell lines. Compound 6a, with the best inhibitory activity against HeLa cells (IC50 = 1.6 ± 0.8 μM), was selected to investigate the induced changes of cell morphology in the HeLa cell line by means of acridine orange (AO)/ethidium bromide (EB) double staining and cell cycle analysis using flow cytometry. The results indicated that compound 6a could induce cell apoptosis and cause G1-phase arrest in the cell division cycle.

  一系列新型的N-(5-苄基-4-(叔丁基)噻唑-2-基)-2-(哌嗪-1-基)乙酰胺被设计、合成并评估其体外抗肿瘤活性。合成化合物的结构通过1H NMR、13C NMR和元素分析进行表征。总体而言，化合物5a、5c和6a对HeLa（人宫颈癌）和A549（人肺癌）细胞系表现出强烈的抗增殖活性。化合物6a在HeLa细胞中的抑制活性最佳（IC50 = 1.6 ± 0.8 μM），被选中通过结合橙（AO）/溴化乙锭（EB）双重染色和流式细胞术进行细胞周期分析，研究其诱导的细胞形态变化。结果表明，化合物6a可以诱导细胞凋亡并导致细胞分裂周期中的G1期停滞。
• N-（5-苄基噻唑-2-基）苯甲酰胺及其医药用途
  申请人：湖南大学

  公开号：CN104771397B

  公开（公告）日：2017-03-08

  本发明涉及化学结构式I所示的N‑（5‑苄基噻唑‑2‑基）苯甲酰胺在制备神经氨酸酶抑制剂中的应用：其中R选自：C1～C2烷基、C3～C4直链或支链烷基；Y1选自：氢、氘、甲基、乙基、氟、氯、溴；Y2、Y4选自：氢、氘、甲基、乙基、氟、氯、溴；Y3选自：氢、氘、甲基、乙基、氟、氯、溴；R1、R5选自：氢、氘、甲基、乙基、甲氧基、乙氧基、氟、氯、溴、硝基、三氟甲基或三氟甲氧基；R2、R4选自：氢、氘、甲基、乙基、羟基、甲氧基、乙氧基、氟、氯、溴、硝基、三氟甲基或三氟甲氧基；R3选自：氢、氘、甲基、乙基、羟基、甲氧基、乙氧基、氟、氯、溴、硝基、三氟甲基或三氟甲氧基。
• N-（4-烷基-5-苄基噻唑-2-基）烯酰胺及其制 备方法与应用
  申请人：南华大学

  公开号：CN105017174B

  公开（公告）日：2017-03-15

  本发明涉及化学结构式Ⅰ所示的N‑（4‑烷基‑5‑苄基噻唑‑2‑基）烯酰胺或其盐：I式中R选自：C1~C2烷基、C3~C4直链或C3~C4支链烷基；Y1、Y3选自：氢、甲基、乙基、羟基、甲氧基、乙氧基、氟、氯、溴或碘；Y2、Y4选自：氢、甲基、乙基；n选自：1、2、3、4、5、6或7；Z选自：氢、甲基或苯基；盐选自：盐酸盐、氢溴酸盐、硫酸盐、磷酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐。N‑（4‑烷基‑5‑苄基噻唑‑2‑基）烯酰胺或其盐在制备抗癌药物中的应用。
• CN105906618
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, synthesis and neuraminidase inhibitory activity of N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)benzamides
  作者：Zhilin Wu、Junmei Peng、Aixi Hu、Jiao Ye、Guoxi Li

  DOI：10.1007/s00044-015-1487-5

  日期：2016.2

  A series of N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)benzamides were synthesized and the structures were characterized by H-1 NMR, MS and elemental analyses. The crystal structures of compounds F5 and F16 were determined by single-crystal X-ray diffraction. The neuraminidase inhibitory activities of compounds F1-F32 were evaluated in vitro at the concentration of 40 mu g/mL. The results indicated that compounds F8, F26 and F32 exhibited most potent inhibitory activity against NA. Molecular docking was performed by LeDock to further explain the structure-activity relationship of compound F26. The docking modeling showed that compound F26 was in good combination with oseltamivir binding sites of NA and could be a potential NA inhibitor agent.