4-(2-amino-1,3-thiazol-4-yl)-2-methoxyphenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-amino-1,3-thiazol-4-yl)-2-methoxyphenol
• 化学式: C₁₀H₁₀N₂O₂S
• 分子量: 222.268
• InChiKey: PMICHXCAAVTBQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  96.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-amino-1,3-thiazol-4-yl)-2-methoxyphenol 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(4-(4-hydroxy-3-methoxyphenyl)thiazol-2-yl)-3-(4-(3-nitrobenzyl)piperazin-1-yl)propanamide
  参考文献：
  名称：

  Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury

  摘要：

  Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.09.068
• 作为产物：
  描述：

  香草乙酮 在 aluminum (III) chloride 、 溴 作用下， 以 乙醚 、 异丙醇 为溶剂， 反应 1.0h， 生成 4-(2-amino-1,3-thiazol-4-yl)-2-methoxyphenol
  参考文献：
  名称：

  Biological and Anti-inflammatory Evaluation of Two Thiazole Compounds in RAW Cell Line: Potential Cyclooxygenase-2 Specific Inhibitors

  摘要：

  两种新型噻唑衍生物CX-32（N-[4-(4-羟基-3-甲氧基苯基)-1,3-噻唑-2-基]乙酰胺）和CX-35（4-(2-氨基-1,3-噻唑-4-基)-2-甲氧基苯酚）在LPS刺激的RAW 264.7细胞系中被研究其抗炎效果。这些化合物的合成、结构分析和纯度通过高效液相色谱法（HPLC）、氢核磁共振（H1 NMR）和碳核磁共振（C13 NMR）进行了评估。通过将LPS激活的RAW细胞与25 µM、50 µM或100 µM的CX-32或CX-35分别孵育，评估了CX-32和CX-35对环氧合酶-2（COX-2）活性的抑制效应。用酶免疫测定法（EIA）评估分泌PGE2的水平，西方印迹法测定COX-2蛋白的水平。最后，进行了细胞活力实验以评估每种化合物的毒性。将LPS激活的RAW细胞与25 μM、50 μM或100 μM的CX-35或CX-32分别处理，抑制了前列腺素的产生，但对COX-2蛋白水平没有影响。此外，CX-35和CX-32将PGE2的产生减少到与用选择性COX-2抑制剂NS 398孵育的LPS激活的RAW细胞相当的水平。此外，CX-32和CX-35均显示出无毒性，因为未处理的Hela细胞的活力与孵育CX-35或CX-32的Hela细胞相似。我们的数据表明，CX-32和CX-35显著阻断了在炎性细胞应激中诱导的前列腺素产生，可能通过特异性COX-2抑制作用；确认这一假设需要进一步研究。

  DOI：

  10.2174/1573406411208030401

文献信息

• Design, synthesis, characterization and antitubercular activity of some nov-el 2, 4-disubstituted thiazole derivatives
  作者：Gobala Krishnan P、Gnanaprakash K、Chandrasekhar KB

  DOI：10.26452/ijrps.v10i2.729

  日期：——

  Literature reviews reveal that thiazole and pyrazine carboxamide derivatives exhibit anticonvulsant, antimicrobial, anticancer and anti-tubercular activities due to the presence of –S-C=N- and-CO–NH- moiety. A series of thiazolyl pyrazine carboxamide derivatives (5a-j) were synthesized by condensation reaction between 2-amino, 4-substituted phenyl 2-amino thiazole and pyrazine 2-carboxylic acid. These synthesized thiazole derivatives (5a-j) were evaluated for their inhibitory activity against Mycobacterium tuberculosis (Mtb), H37Rv using microplate Alamar Blue assay (MABA). The compound, 5c and 5h showed high anti-mycobacterial activity with MIC value of 6.25 µg/ml, and the compound 5g also exhibited anti-mycobacterial activity with MIC value of 12.50 µg/ml. Molecular docking studies of these synthesized molecules with b-Ketoacyl-ACP Synthase (KasA) protein of Mycobacterium tuberculosis (Mtb) have been carried out to understand the mechanism of anti-mycobacterial action.

  文献综述显示，噻唑和吡嗪羧酰胺衍生物由于含有-S-C=N-和-CO-NH-基团而表现出抗癫痫、抗微生物、抗癌和抗结核活性。通过2-氨基、4-取代苯基2-氨基噻唑和吡嗪-2-羧酸之间的缩合反应合成了一系列噻唑基吡嗪羧酰胺衍生物（5a-j）。这些合成的噻唑衍生物（5a-j）通过微板AlaMAr蓝试验（MABA）评估了它们对结核分枝杆菌（Mtb）H37Rv的抑制活性。化合物5c和5h显示出较高的抗分枝杆菌活性，MIC值为6.25 µg/ml，而化合物5g也表现出抗分枝杆菌活性，MIC值为12.50 µg/ml。对这些合成分子与结核分枝杆菌（Mtb）的b-酮酰-ACP合酶（KasA）蛋白的分子对接研究已经进行，以了解抗分枝杆菌作用的机制。