N-(4-(4-methoxyphenyl)thiazol-2-yl)acetamide | 60867-76-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-(4-methoxyphenyl)thiazol-2-yl)acetamide
• 英文别名: N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]acetamide
• CAS: 60867-76-7
• 化学式: C₁₂H₁₂N₂O₂S
• 分子量: 248.305
• InChiKey: XAFPANDNJFYZGN-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-(4-methoxyphenyl)thiazol-2-yl)acetamide 在 哌啶 、 盐酸 、 硫酸 、 溶剂黄146 、 sodium nitrite 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 7.22h， 生成 2-[[2-[[4-(Diethylamino)phenyl]diazenyl]-4-(4-methoxyphenyl)-1,3-thiazol-5-yl]methylidene]indene-1,3-dione
  参考文献：
  名称：

  Thiazole azo dyes with lateral donor branch: Synthesis, structure and second order NLO properties

  摘要：

  Three azo dyes with a thiazole based donor-pi-acceptor structure containing a methoxyphenyl group as the lateral donor branch were synthesized and fully characterized. The formyl azo dye precursor was synthesized using 5-formylaminothiazole derivative as the diazo component and N,N-diethylaninline as the coupling component. Knoevenagel condensation of this precursor with different acceptors, namely, indandione, malononitrile and dicyanovinylindanone afforded the desired nonlinear optical chromophores a-c, respectively.The optical property, thermal stability and second order nonlinear optical activity were evaluated and a single crystal structural characterization was performed for two of the dyes. All nonlinear optical dyes a-c have good nonlinearity and good thermal stability. Compared with dyes a and b, dye c shows more than triple second order nonlinear optical response, the result that makes this molecule an unusual example of asymmetrical 2D charge transfer chromophore. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.08.002
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 碘 、 sodium acetate 作用下， 生成 N-(4-(4-methoxyphenyl)thiazol-2-yl)acetamide
  参考文献：
  名称：

  2-氨基-4-芳基噻唑衍生物的制备、抗菌活性和毒性

  摘要：

  合成了七种 2-氨基-4-芳基-1,3-噻唑 (1a-g) 及其相应的 2-氨基乙酰基 (2a-g) 和 2-氨基乙酰基-5-溴 (3a-g) 衍生物并进行了体外测试针对 11 种参考菌株、三种革兰氏阳性菌和四种革兰氏阴性菌、两种酵母菌和两种霉菌。还使用盐水虾试验评估了化合物的毒性。化合物 1a、1b、1e-g 和 3b 在不同浓度下显示出中等的抗菌活性。结果表明，氨基的乙酰化和噻唑部分 5 位的溴化导致活性丧失。化合物 1a、1e 和 1f 对盐水虾无节幼体的毒性低于 10 ppm。大多数其他化合物表现出中等毒性，LD50 高于 100 ppm。所有化合物的结构均通过 NMR 和 MS 数据确认。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:254–260, 2006; 在线发表于 Wiley InterScience (www.interscience

  DOI：

  10.1002/hc.20182

文献信息

• Structure–activity relationships of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists
  作者：Kwan-Young Jung、Soo-Kyung Kim、Zhan-Guo Gao、Ariel S Gross、Neli Melman、Kenneth A Jacobson、Yong-Chul Kim

  DOI：10.1016/j.bmc.2003.10.041

  日期：2004.2

  adenosine A3 receptors. Molecular modeling study of conformation search and receptor docking experiments to investigate the dramatic differences of binding affinities between two regioisomers of thiadiazole analogues, (39) and (42), suggested possible binding mechanisms in the binding pockets of adenosine receptors.

  4-(4-甲氧基苯基)-2-氨基噻唑和3-(4-甲氧基苯基)-5-氨基噻二唑衍生物已被合成并评估为人类腺苷A3受体的选择性拮抗剂。苯环 4 位的甲氧基和氨基噻唑和氨基噻二唑模板的 N-乙酰基或丙酰基取代显示出对人腺苷 A3 受体的结合亲和力和选择性的极大增加。本系列中最有效的 A3 拮抗剂，N-[3-(4-甲氧基-苯基)-[1,2,4] 噻二唑-5-基]-乙酰胺 (39)，对人体的 Ki 值为 0.79 nM腺苷 A3 受体在参与腺苷 A3 受体信号转导途径之一的 cAMP 生物合成的功能测定中显示出拮抗特性。
• Preparation, antimicrobial activity, and toxicity of 2-amino-4-arylthiazole derivatives
  作者：Pedro Morales-Bonilla、Andrea Pérez-Cardeña、Esther Quintero-Mármol、José Luis Arias-Téllez、Gonzalo J. Mena-Rejón

  DOI：10.1002/hc.20182

  日期：2006.4

  2-aminoacetyl (2a–g) and 2-aminoacetyl-5-bromo (3a–g) derivatives were synthesized and tested in vitro against 11 reference strains, three Gram-positive and four Gram-negative bacteria, two yeasts, and two moulds. Toxicity of the compounds was also evaluated using the brine shrimp test. Compounds 1a, 1b, 1e–g, and 3b showed moderate antimicrobial activity at different concentrations. The results indicated

  合成了七种 2-氨基-4-芳基-1,3-噻唑 (1a-g) 及其相应的 2-氨基乙酰基 (2a-g) 和 2-氨基乙酰基-5-溴 (3a-g) 衍生物并进行了体外测试针对 11 种参考菌株、三种革兰氏阳性菌和四种革兰氏阴性菌、两种酵母菌和两种霉菌。还使用盐水虾试验评估了化合物的毒性。化合物 1a、1b、1e-g 和 3b 在不同浓度下显示出中等的抗菌活性。结果表明，氨基的乙酰化和噻唑部分 5 位的溴化导致活性丧失。化合物 1a、1e 和 1f 对盐水虾无节幼体的毒性低于 10 ppm。大多数其他化合物表现出中等毒性，LD50 高于 100 ppm。所有化合物的结构均通过 NMR 和 MS 数据确认。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:254–260, 2006; 在线发表于 Wiley InterScience (www.interscience
• Synthesis and Biological Activities of 4-Phenyl-5-pyridyl-1,3-thiazole Derivatives as Selective Adenosine A3 Antagonists
  作者：Seiji Miwatashi、Yasuyoshi Arikawa、Tatsumi Matsumoto、Keiko Uga、Naoyuki Kanzaki、Yumi N. Imai、Shigenori Ohkawa

  DOI：10.1248/cpb.56.1126

  日期：——

  To investigate the potency of an adenosine A3 receptor (A3AR) antagonist as an anti-asthmatic drug, a novel series of 4-phenyl-5-pyridyl-1,3-thiazole derivatives was synthesized and evaluated in human adenosine A1, A2A and A3 receptor and rat adenosine A3 receptor binding assays. From investigation of the SAR study, compound 7af was identified as a highly potent human and rat A3AR antagonist. This compound inhibited IB-MECA-induced plasma protein extravasation in the skin of rats and showed good oral absorption. Also, compound 7af significantly inhibited antigen-induced hyper-responsiveness to acetylcholine in actively sensitized Brown Norway rats. These results show that 4-phenyl-5-pyridyl-1,3-thiazole derivatives are potential candidates to enable the evaluation of A3AR antagonists. Further evaluation of this class of compounds may afford a novel anti-inflammatory agent such as an anti-asthmatic drug.

  为了研究腺苷A3受体（A3AR）拮抗剂作为抗哮喘药物的效力，合成了一系列新的4-苯基-5-吡啶基-1,3-噻唑衍生物，并在人体腺苷A1、A2A和A3受体以及大鼠腺苷A3受体的结合实验中进行了评估。通过SAR研究的调查，化合物7af被鉴定为一种对人类和大鼠A3AR高度有效的拮抗剂。该化合物抑制了IB-MECA诱导的大鼠皮肤内血浆蛋白渗出，并显示出良好的口服吸收。此外，化合物7af显著抑制了在活跃致敏的布朗挪威大鼠中抗原诱导的对乙酰胆碱的超反应性。这些结果表明，4-苯基-5-吡啶基-1,3-噻唑衍生物是评估A3AR拮抗剂的潜在候选化合物。进一步评估这类化合物可能提供一种新的抗炎剂，如抗哮喘药物。
• Somei, Masanori; Yamada, Yoshikazu; Kitagawa, Keiichi, Heterocycles, 1997, vol. 45, # 3, p. 434 - 438
  作者：Somei, Masanori、Yamada, Yoshikazu、Kitagawa, Keiichi、Sugaya, Katsuko、Tomita, Yayoi、et. al

  DOI：——

  日期：——
• Some Possible Antihistaminics and Antispasmodics. I. Synthesis of Mannich Bases
  作者：Prithwi Nath Bhargava、Suresh Chandra Sharma

  DOI：10.1246/bcsj.38.909

  日期：1965.6