5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑-2-胺 | 28004-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑-2-胺
• 英文名称: 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine
• 英文别名: 2-amino-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole
• CAS: 28004-59-3
• 化学式: C₁₁H₁₃N₃O₃S
• mdl: MFCD00981236
• 分子量: 267.309
• InChiKey: DJSKNOBOTVECTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑-2-胺 以 吡啶 、 xylene 为溶剂， 生成 5H-(1,3,4)Thiadiazolo(3,2-a)(1,3,5)triazine-5,7(6H)-dione, 6-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-alkoxyphenyl-6-(substituted phenyl)-1,3,4-thiadiazole-[3,2-a]-s-triazin-5,7-diones and 1-(alkyl and substituted phenyl)-3-[5-alkoxyphenyl-1,3,4-thia- and oxadiazol-2-yl]-ureas

  摘要：

  DOI：

  10.1016/0223-5234(89)90010-x
• 作为产物：
  描述：

  1-Benzyl-3-[(3,4,5-trimethoxybenzoyl)amino]thiourea 在 三氯氧磷 作用下， 反应 2.0h， 以34%的产率得到5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  1,3,4-THIADIAZOLES. REGIOSELECTIVE O-DEMETHYLATION ON DEHYDRATIVE CYCLIZATION OF 1-(3,4,5-TRIMETHOXYBENZOYL)4-SUBSTITUTED THIOSEMICARBAZIDES WITH SULPHURIC ACID

  摘要：

  Cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-substituted thiosemicarbazides 2a-g with sulphuric acid at ambient temperature afforded the selectively demethylated products 2-(4-hydroxy-3,5-dimethoxyphenyl)5-substituted amino-1,3,4-thiodiazoles 4a-g. Meanwhile, dehydrative cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-(benzyl or t-butyl)thiosemicarbazides 2h,i with sulphuric acid yielded 2-(4-hydroxy-3,5-dimethoxyphenyl)-5-amino-1,3,4-thiadiazole 5. On the other hand, dehydration of 2h,i by heating with phosphorus oxychloride yielded 2-(3,4,5-trimethoxyphenyl)-5-amino-1,3,4-thiadiazole 6.

  DOI：

  10.1080/10426500490485525

文献信息

• New N -4 piperazinyl derivatives of norfloxacin: design, synthesis, and correlation of calculated physicochemical parameters with antibacterial activity
  作者：Gamal El-Din ABUO-RAHMA、Samar ABBAS、Mai SHOMAN、Ebtihal SAMIR、Rehab ABDEL-BAKY

  DOI：10.3906/kim-1706-16

  日期：——

  A group of $N-$4 piperazinyl derivatives of norfloxacin was synthesized and identified by different spectroscopic techniques. The $N-$4 piperazinyl substituent in target compounds 2a-2k, 3a-3c, and 4a and 4b was designed to have different electronic, steric, and physicochemical properties. The antibacterial activity of the newly synthesized compounds was evaluated against Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, and Staphylococcus aureus strains using norfloxacin as a reference. Results showed that most of the tested compounds had higher activity against E. coli and K. pneumoniae than norfloxacin, whereas only five derivatives were more active against P. aeruginosa. On the other hand, all derivatives were less active than norfloxacin against S. aureus. The biological activity of the target compounds, expressed in log MIC, is correlated with lipophilicity, polarizability, and topology parameters. Results showed that none of the calculated parameters could determine the biological activity. Consequently, the total volume of the molecule, bulkiness at C-7, electronic factors, and lipophilicity are important factors that should be considered in the design of new fluoroquinolones.

  合成了一组$N$-4哌嗪基诺氟沙星衍生物，并通过不同的光谱技术进行鉴定。目标化合物2a-2k、3a-3c、4a和4b中的$N$-4哌嗪基取代基被设计为具有不同的电子、立体和物理化学性质。评估了新合成化合物对铜绿假单胞菌、大肠杆菌、肺炎克雷伯菌和金黄色葡萄球菌菌株的抗菌活性，以诺氟沙星为参照。结果显示，大多数被测化合物对大肠杆菌和肺炎克雷伯菌的活性高于诺氟沙星，而只有五种衍生物对铜绿假单胞菌的活性更高。另一方面，所有衍生物对金黄色葡萄球菌的活性都低于诺氟沙星。目标化合物的生物活性（以对数最低抑菌浓度表示）与亲脂性、极化率和拓扑参数相关。结果表明，计算的参数均不能确定生物活性。因此，分子的总体积、C-7处的体积、电子因素和亲脂性是设计新型氟喹诺酮时应考虑的重要因素。
• Synthesis and antiviral activity of some imidazo[1,2-b][1,3,4]thiadiazole carbohydrate derivatives
  作者：Mirta L. Fascio、Claudia S. Sepúlveda、Elsa B. Damonte、Norma B. D'Accorso

  DOI：10.1016/j.carres.2019.05.003

  日期：2019.7

  Herein we describe the synthesis of imidazo[2,1-b][1,3,4]thiadiazoles from carbohydrates with D-ribo and D-xylo configuration. The antiviral activity of these compounds was tested against Junín virus (the etiological agent of Argentine hemorrhagic fever). The p-chlorophenyl derivatives showed antiviral activity in a range of micromolar concentration.

  本文中，我们描述了由具有D-ribo和D-xylo构型的碳水化合物合成咪唑并[2,1-b] [1,3,4]噻二唑。测试了这些化合物对Junin病毒（阿根廷出血热的病原体）的抗病毒活性。对氯苯基衍生物在微摩尔浓度范围内显示抗病毒活性。
• Synthesis, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives
  作者：Hamada H. H. Mohammed、Samar H. Abbas、El-Shimaa M. N. Abdelhafez、James M. Berger、Satoshi Mitarai、Masayoshi Arai、Gamal El-Din A. A. Abuo-Rahma

  DOI：10.1007/s00706-019-02478-4

  日期：2019.10

  AbstractHerein we report the synthesis of new N-4-piperazinyl thiadiazole and oxadiazole ciprofloxacin derivatives and their antibacterial and antimycobacterial activities. Although thiadiazole ciprofloxacin derivatives compound showed broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative organisms, the oxadiazole derivatives exhibited weaker antibacterial

  摘要本文中，我们报道了新的N -4-哌嗪基噻二唑和恶二唑环丙沙星衍生物的合成及其抗菌和抗分枝杆菌活性。尽管噻二唑环丙沙星衍生物化合物对革兰氏阳性或革兰氏阴性菌的所有测试菌株均具有广谱抗菌活性，但与参考环丙沙星相比，恶二唑衍生物对大多数测试菌株的抗菌和分枝杆菌活性较噻二唑衍生物弱。此外，抗分枝杆菌筛选显示含有噻二唑支架的化合物有效抑制耻垢分枝杆菌MIC分别为1.56和3.13，并适度抑制了耐药菌株。DNA裂解分析表明，噻二唑环丙沙星衍生物抑制超螺旋松弛，尽管程度比环丙沙星要小，并且还增加了产生的切口底物的量。 图形摘要
• Synthesis and Biological Evaluation of Imidazo[2,1-<i>b</i>][1,3,4]thiadiazole-Linked Oxindoles as Potent Tubulin Polymerization Inhibitors
  作者：Ahmed Kamal、M. P. Narasimha Rao、Pompi Das、P. Swapna、Sowjanya Polepalli、Vijaykumar D. Nimbarte、Kishore Mullagiri、Jeshma Kovvuri、Nishant Jain

  DOI：10.1002/cmdc.201400069

  日期：2014.7

  ((E)‐3‐((6‐p‐tolyl‐2‐(3,4,5‐trimethoxyphenyl)imidazo[2,1‐b][1,3,4]thiadiazol‐5‐yl)methylene)indolin‐2‐one), and 15 ((E)‐6‐chloro‐3‐((6‐phenyl‐2‐(3,4,5‐trimethoxyphenyl)imidazo[2,1‐b][1,3,4]thiadiazol‐5‐yl)methylene)indolin‐2‐one) exhibited potent anti‐proliferative activity. Treatment with these three compounds resulted in accumulation of cells in G2/M phase, inhibition of tubulin assembly, and increased

  合成了由A，B，C和D环系统组成的一系列咪唑并[2,1 b ] [1,3,4]噻二唑连接的羟吲哚，并研究了其在多种人类癌细胞系中的抗增殖活性；测试化合物在C环和D环上被不同取代。其中，化合物7（（E）-5-氟-3-3 -（（6-对甲苯基-2-（3,4,5-三甲氧基苯基）-咪唑[2] ，1- b ] [1,3,4]噻二唑-5-基）亚甲基）吲哚-2--1），11（（E）-3-（（6 - p-甲苯基-2-（3,4， 5-三甲氧基苯基）咪唑并[ 2,1- b ] [1,3,4]噻二唑-5-基）亚甲基）吲哚-2--1）和15（（E）-6-氯-3-（（6-苯基-2-（3,4,5-三甲氧基苯基）咪唑[ 2,1- b ] [1,3,4]噻二唑-5-基）亚甲基）吲哚啉- 2‐1）表现出有效的抗增殖活性。用这三种化合物处理可导致细胞处于G 2 / M期积累，抑制微管蛋白装配，并增加细胞周期蛋白B1蛋白水平。化合物7显示的有效的细胞毒性，与IC
• Ultrasound-assisted synthesis and antibacterial activity of novel 1,3,4-thiadiazole-1H-pyrazol-4-yl-thiazolidin-4-one derivatives
  作者：Nagaraju Kerru、Lalitha Gummidi、Sandeep V. H. S. Bhaskaruni、Surya Narayana Maddila、Sreekantha B. Jonnalagadda

  DOI：10.1007/s00706-020-02625-2

  日期：2020.6

  (55–65 min) at 50 °C. All the twelve new thiazolidin-4-one derivatives were fully characterized by spectroscopic techniques and were screened for their antibacterial activity. Among the screened hybrids, derivatives with 4-nitro and 3-nitro groups substituted on the phenyl ring showed fourfold (MBC = 156.3 µg/cm3) and twofold (MBC = 312.5 µg/cm3) stronger potency against Pseudomonas aeruginosa strain as compared

  摘要我们报告了一种有效的多组分方法，用于从吡唑-4-甲醛，5-（取代的苯基）的反应中合成具有生物活性的1,3,4-噻二唑-1 H-吡唑-4-基-噻唑烷-4-酮杂化物超声波下乙醇中的-1,3,4-噻二唑-2-胺和2-巯基乙酸 反应在50°C的短时间内（55-65分钟）可得到所需产物的优异收率（91-97％）。所有十二种新的噻唑烷丁-4-酮衍生物均已通过光谱技术进行了充分表征，并对其抗菌活性进行了筛选。在筛选的杂种中，苯环上被4-硝基和3-硝基取代的衍生物显示出更强的四倍（MBC = 156.3 µg / cm 3）和两倍（MBC = 312.5 µg / cm 3）对与标准环丙沙星相比，铜绿假单胞菌菌株。SAR研究揭示了1,3,4-噻二唑-2-胺部分的苯环上的官能团对于改变细菌活性的重要性。吸电子（NO 2）基团在对位-和间位-位在增强的抗菌活性方面发挥了显著作用。所述方案的突出特征是优异的