2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(5-methylpyridin-2-yl)acetamide | 1239727-54-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(5-methylpyridin-2-yl)acetamide
• 英文别名: 2-(2-amino-1,3,4-thiadi azol-5-ylthio)-N-p-tolyl acetamide；2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-(5-methylpyridin-2-yl)acetamide
• CAS: 1239727-54-8
• 化学式: C₁₀H₁₁N₅OS₂
• 分子量: 281.362
• InChiKey: ZUTDNQQTNUBNHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(5-methylpyridin-2-yl)acetamide 、 甲氧基苯甲酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 4.08h， 以69%的产率得到2-methoxy-N-[5-[2-[(5-methylpyridin-2-yl)amino]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]benzamide
  参考文献：
  名称：

  Novel small molecules as apoptosis inducers: Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation

  摘要：

  Inducing apoptosis is a promising therapeutic approach to overcome cancer. In this study, 30 compounds were synthesized and evaluated for their antiproliferative activity against three tumor cell lines in vitro: A875, H460 and Hela cancer cells by the MTT assay. The most potent analogue 7a, a novel compound was first reported by our group, inhibited the proliferation of A875 cells with an IC50 value of 98 nM. Flow cytometry analysis and morphological analysis suggested that compound 7a had potential anticancer efficacy via G(2)/M cell cycle arrest, which could be attributed to its proliferation and apoptosis, and also in a concentration-dependent manner. The SAR analysis indicated that the substituents R-2 played a crucial role in the antiproliferation activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.076
• 作为产物：
  描述：

  2-氨基-5-甲基吡啶 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(5-methylpyridin-2-yl)acetamide
  参考文献：
  名称：

  新型2-（（5-氨基-1,3,4-噻二唑-2-基）硫基）-N-芳基乙酰胺衍生物的设计，合成，对接研究和脲酶抑制活性评估

  摘要：

  在本文中，设计，合成了新型的2-（（5-氨基-1,3,4-噻二唑-2-基）硫代）-N-芳基乙酰胺衍生物（7a–l），并对其体外脲酶抑制剂进行了评估。活动。从胺，2-氯乙酰氯，肼甲硫基酰胺和二硫化碳中以高分离产率通过三步高效合成化合物。通过将所有合成的化合物和标准抑制剂对接至波豆脲酶的晶体结构中，使用AutoDock4进行了分子对接模拟。化合物的脲酶抑制活性之间的比较图7a-1与IC 50羟基脲（2.85-5.83μM）的硫脲并且与IC标准抑制剂50（分别为22.00和100.00 µM）的摩尔数证明了合成化合物对上述酶的高活性。对接结果与实验结果吻合良好，表明合成的化合物可以与脲酶的活性位点以及所有位点之间良好地相互作用。化合物7j与活性位点之间表现出更有利的相互作用，这证实了其强大的抑制活性，IC 50为2.85 µM。因此，化合物7j可能是进一步评估的有希望的候选者。

  DOI：

  10.1007/s00044-020-02683-5

文献信息

• Novel small molecules as apoptosis inducers: Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation
  作者：Lifeng Zhao、Xiao Li、Lidan Zhang、Tinghong Ye、Yongxia Zhu、Yuquan Wei、Shengyong Yang、Luoting Yu

  DOI：10.1016/j.bmcl.2013.02.076

  日期：2013.4

  Inducing apoptosis is a promising therapeutic approach to overcome cancer. In this study, 30 compounds were synthesized and evaluated for their antiproliferative activity against three tumor cell lines in vitro: A875, H460 and Hela cancer cells by the MTT assay. The most potent analogue 7a, a novel compound was first reported by our group, inhibited the proliferation of A875 cells with an IC50 value of 98 nM. Flow cytometry analysis and morphological analysis suggested that compound 7a had potential anticancer efficacy via G(2)/M cell cycle arrest, which could be attributed to its proliferation and apoptosis, and also in a concentration-dependent manner. The SAR analysis indicated that the substituents R-2 played a crucial role in the antiproliferation activity. (C) 2013 Elsevier Ltd. All rights reserved.
• Design, synthesis, docking study and urease inhibitory activity evaluation of novel 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-arylacetamide derivatives
  作者：Mohammad Nazari Montazer、Mehdi Asadi、Saeed Bahadorikhalili、Faezeh Sadat Hosseini、Arash Amanlou、Mahmood Biglar、Massoud Amanlou

  DOI：10.1007/s00044-020-02683-5

  日期：2021.3

  In this paper, novel 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-arylacetamide derivatives (7a–l) are designed, synthesized, and evaluated in vitro for their urease inhibitor activities. The compounds are synthesized efficiently in three steps in high isolated yields from amines, 2-chloroacetyl chloride, hydrazinecarbothioamide, and carbon disulfide. The molecular docking simulation were performed using

  在本文中，设计，合成了新型的2-（（5-氨基-1,3,4-噻二唑-2-基）硫代）-N-芳基乙酰胺衍生物（7a–l），并对其体外脲酶抑制剂进行了评估。活动。从胺，2-氯乙酰氯，肼甲硫基酰胺和二硫化碳中以高分离产率通过三步高效合成化合物。通过将所有合成的化合物和标准抑制剂对接至波豆脲酶的晶体结构中，使用AutoDock4进行了分子对接模拟。化合物的脲酶抑制活性之间的比较图7a-1与IC 50羟基脲（2.85-5.83μM）的硫脲并且与IC标准抑制剂50（分别为22.00和100.00 µM）的摩尔数证明了合成化合物对上述酶的高活性。对接结果与实验结果吻合良好，表明合成的化合物可以与脲酶的活性位点以及所有位点之间良好地相互作用。化合物7j与活性位点之间表现出更有利的相互作用，这证实了其强大的抑制活性，IC 50为2.85 µM。因此，化合物7j可能是进一步评估的有希望的候选者。