4-ethyl-5-(3-hydroxynaphthalen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione | 219538-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-ethyl-5-(3-hydroxynaphthalen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 3-(4-Ethyl-5-sulfanylidene-1,2,4-triazolidin-3-ylidene)-2-naphthalenone；4-ethyl-3-(3-hydroxynaphthalen-2-yl)-1H-1,2,4-triazole-5-thione
• CAS: 219538-20-2
• 化学式: C₁₄H₁₃N₃OS
• 分子量: 271.343
• InChiKey: MGJTUWIRWFUWOF-UHFFFAOYSA-N

物化性质

• 沸点：
  426.0±47.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二氯苯甲酰氯 、 4-ethyl-5-(3-hydroxynaphthalen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 以 丙酮 为溶剂， 反应 2.0h， 以96%的产率得到1,4-dihydro-1-(2,6-dichlorobenzoyl)-3-(3-hydroxy-2-naphthyl)-4-ethyl-5H-1,2,4-triazoline-5-thione
  参考文献：
  名称：

  Synthesis and preliminary anticancer activity of new 1,4-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-1,2,4-triazoline-5-thiones

  摘要：

  1,4-Dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-L2,4-triazolinc-5-thiones were synthesized. The structures of original eight compounds were confirmed by elemental analysis,H-1 NMR and mass spectral methods. One of the compounds (3a) was tested in vitro for its anticancer activity against 52 human tumor cell lines. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01248-x
• 作为产物：
  描述：

  3-羟基-2-萘酸肼 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 4-ethyl-5-(3-hydroxynaphthalen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  3-羟基-2-萘酰肼的新衍生物：硫代氨基脲和1,2,4-三唑-3-硫酮，其合成与体外抗菌评价

  摘要：

  摘要在本文中，我们描述了我们合成的十二种3-羟基-2-萘酰肼衍生物（六种硫代氨基脲和六种1,2,4-三唑-3-硫酮）。硫代氨基脲衍生物是通过3-羟基-2-萘肼与适当的异硫氰酸酯的缩合反应制备的。通过相应的硫代氨基脲衍生物在碱性介质中的环化反应合成1,2,4-三唑-3-硫酮。所有获得的化合物均已通过1 H NMR和13 C NMR光谱进行了分析，并评估了其对一系列参考微生物的体外抗菌活性，这些参考菌株包括革兰氏阳性细菌，革兰氏阴性细菌和属于酵母假丝酵母的真菌spp。我们的抗菌筛选结果表明，一些新获得的化合物显示出很高的抗菌活性，尤其是对革兰氏阳性细菌。其中，化合物的活性1，2和4是中等至强对葡萄球菌。除此之外，化合物1和2的抗蜡样芽孢杆菌ATCC 10876活性比头孢呋辛高两倍，比氨苄西林高四倍。 图形概要

  DOI：

  10.1007/s13738-016-0911-1

文献信息

• Certain triazole-based compounds, compositions, and uses thereof
  申请人：Hodge Nicholas Carl

  公开号：US20050288347A1

  公开（公告）日：2005-12-29

  Thiotriazole-based chemical entities exhibiting ATP-utilizing enzyme inhibitory activity, methods of using such chemical entities, and compositions comprising such chemical entities, are described.

  描述了具有 ATP 利用酶抑制活性的硫代三唑类化学实体、使用此类化学实体的方法以及包含此类化学实体的组合物。
• Synthesis, structure elucidation and antimicrobial activity of some 3-hydroxy-2-naphthoic acid hydrazide derivatives
  作者：H.N. Dogan、S. Rollas、H. Erdeniz

  DOI：10.1016/s0014-827x(98)00049-4

  日期：1998.7

  In this study, some 1,4-disubstituted thiosemicarbazide, 1,2,4-triazole and 1,3,4-thiadiazole type novel compounds derived from 3-hydroxy-2-naphthoic acid hydrazide were synthesized to screen for their antimicrobial activity. The structures of these substances were elucidated using elemental analysis and UV, H-1 NMR, and mass spectral methods. All of these compounds were tested in vitro for their antibacterial and antifungal activity. (C) 1998 Elsevier Science S.A. All rights reserved.
• Synthesis and preliminary anticancer activity of new 1,4-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-1,2,4-triazoline-5-thiones
  作者：A. Duran、H.N. Dogan、Sevim Rollas

  DOI：10.1016/s0014-827x(02)01248-x

  日期：2002.7

  1,4-Dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-L2,4-triazolinc-5-thiones were synthesized. The structures of original eight compounds were confirmed by elemental analysis,H-1 NMR and mass spectral methods. One of the compounds (3a) was tested in vitro for its anticancer activity against 52 human tumor cell lines. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• New 3-hydroxy-2-naphthoic hydrazide derivatives: thiosemicarbazides and 1,2,4-triazole-3-thiones, their synthesis and in vitro antimicrobial evaluation
  作者：Łukasz Popiołek、Kinga Paruch、Paweł Patrejko、Anna Biernasiuk、Monika Wujec

  DOI：10.1007/s13738-016-0911-1

  日期：2016.10

  evaluated for in vitro antimicrobial activity against a panel of reference strains of microorganisms, including Gram-positive bacteria, Gram-negative bacteria and fungi belonging to yeasts Candida spp. Our antimicrobial screening results indicated that some of the newly obtained compounds showed high antibacterial activity, especially against Gram-positive bacteria. Among them, the activity of compounds 1

  摘要在本文中，我们描述了我们合成的十二种3-羟基-2-萘酰肼衍生物（六种硫代氨基脲和六种1,2,4-三唑-3-硫酮）。硫代氨基脲衍生物是通过3-羟基-2-萘肼与适当的异硫氰酸酯的缩合反应制备的。通过相应的硫代氨基脲衍生物在碱性介质中的环化反应合成1,2,4-三唑-3-硫酮。所有获得的化合物均已通过1 H NMR和13 C NMR光谱进行了分析，并评估了其对一系列参考微生物的体外抗菌活性，这些参考菌株包括革兰氏阳性细菌，革兰氏阴性细菌和属于酵母假丝酵母的真菌spp。我们的抗菌筛选结果表明，一些新获得的化合物显示出很高的抗菌活性，尤其是对革兰氏阳性细菌。其中，化合物的活性1，2和4是中等至强对葡萄球菌。除此之外，化合物1和2的抗蜡样芽孢杆菌ATCC 10876活性比头孢呋辛高两倍，比氨苄西林高四倍。 图形概要