1-ethyl-3-(4H-1,2,4-triazol-4-yl)thiourea | 5102-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-ethyl-3-(4H-1,2,4-triazol-4-yl)thiourea
• 英文别名: N-ethyl-N'-(4H-1,2,4-triazol-4-yl)thiourea；1-ethyl-3-(1,2,4-triazol-4-yl)thiourea
• CAS: 5102-45-4
• 化学式: C₅H₉N₅S
• mdl: MFCD02570975
• 分子量: 171.226
• InChiKey: KIKXOOGOLARHIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯乙酸 、 1-ethyl-3-(4H-1,2,4-triazol-4-yl)thiourea 在 sodium acetate 作用下， 以 乙醇 为溶剂， 生成 3-Aethyl-2-<1,3,4>triazolylimino-thiazolidin-4-on
  参考文献：
  名称：

  Solanki,M.S.; Trivedi,J.P., Journal of the Indian Chemical Society, 1965, vol. 42, p. 817 - 818

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基-1,2,4-三氮唑 、 异硫氰酸乙酯 以 乙腈 为溶剂， 反应 16.0h， 以72%的产率得到1-ethyl-3-(4H-1,2,4-triazol-4-yl)thiourea
  参考文献：
  名称：

  Synthesis, Antimicrobial and Pharmacological Evaluation of Thioureaderivatives of 4H-1,2,4-triazole

  摘要：

  一批4H-1,2,4-三唑衍生物硫脲被高效制备并评估其抗菌、抗真菌和抗病毒活性。所有衍生物的化学身份基于光谱方法确立。分子结构10和21通过X射线晶体学确定。具有苯基（1）、3,4-二氯苯基（2）和p-甲氧基苯基（3）取代基的化合物对真菌种类最为有效。衍生物12对CVB-5显示出显著活性。研究了五个新的4H-1,2,4-三唑硫脲衍生物2、10、12、18和21的中枢神经系统活性。结果证明所有测试的硫脲化合物的活性可能与血清素系统有关。衍生物2、10、12、18作为头部抽动反应（HTR）的抑制剂。21的生物活性也与内源性阿片系统相关。衍生物18降低了自发活动性，10减少了实验室动物的安非他命诱导活动。

  DOI：

  10.2174/1570180811666141001010044

文献信息

• Exploring “Triazole-Thiourea” Based Ligands for the Self-Assembly of Photoluminescent Hg(II) Coordination Compounds
  作者：Houria Benaissa、Nayarassery N. Adarsh、Koen Robeyns、Jakub J. Zakrzewski、Szymon Chorazy、James G. M. Hooper、Filip Sagan、Mariusz P. Mitoraj、Mariusz Wolff、Smaail Radi、Yann Garcia

  DOI：10.1021/acs.cgd.1c00352

  日期：2021.6.2

  This study represents the first explorative investigation on the supramolecular structural diversity in Hg(II) coordination chemistry with triazole-thiourea ligands leading to a variety of mononuclear, binuclear, and coordination polymers: [Hg(L1)2(L1–)2]} (1), [Hg2(L1)2(μ2-I)2I2]·DMSO} (2), [Hg(L2)(μ2-I)I]·MeOH}∝ (3), [Hg2(μ-L3–)4]}∝ (4), [HgCl(L4–)L4]·MeOH} (5), [Hg2(L4)2(μ2-I)2(I)2]·2MeOH} (6), [Hg2(μ2-L5–)4]}∝ (7), [Hg2(μ2-Cl)2(L6–)2(L6)2]} (8), [Hg2(μ2-Br)2(L6–)2(L6)2]} (9), and [Hg2(μ2-I)2(L6–)2(L6)2]} (10). A reaction mechanism was suggested for the unexpected ligand rearrangement occurring in [Hg2I3(μ3-L5′)]}∝ (11). The ligands were fully characterized including by X-ray crystallography and computational means. This includes six new triazole-thiourea based ligands, namely, 1-R-3-(4H-1,2,4-triazol-4-yl)thiourea (where R = methyl (L1), ethyl (L2), propyl (L3), isopropyl (L4), and its polymorph (L4-poly), allyl (L5), ethyl acetate (L6), and its solvate (L6_MeOH)). Under UV light excitation, 7, 10, and 11 exhibit visible photoluminescence of wide origin, ranging from ligand-centered (LC) fluorescence combined with organic-ligand-to-metal charge transfer (LMCT) emissive states in 7 and 10, up to halide-to-metal charge transfer (XMCT) combined with halide-to-ligand charge transfer (XLCT) emissive states in 11. The variable emission mechanisms in the obtained coordination polymers were elucidated by experimental proofs confronted with theoretical calculations of the electronic densities of states, proving that Hg(II) halide coordination polymers involving flexible 1,2,4-triazole-based ligands form a promising class of luminescent molecular materials.

  本研究首次探索了Hg(II)配合物中三唑-硫脲配体的超分子结构多样性,生成了一系列单核、双核和配位聚合物: [Hg(L1)2(L1–)2]} (1), [Hg2(L1)2(μ2-I)2I2]·DMSO} (2), [Hg(L2)(μ2-I)I]·MeOH}∝ (3), [Hg2(μ-L3–)4]}∝ (4), [HgCl(L4–)L4]·MeOH} (5), [Hg2(L4)2(μ2-I)2(I)2]·2MeOH} (6), [Hg2(μ2-L5–)4]}∝ (7), [Hg2(μ2-Cl)2(L6–)2(L6)2]} (8), [Hg2(μ2-Br)2(L6–)2(L6)2]} (9), 和 [Hg2(μ2-I)2(L6–)2(L6)2]} (10)。提出了反应机制,解释了 [Hg2I3(μ3-L5′)]}∝ (11) 中意外的配体重排现象。配体通过X射线晶体学和计算方法得到了充分表征。包括六个新的三唑-硫脲基配体,即1-R-3-(4H-1,2,4-三唑-4-基)硫脲(其中 R = 甲基 (L1), 乙基 (L2), 丙基 (L3), 异丙基 (L4) 及其多晶型物 (L4-poly), 烯丙基 (L5), 乙酸乙酯 (L6), 及其溶剂化物 (L6_MeOH))。在紫外光激发下,7, 10 和 11 显示出可见的宽范围光致发光,从7和10中的配体中心(LC)荧光与有机配体至金属电荷转移(LMCT)发射态,到11中的卤素至金属电荷转移(XMCT)与卤素至配体电荷转移(XLCT)发射态。通过实验证据与态密度的理论计算对比,阐明了所得配位聚合物中可变的发光机制,证明涉及柔性1,2,4-三唑基配体的Hg(II)卤素配位聚合物是一类有前景的发光分子材料。
• Synthesis, Antimicrobial and Pharmacological Evaluation of Thioureaderivatives of 4H-1,2,4-triazole
  作者：Anna Bielenica、Ewa Kedzierska、Sylwia Fidecka、Hanna Maluszynska、Barbara Miroslaw、Anna E. Koziol、Joanna Stefanska、Silvia Madeddu、Gabriele Giliberti、Giuseppina Sanna、Marta Struga

  DOI：10.2174/1570180811666141001010044

  日期：2015.2.4

  A group of 4H-1,2,4-triazole-derived thioureas was efficiently prepared and evaluated for antibacterial, antifungal and antiviral activities.The chemical identity of all derivatives was established on the basis of spectral methods. The molecular structures of 10 and 21 were determined by an X-ray crystallography. Compounds with phenyl (1), 3,4-dichlorophenyl (2) and p-methoxyphenyl (3) substituents were the most promising against fungi species. The derivative 12 has proved to be significantly active against CVB-5. The CNS-activity of five new 4H-1,2,4-triazolo-thiourea derivatives 2, 10, 12, 18 and 21 was investigated. The results proved that activity of all tested thiourea compounds may be connected with the serotonergic system. Derivatives 2, 10, 12, 18 acted as inhibitors of the head twitch responses (HTR).The biological activity of 21 was also linked with the endogenous opioid system. The derivative 18 diminished the spontaneous mobility and 10 reduced the amphetamineinduced activity of laboratory animals.

  一批4H-1,2,4-三唑衍生物硫脲被高效制备并评估其抗菌、抗真菌和抗病毒活性。所有衍生物的化学身份基于光谱方法确立。分子结构10和21通过X射线晶体学确定。具有苯基（1）、3,4-二氯苯基（2）和p-甲氧基苯基（3）取代基的化合物对真菌种类最为有效。衍生物12对CVB-5显示出显著活性。研究了五个新的4H-1,2,4-三唑硫脲衍生物2、10、12、18和21的中枢神经系统活性。结果证明所有测试的硫脲化合物的活性可能与血清素系统有关。衍生物2、10、12、18作为头部抽动反应（HTR）的抑制剂。21的生物活性也与内源性阿片系统相关。衍生物18降低了自发活动性，10减少了实验室动物的安非他命诱导活动。
• Solanki,M.S.; Trivedi,J.P., Journal of the Indian Chemical Society, 1965, vol. 42, p. 817 - 818
  作者：Solanki,M.S.、Trivedi,J.P.

  DOI：——

  日期：——