2-acetyl-N-(4-methoxyphenyl)hydrazinecarbothioamide | 502703-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-acetyl-N-(4-methoxyphenyl)hydrazinecarbothioamide
• 英文别名: 1-acetyl-4-(4-methoxyphenyl)thiosemicarbazide；1-acetamido-3-(4-methoxyphenyl)thiourea
• CAS: 502703-95-9
• 化学式: C₁₀H₁₃N₃O₂S
• 分子量: 239.298
• InChiKey: VCLUTGOSACJOJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetyl-N-(4-methoxyphenyl)hydrazinecarbothioamide 在 sodium hydroxide 作用下， 反应 5.0h， 生成 4-(4-Methoxyphenyl)-5-methyl-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  A novel sulfanyltriazole was discovered as an HIV-1 non-nucleoside reverse transcriptase inhibitor via HTS using a cell-based assay. Chemical modifications and molecular modeling studies were carried out to establish its SAR and understand its interactions with the enzyme. These modifications led to the identification of sulfanyltriazoles with low nanomolar potency for inhibiting HIV-1 replication and promising activities against selected NNRTI resistant mutants. These novel and potent sulfanyltriazoles could serve as advanced leads for further optimization. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.096
• 作为产物：
  描述：

  乙酰肼 、 4-甲氧基苯基 异硫氰酸酯 以 乙醇 为溶剂， 以92%的产率得到2-acetyl-N-(4-methoxyphenyl)hydrazinecarbothioamide
  参考文献：
  名称：

  氨基硫脲和 S-三唑衍生物的抗菌和理化特性

  摘要：

  图形摘要摘要已合成了两个系列氨基硫脲衍生物和三个系列的s-三唑衍生物。测试了所有这些化合物对革兰氏阳性和革兰氏阴性细菌菌株的体外抗菌活性。在测试的氨基硫脲衍生物中，检测到两种具有 3-/4-甲苯基取代（1 l，1 m）的 1-甲酰氨基硫脲的最佳生物活性（MIC 范围在 31.25 和 250 μg/mL 之间）。所有测试的 s-三唑衍生物的抗菌活性都低于它们的无环前体。

  DOI：

  10.1080/10426507.2014.902831

文献信息

• N-(Acetamido)thiourea based simple neutral hydrogen-bonding receptors for anions
  作者：Wen-Xia Liu、Rui Yang、Ai-Fang Li、Zhao Li、Yu-Feng Gao、Xing-Xing Luo、Yi-Bin Ruan、Yun-Bao Jiang

  DOI：10.1039/b910255h

  日期：——

  of a proline derivative 6 bearing a chiral center in the N-amido moiety provide direct evidence for this conformation change upon its binding with anions in MeCN. The amplified effect of substituent X at the N′-phenyl ring of 5 on the anion binding constant supports the conclusion of anion-binding switched charge transfer in the anion binding complex. 1H NMR and absorption titrations for 5 indicated

  N-（乙酰氨基）-N'-苯硫脲（4–6）被发现是有效的阴离子受体，其阴离子亲和力比它们的阴离子亲和力高N-苯甲酰胺基-N'-苯硫脲对应对象（1和2）。这N'-苯硫脲在4–6中的部分被证明是发色团，其最大吸收在。270纳米 已经发现，在阴离子的存在下，在约1μm的吸收。270 nm的4–6（5f除外）in乙腈（MeCN）呈蓝色偏移并增强，而大约在2020年出现红移的肩膀。295 nm，以及大约等渗点。240纳米 1：1的阴离子结合的常数4-6在10，例如6 -10 7中号-1数量级为ACO -在MeCN，被认为是比那些更高1和2，虽然硫脲基的酸度4–6中的-NH质子低于1和2中的-NH质子。1 H NMR数据表明4–6中的N–N单键是扭曲的，但小于1中的N–N单键。和2。建议在阴离子结合后在4–6的N–N单键处发生构象变化，这导致阴离子结合复合物中的平面氢键网络发生电荷转移，其中N-酰基部分
• Sharma, Laxmi Kant; Singh, Sushma; Siddiqui, Journal of the Indian Chemical Society, 2011, vol. 88, # 1, p. 155 - 161
  作者：Sharma, Laxmi Kant、Singh, Sushma、Siddiqui、Singh

  DOI：——

  日期：——
• Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors
  作者：Zhiwei Wang、Baogen Wu、Kelli L. Kuhen、Badry Bursulaya、Truc N. Nguyen、Deborah G. Nguyen、Yun He

  DOI：10.1016/j.bmcl.2006.05.096

  日期：2006.8

  A novel sulfanyltriazole was discovered as an HIV-1 non-nucleoside reverse transcriptase inhibitor via HTS using a cell-based assay. Chemical modifications and molecular modeling studies were carried out to establish its SAR and understand its interactions with the enzyme. These modifications led to the identification of sulfanyltriazoles with low nanomolar potency for inhibiting HIV-1 replication and promising activities against selected NNRTI resistant mutants. These novel and potent sulfanyltriazoles could serve as advanced leads for further optimization. (c) 2006 Elsevier Ltd. All rights reserved.
• Antimicrobial and Physicochemical Characterizations of Thiosemicarbazide and <i>S</i>-Triazole Derivatives
  作者：Edyta Kuśmierz、Agata Siwek、Urszula Kosikowska、Anna Malm、Tomasz Plech、Andrzej Wróbel、Monika Wujec

  DOI：10.1080/10426507.2014.902831

  日期：2014.10.3

  GRAPHICAL ABSTRACT Abstract Two series of thiosemicarbazide derivatives and three series of s-triazole derivatives have been synthesized. All of these compounds were tested for their in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains. Among tested thiosemicarbazide derivatives, the best bioactivity was detected for two 1-formylthiosemicarbazides with 3-/4-tolyl

  图形摘要摘要已合成了两个系列氨基硫脲衍生物和三个系列的s-三唑衍生物。测试了所有这些化合物对革兰氏阳性和革兰氏阴性细菌菌株的体外抗菌活性。在测试的氨基硫脲衍生物中，检测到两种具有 3-/4-甲苯基取代（1 l，1 m）的 1-甲酰氨基硫脲的最佳生物活性（MIC 范围在 31.25 和 250 μg/mL 之间）。所有测试的 s-三唑衍生物的抗菌活性都低于它们的无环前体。