[(3-甲氧基苯基)亚甲基氨基]硫脲 | 51146-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: [(3-甲氧基苯基)亚甲基氨基]硫脲
• 英文名称: 3-methoxybenzaldehyde thiosemicarbazone
• 英文别名: [(E)-(3-methoxyphenyl)methylideneamino]thiourea
• CAS: 51146-74-8
• 化学式: C₉H₁₁N₃OS
• 分子量: 209.272
• InChiKey: FRKKQKDSWAUADS-IZZDOVSWSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  364.0±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3-甲氧基苯基)亚甲基氨基]硫脲 在 三氯化铁 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-(3-甲氧基苯基)-1,2,4-噻二唑-2-胺
  参考文献：
  名称：

  降压噻二唑。1.合成一些具有血管扩张活性的2-芳基-5-肼基-1,3,4-噻二唑。

  摘要：

  已经合成了一些2-芳基-5-肼基-1,3,4-噻二唑并筛选了其降压活性。通常，具有2-取代的苯环的化合物比其3-或4-取代的对应物或含有杂芳基的化合物具有更高的活性。2-甲基苯基和2-乙基苯基衍生物7和18是该系列中最有效的成员。初步研究表明，这些化合物的降压作用归因于对血管平滑肌的直接松弛作用。

  DOI：

  10.1021/jm00400a003
• 作为产物：
  描述：

  氨基硫脲 、 3-甲氧基苯甲醛 以 乙醇 为溶剂， 反应 2.0h， 生成 [(3-甲氧基苯基)亚甲基氨基]硫脲
  参考文献：
  名称：

  作为神经氨酸酶抑制剂的3-（（4-（叔丁基）-2-（2-苄叉肼基）噻唑-5-基）甲基）喹啉-2（1H）-酮的设计，合成和评估

  摘要：

  设计，合成和合成了一系列新颖的3-（（4-（叔丁基）-2-（2-苄叉肼基）噻唑-5-基）甲基）喹啉-2-（1 H）-酮（7a - 7z）评估其抑制流感H1N1病毒神经氨酸酶（NA）的能力。一些化合物显示出中等的流感NA抑制活性。带有7-（2-（2-（2-甲氧基亚苄基）肼基）噻唑骨架的化合物7l是最好的化合物，具有中等的NA抑制活性，IC 50为44.66 µmol / L。结构-活性关系显示出与甲氧基或羟基基团的化合物在邻位，氟和硝基在元苯环对位的氯和溴基更活泼。对接研究表明，化合物7l与一些关键残基（包括Asp151，Glu119，Arg292，Tyr406和Asn347）具有重要的相互作用，并与邻近NA活性位点的430腔结合。

  DOI：

  10.1002/cjoc.201500738

文献信息

• Aryl hydrazones linked thiazolyl coumarin hybrids as potential urease inhibitors
  作者：Uzma Salar、Bakhtawer Qureshi、Khalid Mohammed Khan、Muhammad Arif Lodhi、Zaheer Ul‑Haq、Farman Ali Khan、Fouzia Naz、Muhammad Taha、Shahnaz Perveen、Shafqat Hussain

  DOI：10.1007/s13738-021-02377-8

  日期：2022.4

  Aryl hydrazones bearing thiazolyl coumarin hybrids 1–32 were prepared by following 'one-pot' two-steps reaction scheme. Various arylaldehydes were reacted to thiosemicarbazide under acidic condition to form aryl thiosemicarbazone intermediates which in turn treated with 3-bromoacetyl coumarin under basic condition to afford thiazolyl coumarin hybrids 1–32. All hybrids were recognized by EI- and HREI-MS

  通过遵循“一锅”两步反应方案制备带有噻唑基香豆素杂化物1-32的芳基腙。各种芳醛在酸性条件下与氨基硫脲反应形成芳基氨基氨基硫脲中间体，该中间体又在碱性条件下用 3-溴乙酰香豆素处理，得到噻唑基香豆素杂化物 1-32。所有杂种均通过 EI-和 HREI-MS 以及 1H-和 13C-NMR 光谱技术进行识别。筛选化合物 1-32 对脲酶的体外抑制活性，并在 IC50 = 16.29 ± 1.1-256.30 ± 1.4 µM 范围内显示出良好至中等的抑制潜力。值得指出的是，化合物 21 (IC50 = 16.29 ± 1.1 µM) 被确定为比标准乙酰氧肟酸 (IC50 = 27.0 ± 0.5 µM) 更有效的脲酶抑制剂。衍生物 19 (IC50 = 77.67 ± 1. 5 µM) 和 30 (IC50 = 71.21 ± 1.6 µM) 被发现具有中度活性。构效关系表明-F、-Cl、-
• Synthesis of (E)-2-Benzylidene-N-(3-(3-oxo-2,3-dihydro-4Hbenzo[ b][1,4]oxazin-4-yl)propyl)hydrazine-1-carbothioamides
  作者：Palla Sai Lakshmi、Puligilla Shankaraiah

  DOI：10.14233/ajchem.2023.27601

  日期：——

  A series of novel substituted-(E)-2-benzylidene-N-(3-(3-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4- yl)propyl)hydrazine-1-carbothioamides (9a-j) was synthesized in satisfactory to excellent yield by reacting (Z)-N′-benzylidene hydrazine carbothioamides (8a-j) with 4-(3-bromo-propyl)-2H-benzo[b][1,4]oxazin- 3(4H)-one (5) in K2CO3 and dry N,N-dimethyl formamide. The novel carbothioamides (9a-j) structures

  一系列新型取代-(E)-2-亚苄基-N-(3-(3-氧代-2,3-二氢-4H-苯并[b][1,4]恶嗪-4-基)丙基)肼通过 (Z)-N'-亚苄基肼硫代碳酰胺 (8a-j) 与 4-(3-溴-丙基)-2H-苯并[b] 反应，合成了 -1-硫代碳酰胺 (9a-j)，收率令人满意。 [1,4]恶嗪-3(4H)-酮(5)在K2CO3和干燥N,N-二甲基甲酰胺中。使用 1H NMR、IR 和质谱方法确认了新型硫代碳酰胺 (9a-j) 的结构
• Taniyama et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 993,995
  作者：Taniyama et al.

  DOI：——

  日期：——
• Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors
  作者：Muhammad Adil S. Aslam、Shams-ul Mahmood、Mohammad Shahid、Aamer Saeed、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2011.09.009

  日期：2011.11

  A series of new and novel Schiff base derivatives were synthesized and investigated as potential new inhibitors of Jack bean urease. The most potent compounds were 3f with (K-i = 0.09 mu M) and 3k (K-i = 0.122 mu M). A pure competitive mechanism of inhibition was observed. Molecular docking studies were also performed to illustrate the binding mode of the compounds. Docking studies were performed on both enzymes from Jack bean urease and H. pylori urease. It was observed that both share the same binding mode. The binding sites of the two urease structures also aligned very well indicating the similarity in binding sites of the enzymes. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and Biological Evaluation of 3-thiazolocoumarinyl Schiff-base Derivatives as Cholinesterase Inhibitors
  作者：Rabia Raza、Aamer Saeed、Mubeen Arif、Shamsul Mahmood、Muhammad Muddassar、Ahsan Raza、Jamshed Iqbal

  DOI：10.1111/j.1747-0285.2012.01435.x

  日期：2012.10

  On the basis of the observed biological activity of the coumarins, a new set of 3‐thiazolocoumarinyl Schiff‐base derivatives with chlorine, hydroxy and methoxy functional group substitutions were designed and synthesized. These compounds were tested against acetylcholinesterase from Electrophorus electricus and butyrylcholinesterase from horse serum and their structure–activity relationship was established. Studies revealed them as the potential inhibitors of cholinesterase (acetylcholinesterase and butyrylcholinesterase). The 3f was found to be most potent against acetylcholinesterase with Ki value of 1.05 ± 0.3 μm and 3l showed excellent inhibitory action against butyrylcholinesterase with Ki value of 0.041 ± 0.002 μm. The synthesized compounds were also docked into the active sites of the homology models of acetylcholinesterase and butyrylcholinesterase to predict the binding modes of these compounds. It was predicted that most of the compounds have similar binding modes with reasonable binding affinities. Our docking studies have also shown that these synthesized compounds have better interaction patterns with butyrylcholinesterase over acetylcholinesterase. The main objective of the study was to develop new potent and selective compounds, which might be further optimized to prevent the progression of the Alzheimer’s disease and could provide symptomatic treatment.