N-[(3',4'-dimethoxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine | 59670-49-4

• 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: N-[(3',4'-dimethoxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine
• 英文别名: N-(3,4-dimethoxybenzylidene)-4H-1,2,4-triazol-4-amine；(3,4-dimethoxy-benzylidene)-[1,2,4]triazol-4-yl-amine；1-(3,4-Dimethoxyphenyl)-N-(4H-1,2,4-triazol-4-yl)methanimine；1-(3,4-dimethoxyphenyl)-N-(1,2,4-triazol-4-yl)methanimine
• CAS: 59670-49-4
• 化学式: C₁₁H₁₂N₄O₂
• mdl: MFCD00226623
• 分子量: 232.242
• InChiKey: DKPICALCFHAXGE-UHFFFAOYSA-N

物化性质

• 沸点：
  403.4±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(3',4'-dimethoxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.5h， 生成 3-(4-chloro-3-(trifluoromethyl)phenyl)-1-(3,4-dimethoxybenzyl)-1-(4H-1,2,4-triazol-4-yl)urea
  参考文献：
  名称：

  1,2,4-三唑连接的脲/硫脲偶联物的合成作为细胞毒性和凋亡诱导剂

  摘要：

  一系列新的1,2,4-三唑连接的尿素和硫脲的结合物已被合成并评价它们在体外针对选定的人癌症细胞系即，乳腺癌（MCF-7，MDA-MB-231），肺（细胞毒性A549）前列腺（DU145）和一种小鼠黑素瘤（B16-F10）细胞系，并与参考药物进行比较。在所有测试化合物中，化合物5t对MCF-7乳腺癌细胞系均表现出明显的细胞毒性，IC 50值为7.22±0.47 µM。值得注意的是，化合物5t诱导细胞凋亡使用不同的染色技术（如a啶橙/溴化乙锭（AO / EB），膜联蛋白V-FITC / PI和DAPI）评估了MCF-7的细胞凋亡。此外，克隆形成测定表明化合物5t抑制了MCF-7细胞上的集落形成。此外，流式细胞仪分析还显示化合物5t导致细胞停滞在细胞周期的G0 / G1期。此外，发现该化合物在正常人细胞（L-132）上进行测试时，具有较低的细胞毒性，因此更为安全。

  DOI：

  10.1016/j.bmcl.2018.03.074
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 N-[(3',4'-dimethoxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine
  参考文献：
  名称：

  Synthesis of triazole Schiff bases: Novel inhibitors of nucleotide pyrophosphatase/phosphodiesterase-1

  摘要：

  A series of Schiff base triazoles 1-25 was synthesized and evaluated for their nucleotide pyrophosphatase/ phosphodiesterase-1 inhibitory activities. Among twenty-five compounds, three compounds 10 (IC50 = 132.20 +/- 2.89 mu M), 13 (IC50 = 152.83 +/- 2.39 mu M), and 22 (IC50 = 251.0 +/- 6.64 mu M) were identified as potent inhibitors with superior activities than the standard EDTA (IC50 = 277.69 +/- 2.52 mu M). The newly identified inhibitors may open a new avenue for the development of treatment of phosphodiesterase-I related disorders. These compounds were also evaluated for carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitory potential and were found to be inactive. The compounds showed non-toxic effect towards PC3 cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.032

文献信息

• Antiglycation Activity of Triazole Schiff’s Bases Against Fructosemediated Glycation: In Vitro and In Silico Study
  作者：Muniza Shaikh、Salman Siddiqui、Humaira Zafar、Uzma Naqeeb、Fakiha Subzwari、Rehan Imad、Khalid M. Khan、Muhammad I. Choudhary

  DOI：10.2174/1573406415666190212105718

  日期：2020.5.20

  Objectives: Two classes of previously synthesized traizole Schiff’s bases (4H-1,2,4-triazole-4- Schiff’s bases 1-14, and 4H-1,2,4-triazole-3-Schiff’s bases 15-23) were evaluated for their in vitro antiglycation activity. Methods: In vitro fructose-mediated human serum albumin (HSA) glycation assay was employed to assess the antiglycation activity of triazole Schiff’s bases. The active compounds were subjected

  背景：已知晚期糖基化终产物（AGEs）与糖尿病并发症，神经退行性疾病和衰老的病理生理有关。预防AGEs的形成可能有助于控制这些疾病。 目的：评估了两类先前合成的曲唑席夫碱（4H-1,2,4-三唑-4-席夫碱1-14和4H-1,2,4-三唑-3-席夫碱15-23）。具有体外抗糖化活性 方法：采用果糖介导的人血清白蛋白（HSA）糖基化体外试验来评估三唑席夫碱的抗糖化活性。通过MTT测定法对小鼠成纤维细胞（3T3）细胞系上的活性化合物进行细胞毒性分析。进行了分子对接和模拟研究，以评估化合物与HSA的相互作用和稳定性。分别通过体外α-葡萄糖苷酶抑制作用和DPPH自由基清除试验评估了选定的非细胞毒性化合物的抗高血糖和抗氧化活性。 结果：来自4H-1,2,4-三唑-4-席夫碱的化合物1（IC50 = 47.30±0.38 µM）具有与标准芦丁（IC50 = 54.5±0.05 µM）相当的抗糖化活性，
• Mhaske, Sadhana D.; Takate, Sushama J.; Dhawale, Rhushikesh N., Indian Journal of Heterocyclic Chemistry, 2017, vol. 27, # 1, p. 89 - 97
  作者：Mhaske, Sadhana D.、Takate, Sushama J.、Dhawale, Rhushikesh N.、Akolkar, Hemantkumar N.、Randhavane, Pratibha V.、Karale, Bhausaheb K.

  DOI：——

  日期：——
• Designing, antifungal and structure activity relationship studies of Azomethines and β-lactam derivatives of aza heterocyclic amines
  作者：Diksha Verma、Sunita Sharma、Tanvi Sahni、Harleen Kaur、Sukhmanpreet Kaur

  DOI：10.1016/j.jics.2022.100587

  日期：2022.8
• Synthesis of 1,2,4-triazole-linked urea/thiourea conjugates as cytotoxic and apoptosis inducing agents
  作者：Ramya Tokala、Swarna Bale、Ingle Pavan Janrao、Aluri Vennela、Niggula Praveen Kumar、Kishna Ram Senwar、Chandraiah Godugu、Nagula Shankaraiah

  DOI：10.1016/j.bmcl.2018.03.074

  日期：2018.6

  A new series of 1,2,4-triazole-linked urea and thiourea conjugates have been synthesized and evaluated for their in vitro cytotoxicity against selected human cancer cell lines namely, breast (MCF-7, MDA-MB-231), lung (A549) prostate (DU145) and one mouse melanoma (B16-F10) cell line and compared with reference drug. The compound 5t showed significant cytotoxicity on MCF-7 breast cancer cell line with

  一系列新的1,2,4-三唑连接的尿素和硫脲的结合物已被合成并评价它们在体外针对选定的人癌症细胞系即，乳腺癌（MCF-7，MDA-MB-231），肺（细胞毒性A549）前列腺（DU145）和一种小鼠黑素瘤（B16-F10）细胞系，并与参考药物进行比较。在所有测试化合物中，化合物5t对MCF-7乳腺癌细胞系均表现出明显的细胞毒性，IC 50值为7.22±0.47 µM。值得注意的是，化合物5t诱导细胞凋亡使用不同的染色技术（如a啶橙/溴化乙锭（AO / EB），膜联蛋白V-FITC / PI和DAPI）评估了MCF-7的细胞凋亡。此外，克隆形成测定表明化合物5t抑制了MCF-7细胞上的集落形成。此外，流式细胞仪分析还显示化合物5t导致细胞停滞在细胞周期的G0 / G1期。此外，发现该化合物在正常人细胞（L-132）上进行测试时，具有较低的细胞毒性，因此更为安全。
• Synthesis of triazole Schiff bases: Novel inhibitors of nucleotide pyrophosphatase/phosphodiesterase-1
  作者：Khalid Mohammed Khan、Salman Siddiqui、Muhammad Saleem、Muhammad Taha、Syed Muhammad Saad、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2014.08.032

  日期：2014.11

  A series of Schiff base triazoles 1-25 was synthesized and evaluated for their nucleotide pyrophosphatase/ phosphodiesterase-1 inhibitory activities. Among twenty-five compounds, three compounds 10 (IC50 = 132.20 +/- 2.89 mu M), 13 (IC50 = 152.83 +/- 2.39 mu M), and 22 (IC50 = 251.0 +/- 6.64 mu M) were identified as potent inhibitors with superior activities than the standard EDTA (IC50 = 277.69 +/- 2.52 mu M). The newly identified inhibitors may open a new avenue for the development of treatment of phosphodiesterase-I related disorders. These compounds were also evaluated for carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitory potential and were found to be inactive. The compounds showed non-toxic effect towards PC3 cell lines. (C) 2014 Elsevier Ltd. All rights reserved.