3-nitroacetophenone thiosemicarbazone | 132898-27-2

• 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: 3-nitroacetophenone thiosemicarbazone
• 英文别名: [1-(3-Nitrophenyl)ethylideneamino]thiourea
• CAS: 132898-27-2
• 化学式: C₉H₁₀N₄O₂S
• mdl: MFCD01043478
• 分子量: 238.27
• InChiKey: NFJPLHYZNDOBTD-UHFFFAOYSA-N

物化性质

• 沸点：
  399.4±44.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitroacetophenone thiosemicarbazone 在 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 3-benzyl-2-(2-(1-(3-nitrophenyl)ethylidene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  1,3-噻唑烷丁-4-酮衍生物的合成，生物学评估和定量构效关系。具有高抗真菌效力和低细胞毒性的有前途的化学支架

  摘要：

  参考有关噻唑烷酮支架各种生物学特性的最新研究报告，我们合成了一百多种化合物，这些化合物的特征是1,2噻唑烷酮-4-酮核在C2处衍生化，并带有与（环）脂族连接的肼桥。或杂（芳基）部分，以及它们的N-苄基衍生物。这些分子被作为潜在的抗念珠菌药物进行了分析，显示它们具有与成熟的局部和全身性抗真菌药物（即克霉唑，氟康唑，酮康唑，咪康唑，噻康唑，两性霉素B）相当的生物活性，在某些情况下具有更高的生物学活性。具有最低MIC的化合物进行了进一步测试，以评估其细胞毒性作用（CC 50）在Hep2细胞上，证明了其相对安全性。最后，使用QSAR和3-D QSAR模型预测1,3-噻唑烷丁-4-酮支架的假定化学修饰，以设计针对念珠菌的新的和潜在的更具活性的化合物。

  DOI：

  10.1016/j.ejmech.2017.09.026
• 作为产物：
  描述：

  苯乙酮 在 硫酸 、 硝酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.25h， 生成 3-nitroacetophenone thiosemicarbazone
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates

  摘要：

  The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Ttypanosoma cruzi in in vitro assays (IC50 < 57 mu M), and no mutagenic profile was observed in micro-nucleous tests. Although the in vitro inhibition test showed that 10-mu M doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.022

文献信息

• Synthesis of some new hetarylpyranopyridazines, cinnolines, and hetarylpyridazine derivatives
  作者：M. Abdel-Megid、Y. Gabr、M. A. A. Awas、N. M. Abdel-Fatah

  DOI：10.1007/s10593-010-0433-1

  日期：2009.11

  4-Acetyl-5,6-diphenylpyridazin-3(2H)-one was condensed with 6-chloro-3-formylchromone under different reaction conditions to yield the enone or pyranopyridazine. Both compounds were used in the synthesis of some new hetarylpyranopyridazines. Pyranodipyridazine was obtained via a sequence of reactions of 4-acetyl-5,6-diphenylpyridazin-3(2H)-one with diethyl carbonate, acetic anhydride, and 4-bromobenzenediazonium

  在不同反应条件下，将4-乙酰基-5,6-二苯基哒嗪-3（2H）-1与6-氯-3-甲酰基色酮缩合，生成烯酮或吡喃并哒嗪。两种化合物都用于合成一些新的杂芳基吡喃并哒嗪。吡喃二哒嗪是通过4-乙酰基-5,6-二苯基吡啶并嗪-3（2H）-one与碳酸二乙酯，乙酸酐和4-溴苯重氮的反应序列获得的。哒嗪基丁烷-1,3-二酮与浓硫酸的反应 还研究了H2SO4，POCl3，肼，盐酸羟胺，氰基乙酰胺，硫脲和硫代氨基脲。
• Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma
  作者：Celeste De Monte、Simone Carradori、Daniela Secci、Melissa D'Ascenzio、Paolo Guglielmi、Adriano Mollica、Stefania Morrone、Susanna Scarpa、Anna Maria Aglianò、Sabrina Giantulli、Ida Silvestri

  DOI：10.1016/j.ejmech.2015.10.023

  日期：2015.11

  Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis, molecular docking, acetylcholinesterase and butyrylcholinesterase inhibitory potential of thiazole analogs as new inhibitors for Alzheimer disease
  作者：Fazal Rahim、Muhammad Tariq Javed、Hayat Ullah、Abdul Wadood、Muhammad Taha、Muhammad Ashraf、Qurat-ul-Ain、Muhammad Anas Khan、Fahad Khan、Salma Mirza、Khalid M. Khan

  DOI：10.1016/j.bioorg.2015.08.002

  日期：2015.10

  A series of thirty (30) thiazole analogs were prepared, characterized by H-1 NMR, C-13 NMR and EI-MS and evaluated for Acetylcholinesterase and butyrylcholinesterase inhibitory potential. All analogs exhibited varied butyrylcholinesterase inhibitory activity with IC50 value ranging between 1.59 +/- 0.01 and 389.25 +/- 1.75 mu M when compared with the standard eserine (IC50, 0.85 +/- 0.0001 mu M). Analogs 15, 7, 12, 9, 14, 1, 30 with IC50 values 1.59 +/- 0.01, 1.77 +/- 0.01, 6.21 +/- 0.01, 7.56 +/- 0.01, 8.46 +/- 0.01, 14.81 +/- 0.32 and 16.54 +/- 0.21 mu M respectively showed excellent inhibitory potential. Seven analogs 15, 20, 19, 24, 28, 30 and 25 exhibited good acetylcholinesterase inhibitory potential with IC50 values 21.3 +/- 0.50, 35.3 +/- 0.64, 36.6 +/- 0.70, 44.81 +/- 0.81, 46.36 +/- 0.84, 48.2 +/- 0.06 and 48.72 +/- 0.91 mu M respectively. All other analogs also exhibited well to moderate enzyme inhibition. The binding mode of these compounds was confirmed through molecular docking. (C) 2015 Elsevier Inc. All rights reserved.
• Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates
  作者：Lorena Blau、Renato Farina Menegon、Gustavo H.G. Trossini、João Vitor Dutra Molino、Drielli Gomes Vital、Regina Maria Barretto Cicarelli、Gabriela Duó Passerini、Priscila Longhin Bosquesi、Chung Man Chin

  DOI：10.1016/j.ejmech.2013.04.022

  日期：2013.9

  The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Ttypanosoma cruzi in in vitro assays (IC50 < 57 mu M), and no mutagenic profile was observed in micro-nucleous tests. Although the in vitro inhibition test showed that 10-mu M doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis, biological evaluation and quantitative structure-active relationships of 1,3-thiazolidin-4-one derivatives. A promising chemical scaffold endowed with high antifungal potency and low cytotoxicity
  作者：Simone Carradori、Bruna Bizzarri、Melissa D'Ascenzio、Celeste De Monte、Rossella Grande、Daniela Rivanera、Alessanda Zicari、Emanuela Mari、Manuela Sabatino、Alexandros Patsilinakos、Rino Ragno、Daniela Secci

  DOI：10.1016/j.ejmech.2017.09.026

  日期：2017.11

  hundred compounds characterized by a 1,3-thiazolidin-4-one nucleus derivatised at the C2 with a hydrazine bridge linked to (cyclo)aliphatic or hetero(aryl) moieties, and their N-benzylated derivatives. These molecules were assayed as potential anti-Candida agents and they were shown to possess comparable, and in some cases higher biological activity than well-established topical and systemic antimycotic drugs

  参考有关噻唑烷酮支架各种生物学特性的最新研究报告，我们合成了一百多种化合物，这些化合物的特征是1,2噻唑烷酮-4-酮核在C2处衍生化，并带有与（环）脂族连接的肼桥。或杂（芳基）部分，以及它们的N-苄基衍生物。这些分子被作为潜在的抗念珠菌药物进行了分析，显示它们具有与成熟的局部和全身性抗真菌药物（即克霉唑，氟康唑，酮康唑，咪康唑，噻康唑，两性霉素B）相当的生物活性，在某些情况下具有更高的生物学活性。具有最低MIC的化合物进行了进一步测试，以评估其细胞毒性作用（CC 50）在Hep2细胞上，证明了其相对安全性。最后，使用QSAR和3-D QSAR模型预测1,3-噻唑烷丁-4-酮支架的假定化学修饰，以设计针对念珠菌的新的和潜在的更具活性的化合物。