3,4-dichloroacetophenone thiosemicarbazone | 18087-41-7

• 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: 3,4-dichloroacetophenone thiosemicarbazone
• 英文别名: 1-(3,4-dichlorophenyl)-ethylidenethiosemicarbazone；[1-(3,4-Dichlorophenyl)ethylideneamino]thiourea
• CAS: 18087-41-7
• 化学式: C₉H₉Cl₂N₃S
• mdl: MFCD00276349
• 分子量: 262.163
• InChiKey: WLYQLQVFJXFMJD-UHFFFAOYSA-N

物化性质

• 熔点：
  196.0-197.9 °C
• 沸点：
  385.8±52.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 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：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dichloroacetophenone thiosemicarbazone 以 乙醇 、 水 、 丙酮 为溶剂， 反应 123.0h， 生成
  参考文献：
  名称：

  Exploring the Versatility of Cycloplatinated Thiosemicarbazones as Antitumor and Antiparasitic Agents

  摘要：

  Tridentate cycloplatinated thiosemicarbazone complexes have been prepared from a biologically significant ligand, 3,4-dichloroacetophenone thiosemicarbazone (1). The tetranuclear complex 2 was prepared by reaction of the ligand with K-2[PtCl4]. Two mononuclear (3 and 4) and two dinuclear (5 and 6) complexes were isolated upon cleavage of the Pt-S-bridging bonds of the tetranuclear complex 2 with the appropriate phosphane ligand. Each complex was characterized using various analytical and spectroscopic techniques, and the molecular structures of 2-4 were also elucidated. The in vitro antiparasitic activities of these complexes against Plasmodium falciparum strains (D10 (chloroquine sensitive) and Dd2 (chloroquine resistant)) and Trichomonas vaginalis have been determined. Preliminary studies into their potential plasmodial target in the form of beta-hematin formation inhibition assays were also completed. Preliminary results suggest that ligand 1 and complex 3 do not hinder formation of beta-hematin. The antiproliferative activity of the complexes against the cisplatin-senstive A2780 and cisplatin-resistant A2780cisR human ovarian cancer cell lines has been evaluated. The complexes were found to exhibit moderate to weak inhibitory activities.

  DOI：

  10.1021/om300334z
• 作为产物：
  描述：

  氨基硫脲 、 3,4-二氯苯乙酮 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 3,4-dichloroacetophenone thiosemicarbazone
  参考文献：
  名称：

  新设计的 2-(2-亚芳基肼基)-4-芳基噻唑的合成、抗 HIV 活性、分子模型研究和 QSAR

  摘要：

  摘要 考虑到 1,3-噻唑类化合物在药物化学方面的优势，为了获得更显着的生物轮廓，通过环化反应合成 2-(2-亚芳基肼基)-4-芳基噻唑类化合物 6-43 成为可能。缩氨基硫脲和 α-溴苯乙酮。缩氨基硫脲 5a-m 依次由取代的苯甲醛或苯乙酮和缩氨基硫脲合成。进行反应条件的优化以得到良好产率的目标分子。使用 MTT 测定法在体外评估了所有新化合物对 MT4 细胞中 HIV-1 和 HIV-2 复制的抗病毒活性。筛选结果表明，化合物 32-34 是该系列中唯一抑制细胞培养物中 HIV-1 和 HIV-2 复制的化合物，IC50 > 2.71，分别 >2.19 和 >1.71 μM。还研究了化合物 32 和 34 与人类免疫缺陷病毒逆转录酶 (HIV RT) 的一些氨基酸的分子对接。通过多元线性回归（MRL）和遗传函数逼近（GFA）两种方法获得了新合成的同类物之间的初步量子构效关系（QSAR）。

  DOI：

  10.1016/j.molstruc.2019.07.113

文献信息

• Structural design, synthesis and pharmacological evaluation of thiazoles against Trypanosoma cruzi
  作者：Gevanio Bezerra de Oliveira Filho、Marcos Veríssimo de Oliveira Cardoso、José Wanderlan Pontes Espíndola、Dayane Albuquerque Oliveira e Silva、Rafaela Salgado Ferreira、Pollyanne Lacerda Coelho、Pâmela Silva dos Anjos、Emanuelle de Souza Santos、Cássio Santana Meira、Diogo Rodrigo Magalhaes Moreira、Milena Botelho Pereira Soares、Ana Cristina Lima Leite

  DOI：10.1016/j.ejmech.2017.09.047

  日期：2017.12

  (Discrete Typing Units). Therefore, new drugs to treat this disease are necessary. Thiazole compounds have been described as potent trypanocidal agents. Here we report the structural planning, synthesis and anti-T. cruzi evaluation of a new series of 1,3-thiazoles (7–28), which were designed by placing this heterocycle instead of thiazolidin-4-one ring. The synthesis was conducted in an ultrasonic bath

  恰加斯病是美洲大陆最严重的健康问题之一。苯并硝唑（BDZ）和尼呋替莫（NFX）是唯一获准用于治疗的药物，除了在T. cruzi DTU（Discrete Typing Units）之间的易感性不同之外，在慢性阶段还表现出强烈的副作用和无效性。因此，治疗这种疾病的新药是必要的。噻唑化合物已被描述为有效的锥虫杀虫剂。在这里，我们报告了一系列新的1,3-噻唑类化合物的结构规划，合成和抗T. cruzi评估（7–28），这是通过放置该杂环而不是噻唑烷丁4一环来设计的。在室温下在超声浴中以2-丙醇为溶剂进行合成。通过改变连接在苯基和噻唑环上的取代基，观察到取代基保留，增强或大大提高了它们的抗克鲁维氏球菌活性。在一些情况下，在噻唑（化合物的5位甲基9，12和23）增加的杀锥虫属性。苯基交换为吡啶基杂环导致活性增加，从而产生最有效的抗锥虫病菌形式的化合物（14，IC 50trypo = 0.37μM）。
• Structural design, synthesis and pharmacological evaluation of 4-thiazolidinones against Trypanosoma cruzi
  作者：Gevanio Bezerra de Oliveira Filho、Marcos Veríssimo de Oliveira Cardoso、José Wanderlan Pontes Espíndola、Luiz Felipe Gomes Rebello Ferreira、Carlos Alberto de Simone、Rafaela Salgado Ferreira、Pollyanne Lacerda Coelho、Cássio Santana Meira、Diogo Rodrigo Magalhaes Moreira、Milena Botelho Pereira Soares、Ana Cristina Lima Leite

  DOI：10.1016/j.bmc.2015.10.048

  日期：2015.12

  Chagas disease is an infection caused by protozoan Trypanosoma cruzi, which affects approximately 810 million people worldwide. Benznidazole is the only drug approved for treatment during the acute and asymptomatic chronic phases of Chagas disease; however, it has poor efficacy during the symptomatic chronic phase. Therefore, the development of new pharmaceuticals is needed. Here, we employed the bioisosterism to modify a potent antiparasitic and cruzain-inhibitor aryl thiosemicarbazone (4) into 4-thiazolidinones (7-21). Compounds (7-21) were prepared by using a straightforward synthesis and enabled good to excellent yields. As a chemical elucidation tool, X-ray diffraction of compound (10) revealed the geometry and conformation of this class compounds. The screening against cruzain showed that 4-thiazolidinones were less active than thiosemicarbazone (4). However, the antiparasitic activity in Y strain trypomastigotes and host cell cytotoxicity in J774 macrophages revealed that compounds (10 and 18-21) are stronger and more selective antiparasitic agents than thiosemicarbazone (4). Specifically, compounds (18-20), which carry a phenyl at position N3 of heterocyclic ring, were the most active ones, suggesting that this is a structural determinant for activity. In infected macrophages, compounds (18-20) reduced intracellular amastigotes, whereas Benznidazole did not. In T. cruzi-infected mice treated orally with 100 mg/kg of compound (20), a decreased of parasitemia was observed. In conclusion, we demonstrated that the conversation of thiosemicarbazones into 4-thiazolidinones retains pharmacological property while enhances selectivity. (C) 2015 Elsevier Ltd. All rights reserved.
• Cyclopalladated complexes containing tridentate thiosemicarbazone ligands of biological significance: Synthesis, structure and antimalarial activity
  作者：Prinessa Chellan、Shereen Nasser、Livia Vivas、Kelly Chibale、Gregory S. Smith

  DOI：10.1016/j.jorganchem.2010.06.010

  日期：2010.9

  The C-H activation reaction of two aryl-derived thiosemicarbazones with K-2[PdCl4] affords tetranuclear cyclopalladated complexes (3 and 4) where the thiosemicarbazone ligand acts as a tridentate donor [C,N,S] coordinated to palladium via the ortho-carbon of the aryl ring, imine nitrogen and thiolato sulfur. The palladiumesulfur bridging coordination bonds give rise to a Pd4S4 core. These Pd-S-bridging bonds were cleaved with a variety of mono-and bis-phosphines to give a series of mono, di and tetranuclear organopalladium complexes (5-12) where the phosphorus atom coordinates to palladium trans to the imine nitrogen. All of the complexes were fully characterized using various analytical and spectroscopic techniques. These palladium complexes along with their free ligands were evaluated as bioorganometallic antimalarial agents against two Plasmodium falciparum strains, 3D7 (chloroquine sensitive) and K1 (chloroquine and pyrimethamine resistant). Some of the complexes were found to be moderate inhibitors of parasite growth and were more active than the corresponding free ligand. (C) 2010 Elsevier B. V. All rights reserved.
• Synthesis, anti-HIV activity, molecular modeling study and QSAR of new designed 2-(2-arylidenehydrazinyl)-4-arylthiazoles
  作者：Amna Rauf、Muhammad K. Kashif、Bahjat A. Saeed、Najim A. Al-Masoudi、Shahid Hameed

  DOI：10.1016/j.molstruc.2019.07.113

  日期：2019.12

  Abstract Taking into consideration the eminence of 1,3-thiazoles in medicinal chemistry and in a view of procuring more pronounced biological contour, the synthesis of 2-(2-arylidenehydrazinyl)-4-arylthiazoles 6–43 was made possible by the cyclization reaction of thiosemicarbazones and α-bromoacetophenones. The thiosemicarbazones 5a-m were in turn synthesized from substituted benzaldehydes or acetophenones

  摘要 考虑到 1,3-噻唑类化合物在药物化学方面的优势，为了获得更显着的生物轮廓，通过环化反应合成 2-(2-亚芳基肼基)-4-芳基噻唑类化合物 6-43 成为可能。缩氨基硫脲和 α-溴苯乙酮。缩氨基硫脲 5a-m 依次由取代的苯甲醛或苯乙酮和缩氨基硫脲合成。进行反应条件的优化以得到良好产率的目标分子。使用 MTT 测定法在体外评估了所有新化合物对 MT4 细胞中 HIV-1 和 HIV-2 复制的抗病毒活性。筛选结果表明，化合物 32-34 是该系列中唯一抑制细胞培养物中 HIV-1 和 HIV-2 复制的化合物，IC50 > 2.71，分别 >2.19 和 >1.71 μM。还研究了化合物 32 和 34 与人类免疫缺陷病毒逆转录酶 (HIV RT) 的一些氨基酸的分子对接。通过多元线性回归（MRL）和遗传函数逼近（GFA）两种方法获得了新合成的同类物之间的初步量子构效关系（QSAR）。
• Exploring the Versatility of Cycloplatinated Thiosemicarbazones as Antitumor and Antiparasitic Agents
  作者：Prinessa Chellan、Kirkwood M. Land、Ajit Shokar、Aaron Au、Seung Hwan An、Catherine M. Clavel、Paul J. Dyson、Carmen de Kock、Peter J. Smith、Kelly Chibale、Gregory S. Smith

  DOI：10.1021/om300334z

  日期：2012.8.27

  Tridentate cycloplatinated thiosemicarbazone complexes have been prepared from a biologically significant ligand, 3,4-dichloroacetophenone thiosemicarbazone (1). The tetranuclear complex 2 was prepared by reaction of the ligand with K-2[PtCl4]. Two mononuclear (3 and 4) and two dinuclear (5 and 6) complexes were isolated upon cleavage of the Pt-S-bridging bonds of the tetranuclear complex 2 with the appropriate phosphane ligand. Each complex was characterized using various analytical and spectroscopic techniques, and the molecular structures of 2-4 were also elucidated. The in vitro antiparasitic activities of these complexes against Plasmodium falciparum strains (D10 (chloroquine sensitive) and Dd2 (chloroquine resistant)) and Trichomonas vaginalis have been determined. Preliminary studies into their potential plasmodial target in the form of beta-hematin formation inhibition assays were also completed. Preliminary results suggest that ligand 1 and complex 3 do not hinder formation of beta-hematin. The antiproliferative activity of the complexes against the cisplatin-senstive A2780 and cisplatin-resistant A2780cisR human ovarian cancer cell lines has been evaluated. The complexes were found to exhibit moderate to weak inhibitory activities.