1-(4-chlorophenyl)-3-(furan-3-ylmethyl)thiourea | 32564-38-8

• 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: 1-(4-chlorophenyl)-3-(furan-3-ylmethyl)thiourea
• 英文别名: 1-(4-chlorophenyl)-3-(furan-2-ylmethyl)thiourea；1-(4-chloro-phenyl)-3-furfuryl-thiourea
• CAS: 32564-38-8
• 化学式: C₁₂H₁₁ClN₂OS
• mdl: MFCD00124020
• 分子量: 266.751
• InChiKey: QTEYPAXEBVFYCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-3-(furan-3-ylmethyl)thiourea 在 N-甲基吗啉 、 tin(II) chloride dihdyrate 、 sodium acetate 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 benzyl ((2S)-1-((4-((Z)-2-((4-chlorophenyl)imino)-3-(furan-2-ylmethyl)-4-oxothiazolidin-5-yl)phenyl)amino)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Inhibitors of HCV NS5A: From Iminothiazolidinones to Symmetrical Stilbenes

  摘要：

  The iminothiazolidinone BMS-858 (2) was identified as a specific inhibitor of HCV replication in a genotype 1b replicon assay via a high-throughput screening campaign. A more potent analogue, BMS-824 (18), was used in resistance mapping studies, which revealed that inhibitory activity was related to disrupting the function of the HCV nonstructural protein 5A. Despite the development of coherent and interpretable SAIL, it was subsequently discovered that in DMSO 18 underwent an oxidation and structural rearrangement to afford the thiohydantoin 47, a compound with reduced HCV inhibitory activity. However, HPLC bioassay fractionation studies performed after incubation of 18 in assay media led to the identification of fractions containing a dimeric species 48 that exhibited potent antiviral activity. Excision of the key elements hypothesized to be responsible for antiviral activity based on SAR observations reduced 48 to a simplified, symmetrical, pharmacophore realized most effectively with the stilbene 55, a compound that demonstrated potent inhibition of HCV in a genotype 1b replicon with an EC50 = 86 pM.

  DOI：

  10.1021/ml1002647
• 作为产物：
  描述：

  2-呋喃甲胺 、 4-氯异硫氰酸苯酯 以 乙腈 为溶剂， 生成 1-(4-chlorophenyl)-3-(furan-3-ylmethyl)thiourea
  参考文献：
  名称：

  从基于硫脲的化合物到四唑衍生物的合成转变：合成的新型 N-(呋喃-2-基甲基)-1H-四唑-5-胺衍生物的结构和生物学评价

  摘要：

  合成了 N-(呋喃-2-基甲基)-1H-四唑-5-胺的 12 种新型衍生物。对得到的化合物8，分离出其对应的底物单晶，完成X射线衍射实验。在研究初期，进行了基于计算机结构的药理预测。使用标准和临床菌株筛选所有化合物的抗菌和抗分枝杆菌活性。与正常 (HaCaT) 细胞系相比，通过使用 MTT 方法评估了针对一组人类癌细胞系的细胞毒活性。发现所有检查的衍生物对正常细胞系无细胞毒性。在研究组中，化合物 6 在抗菌研究中显示出最有希望的结果。它抑制了四种医院表皮葡萄球菌的生长，当以 4 µg/mL 的量应用时。然而，对化合物 6 的存在最敏感的是表皮葡萄球菌 T 5501 851/19 临床菌株，其 MIC 值仅为 2 µg/mL。最后，基于来自该研究和我们之前工作的先导化合物建立了药效团模型。

  DOI：

  10.3390/molecules26020323

文献信息

• Synthesis, Structural Studies and Biological Evaluation of Halogen Derivatives of 1,3-Disubstituted Thiourea
  作者：Anna Bielenica、Karolina Stepien、Aleksandra Sawczenko、Tadeusz Lis、Anna E. Koziol、Silvia Madeddu、David Collu、Filippo Iuliano、Anita Kosmider、Marta Struga

  DOI：10.2174/1570180814666170106121025

  日期：2017.6.6

  mitochondrial dehydrogenase, whereas release of lactate dehydrogenase from the cytosol to culture medium was a marker of the cell death. Results: The X-ray crystallography studies showed the conformations adopted by the molecules 2a, 7a, 2b and 7b. Compounds 1a and 14a proved cytotoxic against MT-4 cells and different other cell lines derived from human haematological tumors (CC50 < 10 μM). They influenced on

  背景：卤素取代的硫脲衍生物具有充分证明的抗微生物，抗病毒和抗癌特性。 目的：这项工作评估了新合成的氟化硫脲化合物的抗菌和细胞毒性活性。 方法：通过4-氨基-1-苄基哌啶（1a-14a）或糠胺（1b-14b）与氟化异硫氰酸酯的缩合反应获得两个系列的硫脲。抗HIV-1活性评估是基于MTT方法测定的，在成对生长的MT-4细胞中病毒诱导的细胞致病性的抑制作用。根据CLSI指南，使用Mueller-Hinton II琼脂培养基在标准条件下通过圆盘扩散法检查抗菌效力。使用Mueller-Hinton琼脂和2％葡萄糖和0.5μg/ mL亚甲基蓝染料培养基评估抗真菌作用。HaCaT和A549细胞的生存能力通过线粒体脱氢酶测定MTT盐转化率来评估，而乳酸脱氢酶从胞质溶胶释放到培养基中是细胞死亡的标志。 结果：X射线晶体学研究表明分子2a，7a，2b和7b所采用的构象。化合物1a和14a被证明对MT-4细胞和
• [EN] NOVEL REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE TRANSCRIPTASE INVERSE
  申请人：UNIV RAMOT

  公开号：WO2009069132A2

  公开（公告）日：2009-06-04

  Compounds that are capable of inhibiting an activity of a reverse transcriptase are disclosed. Further disclosed are pharmaceutical compositions containing these compounds, and methods of inhibiting an activity of reverse transcriptase and/or of a mutant thereof and of treating an infection caused by a retrovirus, utilizing these compounds. The disclosed compounds are either identified by computational means or are designed and newly prepared based on structural features identified, at least in part, by computational means. Thus, further disclosed is a method of identifying candidate compounds for inhibiting an activity of a wild type reverse transcriptase and/or for treating a viral infection caused by a retrovirus.
• Inhibitors of HCV NS5A: From Iminothiazolidinones to Symmetrical Stilbenes
  作者：Jeffrey L. Romine、Denis R. St. Laurent、John E. Leet、Scott W. Martin、Michael H. Serrano-Wu、Fukang Yang、Min Gao、Donald R O’Boyle、Julie A. Lemm、Jin-Hua Sun、Peter T. Nower、Xiaohua (Stella) Huang、Milind S. Deshpande、Nicholas A. Meanwell、Lawrence B. Snyder

  DOI：10.1021/ml1002647

  日期：2011.3.10

  The iminothiazolidinone BMS-858 (2) was identified as a specific inhibitor of HCV replication in a genotype 1b replicon assay via a high-throughput screening campaign. A more potent analogue, BMS-824 (18), was used in resistance mapping studies, which revealed that inhibitory activity was related to disrupting the function of the HCV nonstructural protein 5A. Despite the development of coherent and interpretable SAIL, it was subsequently discovered that in DMSO 18 underwent an oxidation and structural rearrangement to afford the thiohydantoin 47, a compound with reduced HCV inhibitory activity. However, HPLC bioassay fractionation studies performed after incubation of 18 in assay media led to the identification of fractions containing a dimeric species 48 that exhibited potent antiviral activity. Excision of the key elements hypothesized to be responsible for antiviral activity based on SAR observations reduced 48 to a simplified, symmetrical, pharmacophore realized most effectively with the stilbene 55, a compound that demonstrated potent inhibition of HCV in a genotype 1b replicon with an EC50 = 86 pM.
• Synthetic Transition from Thiourea-Based Compounds to Tetrazole Derivatives: Structure and Biological Evaluation of Synthesized New N-(Furan-2-ylmethyl)-1H-tetrazol-5-amine Derivatives
  作者：Daniel Szulczyk、Anna Bielenica、Piotr Roszkowski、Michał A. Dobrowolski、Wioletta Olejarz、Sebastian Kmiecik、Małgorzata Podsiad、Marta Struga

  DOI：10.3390/molecules26020323

  日期：——

  lines, by using the MTT method. All examined derivatives were found to be noncytotoxic against normal cell lines. Within the studied group, compound 6 showed the most promising results in antimicrobial studies. It inhibited four hospital S. epidermidis rods’ growth, when applied at the amount of 4 µg/mL. However, the most susceptible to the presence of compound 6 was S. epidermidis T 5501 851/19 clinical

  合成了 N-(呋喃-2-基甲基)-1H-四唑-5-胺的 12 种新型衍生物。对得到的化合物8，分离出其对应的底物单晶，完成X射线衍射实验。在研究初期，进行了基于计算机结构的药理预测。使用标准和临床菌株筛选所有化合物的抗菌和抗分枝杆菌活性。与正常 (HaCaT) 细胞系相比，通过使用 MTT 方法评估了针对一组人类癌细胞系的细胞毒活性。发现所有检查的衍生物对正常细胞系无细胞毒性。在研究组中，化合物 6 在抗菌研究中显示出最有希望的结果。它抑制了四种医院表皮葡萄球菌的生长，当以 4 µg/mL 的量应用时。然而，对化合物 6 的存在最敏感的是表皮葡萄球菌 T 5501 851/19 临床菌株，其 MIC 值仅为 2 µg/mL。最后，基于来自该研究和我们之前工作的先导化合物建立了药效团模型。