1-(4-bromophenyl)-3-(4-methoxyphenyl)thiourea | 97272-09-8

• 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-bromophenyl)-3-(4-methoxyphenyl)thiourea
• CAS: 97272-09-8
• 化学式: C₁₄H₁₃BrN₂OS
• 分子量: 337.24
• InChiKey: LNOOFRRAHAPHGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3-(4-methoxyphenyl)thiourea 在 碘 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  使用碘对四唑和相关杂环进行串联区域选择性合成†

  摘要：

  已经开发了一种一锅串联方法，用于从异硫氰酸芳基酯合成四唑化合物。异硫氰酸芳基酯与氨，和芳基胺（R-NH 2）提供了单，1,3-二取代的对称和不对称的硫脲，这些硫脲在用分子碘（I 2）脱硫后，形成了相应的杂亚异丙基苯（氰胺或碳二亚胺）。在原位上与后续处理中产生的杂累叠氮化钠在室温下得到相应的四唑。对于非对称1,3-二取代的硫脲产物区域选择性被发现与所述碱度（对相关联ķ一个附接至硫脲母体胺的）。芳基-仲-烷基不对称硫脲得到的是硫酰胺基胍基产物，而不是由HgCl 2介导的反应产生的5-氨基四唑。双-thioureas从芳基异硫氰酸酯和衍生肼 仅给予噻二唑。

  DOI：

  10.1039/c0ob01007c
• 作为产物：
  描述：

  4-甲氧基二苯胺 、 4-溴苯基异硫氰酸酯 以 乙腈 为溶剂， 反应 12.0h， 以65%的产率得到1-(4-bromophenyl)-3-(4-methoxyphenyl)thiourea
  参考文献：
  名称：

  （4-甲氧基苯基）-1H-四唑-5-胺区域异构体的开发作为新型的选择性抗结核药。

  摘要：

  从其相应的硫脲类似物（1-9）合成了一系列卤代（4-甲氧基苯基）-1H-四唑-5-胺区域异构体（1a-9a，1b-9b）。通过1a，1b和5a的X射线晶体学研究证实了合成途径。测试了标题衍生物对标准，“野生型”和非典型分枝杆菌的体外抗结核活性。最高的治疗潜能归因于N-（溴苯基）四唑异构体8a和9a。它们对耐多药结核分枝杆菌的生长有抑制作用。210比一线抗结核药强8-16倍。与现有药物相比，其他新的四唑衍生化合物对这种病原体也有更多或同等效力。在非结核菌菌株中，分枝杆菌对大多数四唑衍生物的存在最敏感。发现9a和链霉素之间具有协同相互作用，以及8a和9a与异烟肼，利福平和乙胺丁醇成对的可加性。所研究的化合物均未显示出对正常和癌细胞系的抗菌或细胞毒性特性，这表明它们具有高度选择性的抗分枝杆菌作用。

  DOI：

  10.1016/j.ejmech.2019.111882

文献信息

• Synthesis and uncoupling activities of hydrophobic thioureas.
  作者：SEIJU KUBOTA、KISAKO HORIE、HEMANTK. MISRA、KOUHEI TOYOOKA、MASAYUKI UDA、MASAYUKI SHIBUYA、HIROSHI TERADA

  DOI：10.1248/cpb.33.662

  日期：——

  Various N-aryl-N'-phenylthioureas, N, N'-diarylthioureas and N-(1, 2, 4-triazol-3-yl)-N'-arylthioureas were prepared and examined for uncoupling activities. The results indicate that substitution at the 4-position of the phenyl groups of diaryl thioureas is very important for uncoupling activities. Diphenyl thioureas substituted with two or more halogen atoms exhibited strong activities. The highest activity was exhibited by a compound containing nitro groups on both phenyl groups. These results indicate that the hydrophobicity and acidic nature of the compound are of primary importance for uncoupling activities. A remarkable decrease in activity was observed with the thioureas which were substituted with pyridine and 1, 2, 4-triazole rings. The reaction of phenyl isothiocyanate with 3-amino-1, 2, 4-triazole was also studied.

  制备并测试了各种N-芳基-N'-苯基硫脲、N,N'-二芳基硫脲和N-(1,2,4-三唑-3-基)-N'-芳基硫脲的解偶联活性。结果表明，对于解偶联活性而言，二芳基硫脲的苯基4-位取代非常重要。含有两个或更多卤素原子的二苯基硫脲表现出强烈的活性。在两个苯基上都含有硝基的化合物显示出最高的活性。这些结果表明，化合物对疏水性和酸性对于解偶联活性具有首要重要性。当硫脲被吡啶和1,2,4-三唑环取代时，活性显著下降。还研究了苯基异硫氰酸酯与3-氨基-1,2,4-三唑的反应。
• A NEW AND EFFICIENT SOLID STATE SYNTHESIS OF DIARYL THIOUREAS
  作者：Jian-Ping Li、Yu-Lu Wang、Hong Wang、Qian-Fu Luo、Xiao-Yang Wang

  DOI：10.1081/scc-100103270

  日期：2001.1

  Fourteen diaryl thioureas which are physiologically active have been synthesized in the solid state at room temperature. The reaction needs only simple equipment and gives excellent yields.

  已在室温下以固态合成了十四种具有生理活性的二芳基硫脲。该反应只需要简单的设备，产率极好。
• A simple and straightforward synthesis of phenyl isothiocyanates, symmetrical and unsymmetrical thioureas under ball milling
  作者：Ze Zhang、Hao-Hao Wu、Ya-Jun Tan

  DOI：10.1039/c3ra43252a

  日期：——

  anilines were efficiently transformed into isothiocyanates (in presence of 5.0 equiv. CS2) or symmetrical thioureas (in presence of 1.0 equiv. CS2), without using any other harsh or toxic decomposition reagent. Some in situ generated isothiocyanates can directly “click” with other amines to afford unsymmetrical thioureas.

  推动者 酸值在球磨下，无需使用任何其他刺激性或有毒的分解试剂，即可将苯胺有效地转化为异硫氰酸酯（存在5.0当量CS 2）或对称硫脲（存在1.0当量CS 2）。一些原位生成的异硫氰酸酯可以直接与其他胺“点击”，从而提供不对称的硫脲。
• Synthesis and Erythroid Induction Activity of New Thiourea Derivatives
  作者：Hina Siddiqui、Sarah Shafi、Hamad Ali、Syed Ghulam Musharraf

  DOI：10.2174/1573406416666200514085623

  日期：2020.12.30

  The use of medicinal agents to augment the fetal hemoglobin (HbF) accretion is an important approach for the treatment of sickle-cell anemia and β-thalassemia. HbF inducers have the potential to reduce the clinical symptoms and blood transfusion dependence in the patients of β- hemoglobinopathies.

  The current study was aimed to examine the erythroid induction potential of newly synthesized thiourea derivatives.

  Thiourea derivatives 1-27 were synthesized by using environmentally friendly methods. Compounds 3, 10 and 22 were found to be new. The structures of synthesized derivatives were deduced by using various spectroscopic techniques. These derivatives were then evaluated for their erythroid induction using the human erythroleukemic K562 cell line, as a model. The benzidine-H2O2 assay was used to evaluate erythroid induction, while HbF expression was studied through immunocytochemistry using the Anti-HbF antibody. Cytotoxicity of compounds 1-27 was also evaluated on mouse fibroblast 3T3 cell line and cancer Hela cell line using MTT assay.

  All the compounds (1-27) have not been reported for their erythroid induction activity previously. Compounds 1, 2, and 3 were found to be the potent erythroid inducing agents with % induction of 45± 6.9, 44± 5.9, and 41± 6.1, at 1.56, 0.78, and 0.78 μM concentrations, respectively, as compared to untreated control (12 ± 1 % induction). Furthermore, compound 1, 2, and 3 significantly induced fetal hemoglobin the expression up to 4.2-fold, 4.06-fold, and 3.52-fold, respectively, as compared to untreated control. Moreover, the compounds 1-4, 6-9, 11, 12, 15, 17, 19, 22, 23, and 25 were found to be non-cytotoxic against the 3T3 cell line.

  This study signifies that the compounds reported here may serve as the starting point for the designing and development of new fetal hemoglobin inducers for the treatment of β- hemoglobinopathies.

  背景：利用药物促进胎儿血红蛋白（HbF）增加是治疗镰状细胞贫血和β地中海贫血的重要方法。HbF诱导剂有潜力减少β-血红蛋白病患者的临床症状和依赖输血的情况。 目的：本研究旨在检验新合成硫脲衍生物的红细胞诱导潜力。 方法：利用环保方法合成了硫脲衍生物1-27。发现化合物3、10和22是新合成的。通过各种光谱技术推导出合成衍生物的结构。然后利用人类红细胞白血病K562细胞系作为模型评估它们的红细胞诱导作用。利用苯胺-H2O2试验评估红细胞诱导作用，利用抗HbF抗体进行免疫细胞化学研究HbF表达。还利用MTT试验评估化合物1-27对小鼠成纤维细胞3T3细胞系和癌细胞Hela细胞系的细胞毒性。 结果：所有化合物（1-27）以前未报道其红细胞诱导活性。化合物1、2和3被发现是有效的红细胞诱导剂，其诱导率分别为45±6.9、44±5.9和41±6.1，在浓度为1.56、0.78和0.78μM时，相比未处理对照（12±1%诱导）。此外，化合物1、2和3显著提高了胎儿血红蛋白的表达，分别比未处理对照提高了4.2倍、4.06倍和3.52倍。此外，化合物1-4、6-9、11、12、15、17、19、22、23和25对3T3细胞系表现出非细胞毒性。 结论：本研究表明，这里报道的化合物可能成为设计和开发新的胎儿血红蛋白诱导剂用于治疗β-血红蛋白病的起点。
• Molecular modeling and synthesis of some new 2-imino-4-thiazolidinone derivatives with promising TNF-α inhibitory activity
  作者：Yakub Ali、Mohammad Sarwar Alam、Hinna Hamid、Asif Husain、Abhijeet Dhulap、Firasat Hussain、Sameena Bano、Chetna Kharbanda

  DOI：10.1039/c5nj00078e

  日期：——

  Out of 32 novel 2-imino-4-thiazolidinones, compounds3f&3gshowed potent anti-inflammatory activity without causing any damage to the stomach.

  在32种新型2-亚氨基-4-噻唑啉酮中，化合物3f和3g显示出强效的抗炎活性，而不会对胃造成任何损害。