5-(2-methoxyphenyl)-1,3,4-thiadiazole-2-thiol | 108413-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(2-methoxyphenyl)-1,3,4-thiadiazole-2-thiol
• 英文别名: 1,3,4-Thiadiazole-2(3H)-thione, 5-(2-methoxyphenyl)-；5-(2-methoxyphenyl)-3H-1,3,4-thiadiazole-2-thione
• CAS: 108413-63-4
• 化学式: C₉H₈N₂OS₂
• 分子量: 224.307
• InChiKey: GOOHMBZERNIEHB-UHFFFAOYSA-N

物化性质

• 沸点：
  348.0±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)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-methoxyphenyl)-1,3,4-thiadiazole-2-thiol 、 13-chloro-(+)-nootkatone 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests

  摘要：

  DOI：

  10.1021/acs.jafc.1c05853
• 作为产物：
  描述：

  2-甲氧基苯甲酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-(2-methoxyphenyl)-1,3,4-thiadiazole-2-thiol
  参考文献：
  名称：

  带有 1,3,4-噻二唑部分的苯并噻唑衍生物的合成和生物活性

  摘要：

  摘要 设计、合成了一系列带有 1,3,4-噻二唑部分的苯并噻唑衍生物，并评估了它们的抗菌、抗真菌和抗病毒活性。生物测定结果表明，大多数目标化合物对烟草花叶病毒（TMV）表现出良好的抗病毒活性和对米黄单胞菌的抗菌活性。oryzae (Xoo) 和青枯病菌 (Rs)。特别是，标题化合物 5k (N-(5-甲氧基苯并[d]噻唑-2-基)-2-((5-(2-甲苯基)-1,3,4-噻二唑-2-基)硫代)乙酰胺)和标题化合物5a(N-(5-硝基苯并[d]噻唑-2-基)-2-((5-(4-(三氟甲基)苯基)-1)的抗-Rs作用) ,3,4-噻二唑-2-基）硫代）乙酰胺）在 100 µg/mL 时分别达到 52.4% 和 71.6%，优于双甲噻唑（32.0% 和 52.3%）。此外，标题化合物5i (N-(5-甲氧基苯并[d]噻唑-2-基)-2-((5-(4-硝基苯基)-1,3,4-噻二唑-2-基)的保护和灭活活性)硫）乙酰胺）对

  DOI：

  10.1080/10426507.2018.1539992

文献信息

• Synthesis and antiviral activity of novel thioether derivatives containing 1,3,4-oxadiazole/thiadiazole and emodin moieties
  作者：Liangrun Dong、Baojing Song、Jian Wu、Zengxue Wu、Yunying Zhu、Xuewen Chen、Deyu Hu

  DOI：10.1080/10426507.2015.1114944

  日期：2016.6.2

  ABSTRACT ABSTRACT A series of novel thioether derivatives containing 1,3,4-oxadiazole/thiadiazole and emodin moieties were designed and synthesized. The structures of the target compounds were confirmed by 1H NMR, 13C NMR, Infrared, and elemental analysis. The results of bioactivity analysis showed that most of the target compounds exhibited moderate to good antiviral activity against tobacco mosaic virus

  图形摘要 摘要 设计并合成了一系列含有 1,3,4-恶二唑/噻二唑和大黄素部分的新型硫醚衍生物。目标化合物的结构经1H NMR、13C NMR、红外和元素分析确证。生物活性分析结果表明，大多数目标化合物在浓度为500 mg/L时对烟草花叶病毒表现出中等至良好的抗病毒活性。尤其是标题化合物中Y2、Y8和Y10在体内具有明显的治疗活性，抑制率分别为50.51、52.08和54.62%，与宁南霉素（53.40%）相似。
• Synthesis and antibacterial activity of novel lincomycin derivatives. II. Exploring (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives
  作者：Ko Kumura、Yoshinari Wakiyama、Kazutaka Ueda、Eijiro Umemura、Takashi Watanabe、Megumi Kumura、Takuji Yoshida、Keiichi Ajito

  DOI：10.1038/ja.2016.139

  日期：2017.5

  The synthesis and antibacterial activity of (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives are described. These derivatives were mainly prepared by the Mitsunobu reaction of 2,3,4-tris-O-(trimethylsilyl)lincomycin and the corresponding thiols. Exploring structure-activity relationships of the substituent at the 5 position of a thiadiazole ring revealed that compounds with

  描述了（7S）-7-（5-芳基-1,3,4-噻二唑-2-基-硫基）-7-脱氧林可霉素衍生物的合成和抗菌活性。这些衍生物主要是通过2,3,4-三-O-（三甲基甲硅烷基）林可霉素与相应的硫醇的Mitsunobu反应制备的。探索噻二唑环的5位上的取代基的构效关系，发现具有邻位取代苯基的化合物与具有未取代的报道的化合物（1）相比，具有erm基因的肺炎链球菌和化脓性链球菌显示出改善的抗菌活性。苯环。
• Synthesis and Antifungal Activity of 5-Chloro-6-Phenylpyridazin-3(2H)-one Derivatives
  作者：Jian Wu、Baoan Song、Hongjun Chen、Pinaki Bhadury、Deyu Hu

  DOI：10.3390/molecules14093676

  日期：——

  An effective method has been developed for the preparation under mild conditions of novel pyridazine derivatives from the easily accessible starting materials mucochloric acid and benzene. All the synthesized compounds were fully characterized and some of them displayed good antifungal activities against G. zeae, F. oxysporum and C. mandshurica in preliminary antifungal activity tests.

  开发了一种在温和条件下以容易获得的起始原料粘氯酸和苯制备新型哒嗪衍生物的有效方法。所有合成的化合物都得到了充分的表征，并且在初步的抗真菌活性测试中，其中一些化合物对玉米、尖孢镰刀菌和曼果镰刀菌表现出良好的抗真菌活性。
• Synthesis, antifungal activity and 3D-QSAR study of novel nopol-based 1,3,4-thiadiazole–thioether compounds
  作者：Xiu Wang、Wen-Gui Duan、Gui-Shan Lin、Ming Chen、Fu-Hou Lei

  DOI：10.1007/s11164-021-04510-x

  日期：2021.10

  A series of novel nopol derivatives containing 1,3,4-thiadiazole–thioether moiety were synthesized from β-pinene, which is a natural, abundant and renewable biomass resource. Their structures were characterized by FT-IR, 1H NMR, 13C NMR, ESI–MS and elemental analysis. In vitro antifungal activity of the target compounds was preliminarily evaluated against eight tested plant pathogens, including Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis and Colleterichum orbicalare. The bioassay results revealed that, at the concentration of 50 μg/mL, all the target compounds showed certain inhibition activity against the eight tested fungi. Compounds 5f (R = m–OCH3), 5i (R = m–F) and 5r (R = m–I) had excellent inhibition rates of 77.8%, 88.9% and 77.8%, respectively, against P. piricola, showing much better antifungal activity than that of the positive control chlorothalonil. Meanwhile, compound 5 m (R = p–Cl) displayed antifungal activity of 80.7% against R. solani. Furthermore, the analysis of three-dimensional quantitative structure–activity relationship (3D-QSAR) was performed for the relationship between the structures of the target compounds and their antifungal activity against P. piricola by CoMFA method. A reasonable CoMFA model (n = 6; q2 = 0.597; r2 = 0.985) was established.

  一系列包含1,3,4-噻二唑-硫醚基团的新型nopol衍生物是从β-松油烯合成的，这是一种天然、丰富且可再生的生物质资源。其结构通过FT-IR、1H NMR、13C NMR、ESI-MS和元素分析进行了表征。针对八种植物病原菌的体外抗真菌活性进行了初步评估，包括黄瓜纹枯病菌（Fusarium oxysporum f. sp. cucumerinum）、落花生斑点病菌（Cercospora arachidicola）、梨果病病菌（Physalospora piricola）、马铃薯晚疫病病菌（Alternaria solani）、玉米镰刀菌（Gibberella zeae）、水稻稻瘟病菌（Rhizoctonia solani）、玉米大斑病菌（Bipolaris maydis）和圆孢纹枯病菌（Colletotrichum orbicalare）。生物测定结果显示，在50 μg/mL的浓度下，所有目标化合物对这八种测试真菌均表现出一定的抑制活性。化合物5f（R = m-OCH3）、5i（R = m-F）和5r（R = m-I）对P. piricola的抑制率分别为77.8%、88.9%和77.8%，表现出比阳性对照氯硝噻啶更优越的抗真菌活性。同时，化合物5m（R = p-Cl）对R. solani表现出80.7%的抗真菌活性。此外，通过CoMFA方法对目标化合物的结构与其对P. piricola的抗真菌活性之间的关系进行了三维定量构效关系（3D-QSAR）分析，建立了合理的CoMFA模型（n = 6; q2 = 0.597; r2 = 0.985）。
• Lincomycin Derivatives and Antimicrobial Agents Comprising the Same as Active Ingredient
  申请人：Umemura Eijirou

  公开号：US20090156512A1

  公开（公告）日：2009-06-18

  This invention provides compounds of formula (I) or its pharmacologically acceptable salt or solvate, wherein A represents aryl or a monocyclic or bicyclic heterocyclic group, R 1 represents a halide, nitro, substituted C 1-6 alkyl, optionally substituted amino, C 1-6 alkyloxycarbonyl, optionally substituted aryl, a heterocyclic group, or heterocyclic carbonyl, R 2 represents a hydrogen atom or C 1-6 alkyl, R 3 represents C 1-6 alkyl, all of R 4 , R 5 , and R 6 represent a hydrogen atom, R 7 represents C 1-6 alkyl, m is 1 or 2, and n is 1. The compounds are novel lincomycin derivatives having a potent activity against resistant pneumococci. The compounds can be used as an antimicrobial agent and are useful for preventing or treating bacterial infectious diseases.

  本发明提供了式（I）的化合物或其药理学上可接受的盐或溶剂，其中A代表芳基或单环或双环杂环基，R1代表卤素、硝基、取代的C1-6烷基、可选取代的氨基、C1-6烷氧羰基、可选取代的芳基、杂环基或杂环羰基，R2代表氢原子或C1-6烷基，R3代表C1-6烷基，R4、R5和R6均代表氢原子，R7代表C1-6烷基，m为1或2，n为1。这些化合物是新型的林可霉素衍生物，对耐药性肺炎球菌具有强大的活性。这些化合物可以用作抗微生物剂，并且对于预防或治疗细菌感染性疾病是有用的。