5-苯基-1,3,4-噻二唑-2-硫醇 | 5585-19-3

• 物质功能分类: 化学试剂 - 有机试剂 - 硫醇盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-苯基-1,3,4-噻二唑-2-硫醇
• 英文名称: 2-phenyl-1,3,4-thiadiazole-5(4H)-thione
• 英文别名: 2-Phenyl-1,3,4-thiadiazoline-5-thione；5-phenyl-1,3,4-thiadiazole-2(3H)-thione；5-phenyl-1,3,4-thiadiazol-2-thione；5-Phenyl-1,3,4-thiadiazole-2-thiol；5-phenyl-3H-1,3,4-thiadiazole-2-thione
• CAS: 5585-19-3
• 化学式: C₈H₆N₂S₂
• mdl: MFCD01681863
• 分子量: 194.281
• InChiKey: ZTLMHGOWADYAHM-UHFFFAOYSA-N

物化性质

• 熔点：
  213-215℃
• 沸点：
  298.8±23.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-苯基-1,3,4-噻二唑-2-硫醇 在 hydrazine hydrate monohydrate 作用下， 生成 (5-苯基-1,3,4-噻二唑-2-基)肼
  参考文献：
  名称：

  Synthesis and spectral characterization of Zn(II) microsphere series for antimicrobial application

  摘要：

  Microsphere series have been synthesized by reacting zinc(II) acetate dihydrate with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole/oxadiazole/triazole with salicylaldehyde. Elemental analysis suggests that the complexes have 1:2 and 1:1 stoichiometry of the type [Zn(L)(2)(H2O)(2)] and [Zn(L')(2)(H2O)(2)]; LH = Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thia/oxadiazole with salicylaldehyde; L'H-2 = Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1,2,4-triazole and salicylaldehyde and were characterized by elemental analyses, IR, H-1 NMR and C-13 NMR spectral data. Scanning electron microscopy (SEM) showed that synthesized materials have microsphere like structure and there EDX analysis comparably matches with elemental analysis. For the antimicrobial application Schiff bases and their zinc(II) complexes were screened for four bacteria e.g. Bacillus subtilis, Pseudomonas aeruginosa, Salmonella typhi, Streptococcus pyogenes and four fungi e.g. Cyrtomium falcatum, Aspergillus niger, Fusarium oxysporium and Curvularia pallescence by the reported method. Schiff base and Zn(II) compounds showed significant antimicrobial activities. However, activities increase upon chelation. Thermal analysis (TGA) data of compound (10) showed its stability up to 300 degrees C. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.06.009
• 作为产物：
  描述：

  2-氨基-5-苯基-1,3,4-噻二唑 在 铜 盐酸 、 硫脲 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 5-苯基-1,3,4-噻二唑-2-硫醇
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activity of 5-Aryl-1,3,4-thiadiazole Derivatives

  摘要：

  DOI：

  10.1211/146080800128735430

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 biological evaluation of novel disulfides incorporating 1,3,4-thiadiazole scaffold as promising antitumor agents
  作者：Sha Li、Hai-Xin Wang、Hai-Ying Liu、Fen Jing、Xiao-Yun Fu、Cai-Wen Li、Yan-Ping Shi、Bao-Quan Chen

  DOI：10.1007/s00044-019-02389-3

  日期：2019.9

  and A549 lines. Bioassay indicated that some compounds showed stronger antitumor effects than reference drugs PX-12 and 5-fluorouracil. Among these screened compounds, compound 7h showed excellent biological activities in inhibiting SMMC-7721 cell proliferation with IC50 at 1.93 ± 0.08 μM. Compounds 7k and 7i manifested highly effective growth inhibitory activity versus MCF-7 cells, with IC50 at 3.04 ± 0

  在本研究中，制备了十四个含二硫基的2,5-二取代的1,3,4-噻二唑衍生物。通过IR，NMR，MS和元素分析鉴定了所得化合物7a – 7n。使用针对SMMC-7721，MCF-7和A549品系的标准CCK-8分析法研究了它们的体外抗增殖特性。生物测定表明，某些化合物显示出比参考药物PX-12和5-氟尿嘧啶更强的抗肿瘤作用。在这些筛选出的化合物中，化合物7h以1.93±0.08μM的IC 50抑制SMMC-7721细胞增殖具有优异的生物学活性。化合物7k和7i与MCF-7细胞相比，具有明显的高效生长抑制活性，IC 50分别为3.04±0.09和3.54±0.17μM。对于A549细胞，发现化合物7m具有最高的抗肿瘤效力，IC 50为3.67±0.13μM。
• [EN] OXA- AND THIA-DIAZOLES USEFUL IN THE TREATMENT OF TUBERCULOSIS<br/>[FR] OXADIAZOLES ET THIADIAZOLES UTILES DANS LE TRAITEMENT DE LA TUBERCULOSE
  申请人：UNIVERZITA KARLOVA V PRAZE FARMACEUTICKA FAKULTA V HRADCI KRALOVE

  公开号：WO2014161516A1

  公开（公告）日：2014-10-09

  A substituted diazole of genera l formula (1) wherein X is 0 or S; R is selected from the group consisting of: H, NH2-, C1-C11n alkyl, cyclohexyl-, benzyl-, phenyl-, pyridyl- or phenyl- substituted, in positions 2, 3, 4 or 5, by one or more electron-acceptor groups comprising -N02, -N(a lkyl)3, -CF3, CC13, -CN, -COOH, -COOAlk, -COOAr, -CHO, -COAlk, -COAr, -F, -CI, -Br, -I, and/or electron-donor groups comprising -NH2, -N Halkyl, -N(alkyl)2, -OH, -Oalkyl, -Oaryl, -NHCOCH3, -NHCOalkyl; -NHCOaryl; -alkyl, -aryl, wherein when R1 and R3 is -N02, then R2 a R4 is -H, or when R1 and R3 is -H, then R2 and R4 is -N02. These compounds can be prepared by easy synthesis and have low toxicity and significant activity against mycobacteria including their multiresistant strains. The invention provides also a pharmaceutical preparation having substituted diazole of formula (I) as the active ingredient, as well as the use of this substituted diazole as antituberculotic.

  一种通式(1)的取代二唑，其中X是0或S；R选自包括以下组：H，NH2-，C1-C11n烷基，环己基-，苄基-，苯基-，吡啶基-或苯基-，在2、3、4或5的位置上，被一个或多个电子受体基团取代，包括-N02，-N(烷基)3，-CF3，CC13，-CN，-COOH，-COOAlk，-COOAr，-CHO，-COAlk，-COAr，-F，-CI，-Br，-I，和/或电子供体基团包括-NH2，-NHalkyl，-N(alkyl)2，-OH，-Oalkyl，-Oaryl，-NHCOCH3，-NHCOalkyl；-NHCOaryl；-烷基，-芳基，其中当R1和R3是-N02，那么R2是R4是-H，或者当R1和R3是-H，那么R2和R4是-N02。这些化合物可以通过简单的合成法制备，并且具有低毒性和对包括多药耐药株在内的分枝杆菌的显著活性。本发明还提供了一种以通式(I)的取代二唑作为活性成分的药物制剂，以及将这种取代二唑用作抗结核药的应用。
• Efficient formation of C–S bond using heterocyclic thiones and arynes
  作者：Yu An、Gang Xu、Menglu Cai、Shihui Wang、Xiao zhong Wang、Yingqi Chen、Liyan Dai

  DOI：10.1016/j.tet.2020.131829

  日期：2021.1

  their diverse biological activities and medicinal prospects. Here, a facile method was reported. An arylation of 1,3,4-oxa(thia)diazol-2-thiones reacting with arynes to build C(aryl)-S bonds in the presence of CsF had good yields and excellent selectivity. The reaction was completed in short time without using expensive reagents and catalysts. Present reaction system is an efficient procedure to process

  苯硫基杂环化合物因其多样的生物学活性和医学前景而被广泛使用。在此，报道了一种简便的方法。在CsF存在下，与芳烃反应形成芳基-S键的1,3,4-氧杂噻唑并噻吩-2-硫酮的芳基化反应具有良好的收率和优异的选择性。反应在短时间内完成，无需使用昂贵的试剂和催化剂。目前的反应体系是一种处理苯硫基杂环化合物的有效方法，它揭示了一种可持续的方法，并在未来的有机合成中具有更好的应用前景。
• Some Reactions of 2-Aryl-4-chloromethyl-1,3,4-thiadiazoline-5-thiones
  作者：Ahmed A. El-Barbary、Hamdy A. Hammouda

  DOI：10.1002/ardp.19843170611

  日期：——

  Some 2‐aryl‐1,3,4‐thiadiazoline‐5‐thiones 1 react with formaldehyde to give the compounds 2, which react with thionyl chloride to afford the compounds 3. The latter react with phenols, thiophenol and related compounds giving 4. With amines, 3 yield the 2‐aryl‐4‐alkyl(aryl)aminomethyl‐1,3,4‐thiadiazoline‐5‐thiones 7. Some of the compounds described were screened bacteriologically.

  一些2-芳基-1,3,4-噻二唑啉-5-硫酮1与甲醛反应得到化合物2，再与亚硫酰氯反应得到化合物3，后者与苯酚、苯硫酚及相关化合物反应得到4。使用胺，3 产生 2-芳基-4-烷基（芳基）氨基甲基-1,3,4-噻二唑啉-5-硫酮 7。一些描述的化合物经过细菌学筛选。