2-(3-chlorophenyl)-1,3,4-thiadiazole-5-thiol

• 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: 2-(3-chlorophenyl)-1,3,4-thiadiazole-5-thiol
• 英文别名: 5-(3-Chlorophenyl)-1,3,4-thiadiazole-2-thiol；5-(3-chlorophenyl)-3H-1,3,4-thiadiazole-2-thione
• 化学式: C₈H₅ClN₂S₂
• 分子量: 228.726
• InChiKey: SWGXUOSCGPQWJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 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

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)-benzene 、 2-(3-chlorophenyl)-1,3,4-thiadiazole-5-thiol 在 sodium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  含噻二唑单元的氯代丙烯衍生物的制备和用途

  摘要：

  本发明涉及一种含噻二唑单元的氯代丙烯衍生物(I)的制备和用途。以巯基取代的噻二唑中间体(II)与氯代丙烯化合物(III)反应得到。所述含噻二唑单元的氯代丙烯衍生物对有害昆虫具有良好的防治效果。

  公开号：

  CN113636987B
• 作为产物：
  描述：

  间氯苯甲酸甲酯 在 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 2-(3-chlorophenyl)-1,3,4-thiadiazole-5-thiol
  参考文献：
  名称：

  Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and Thiadiazoles as Selective Antitubercular Agents Active Against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  Herein, we report the discovery and structure activity relationships of 5-substituted-2-[(3,5-dinitrobenzyl)-sulfanyl]-1,3,4-oxadiazoles and 1,3,4-thiadiazoles as a new class of antituberculosis agents. The majority of these compounds exhibited outstanding in vitro activity against Mycobacterium tuberculosis CNCTC My 331/88 and six multidrug-resistant clinically isolated strains of M. tuberculosis, with minimum inhibitory concentration values as low as 0.03 mu M (0.011-0.026 mu g/mL). The investigated compounds had a highly selective antimycobacterial effect because they showed no activity against the other bacteria or fungi tested in this study. Furthermore, the investigated compounds exhibited low in vitro toxicities in four proliferating mammalian cell lines and in isolated primary human hepatocytes. Several in vitro genotoxicity assays indicated that the selected compounds have no mutagenic activity. The oxadiazole and thiadiazole derivatives with the most favorable activity/toxicity profiles also showed potency comparable to that of rifampicin against the nonreplicating streptomycin-starved M. tuberculosis 18b-Lux strain, and therefore, these derivatives, are of particular interest.

  DOI：

  10.1021/acs.jmedchem.5b00608

文献信息

• Heterocyclic amplifiers of phleomycin. V. Thiadiazolylpyridines and related compounds; preliminary antitumour results
  作者：AN Aliano、TE Allen、DJ Brown、WB Cowden、GW Grigg、D Kavulak、S Lan

  DOI：10.1071/ch9842385

  日期：——

  Syntheses are described for N,N-dimethyl-2-[5'-(pyridin-2''-yl)-1',3',4'-thiadiazol-2'-ylthio]ethylamine; the homologous propylamine; the N,N-diethyl homologue; the 5'-phenyl analogue; and some substituted phenyl, pyrazinyl and pyrimidinyl analogues. Unlike the pyridin-4''-yl isomer previously described, these compounds proved but mediocre amplifiers of phleomycin-G in vitro against Escherichia coli. Testing in vivo against Ehrlich's tumour in mice was therefore confined to the pyridin-4''-yl compound and to N,N-dimethyl-2-(6'-methyl-2'-phenylpyrimidin-4'-ylthio)ethylamine: the first showed considerable amplifying power towards two phleomycins and a bleomycin; the second, only marginally less amplification towards the same phleomycins.

  合成方法如下 N,N-二甲基-2-[5'-(吡啶-2''-基)-1',3',4'-噻二唑-2'-基硫基]乙胺 同系物丙胺；N,N-二乙基同系物； 5'-苯基类似物；以及一些取代的苯基、吡嗪基和嘧啶基类似物 和嘧啶类似物。与 与之前描述的吡啶-4''-基异构体不同，这些化合物被证明只是 与之前描述的吡啶-4''-基异构体不同，这些化合物在体外对大肠杆菌 体外对大肠杆菌的作用。 因此，针对小鼠艾氏肿瘤的体内试验仅限于吡啶-4''-基 化合物和 N,N-二甲基-2-(6'-甲基-2'-苯基嘧啶-4'-基硫基)乙胺：前者对两种噬菌体显示出相当大的扩增能力。 对两种酞霉素和一种博莱霉素显示出相当大的扩增能力。 和一种博莱霉素的扩增能力相当强；第二种对相同的 对相同的 霉素的放大能力。
• Synthesis and Fungicidal Activity of Some 5-Membered Heterocyclic Derivatives Containing Benzimidazoles
  作者：Lallan Mishra、V. K. Singh、N. K. Dubey、A. K. Mishra

  DOI：10.1271/bbb.57.989

  日期：1993.1

  2-Chloromethyl-5H/methyl benzimidazoles were condensed with different 2-substituted 5-mercapto-1,3,4-oxadiazoles and thiadiazoles, and 4-amino 2-substituted 5-mercapto-1,2,4-triazoles. The synthesized compounds were characterized and evaluated for their fungicidal activities, and few were found to be better fungicides than those commercially used.

  将2-氯甲基-5H /甲基苯并咪唑与不同的2-取代的5-巯基-1,3,4-恶二唑和噻二唑，以及4-氨基2-取代的5-巯基-1,2,4-三唑缩合。表征并评价了合成化合物的杀真菌活性，发现很少有比市售化合物更好的杀真菌剂。
• Efficient copper-catalyzed C–S cross-coupling of heterocyclic thiols with aryl iodides
  作者：Liang-Feng Niu、Yan Cai、Chao Liang、Xin-Ping Hui、Peng-Fei Xu

  DOI：10.1016/j.tet.2011.02.064

  日期：2011.4

  A copper-catalyzed cross-coupling of heterocyclic thiols with aryl iodides is reported. The reaction was carried out in the presence of CuI (5 mol %), 1,10-phenanthroline (10 mol %) and K2CO3 (1.3 equiv) in DMF at 120 °C. A variety of heterocyclic sulfides were prepared in high selectivities and yields.

  据报道，铜催化的杂环硫醇与芳基碘化物的交叉偶联。反应在120℃下在CuI（5mol％），1，10-菲咯啉（10mol％）和K 2 CO 3（1.3当量）的存在下在DMF中进行。以高选择性和高产率制备了各种杂环硫化物。
• 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）。
• Fabrication of magnetic amino-functionalized nanoparticles for S-arylation of heterocyclic thiols
  作者：Yanhong Liu、Lincheng Zhou、Xinping Hui、Zhenwen Dong、Hao Zhu、Yanming Shao、Yanfeng Li

  DOI：10.1039/c4ra08782h

  日期：——

  The aminosilane coupling agent and polyethylene imine-600 were loaded onto magnetic nanoparticles to obtain magnetic nanoligands (MNLs) A, B, C and D.

  氨基硅烷偶联剂和聚乙烯亚胺-600被加载到磁性纳米颗粒上，以获得磁性纳米配体（MNLs）A、B、C和D。