5-(pyridin-2-yl)-3H-1,3,4-thiadiazole-2-thione | 28819-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(pyridin-2-yl)-3H-1,3,4-thiadiazole-2-thione
• 英文别名: 2-(2'-pyridyl)-1,3,4-thiadiazolin-5-thione；5-(2-pyridyl)-2-mercapto-1,3,4-thiadiazole；5-(pyridin-2-yl)-1,3,4-thiadiazole-2-thiol；5-pyridin-2-yl-3H-[1,3,4]thiadiazole-2-thione；2-mercapto-5-pyrid-2-yl-1,3,4-thiadiazole；5α-Pyridyl-1,3,4-thiadiazolin-2-thion；5-pyridin-2-yl-3H-1,3,4-thiadiazole-2-thione
• CAS: 28819-37-6
• 化学式: C₇H₅N₃S₂
• 分子量: 195.269
• InChiKey: NURSZUJTABWSTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  94.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(pyridin-2-yl)-3H-1,3,4-thiadiazole-2-thione 在 potassium carbonate 、 一水合肼 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 96.0h， 生成 (5-Pyridin-2-yl-[1,3,4]thiadiazol-2-ylsulfanyl)-acetic acid [1-(2-nitro-phenyl)-meth-(Z)-ylidene]-hydrazide
  参考文献：
  名称：

  Synthesis and antimycobacterial activity of [5-(pyridin-2-yl)-1,3,4-thiadiazol-2-ylthio]acetic acid arylidene-hydrazide derivatives

  摘要：

  [5-(Pyridin-2-yl)-1,3,4-thiadiazol-2-ylthio]acetic acid arylidene-hydrazide derivatives were synthesized and tested for their in vitro antimycobacterial activity. Some compounds showed a feable activity against a strain of Mycobacterium tuberculosis and a strain of Mycobacterium avium. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01097-7
• 作为产物：
  描述：

  2-吡啶甲酰肼 在 盐酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 5-(pyridin-2-yl)-3H-1,3,4-thiadiazole-2-thione
  参考文献：
  名称：

  含五杂环支架的吲哚衍生物的合成和生物学评价作为 A549 和 K562 细胞的新型抗癌剂

  摘要：

  摘要 在此，一系列新的 2- chloro- N- (5-(2-oxoindolin-3-yl)-4 H -pyrazol-3-yl) 乙酰胺衍生物包含 1,3,4 - thiadiazole ( 10a – i ) 和4 H -1,2,4-triazol-4-amine ( 11a – r ) 部分被设计、合成为新型抗癌药物。抗增殖活性值表明化合物10b是最有效的衍生物，对 A549 和 K562 细胞的 IC 50值分别为 12.0 nM 和 10 nM。10 b的机理调查和对接研究表明它具有良好的凋亡特性和剂量依赖性的 A549 和 K562 细胞生长停滞，阻断细胞周期进入 G2/M 期。有趣的是，10 b通过调节 EGFR 和 p53-MDM2 介导的途径抑制了 A549 和 K562 细胞的生长。

  DOI：

  10.1080/14756366.2022.2163393

文献信息

• 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。
• 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, Singlet Oxygen Photogeneration and DNA Photocleavage of Porphyrins with Nitrogen Heterocycle Tails
  作者：Yun-Man Zheng、Kai Wang、Tian Li、Xiu-Lan Zhang、Zao-Yin Li

  DOI：10.3390/molecules16053488

  日期：——

  Eight novel compounds were prepared by reaction of 5-(bromo- propoxyphenyl)-10,15,20-triphenylporphyrin with oxazole thiols, 1,3,4-oxadiazole thiols and 1,3,4-thiadiazole thiols, and their structures confirmed by UV-vis, IR, 1H-NMR, MS and elemental analysis. The assessment of indirectly measured 1O2 production rates against 5,10,15,20-tetraphenyl porphyrin (H2TPP) were described and the relative singlet oxygen production yields were：porphyrin 5 > porphyrins 1, 3, 4, 6-8, H2TPP > porphyrin 2. Porphyrin 4 and porphyrin 7 showed substantial photocleavage activities toward DNA, with over 75% cleavage observed at 40 µM. It suggested that these those porphyrins with nitrogen heterocycle tails are potential photosensitive agents.

  通过5-(溴丙氧基苯基)-10,15,20-三苯基卟啉与恶唑硫醇、1,3,4-恶二唑硫醇和1,3,4-噻二唑硫醇反应制备了8个新化合物，其结构通过UV-vis、IR、1H-NMR、MS 和元素分析。描述了对5,10,15,20-四苯基卟啉(H2TPP)间接测量的1O2产率的评估，相对单线态氧产率为：卟啉5 > 卟啉1, 3, 4, 6-8, H2TPP > 卟啉2. 卟啉 4 和卟啉 7 对 DNA 表现出显着的光裂解活性，在 40 µM 时观察到超过 75% 的裂解。这表明这些带有氮杂环尾部的卟啉是潜在的光敏剂。
• 2-mercapto-5-pyridyl-1,3,4-oxadiazoles and
  申请人：Ciba-Geigy Corporation

  公开号：US04894380A1

  公开（公告）日：1990-01-16

  The invention relates to 2-mercapto-5-pyridyl-1,3,4-oxadiazoles and 2-mercapto-5-pyridyl-1,3,4-thiadiazoles of the formula I ##STR1## wherein X is oxygen or sulfur, R' is C.sub.1 -C.sub.3 alkyl which is substituted by bromine, fluorine, C.sub.1 -C.sub.3 alkoxy or cyano; unsubstituted or halogen-substituted C.sub.3 -C.sub.7 alkenyl; unsubstituted or halogen-substituted C.sub.4 -C.sub.7 alkynyl, R is C.sub.1 -C.sub.3 alkyl, unsubstituted C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkoxy which is substituted by halogen or C.sub.1 -C.sub.3 alkoxy; unsubstituted or halogen-substituted C.sub.3 -C.sub.7 alkenyl; C.sub.3 -C.sub.7 alkynyl, C.sub.1 -C.sub.3 alkylthio, halogen, cyano, hydroxy, amino or amino which is substituted by one or two C.sub.1 -C.sub.3 alkyl groups; or is aminocarbonyl; and n is 0, 1, 2, 3 or 4, to the preparation of the compounds of formula I and to novel intermediates for the synthesis of these compounds. The compounds of formula I have nematicidal properties. The invention further relates to nematicidal compositions which contain at least one compound of formula I as active component, and to methods of using said compounds and of the compositions containing them for controlling nematodes.

  本发明涉及式I的2-巯基-5-吡啶基-1,3,4-噁唑和2-巯基-5-吡啶基-1,3,4-噻唑，其中X为氧或硫，R'为C.sub.1-C.sub.3烷基，该烷基被溴、氟、C.sub.1-C.sub.3烷氧基或氰基取代；未取代或卤素取代的C.sub.3-C.sub.7烯基；未取代或卤素取代的C.sub.4-C.sub.7炔基，R为C.sub.1-C.sub.3烷基，未取代的C.sub.1-C.sub.3烷氧基或被卤素或C.sub.1-C.sub.3烷氧基取代的C.sub.1-C.sub.3烷氧基；未取代或卤素取代的C.sub.3-C.sub.7烯基；C.sub.3-C.sub.7炔基，C.sub.1-C.sub.3烷硫基，卤素，氰基，羟基，氨基或被1个或2个C.sub.1-C.sub.3烷基取代的氨基；或为氨基甲酰基；n为0、1、2、3或4，用于制备式I化合物以及用于合成这些化合物的新中间体。式I化合物具有线虫杀性。本发明还涉及含有至少一种式I化合物作为活性成分的线虫杀剂组合物，以及使用该化合物和含有它们的组合物控制线虫的方法。
• 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。