5-methyl-N-phenyl-1,3,4-thiadiazol-2-amine | 7159-68-4

• 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: 5-methyl-N-phenyl-1,3,4-thiadiazol-2-amine
• CAS: 7159-68-4
• 化学式: C₉H₉N₃S
• mdl: MFCD00598436
• 分子量: 191.257
• InChiKey: GMLHQAXHARHDDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methyl-N-phenyl-1,3,4-thiadiazol-2-amine 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 5-Phenylamino-2-<4-trimethylammonio-styryl>-1.3.4-thiadiazol
  参考文献：
  名称：

  Tripathy,P.B.; Rout,M.R., Journal of the Indian Chemical Society, 1960, vol. 37, p. 414 - 419

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰氨基-3-苯基硫脲 在 硫酸 作用下， 反应 0.5h， 以66%的产率得到5-methyl-N-phenyl-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis of some 1,3,4-thiadiazole derivatives as inhibitors of Entamoeba histolytica

  摘要：

  In the quest for potent anti-amoebic agents, some 1,3,4-thiadiazole derivatives were synthesized and characterized by spectral data. The purity of the compounds was confirmed by elemental analysis. All the compounds were screened in vitro against HM1:IMSS strain of Entamoeba histolytica by microdilution method. The results revealed that compounds 1 (IC50 = 0.670 mu M), 3 (IC50 = 1.60 mu M) and 8 (IC50 = 0.522 mu M) had much better anti-amoebic activity than the reference drug metronidazole (IC50 = 1.80 mu M). Further, cytotoxicity of the compounds having IC50 value less than metronidazole was assessed by MTT assay on human breast cancer MCF-7 cell line and all the compounds were found low cytotoxic in the concentration range of 2.5-250 mu M. Preliminary results indicate that these three compounds (1, 3 and 8) may be subjected to further investigations and it may be hoped that the present study will stimulate efforts towards the development of novel effective anti-amoebic agents.

  DOI：

  10.1007/s00044-012-0107-x

文献信息

• Mesoionic Purinone Analogs IV: Synthesis and In Vitro Antibacterial Properties of Mesoionic Thiazolo[3,2-a]pyrimidin-5,7-diones and Mesoionic 1,3,4-Thiadiazolo[3,2-a]pyrimidin-5,7-diones
  作者：R.A. Coburn、R.A. Glennon

  DOI：10.1002/jps.2600621110

  日期：1973.11

  Derivatives of two members of a new and unusual class of heterocycles, termed mesoionic purinone analogs, were synthesized and examined for in vitro antibacterial activity. Mesoionic thiazolo[3,2-a]pyrimidin-5,7-diones and mesoionic 1,3,4-thiadiazolo[3,2-a]pyrimidin-5,7-diones, which are isoconjugate with xanthine, were found to exhibit antibacterial activity against both Gram-negative and Gram-positive

  合成了新的和异常的一类杂环的两个成员的衍生物，称为中离子嘌呤酮类似物，并检查了其体外抗菌活性。发现与黄嘌呤同缀合物的中离子噻唑并[3,2-a]嘧啶-5,7-二酮和中离子1,3,4-噻二唑并[3,2-a]嘧啶-5,7-二酮与黄嘌呤同构。对革兰氏阴性和革兰氏阳性生物均具有抗菌活性。几个中离子的1,3,4-噻二唑并[3,2-a]嘧啶-5,7-二酮对寻常变形杆菌和金黄色葡萄球菌具有显着水平的活性。
• Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
  作者：Daniel Moser、Yaya Duan、Feng Wang、Yuanhong Ma、Matthew J. O'Neill、Josep Cornella

  DOI：10.1002/anie.201806271

  日期：2018.8.20

  The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry‐BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C−N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C−O, C−N, C−S, or C−SO2R bonds are disclosed herein. In contrast to C−N activation through diazotization

  提出了使用四氟硼酸吡啶鎓试剂（Pyry-BF 4）对氨基杂环进行官能化的方法。该试剂可与多种杂环胺有效地缩合，并为亲核芳香族取代反应准备C-N键。本文公开了用于形成CO，CN，CS或CS 2 R键的60多个例子。与通过重氮化和多烷基化进行CN活化相反，该方法的特点是条件温和且对官能团的耐受力强。除小分子衍生化外，Pyry-BF 4还允许以后期方式引入官能团，以提供高度官能化的结构。
• Bis(1,3,4-Thiadiazolo)-1,3,5-triaziniumHalides: Access to Highly Substituted Aromatic Guanidines
  作者：Ernst Anders、Kurt Wermann、Martin Walther、Helmar Görls

  DOI：10.1055/s-2003-40844

  日期：——

  The reaction of bis(1,3,4-thiadiazolo)-1,3,5-triazinium halides with primary aromatic amines in CHCl3/Et3N yields new highly substituted aromatic guanidines (up to 90% yield).

  双(1,3,4-噻二唑)-1,3,5-三嗪卤化物与芳香族伯胺在CHCl3/Et3N中反应生成新的高度取代的芳香族胍（产率高达90%）。
• OCT3 ACTIVITY INHIBITOR CONTAINING IMIDAZOPYRIDINE DERIVATIVE AS ACTIVE COMPONENT, AND OCT3 DETECTION AGENT
  申请人：Shin Nippon Biomedical Laboratories, Ltd.

  公开号：EP2939675A1

  公开（公告）日：2015-11-04

  [Problem] To provide an OCT3 activity inhibitor having a different basic skeleton than that of conventional OCT3 activity inhibitors. [Solution] This inhibitor of organic cation transporter 3 (OCT3) contains, as an active component, an imidazo[1,2-a]pyridine derivative, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof

  [问题]提供一种 OCT3 活性抑制剂，其基本骨架不同于传统的 OCT3 活性抑制剂。 解决方案]这种有机阳离子转运体 3 (OCT3) 抑制剂的活性成分包括咪唑并[1,2-a]吡啶衍生物、其药学上可接受的盐或其药学上可接受的溶液
• Sen,A.B.; Gupta,S.K., Journal of the Indian Chemical Society, 1962, vol. 39, p. 628 - 634
  作者：Sen,A.B.、Gupta,S.K.

  DOI：——

  日期：——