5-{[(3,4-Dichlorophenyl)methyl]sulfanyl}-1,3,4-thiadiazol-2-amine

• 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-{[(3,4-Dichlorophenyl)methyl]sulfanyl}-1,3,4-thiadiazol-2-amine
• 英文别名: 5-[(3,4-dichlorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-amine
• 化学式: C₉H₇Cl₂N₃S₂
• mdl: MFCD02215565
• 分子量: 292.213
• InChiKey: CWHKSVGUSBSCQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-{[(3,4-Dichlorophenyl)methyl]sulfanyl}-1,3,4-thiadiazol-2-amine 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.5h， 生成 N-(5-((3,4-dichlorobenzyl)thio)-1,3,4-thiadiazol-2-yl)-2-((4-(phenylamino)quinazolin-2-yl)thio)acetamide
  参考文献：
  名称：

  含1,3,4-噻二唑的4-氨基喹唑啉衍生物的合成及体外抗肿瘤活性评价

  摘要：

  为了寻找高效、低毒的新型抗肿瘤药物，设计、合成了一系列含有1,3,4-噻二唑基团的新型4-氨基喹唑啉衍生物，并评估了其对四种人类癌细胞株的抗增殖活性（H1975， PC-3、MCF-7 和 HGC-27）在体外使用 MTT 测定。其中，化合物N-(5-((3,5-二氯苄基)硫代)-1,3,4-噻二唑-2-基)-2-((4-(苯氨基)喹唑啉-2-基)硫代)乙酰胺 ( 15o ) 对四种测试的癌细胞系显示出良好的抗肿瘤增殖活性，IC 50PC-3 细胞的值为 1.96 ± 0.15 μM。抗肿瘤活性明显优于吉非替尼。进一步的机制研究表明，化合物15o以浓度依赖性和时间依赖性方式抑制PC-3肿瘤细胞的迁移能力，阻断S期细胞周期。同时细胞克隆实验进一步证明，化合物15o显着抑制PC-3细胞集落形成，2.0 μM抑制率高达92%。

  DOI：

  10.1007/s00044-022-02913-y
• 作为产物：
  描述：

  2-氨基-5-巯基-1,3,4-噻二唑 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.5h， 生成 5-{[(3,4-Dichlorophenyl)methyl]sulfanyl}-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis and biological assessment of ciprofloxacin-derived 1,3,4-thiadiazoles as anticancer agents

  摘要：

  The quinolone-3-carboxylic acid scaffold is essential structure for antibacterial activity of fluoroquinolones such as ciprofloxacin. Modification of 3-carboxylic functionality in this structure can be used for switching its activity from antibacterial to anticancer. Accordingly, a series of C-3 modified ciprofloxacin derivatives containing N-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-carboxamide moiety was synthesized as novel anticancer agents. Most of compounds showed significant activity against MCF-7, A549 and SKOV-3 cancer cells in the MTT assay. In particular, compounds 13a-e and 13g were found to be as potent as standard drug doxorubicin against MCF-7 cell line (IC50s = 3.26-3.90 µM). Furthermore, the 4-fluorobenzyl derivatives 13h and 14b with IC50 values of 3.58 and 2.79 µM exhibited the highest activity against SKOV-3 and A549 cells, being as potent as doxorubicin. Two promising compounds 13e and 13g were further tested for their apoptosis inducing activity and cell cycle arrest. Both compounds could significantly induce apoptosis in MCF-7 cells, while compound 13e was more potent apoptosis inducer resulting in an 18-fold increase in the proportion of apoptotic cells at the IC50 concentration in MCF-7 cells. The cell cycle analysis revealed that compounds 13e and 13g could increase cell portions in the sub-G1 phase, inducing oligonucleosomal DNA fragmentation and apoptosis confirmed by comet assay.

  DOI：

  10.1016/j.bioorg.2020.104383

文献信息

• Compounds for the treatment of neurodegenerative disorders
  申请人：Chen L. Yuhpyng

  公开号：US20050043372A1

  公开（公告）日：2005-02-24

  The present invention relates to compounds of the Formula wherein R 3 , R 5 , R 7 , U, X, Y and Z are as defined. Compounds of the Formula I have activity inhibiting production of Aβ-peptide. This invention also relates to pharmaceutical compositions and methods of treating diseases, for example, neurodegenerative diseases, e.g., Alzheimer's disease, in a mammal comprising compounds of the Formula I.

  本发明涉及具有以下结构的化合物，其中R3、R5、R7、U、X、Y和Z如所定义。公式I的化合物具有抑制Aβ肽产生活性。本发明还涉及含有公式I化合物的药物组合物和治疗疾病的方法，例如，神经退行性疾病，例如阿尔茨海默病，在哺乳动物中。
• COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS
  申请人：Chen Yuhpyng L.

  公开号：US20080249094A1

  公开（公告）日：2008-10-09

  The present invention relates to compounds of the Formula wherein R 3 , R 5 , R 7 , U, X, Y and Z are as defined. Compounds of the Formula I have activity inhibiting production of Aβ-peptide. This invention also relates to pharmaceutical compositions and methods of treating diseases, for example, neurodegenerative diseases, e.g., Alzheimer's disease, in a mammal comprising compounds of the Formula I.

  本发明涉及公式I中的化合物，其中R3、R5、R7、U、X、Y和Z如定义所述。公式I的化合物具有抑制Aβ-肽生成活性。本发明还涉及制备公式I化合物的制药组合物和治疗疾病的方法，例如，神经退行性疾病，例如阿尔茨海默病，在哺乳动物中包括公式I的化合物。
• Discovery of indole-3-acetic acid derivatives containing 1,3,4-thiadiazole thioether and amide moieties as novel antibacterial agents
  作者：Chenghao Tang、Jiali Shao、Chou Si、Xiumei Yang、Xiuhong Hu、Pei Li、Xiang Wang

  DOI：10.1007/s10593-024-03298-z

  日期：2024.2

  A series of twenty one novel compounds derived from indole-3-acetic acid, the structure of which includes 1,3,4-thiadiazole, thioether, and amide moieties were designed, synthesized, and evaluated for their in vitro antibacterial activity against three bacterial strains. The bioassay results showed that among the synthesized compounds, N-5-[(2-fluorobenzyl)sulfanyl]-1,3,4-thiadiazol-2-yl}-3-(1H-i

  设计、合成了一系列二十一种源自吲哚-3-乙酸的新型化合物，其结构包括1,3,4-噻二唑、硫醚和酰胺部分，并评估了它们对三种细菌的体外抗菌活性。菌株。生物测定结果表明，合成的化合物中，N -5-[(2-氟苄基)硫基]-1,3,4-噻二唑-2-基}-3-(1 H-吲哚-3-基)-丙酰胺对丁香假单胞菌pv.具有最佳抑制率。猕猴桃和N- 5-[(4-氯苄基)硫基]-1,3,4-噻二唑-2-基}-3-(1H-吲哚-3-基)丙酰胺对米黄单胞菌的抑制率最好光伏。oryzae和Xanthomonas axonopodis pv. citri，在所有情况下均优于杀菌剂噻二唑铜和双噻唑。
• EP1658072A4
  申请人：——

  公开号：EP1658072A4

  公开（公告）日：2009-03-25
• US7253195B2
  申请人：——

  公开号：US7253195B2

  公开（公告）日：2007-08-07