4-氨基-3-(4-氯苯基)-5-疏基-4H-1,2,4-噻唑 | 68468-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氨基-3-(4-氯苯基)-5-疏基-4H-1,2,4-噻唑
• 英文名称: 4-amino-5-mercapto-3-(4-chlorophenyl)-1,2,4-triazole
• 英文别名: 4-amino-5-(4-chlorophenyl)-4H-1,2,4-triazole-3-thiol；3-(p-chlorophenyl)-4-amino-5-mercapto-1,2,4-triazole；4-amino-5-(4-chlorophenyl)-3-mercapto-1,2,4-triazole；4-amino-5-(4-chlorophenyl)-1,2,4-triazole-3-thiol
• CAS: 68468-95-1
• 化学式: C₈H₇ClN₄S
• mdl: MFCD00269263
• 分子量: 226.689
• InChiKey: OBKJAIJYUZQJFR-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176°C
• 沸点：
  336.5±44.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  85.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氨基-3-(4-氯苯基)-5-疏基-4H-1,2,4-噻唑 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, spectral characterization and biological activity of zinc(II) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases

  摘要：

  New Zn(II) complexes have been synthesized by the reactions of zinc(II) acetate with Schiff bases derived from 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde, 2-hydroxyacetophenone or indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non-electrolytes. Elemental analyses suggest that the complexes have 1:1 stoichiometry of the type [ZnL(H(2)O)(2)], [ZnL'(OAc)(2)(H(2)O)(2)] (L=dianionic Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and 2-hydroxyacetophenone or indoline-2,3-dione; L'=neutral Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde) and they were characterized by FT-IR, (1)H NMR, (13)C NMR and FAB mass. All these Schiff bases and their complexes have also been screened for their antibacterial activities against Bacillus subtilis, Escherichia coli and antifungal activities against Colletotrichum falcatum, Aspergillus niger, Fusarium oxysporium and Carvularia pallescence by petriplates methods.

  DOI：

  10.1016/j.saa.2011.08.019
• 作为产物：
  描述：

  对氯苯甲酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 生成 4-氨基-3-(4-氯苯基)-5-疏基-4H-1,2,4-噻唑
  参考文献：
  名称：

  Recurrent neural network (RNN) model accelerates the development of antibacterial metronidazole derivatives

  摘要：

  利用递归神经网络模型生成抗菌甲硝唑衍生物。

  DOI：

  10.1039/d2ra01807a

文献信息

• Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study
  作者：Weifeng Ma、Peng Chen、Xiansen Huo、Yufeng Ma、Yanhong Li、Pengcheng Diao、Fang Yang、Shengquan Zheng、Mengjin Hu、Wenwei You、Peiliang Zhao

  DOI：10.1016/j.ejmech.2020.112847

  日期：2020.12

  Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over

  基于我们先前的工作，我们报道了CA-4的52种新的基于三唑并噻二嗪的类似物的设计，合成和生物学评估，以及它们的初步结构-活性关系。在合成的化合物中，Iab被发现是最有效的衍生物，在体外具有IC 50值（从几位数到几位数纳摩尔），并且对正常人胚胎肾HEK-293细胞也表现出优异的选择性（IC 50 > 100μM ）。进一步的机理研究表明，Iab显着阻断微管蛋白聚合并破坏A549细胞的细胞内微管网络。此外，艾伯通过调节p-cdc2和cyclin B1的表达诱导G2 / M细胞周期阻滞，并通过上调裂解的PARP和caspase-3的表达以及下调Bcl-2引起细胞凋亡。重要的是，在体内，Iab有效抑制异种移植小鼠模型中A549肺癌的肿瘤生长，而没有明显的毒性迹象，从而证实了其作为有望用于癌症治疗的潜力。
• 4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors
  作者：Laurent Gavara、Laurent Sevaille、Filomena De Luca、Paola Mercuri、Carine Bebrone、Georges Feller、Alice Legru、Giulia Cerboni、Silvia Tanfoni、Damien Baud、Giuliano Cutolo、Benoît Bestgen、Giulia Chelini、Federica Verdirosa、Filomena Sannio、Cecilia Pozzi、Manuela Benvenuti、Karolina Kwapien、Marina Fischer、Katja Becker、Jean-Marie Frère、Stefano Mangani、Nohad Gresh、Dorothée Berthomieu、Moreno Galleni、Jean-Denis Docquier、Jean-François Hernandez

  DOI：10.1016/j.ejmech.2020.112720

  日期：2020.12

  potent, they represented a promising basis for the development of broad-spectrum MBL inhibitors. Here, we synthesized and characterized a large number of 4-amino-1,2,4-triazole-3-thione-derived Schiff bases. Compared to the previous series, the presence of an aryl moiety at position 4 afforded an average 10-fold increase in potency. Among 90 synthetic compounds, more than half inhibited at least one

  产生金属β-内酰胺酶（MBL）的革兰氏阴性菌对β-内酰胺抗生素的耐药性代表着重大的医学威胁，并且迫切需要开发临床上有用的抑制剂。我们先前报道了MBL催化位点中的5个取代的4-氨基/ H-1,2,4-三唑-3-硫酮化合物的原始结合模式。此外，我们表明，尽管具有中等效力，但它们代表了广谱MBL抑制剂开发的有希望的基础。在这里，我们合成和表征了大量的4-氨基-1,2,4-三唑-3-硫酮衍生的席夫碱。与先前的系列相比，在4位上存在芳基部分可使效力平均提高10倍。在90种合成化合物中，超过一半的化合物抑制了至少六个被测MBL（L1，VIM-4，VIM-2，NDM-1，IMP-1，K i的值在μM至亚μM范围内。几种是广谱抑制剂，也可以抑制临床上最相关的VIM-2和NDM-1。活性化合物通常在位置5处包含卤代，双环芳基或酚基部分，以及在邻苯甲酸，2,4-二羟基苯基，对苄氧基苯基或3-（m-苯甲酰基）-
• Potential Broad Spectrum Anthelmintics IV: Design, Synthesis, and Antiparasitic Screening of Certain 3,6-Disubstituted- (7H) -s -triazolo- [3,4-b][1,3,4]thiadiazine Derivatives
  作者：M.A. El-Dawy、A.-Mohsen M.E. Omar、Abla M. Ismail、A.A.B. Hazzaa

  DOI：10.1002/jps.2600720111

  日期：1983.1

  Abstract A series of 3,6-disubstituted-(7H)-s-triazolo[3,4-b][l,3,4]- thiadiazine derivatives were prepared. The compounds were designed to obtain structural similarities and/or bear isosteric relation with certain fused systems encountered in some well-known antiparasitic drugs. The substituents in all products were selected according to the Topliss scheme. Preliminary screening for antiparasitic

  摘要制备了一系列3,6-二取代-（7H）-s-三唑并[3,4-b] [1,3,4]-噻二嗪衍生物。设计这些化合物以获得与某些众所周知的抗寄生虫药物中遇到的某些融合系统的结构相似性和/或具有等位关系。根据Topliss方案选择所有产物中的取代基。使用A虫（Ascaris vitulorum）初步筛选抗寄生虫活性表明，6取代的衍生物通常比3取代的衍生物更具活性，并且π效应比σ效应更为明显。
• Design, synthesis and biological evaluation of flexible and rigid analogs of 4H-1,2,4-triazoles bearing 3,4,5-trimethoxyphenyl moiety as new antiproliferative agents
  作者：Mahsa Ansari、Mohammad Shokrzadeh、Saeed Karima、Shima Rajaei、Seyedeh Mahdieh Hashemi、Hassan Mirzaei、Marjan Fallah、Saeed Emami

  DOI：10.1016/j.bioorg.2019.103300

  日期：2019.12

  Several flexible and rigid analogs of 4H-1,2,4-triazoles (compounds 8a-g and 9a-g) bearing trimethoxyphenyl pharmacophoric unit, were designed and synthesized as potential anticancer agents. The in vitro cytotoxic assay indicated that both flexible and rigid analogs (8 and 9, respectively) can potentially inhibit the growth of cancerous cells (A549, MCF7, and SKOV3), with IC50 values less than 5.0 µM

  设计并合成了带有三甲氧基苯基药效单元的4 H -1,2,4-三唑的几种柔性和刚性类似物（化合物8a-g和9a-g），并将其合成为潜在的抗癌药。体外细胞毒性试验表明，柔性和刚性类似物（分别为8和9）都可以潜在地抑制癌细胞（A549，MCF7和SKOV3）的生长，IC 50值小于5.0 µM。此外，作为化合物9的区域异构体的化合物10a-1显示出显着的细胞毒性活性，IC 50值为0.30至5.0μM。刚性类似物9a，10h和10k分别比依托泊苷对MCF7，SKOV3和A549细胞更有效。这些化合物对癌细胞显示出比正常细胞高的选择性，因为它们对L929细胞没有明显的细胞毒性。另外，代表性化合物9a和10h可以微摩尔水平抑制微管蛋白聚合。通过测定秋水仙碱-微管蛋白荧光的变化，表明化合物10h可与秋水仙碱口袋处的微管蛋白结合。分子对接研究进一步证实了有前途的化合物9a，10h和10k的抑制活性 通过
• Synthesis and Structure of Novel 1,2,4-triazole Derivatives Containing the 2,4-dinitrophenylthio Group
  作者：Qichun Ding、Xinxiang Lei、Jianyu Jin、Lixue Zhang、Huiai Du、Haile Zhang

  DOI：10.3184/030823409x401961

  日期：2009.2

  Some novel 1,2,4-triazole derivatives containing the 2,4-dinitrophenylthio group have been synthesised in high yields by means of the reactions of 3-substituted-4-amino −1 H-1,2,4-triazole-5(4 H)-thiones or ( E)-3-aryl-4-(benzylideneamino)-1 H-1,2,4-triazole-5(4 H)-thiones with 1-chloro-2,4-dinitrobenzene. The ( E)-3-aryl-4-(benzylideneamino)-1 H-1,2,4-triazole-5(4 H)-thiones were prepared by the reaction of 4-amino-3-aryl-2 H-1,2,4-triazole-3(4 H)-thiones and diverse aromatic aldehydes. The 2, 4-dinitrophenyl group linked to the S atom, not to the N atom, was confirmed by the crystal structures. The structures of all the compounds were determined by elemental analysis, IR, MS, ¹H NMR and ¹³C NMR.

  通过 3-取代-4-氨基-1 H-1,2,4-三唑-5(4 H)-硫酮或 ( E)-3- 芳基-4-(亚苄基氨基)-1 H-1,2,4-三唑-5(4 H)-硫酮与 1-氯-2,4-二硝基苯的反应，高产合成了一些含有 2,4-二硝基苯硫基的新型 1,2,4-三唑衍生物。4- 氨基-3-芳基-2 H-1,2,4-三唑-3(4 H)-硫酮与多种芳香醛反应制备了(E)-3-芳基-4-(苄亚氨基)-1 H-1,2,4-三唑-5(4 H)-硫酮。晶体结构证实，2, 4-二硝基苯基与 S 原子而非 N 原子相连。所有化合物的结构都是通过元素分析、红外光谱、质谱、1H NMR 和 13C NMR 确定的。