1-(3,4-dichlorophenyl)-4-vinyl-1H-1,2,3-triazole | 1325725-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3,4-dichlorophenyl)-4-vinyl-1H-1,2,3-triazole
• 英文别名: 1-(3,4-Dichlorophenyl)-4-vinyl-triazole；1-(3,4-dichlorophenyl)-4-ethenyltriazole
• CAS: 1325725-23-2
• 化学式: C₁₀H₇Cl₂N₃
• 分子量: 240.092
• InChiKey: LBLHZTKXKDLRGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3,4-dichlorophenyl)-4-vinyl-1H-1,2,3-triazole 在 吡啶 、 ammonium cerium (IV) nitrate 、 碳酸氢钠 、 锌 作用下， 以 乙腈 为溶剂， 反应 123.0h， 生成 2-(1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)-2,3-dihydronaphtho[2,3-b]furan-4,9-diyl diacetate
  参考文献：
  名称：

  Diacetate Naphthoquinone Derivatives Tethered to 1,2,3-Triazoles: Synthesis and Cytotoxicity Evaluation in Caco-2 Cells

  摘要：

  由萘醌制备的乙酰化化合物被报道为抗肿瘤前药。在探索萘醌和三唑核的合成多样性时，我们在此报告了一种简单有效的合成路线，以制备一系列16个1,2,3-三唑-萘醌乙酰衍生物的原型前药。化合物10a-10h和11a-11h是通过在碱性介质中，利用硝酸铈铵（CAN）促进的罗森和4-乙烯基-1H-1,2,3-三唑之间的氧化环加成反应，然后在过量的金属锌和乙酸酐中还原乙酰化萘醌制备的，产率高达>98%。所有衍生物均表现出血液相容性，化合物11e对Caco-2细胞展示了最有前途的特异性指数。分子对接表明，这些化合物可能通过抑制至少一种拓扑异构酶II亚型来发挥其细胞毒活性。

  DOI：

  10.21577/0103-5053.20210123
• 作为产物：
  描述：

  4-azido-1,2-dichlorobenzene 在 copper(ll) sulfate pentahydrate 、 sodium hydride 、 sodium ascorbate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 生成 1-(3,4-dichlorophenyl)-4-vinyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Novel 1,2,3-Triazole Derivatives for Use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain

  摘要：

  The purpose of this study was to prepare various 4-substituted N-phenyl-1,2,3-triazole derivatives using click chemistry. The derivatives were screened in vitro for antimicrobial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar Blue susceptibility test. The activity was expressed as the minimum inhibitory concentration (MIC) in mu g/mL (mu M). Derivatives of isoniazid (INH), (E)-N'-[(1-aryl)-1H-1,2,3-triazole-4-yl)methylene] isonicotinoyl hydrazides, exhibited significant activity with MIC values ranging from 2.5 to 0.62 mu g/mL. In addition, they displayed low cytotoxicity against liver cells (hepatoma HepG2) and kidney cells (BGM), thereby providing a high therapeutic index. The results demonstrated the potential and importance of developing new INH derivatives to treat mycobacterial infections.

  DOI：

  10.1021/jm2003624

文献信息

• Synthesis and evaluation of the cytotoxic activity of Furanaphthoquinones tethered to 1H-1,2,3-triazoles in Caco-2, Calu-3, MDA-MB231 cells
  作者：Dora C.S. Costa、Gabriella Silva de Almeida、Vitor Won-Held Rabelo、Lucio Mendes Cabral、Plínio Cunha Sathler、Paula Alvarez Abreu、Vitor Francisco Ferreira、Luiz Cláudio Rodrigues Pereira da Silva、Fernando de C. da Silva

  DOI：10.1016/j.ejmech.2018.07.018

  日期：2018.8

  are structural pharmacophore that is known to impart several cancer cells. This work shows a synthetic methodology to obtain hybrid molecules involving naphthoquinone and triazol scaffold as multiple ligands. A simple and efficient synthetic route was used to prepare a series of sixteen compounds being eight 2-(1-aryl-1H-1,2,3-triazol-4-yl)-2,3-dihydronaphtho[1,2 b]furan-4,5-diones and eight 2-(1-aryl-1H-1

  萘醌和1,2,3-三唑是已知可赋予几种癌细胞的结构药效团。这项工作显示了一种合成方法，可获得涉及萘醌和三唑支架作为多个配体的杂合分子。一种简单有效的合成方法用于制备一系列十六种化合物，即八种2-（1-芳基-1 H -1,2,3-三唑-4-基）-2,3-二氢萘并[1,2 b ]呋喃-4,5-二酮和八个2-（1-芳基-1 H -1,2,3-三唑-4-基）-2,3-二氢萘并[2,3- b ]呋喃-4,9 -diones。这些化合物已在MDA-MB231，Caco-2和Calu-3人类癌细胞中进行了测试，其中7a在本研究中最敏感的细胞系Caco-2细胞上，它是最有选择性的化合物。计算机研究表明，拓扑异构酶I和IIα的阻断可能是7a在Caco-2细胞中产生细胞毒性作用的作用机制之一。
• Novel 1,2,3-Triazole Derivatives for Use against <i>Mycobacterium tuberculosis</i> H37Rv (ATCC 27294) Strain
  作者：Nubia Boechat、Vitor F. Ferreira、Sabrina B. Ferreira、Maria de Lourdes G. Ferreira、Fernando de C. da Silva、Monica M. Bastos、Marilia dos S. Costa、Maria Cristina S. Lourenço、Angelo C. Pinto、Antoniana U. Krettli、Anna Caroline Aguiar、Brunno M. Teixeira、Nathalia V. da Silva、Priscila R. C. Martins、Flavio Augusto F. M. Bezerra、Ane Louise S. Camilo、Gerson P. da Silva、Carolina C. P. Costa

  DOI：10.1021/jm2003624

  日期：2011.9.8

  The purpose of this study was to prepare various 4-substituted N-phenyl-1,2,3-triazole derivatives using click chemistry. The derivatives were screened in vitro for antimicrobial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar Blue susceptibility test. The activity was expressed as the minimum inhibitory concentration (MIC) in mu g/mL (mu M). Derivatives of isoniazid (INH), (E)-N'-[(1-aryl)-1H-1,2,3-triazole-4-yl)methylene] isonicotinoyl hydrazides, exhibited significant activity with MIC values ranging from 2.5 to 0.62 mu g/mL. In addition, they displayed low cytotoxicity against liver cells (hepatoma HepG2) and kidney cells (BGM), thereby providing a high therapeutic index. The results demonstrated the potential and importance of developing new INH derivatives to treat mycobacterial infections.
• Diacetate Naphthoquinone Derivatives Tethered to 1,2,3-Triazoles: Synthesis and Cytotoxicity Evaluation in Caco-2 Cells
  作者：Dora Costa、Adriane Francisco、Beatriz Matuck、Priscila Furtado、Alana de Oliveira、Vitor Rabelo、Plínio Sathler、Paula Abreu、Vitor Ferreira、Luiz Cláudio da Silva、Fernando da Silva

  DOI：10.21577/0103-5053.20210123

  日期：——

  3-triazoles-naphthoquinodoic acetyl derivatives. The compounds 10a-10h and 11a-11h were obtained by oxidative cycloaddition reaction between lawsone and 4-vinyl-1H-1,2,3-triazoles promoted by ceric ammonium nitrate (CAN) in alkaline medium followed by reductive acetylation of the quinones in excess of metallic zinc and acetic anhydride in yields up to > 98%. All derivatives revealed to be hemocompatible

  由萘醌制备的乙酰化化合物被报道为抗肿瘤前药。在探索萘醌和三唑核的合成多样性时，我们在此报告了一种简单有效的合成路线，以制备一系列16个1,2,3-三唑-萘醌乙酰衍生物的原型前药。化合物10a-10h和11a-11h是通过在碱性介质中，利用硝酸铈铵（CAN）促进的罗森和4-乙烯基-1H-1,2,3-三唑之间的氧化环加成反应，然后在过量的金属锌和乙酸酐中还原乙酰化萘醌制备的，产率高达>98%。所有衍生物均表现出血液相容性，化合物11e对Caco-2细胞展示了最有前途的特异性指数。分子对接表明，这些化合物可能通过抑制至少一种拓扑异构酶II亚型来发挥其细胞毒活性。