1-(2,5-dichlorophenyl)-1H-1,2,3-triazole-4-carbaldehyde | 1325724-93-3

• 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-(2,5-dichlorophenyl)-1H-1,2,3-triazole-4-carbaldehyde
• 英文别名: 1-(2,5-dichlorophenyl)triazole-4-carbaldehyde
• CAS: 1325724-93-3
• 化学式: C₉H₅Cl₂N₃O
• 分子量: 242.064
• InChiKey: VQGMWWGNZNNIKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  426.5±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,5-dichlorophenyl)-1H-1,2,3-triazole-4-carbaldehyde 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 7-(1-(2,5-dichlorophenyl)-1H-1,2,3-triazol-4-yl)-5H-dibenzo[b,h]xanthene-5,6,8,13(7H)-tetraone
  参考文献：
  名称：

  乳腺癌细胞系MCF-7中1H-1,2,3-三唑连接的1H-二苯并[b，h]黄嘌呤作为ROS介导的凋亡诱导因子的设计，合成和生物学评估。

  摘要：

  背景技术低分子量的1,2,3-三唑和萘醌具有多种类型的生物活性，例如抗癌，HIV和细菌。但是，在某些情况下，这两个原子核的结合大大增加了它们的生物活性。目的在这项工作中，我们决定研究与1,2,3-三唑结合的双萘醌和黄酮类化合物的合成和筛选，以对抗癌细胞系，特别是人乳腺癌细胞系MCF-7。结果从Lawone和芳基-1H-1,2,3-三唑-4-甲醛（10a-h）开始，一些新的7-（1-芳基-1H-1,2,3-三唑-4-基）-6H -二苯并[b，h] x吨-5,6,8,13（7H）-四酮（12a-h）和3,3'-（（1-芳基-1H-1,2,3-三唑-4-基）亚甲基）双（2-羟基萘-1）合成4-二酮）11a-h，并以人乳腺癌细胞系MCF-7和非肿瘤细胞系MCF10A为对照评价其细胞毒性活性。我们进行了细胞活力，细胞增殖，细胞内ATP含量和细胞流式细胞术测试，以确定活性氧（ROS）的形成。结论基于这

  DOI：

  10.2174/1573406414666180524071409
• 作为产物：
  描述：

  2,5-二氯苯胺 在 盐酸 、 copper(II) sulfate 、 sodium ascorbate 、 sodium nitrite 、 2-碘酰基苯甲酸 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 生成 1-(2,5-dichlorophenyl)-1H-1,2,3-triazole-4-carbaldehyde
  参考文献：
  名称：

  Synthesis of 1H-1,2,3-triazoles and Study of their Antifungal and Cytotoxicity Activities

  摘要：

  我们在此报告了十五种1,2,3-三唑类化合物对白色念珠菌、克鲁斯念珠菌、副念珠菌、酵母念珠菌、热带念珠菌、都柏林念珠菌、红癣菌、犬小癣菌和黑曲霉的抗真菌活性结果。所有的1,2,3-三唑都是通过在铜(I)催化下，芳香叠氮化合物与炔烃之间的1,3-极性环化反应合成的，其中一些化合物表现出了抗真菌活性且具有较低的细胞毒性。结果证明了开发具有抗真菌活性的新的1,2,3-三唑类化合物的潜力和重要性。

  DOI：

  10.2174/1573406411309080010

文献信息

• Synthesis of 1H-1,2,3-triazoles and Study of their Antifungal and Cytotoxicity Activities
  作者：Iara da Silva、Prisicila Martins、Emanuelly da Silva、Sabrina Ferreira、Vitor Ferreira、Karen C. da Costa、Marne de Vasconcellos、Emerson Lima、Fernando C. da Silva

  DOI：10.2174/1573406411309080010

  日期：2013.10.1

  We report herein the results of antifungal activity of fifteen 1,2,3-triazoles against Candida albicans, Candida krusei, Candida parapsilosis, Candida kefyr, Candida tropicalis, Candida dubliniensis, Tricophyton rubrum, Microporum canis and Aspergillus niger. All of the 1,2,3-triazoles were prepared from 1,3-dipolar cyclizations between aryl azides and alkynes catalyzed by Cu(I), and several of the compounds exhibited antifungal activity with low cytotoxicity. The results demonstrated the potential and importance of developing new 1,2,3-triazoles compounds with antifungal activity.

  我们在此报告了十五种1,2,3-三唑类化合物对白色念珠菌、克鲁斯念珠菌、副念珠菌、酵母念珠菌、热带念珠菌、都柏林念珠菌、红癣菌、犬小癣菌和黑曲霉的抗真菌活性结果。所有的1,2,3-三唑都是通过在铜(I)催化下，芳香叠氮化合物与炔烃之间的1,3-极性环化反应合成的，其中一些化合物表现出了抗真菌活性且具有较低的细胞毒性。结果证明了开发具有抗真菌活性的新的1,2,3-三唑类化合物的潜力和重要性。
• 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.
• 1-Phenyl-1H- and 2-phenyl-2H-1,2,3-triazol derivatives: Design, synthesis and inhibitory effect on alpha-glycosidases
  作者：Daniel Gonzaga、Mario Roberto Senger、Fernando de Carvalho da Silva、Vitor Francisco Ferreira、Floriano Paes Silva

  DOI：10.1016/j.ejmech.2013.12.039

  日期：2014.3

  Due to aging and increasingly overweight in human population, the incidence of non-insulin dependent diabetes mellitus (NIDDM or Type 2 DM) is increasing considerably. Therefore, searching for new alpha-glycosidase inhibitors (GIs) capable of slowing down carbohydrate assimilation by humans is an important strategy towards control of NIDDM. In this report, we disclose the search for new easily accessible synthetic triazoles as anti-diabetic compounds. Two series of non-glycosid triazoles were synthesized (series A and B) and screened against baker's yeast alpha-glucosidase (MAL12) and porcine pancreatic alpha-amylase activity (PPA). Of the 60 compounds tested at 500 mu M, were considered hits (>= 60% inhibition) six triazoles against MAL12 and three against PPA, with the inhibition reaching up to 99.4% on MAL12 and 88.6% on PPA. The IC50 values were calculated for both enzymes and ranged from 54 to 482 mu M for MAL12 and 145 to 282 mu M for PPA. These results demonstrated the potential activity of simple and non-glycosidic triazoles as an important novel class of GIs for the development of drugs to treat Type 2 DM. (C) 2014 Elsevier Masson SAS. All rights reserved.
• 1-Aryl-1 H - and 2-aryl-2 H -1,2,3-triazole derivatives blockade P2X7 receptor in vitro and inflammatory response in vivo
  作者：Daniel Tadeu Gomes Gonzaga、Leonardo Braga Gomes Ferreira、Thadeu Estevam Moreira Maramaldo Costa、Natalia Lidmar von Ranke、Paulo Anastácio Furtado Pacheco、Ana Paula Sposito Simões、Juliana Carvalho Arruda、Luiza Pereira Dantas、Hércules Rezende de Freitas、Ricardo Augusto de Melo Reis、Carmen Penido、Murilo Lamim Bello、Helena Carla Castro、Carlos Rangel Rodrigues、Vitor Francisco Ferreira、Robson Xavier Faria、Fernando de Carvalho da Silva

  DOI：10.1016/j.ejmech.2017.08.034

  日期：2017.10

  Fifty-one 1,2,3-triazole derivatives were synthesized and evaluated with respect to P2X7 receptor (P2X7R) activity and its associated pore. These triazoles were screened in vitro for dye uptake assay and its cytotoxicity against mammalian cell types. Seven 1,2,3-triazole derivatives (5e, 6e, 8h, 9d, 9i, 11, and 12) potently blocked P2X7 receptor pore formation in vitro (J774.G8 cells and peritoneal

  合成了五十一种1,2,3-三唑衍生物，并就P2X7受体（P2X7R）活性及其相关的孔进行了评估。对这些三唑进行了体外筛选，以进行染料吸收测定及其对哺乳动物细胞类型的细胞毒性。七个1,2,3-三唑衍生物（5e，6e，8h，9d，9i，11和12）在体外有效阻断了P2X7受体的孔形成（J774.G8细胞和腹膜巨噬细胞）。显示的所有阻断剂IC 50其值低于500 nM，并且在两种细胞类型中均具有低毒性。这七个选定的三唑抑制了P2X7R介导的白介素1（IL-1β）释放。特别是，化合物9d是最有效的P2X7R阻滞剂。另外，在小鼠的由ATP或角叉菜胶给药引起的炎症反应的小鼠急性模型中，化合物9d促进了有效的阻断反应。同样，9d也降低了小鼠LPS诱导的胸膜炎细胞性。在计算机上的预测表明，当将该分子与市售类似物进行比较时，该分子适合发展抗炎剂。电生理研究表明9d作用的竞争机制阻断P2X7受体。为了观察优先
• Design, Synthesis and Biological Evaluation of 1H-1,2,3-Triazole-Linked-1H-Dibenzo[b,h]xanthenes as Inductors of ROS-Mediated Apoptosis in the Breast Cancer Cell Line MCF-7
  作者：Carolina S. Bortolot、Luana da S.M. Forezi、Roberta K.F. Marra、Marcelo I.P. Reis、Bárbara V.F.e Sá、Ricardo I. Filho、Zeinab Ghasemishahrestani、Mauro Sola-Penna、Patricia Zancan、Vitor F. Ferreira、Fernando de C. da Silva

  DOI：10.2174/1573406414666180524071409

  日期：2019.2.12

  molecular weight 1,2,3-triazoles and naphthoquinones are endowed with various types of biological activity, such as against cancer, HIV and bacteria. However, in some cases, the conjugation of these two nuclei considerably increases their biological activities. OBJECTIVE In this work, we decided to study the synthesis and screening of bis-naphthoquinones and xanthenes tethered to 1,2,3-triazoles against cancer

  背景技术低分子量的1,2,3-三唑和萘醌具有多种类型的生物活性，例如抗癌，HIV和细菌。但是，在某些情况下，这两个原子核的结合大大增加了它们的生物活性。目的在这项工作中，我们决定研究与1,2,3-三唑结合的双萘醌和黄酮类化合物的合成和筛选，以对抗癌细胞系，特别是人乳腺癌细胞系MCF-7。结果从Lawone和芳基-1H-1,2,3-三唑-4-甲醛（10a-h）开始，一些新的7-（1-芳基-1H-1,2,3-三唑-4-基）-6H -二苯并[b，h] x吨-5,6,8,13（7H）-四酮（12a-h）和3,3'-（（1-芳基-1H-1,2,3-三唑-4-基）亚甲基）双（2-羟基萘-1）合成4-二酮）11a-h，并以人乳腺癌细胞系MCF-7和非肿瘤细胞系MCF10A为对照评价其细胞毒性活性。我们进行了细胞活力，细胞增殖，细胞内ATP含量和细胞流式细胞术测试，以确定活性氧（ROS）的形成。结论基于这