2-(1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)propan-2-ol | 1567324-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)propan-2-ol
• 英文别名: 2-[1-(7-Chloro-4-quinolyl)triazol-4-yl]propan-2-ol；2-[1-(7-chloroquinolin-4-yl)triazol-4-yl]propan-2-ol
• CAS: 1567324-72-4
• 化学式: C₁₄H₁₃ClN₄O
• 分子量: 288.736
• InChiKey: ZXKXUYNTVGNGFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)propan-2-ol
  参考文献：
  名称：

  7-氯喹啉三唑：叠氮化物-炔烃环加成点击化学合成，抗疟活性，细胞毒性和SAR研究

  摘要：

  通过在4-叠氮基-7-氯喹啉和几个炔烃之间进行铜催化的环加成（CuAAC）点击化学反应，合成了三唑部分具有不同取代基的二十七种7-氯喹啉三唑衍生物。对所有合成化合物的体外抗恶性疟原虫（W2）活性和对Hep G2A16细胞的细胞毒性进行了评估。所有产品 均显示出低细胞毒性（CC 50 > 100μM），其中五种产品显示出中等的抗疟活性（IC 50从9.6到40.9μM）。作为氯喹类似物，预计这些化合物可能会抑制血红素聚合，因此进行了SAR研究，目的是解释其抗疟原性。可以根据获得的结果设计新的结构变化。

  DOI：

  10.1016/j.ejmech.2013.11.022

文献信息

• Synthesis, Biological Evaluation and In Silico Computational Studies of 7-Chloro-4-(1<i>H</i>-1,2,3-triazol-1-yl)quinoline Derivatives: Search for New Controlling Agents against <i>Spodoptera frugiperda</i> (Lepidoptera: Noctuidae) Larvae
  作者：Doris Natalia Rosado-Solano、Mario Alberto Barón-Rodríguez、Pedro Luis Sanabria Florez、Luz Karime Luna-Parada、Carlos Eduardo Puerto-Galvis、Andrés Felipe Zorro-González、Vladimir V. Kouznetsov、Leonor Yamile Vargas-Méndez

  DOI：10.1021/acs.jafc.9b01067

  日期：2019.8.21

  derivatives were evaluated against the maize armyworm, Spodoptera frugiperda (J.E. Smith). These hybrids were prepared through a copper-catalyzed azide alkyne cycloaddition (CuAAC, known as a click reaction) and displayed larvicidal properties with LD50 values below 3 mg/g insect, and triazolyl-quinoline hybrid 6 showed an LD50 of 0.65 mg/g insect, making it 2-fold less potent than methomyl, which was

  评价了五种7-氯-4-（1 H -1,2,3-三唑-1-基）喹啉衍生物对玉米粘虫Spodoptera frugiperda（JE Smith）的杀虫和拒食活性。这些杂化物是通过铜催化的叠氮化物炔烃环加成反应（CuAAC，称为点击反应）制备而成的，具有幼虫特性，LD 50值低于3 mg / g昆虫，三唑基喹啉杂化物6的LD 50为0.65 mg / g。克杀虫剂，使其效力比用作参照杀虫剂的灭多威低2倍（LD 50 = 0.34 mg / g杀虫剂）。化合物4是活性最高的拒食衍生物（CE 50= 162.1μg/ mL），在250–1000μg/ mL的浓度下具有良好的拒食指数（56–79％）。另外，三唑基-喹啉杂化4 - 8表现出对商业乙酰胆碱酯酶弱的抑制活性，从电盘electricus（电鳗的AChE）（IC 50 = 27.7微克/毫升），以及对低的抗胆碱酯酶活性草地夜蛾幼虫匀浆（IC 50
• New Compounds Hybrids 1 <i>H</i> ‐1,2,3‐Triazole‐Quinoline Against <i>Plasmodium falciparum</i>
  作者：Núbia Boechat、Maria de Lourdes G. Ferreira、Luiz C. S. Pinheiro、Antônio M. L. Jesus、Milene M. M. Leite、Carlos C. S. Júnior、Anna C. C. Aguiar、Isabel M. Andrade、Antoniana U. Krettli

  DOI：10.1111/cbdd.12321

  日期：2014.9

  Malaria is one of the most prevalent parasitic diseases in the world. The global importance of this disease, current vector control limitations, and the absence of an effective vaccine make the use of therapeutic antimalarial drugs the main strategy to control malaria. Chloroquine is a cost‐effective antimalarial drug with a relatively robust safety profile, or therapeutic index. However, chloroquine is no longer used alone to treat patients with Plasmodium falciparum due to the emergence and spread of chloroquine‐resistant strains, which have also been reported for Plasmodium vivax. However, the activity of 1,2,3‐triazole derivatives against chloroquine‐sensitive and chloroquine‐resistant strains of P. falciparum has been reported in the literature. To enhance the anti‐P. falciparum activity of quinoline derivatives, we synthesized 11 new quinoline‐1H‐1,2,3‐triazole hybrids with different substituents in the 4‐positions of the 1H‐1,2,3‐triazole ring, which were assayed against the W2‐chloroquine‐resistant P. falciparum clone. Six compounds exhibited activity against the P. falciparum W2 clone, chloroquine‐resistant, with IC50 values ranging from 1.4 to 46 μm. None of these compounds was toxic to a normal monkey kidney cell line, thus exhibiting good selectivity indexes, as high 351 for one compound (11).
• 7-Chloroquinolinotriazoles: Synthesis by the azide–alkyne cycloaddition click chemistry, antimalarial activity, cytotoxicity and SAR studies
  作者：Guilherme R. Pereira、Geraldo Célio Brandão、Lucas M. Arantes、Háliton A. de Oliveira、Renata Cristina de Paula、Maria Fernanda A. do Nascimento、Fábio M. dos Santos、Ramon K. da Rocha、Júlio César D. Lopes、Alaíde Braga de Oliveira

  DOI：10.1016/j.ejmech.2013.11.022

  日期：2014.2

  triazole moiety were synthesized via copper-catalyzed cycloaddition (CuAAC) click chemistry between 4-azido-7-chloroquinoline and several alkynes. All the synthetic compounds were evaluated for their in vitro activity against Plasmodium falciparum (W2) and cytotoxicity to Hep G2A16 cells. All the products disclosed low cytotoxicity (CC50 > 100 μM) and five of them have shown moderate antimalarial activity

  通过在4-叠氮基-7-氯喹啉和几个炔烃之间进行铜催化的环加成（CuAAC）点击化学反应，合成了三唑部分具有不同取代基的二十七种7-氯喹啉三唑衍生物。对所有合成化合物的体外抗恶性疟原虫（W2）活性和对Hep G2A16细胞的细胞毒性进行了评估。所有产品 均显示出低细胞毒性（CC 50 > 100μM），其中五种产品显示出中等的抗疟活性（IC 50从9.6到40.9μM）。作为氯喹类似物，预计这些化合物可能会抑制血红素聚合，因此进行了SAR研究，目的是解释其抗疟原性。可以根据获得的结果设计新的结构变化。