Citation: MUHAMMAD Naeem Ahmed, SHAHID Hameed, KHAWAJA Ansar Yasin, IFZAN Arshad, SAFEENA Zafar, MUHAMMAD Nawaz Tahir. Synthesis, Crystal Structure and Antimicrobial Activity of Ethyl 2-(1-cyclohexyl-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate[J]. Chinese Journal of Structural Chemistry, ;2014, 33(11): 1666-1672. doi: 10.14102/j.cnki.0254-5861.2011-0370 shu

Synthesis, Crystal Structure and Antimicrobial Activity of Ethyl 2-(1-cyclohexyl-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate

a.
a. Department of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan;
b.
b. Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan;
c.
c. Department of Pharmacy, Faculty of Biological Sciences, Quaid-i-Azam University, Islamabad 45320, Pakistan;
d.
d. University of Sargodha, Department of Physics, Sargodha

Corresponding author: MUHAMMAD Naeem Ahmed,
Received Date: 14 May 2014
Available Online: 19 October 2014
Fund Project: This project was supported by Higher Education Commission (HEC) Govt. of Pakistan (HEC)

A novel 1,4,5-trisubstituted 1,2,3-triazole (C₁₈H₂₁N₃O₃) was synthesized by a one-pot three component reaction of 1-azidocyclohexane, 1-copper(Ⅰ) phenylethyne and ethoxalyl chloride at room temperature. The molecular structure was determined by single-crystal X-ray analysis. The compound crystallizes in the monoclinic system, space group P2₁/n with a=12.8167(9), b=8.0966(6), c=16.7079(9)Å, β=98.716(2)°, Z=4 and V=1713.8(2). In the crystal, the molecules are related by inversion and paired into dimers via C-H…O and C-O…C interactions involving (oxo) acetate groups. Furthermore, X-ray analysis results are compared with the optimized structure computed by using B3LYP method with 6-311G basis set. The calculated results showed that optimized geometry can well reproduce the crystal structure parameters. The bioassay results indicate that the compound has good antibacterial and antifungal activities.
- click chemistry,
- triazole,
- cyclohexyl,
- oxoacetate,
- XRD,
- antimicrobial
1. [1]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
2. [2]
  Zixu Xie , Pengfei Zhang , Ziyao Zhang , Chen Chen , Xing Wang . The choice of antimicrobial polymers: Hydrophilic or hydrophobic?. Chinese Chemical Letters, 2024, 35(9): 109768-. doi: 10.1016/j.cclet.2024.109768
3. [3]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
4. [4]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
5. [5]
  Yue Mao , Zhonghang Chen , Tiankai Sun , Wenyue Cui , Peng Cheng , Wei Shi . Luminescent coordination polymers with mixed carboxylate and triazole ligands for rapid detection of chloroprene metabolite. Chinese Journal of Structural Chemistry, 2024, 43(9): 100353-100353. doi: 10.1016/j.cjsc.2024.100353
6. [6]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
7. [7]
  Yaxian Liang , Qingyi Li , Liwei Hu , Ruohan Zhai , Fan Liu , Lin Tan , Xiaofei Wang , Huixu Xie . Environmentally friendly polylysine gauze dressing for an innovative antimicrobial approach to infected wound management. Chinese Chemical Letters, 2024, 35(10): 109459-. doi: 10.1016/j.cclet.2023.109459
8. [8]
  Hao Sun , Shengke Li , Qian Liu , Minzan Zuo , Xueqi Tian , Kaiya Wang , Xiao-Yu Hu . Supramolecular prodrug vesicles for selective antimicrobial therapy employing a chemo-photodynamic strategy. Chinese Chemical Letters, 2025, 36(3): 109999-. doi: 10.1016/j.cclet.2024.109999
9. [9]
  Yunfen Gao , Liying Wang , Chufan Zhou , Yi Zhao , Hai Huang , Jun Wu . Low-dimensional antimicrobial nanomaterials in anti-infection treatment and wound healing. Chinese Chemical Letters, 2025, 36(3): 110028-. doi: 10.1016/j.cclet.2024.110028
10. [10]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
11. [11]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
12. [12]
  Peiwen Liu , Fang Zhao , Jing Zhang , Yunpeng Bai , Jinxing Ye , Bo Bao , Xinggui Zhou , Li Zhang , Changlu Zhou , Xinhai Yu , Peng Zuo , Jianye Xia , Lian Cen , Yangyang Yang , Guoyue Shi , Lin Xu , Weiping Zhu , Yufang Xu , Xuhong Qian . Micro/nano flow chemistry by Beyond Limits Manufacturing. Chinese Chemical Letters, 2024, 35(5): 109020-. doi: 10.1016/j.cclet.2023.109020
13. [13]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
14. [14]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Qiang Sun , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Li Wang . Recent progress on surface chemistry Ⅱ: Property and characterization. Chinese Chemical Letters, 2025, 36(1): 110100-. doi: 10.1016/j.cclet.2024.110100
15. [15]
  Yingxiao Zong , Yangfei Wei , Xiaoqing Liu , Junke Wang , Huanfang Guo , Junli Wang , Zhuangzhi Shi , Tao Tu , Cheng Yang , Chongyang Wang , Leyong Wang . The 4^th CCL Organic Chemistry Forum held in Zhangye. Chinese Chemical Letters, 2024, 35(8): 109743-. doi: 10.1016/j.cclet.2024.109743
16. [16]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
17. [17]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
18. [18]
  Bingwei Wang , Yihong Ding , Xiao Tian . Benchmarking model chemistry composite calculations for vertical ionization potential of molecular systems. Chinese Chemical Letters, 2025, 36(2): 109721-. doi: 10.1016/j.cclet.2024.109721
19. [19]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
20. [20]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818

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