Citation: Xu-Min CAI, A-Liang LI, Yu-Ting LIN, Wen-Yan WANG, Shi-Fa WANG, Wen GU. Synthesis, Crystal Structure and Antibacterial Activity of New N-(1H-benzo[d]imidazol-2-yl)benzenesulfonamide Derivatives of Dehydroabietic Acid[J]. Chinese Journal of Structural Chemistry, ;2020, 39(8): 1539-1545. doi: 10.14102/j.cnki.0254–5861.2011–2640 shu

Synthesis, Crystal Structure and Antibacterial Activity of New N-(1H-benzo[d]imidazol-2-yl)benzenesulfonamide Derivatives of Dehydroabietic Acid

Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-forest Biomass, Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

Corresponding author: Xu-Min CAI, njguwen@163.com Wen GU, xumin.cai@njfu.edu.cn
Received Date: 15 October 2019
Accepted Date: 8 February 2020

Fund Project: the National Natural Science Foundation of China 31770616the National Natural Science Foundation of China 21601087the Natural Science Foundation for Colleges and Universities in Jiangsu Province 17KJA220002Top-notch Academic Programs Project of Jiangsu Higher Education Institutions PPZY2015C221

Figures(2)

The title compounds (7a~7g) were synthesized from dehydroabietic acid and characterized by spectroscopic methods including HR-MS, ¹H- and ¹³C-NMR. The crystal structure of compound 7g determined by single-crystal X-ray diffractio is of monoclinic system, space group P2₁ with a = 12.282(3), b = 9.940(2), c = 22.656(5) Å, β = 103.06(3)°, Z = 2, V = 2694.4(10) Å³, M_r = 1182.95, D_c = 1.458 Mg/m³, S = 1.000, μ = 1.649 mm^-1, F(000) = 1216, the final R = 0.0791 and wR = 0.1853 for 4098 observed reflections (I > 2σ(I)). The preliminary antibacterial assay showed that compound 7g exhibits significant inhibitory against Bacillus subtilis, Staphylococcus aureus and Methicillin-resistant S. aureus (MRSA) with MIC values of 1.9~7.8 μg/mL.
- dehydroabietic acid,
- benzimidazole,
- sulfonamide,
- crystal structure,
- antibacterial activity
1. [1]
  Kurasaki, H.; Tsuda, K.; Shinoyama, M.; Takaya, N.; Yamaguchi, Y.; Kishii, R.; Iwase, K.; Ando, N.; Nomura, M.; Kohno, Y. LpxC inhibitors: design, synthesis, and biological evaluation of oxazolidinones as gram-negative antibacterial agents. ACS Med. Chem. Lett. 2016, 7, 623−628. doi: 10.1021/acsmedchemlett.6b00057
2. [2]
  Devasahayam, G.; Scheld, W. M.; Hoffman, P. S. Newer antibacterial drugs for a new century. Expert Opin. Investig. Drugs 2010, 19, 215−234. doi: 10.1517/13543780903505092
3. [3]
  Chalothorn, T.; Rukachaisirikul, V.; Phongpaichit, S.; Pannara, S.; Tansakul, C. Synthesis and antibacterial activity of emodin and its derivatives against methicillin-resistant Staphylococcus Aureus. Tetra. Lett. 2019, 60, 151004, 1−5.
4. [4]
  Li, X.; Ma, S. Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ. Eur. J. Med. Chem. 2015, 95, 1−15. doi: 10.1016/j.ejmech.2015.03.026
5. [5]
  Aviles, E.; Prudhomme, J.; Le Roch, K. G.; Franzblau, S. G.; Chandrasena, K.; Mayer, A. M. S.; Rodriguez, A. D. Synthesis and preliminary biological evaluation of a small library of hybrid compounds based on Ugi isocyanide multicomponent reactions with a marine natural product scaffold. Bioorg. Med. Chem. Lett. 2015, 25, 5339−5343. doi: 10.1016/j.bmcl.2015.09.033
6. [6]
  Leandro, L. F.; Cardoso, M. J.; Silva, S. D.; Souza, M. G.; Veneziani, R. C.; Ambrosio, S. R.; Martins, C. H. Antibacterial activity of Pinus elliottii and its major compound, dehydroabietic acid, against multidrug-resistant strains. J. Med. Microbiol. 2014, 63, 1649−1653. doi: 10.1099/jmm.0.081711-0
7. [7]
  Chen, N. Y.; Duan, W. G.; Lin, G. S.; Liu, L. Z.; Zhang, R.; Li, D. P. Synthesis and antifungal activity of dehydroabietic acid-based 1, 3, 4-thiadiazole-thiazolidinone compounds. Mol. Divers. 2016, 20, 897−905. doi: 10.1007/s11030-016-9691-x
8. [8]
  Hou, W.; Luo, Z.; Zhang, G. J.; Cao, D. H.; Li, D.; Ruan, H. Q.; Ruan, B. F. H.; Su, L.; Xu, H. T. Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1, 2, 3-triazole dehydroabietic acid hybrids. Eur. J. Med. Chem. 2017, 138, 1042−1052. doi: 10.1016/j.ejmech.2017.07.049
9. [9]
  Vahermo, M.; Krogerus, S.; Nasereddin, A.; Kaiser, M.; Brun, R.; Jaffe, C. L.; Yli-Kauhaluoma, J.; Moreira, V. M. Antiprotozoal activity of dehydroabietic acid derivatives against Leishmania donovani and Trypanosoma cruzi. Med. Chem. Comm. 2016, 7, 457−463.
10. [10]
  Roa-Linares, V. C.; Brand, Y. M.; Agudelo-Gomez, L. S.; Tangarife-Castano, V.; Betancur-Galvis, L. A.; Gallego-Gomez, J. C.; Gonzalez, M. A. Anti-herpetic and anti-dengue activity of abietane ferruginol analogues synthesized from (+)-dehydroabietylamine. Eur. J. Med. Chem. 2016, 108, 79−88. doi: 10.1016/j.ejmech.2015.11.009
11. [11]
  Kang, M. S.; Hirai, S.; Goto, T.; Kuroyanagi, K.; Lee, J. Y.; Uemura, T.; Ezaki, Y.; Takahashi, N.; Kawada, T. Dehydroabietic acid, a phytochemical, acts as ligand for PPARs in macrophages and adipocytes to regulate inflammation. Biochem. Biophys. Res. Commun. 2008, 369, 333−338. doi: 10.1016/j.bbrc.2008.02.002
12. [12]
  Kim, J.; Kang, Y. G.; Lee, J. Y.; Choi, D. H.; Cho, Y. U.; Shin, J. M.; Park, J. S.; Lee, J. H.; Kim, W. G.; Seo, D. B.; Lee, T. R.; Miyamoto, Y.; No, K. T. The natural phytochemical dehydroabietic acid is an anti-aging reagent that mediates the direct activation of SIRT1. Mol. Cell Endocrinol. 2015, 412, 216−225. doi: 10.1016/j.mce.2015.05.006
13. [13]
  Zapata, B.; Rojas, M.; Betancur-Galvis, L.; Mesa-Arango, A. C.; Perez-Guaita, D.; Gonzalez, M. A. Cytotoxic, immunomodulatory, antimycotic, and antiviral activities of semisynthetic 14-hydroxyabietane derivatives and triptoquinone C-4 epimers. Med. Chem. Comm. 2013, 4, 1239−1246. doi: 10.1039/c3md00151b
14. [14]
  Zhang, W. M.; Yao, Y.; Yang, T.; Wang, X. Y.; Zhu, Z. Y.; Xu, W. T.; Lin, H. X.; Gao, Z. B.; Zhou, H.; Yang, C. G.; Cui, Y. M. The synthesis and antistaphylococcal activity of N-sulfonaminoethyloxime derivatives of dehydroabietic acid. Bioorg. Med. Chem. Lett. 2018, 28, 1943−1948. doi: 10.1016/j.bmcl.2018.03.062
15. [15]
  Berger, M.; Roller, A.; Maulide, N. Synthesis and antimicrobial evaluation of novel analogues of dehydroabietic acid prepared by C−H-activation. Eur. J. Med. Chem. 2017, 126, 937−943. doi: 10.1016/j.ejmech.2016.12.012
16. [16]
  Liu, M. L.; Pan, X. Y.; Yang, T.; Zhang, W. M.; Wang, T. Q.; Wang, H. Y.; Lin, H. X.; Yang, C. G.; Cui, Y. M. The synthesis and antistaphylococcal activity of dehydroabietic acid derivatives: modifications at C-12. Bioorg. Med. Chem. Lett. 2016, 26, 5492−5496. doi: 10.1016/j.bmcl.2016.10.018
17. [17]
  Shrivastava, N.; Naim, M. J.; Alam, M. J.; Nawaz, F.; Ahmed, S.; Alam, O. Benzimidazole scaffold as anticancer agent: synthetic approaches and structure-activity relationship. Arch. Pharm. Chem. Life Sci. 2017, 350, e1700040−80.
18. [18]
  Liu, H. B.; Gao, W. W.; Tangadanchu, V. K. R.; Zhou, C. H.; Geng, R. X. Novel aminopyrimidinyl benzimidazoles as potentially antimicrobial agents: design, synthesis and biological evaluation. Eur. J. Med. Chem. 2018, 143, 66−84. doi: 10.1016/j.ejmech.2017.11.027
19. [19]
  Ranjan, N.; Story, S.; Fulcrand, G.; Leng, F. F.; Ahmad, M.; King, A.; Sur, S.; Wang, W. D.; Tse-Dinh, Y. C.; Arya, D. P. Selective inhibition of Escherichia coli RNA and DNA topoisomerase I by Hoechst 33258 derived mono- and bisbenzimidazoles. J. Med. Chem. 2017, 60, 4904−4922. doi: 10.1021/acs.jmedchem.7b00191
20. [20]
  Gitto, R.; De Luca, L.; Mancuso, F.; Del Prete, S.; Vullo, D.; Supuran, C. T.; Capasso, C. Seeking new approach for therapeutic treatment of cholera disease via inhibition of bacterial carbonic anhydrases: experimental and theoretical studies for sixteen benzenesulfonamide derivatives. J. Enzym. Inhib. Med. Ch. 2019, 34, 1186−1192. doi: 10.1080/14756366.2019.1618292
21. [21]
  Bua, S.; Osman, S. M.; Del Prete, S.; Capasso, C.; Al Othman, Z.; Nocentini, A.; Supuran, C. T. Click-tailed benzenesulfonamides as potent bacterial carbonic anhydrase inhibitors for targeting Mycobacterium tuberculosis and Vibrio cholerae. Bioorg. Chem. 2019, 86, 183−186. doi: 10.1016/j.bioorg.2019.01.065
22. [22]
  Chen, H.; Geng, Y.; Wang, S. F.; Gu, W. Syntheses, crystal structures and antibacterial activities of two new methyl 12-alkylamino-13, 14-dinitrodeisopropyl-dehydroabietates. Chin. J. Struct. Chem. 2019, 38, 257−262.
23. [23]
  Gu, W.; Miao, T. T.; Wang, S. F.; Hao, Y.; Zhang, K. P.; Jin, X. Y. Synthesis, crystal structure and antitumor activity of a new 3H-phenanthro-[2, 1-d]imidazole derivative of dehydroabietic acid. Chin. J. Struct. Chem. 2015, 34, 1440−1445.
24. [24]
  Gu, W.; Wang, S. F. Synthesis and antimicrobial activities of novel 1H-dibenzo[a, c]carbazoles from dehydroabietic acid. Eur. J. Med. Chem. 2010, 45, 4692−4696. doi: 10.1016/j.ejmech.2010.07.038
25. [25]
  Ye, J.; Xuan, W. J.; Hu, A. X. Synthesis, crystal structure and fungicidal activity of (Z)-3, 3-dimethyl-1-(1H-1, 2, 4-triazol-1-yl)butan-2-one O-2-chlorobenzyl oxime nitrate. Chin. J. Struct. Chem. 2011, 30, 1265−1268.
26. [26]
  Meng, L.; Shi, D. Q. Synthesis, crystal structure and biological activities of O-[(Z)-2-methylbenzyl] 1-phenyl-2-(1H-1, 2, 4-triazol-1-yl)ethanone oxime. Chin. J. Struct. Chem. 2009, 28, 307−310.
1. [1]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
2. [2]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
3. [3]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
4. [4]
  Jing FENG , Renshu WANG , Hu WANG , Hailong LIU . Co(Ⅱ) and Ni(Ⅱ) complexes of 3,3-diphenylpropionic acid and 2,2′-dipyridylamine: Structures and biological activities. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 617-631. doi: 10.11862/CJIC.20250265
5. [5]
  Xinzhe ZHANG , Jiarong XU , Mochou GAO , Yage LIU , Yanbao ZHAO , Jingzeng CUI , Xueyan ZOU . Silver chloride/chitosan-based chloramine nanohybrid with excellent antibacterial activity: Design and structure characterization as well as Ag⁺-Cl^- synergistic antibacterial effect. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 428-438. doi: 10.11862/CJIC.20250123
6. [6]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150
7. [7]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
8. [8]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
9. [9]
  Lifang HE , Yaoze LUO , Qiying SHI , Jianxin TANG , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244
10. [10]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
11. [11]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
12. [12]
  Chengyu JIANG , Xufeng LIU . Synthesis, structural characterization, electrocatalytic proton reduction, and fungicidal activity of thiazole-containing di-iron complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 355-364. doi: 10.11862/CJIC.20250253
13. [13]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
14. [14]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
15. [15]
  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
16. [16]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
17. [17]
  Yukun CHEN , Kexin FENG , Bolun ZHANG , Wentao SONG , Jianjun ZHANG . Syntheses, crystal structures, and diametrically opposed mechanically-stimulated luminescence response of two Mg(Ⅱ) metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1227-1234. doi: 10.11862/CJIC.20240448
18. [18]
  Yinxia SUN , Liping LIU , Xue BAI , Yu SUN , Wanhong SUN , Zhepeng DENG , Jianghai CHEN , Jianjun WANG , Li XU , Shuzhen ZHANG . Synthesis and crystal structures of Co(Ⅱ)/Cu(Ⅱ) coordination polymers based on solvent and ligand concentration regulation strategy. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 340-354. doi: 10.11862/CJIC.20250226
19. [19]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
20. [20]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1334)
HTML views(21)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142