2-Ferrocene-4-amine-1H-benzo[d]imidazole and their derivatives: Synthesis, biological and docking study

被引:0
|
作者
Kawad, Mukesh [1 ,4 ]
Sangani, Sagar [1 ,4 ]
Parmar, Jigneshkumar [1 ]
Dabhi, Ranjitsinh C. [2 ]
Arya, Prashant S. [3 ]
Teraiya, Nishith [5 ]
Ahmed, Sarfaraz [6 ]
Ameta, Rakesh Kumar [1 ,7 ]
机构
[1] KSV Univ, Dept Chem, SMMPISR, Gandhinagar, Gujarat, India
[2] Gujarat Univ, Univ Sch Sci, Dept Chem, Ahmedabd 380009, Gujarat, India
[3] UPL Univ Sustainable Technol, SRICT Inst Sci & Res, Vataria 393135, Gujarat, India
[4] Piramal Pharm Solut, Plot 18, Ahmadabad, Gujarat, India
[5] Kadi Sarva Vishvavidhyalaya, KB Inst Pharmaceut Educ & Res, Dept Pharmaceut Chem, Gandhinagar 382023, Gujarat, India
[6] King Saud Univ, Coll Pharm, Dept Pharmacognosy, POB 2457, Riyadh 11451, Saudi Arabia
[7] Gandhinagar Univ, Gandhinagar Inst Sci, Dept Chem, Gandhinagar 382721, Gujarat, India
关键词
Organometallic; 2-Ferrocene-4-amine-1H-benzo[d]imidazole; DNA binding; Docking; Cytotoxicity; Antimicrobial; FERROCENE; COMPLEXES; FERROCIPHENOLS;
D O I
10.1016/j.poly.2024.117242
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An organometallic series based on 2-ferrocene-4-amine-1H-benzo[d]imidazole derivative has been synthesized and characterized through FTIR, H/CNMR, and LCMS. Their antimicrobial activity was assessed by testing them against B. subtills, Staphylococcus aureus, E. faecalis, S. marcescens, E. coli, K. pneumoniae, C. albicans, A. niger, Mucor sp. where they showed good zone of inhibition (ZOI) as compared to standards. The cytotoxicity of synthesized compounds was tested against Hela (cervical) and MCF-7 (breast) cancer cell lines where compound 5a and 5b displayed equivalent potency to the standard while 5e demonstrated highest cytotoxicity against both cell lines. Their comparative docking analysis with DNA suggested that docking score of 5e was -7.4 kcal/mol versus -6 kcal/mol of ethidium bromide, indicating that our designed compound acts via DNA intercalation.
引用
收藏
页数:8
相关论文
共 50 条
  • [1] Design, Synthesis, Molecular Docking and Biological Studies of 4H-Benzo[d][1,3]oxazin-4-one Derivatives and Their Uses in Heterocyclic Synthesis
    Mohareb, Rafat Milad
    Mohamed, Abeer Abdelazeem
    Ibrahim, Rehab A.
    CHEMISTRYSELECT, 2022, 7 (21):
  • [2] Synthesis and Pharmacological Evaluation of Some Amide Functionalized 1H-Benzo[d]imidazole-2-thiol Derivatives as Antimicrobial Agents
    Singu, Padma S.
    Kanugala, Sirisha
    Dhawale, Sachin A.
    Kumar, C. Ganesh
    Kumbhare, Ravindra M.
    CHEMISTRYSELECT, 2020, 5 (01): : 117 - 123
  • [3] Synthesis and evaluation of in vitro antimycobacterial activity of novel 1H-benzo[d]imidazole derivatives and analogues
    Gobis, Katarzyna
    Foks, Henryk
    Serocki, Marcin
    Augustynowicz-Kopec, Ewa
    Napiorkowska, Agnieszka
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 89 : 13 - 20
  • [4] SYNTHESIS AND OPTICAL PROPERTIES OF 2,2′-BIIMIDAZOLE AND BENZO[d]IMIDAZOLE DERIVATIVES: CHANGING π-CONJUGATION BY PHOTOEXCITATION
    Matsumoto, Shoji
    Zhao, Yu
    Akazome, Motohiro
    HETEROCYCLES, 2014, 88 (01) : 261 - 273
  • [5] A New Route for the Synthesis of Trichloromethyl-1H-Benzo[d]imidazole and (1,2,3-Triazol)-1H-Benzo[d]imidazole Derivatives via Copper-Catalyzed N-Arylation and Huisgen Reactions
    Nematpour, Manijeh
    CURRENT ORGANIC CHEMISTRY, 2025, 29 (07) : 591 - 598
  • [6] 4-(4-Bromophenyl)-thiazol-2-amine derivatives: synthesis, biological activity and molecular docking study with ADME profile
    Sharma, Deepika
    Kumar, Sanjiv
    Narasimhan, Balasubramanian
    Ramasamy, Kalavathy
    Lim, Siong Meng
    Shah, Syed Adnan Ali
    Mani, Vasudevan
    BMC CHEMISTRY, 2019, 13
  • [7] 4-(4-Bromophenyl)-thiazol-2-amine derivatives: synthesis, biological activity and molecular docking study with ADME profile
    Deepika Sharma
    Sanjiv Kumar
    Balasubramanian Narasimhan
    Kalavathy Ramasamy
    Siong Meng Lim
    Syed Adnan Ali Shah
    Vasudevan Mani
    BMC Chemistry, 13
  • [8] Design, Synthesis, Biological Evaluation, and Docking Study of Novel 4-Anilinoquinazolines Derivatives as Anticancer Agents
    Moghadam, Azmian Fatemeh
    Kefayati, Hassan
    Evazalipour, Mehdi
    Ghasemi, Saeed
    IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2022, 41 (02): : 353 - 367
  • [9] Synthesis, cytotoxicity and apoptosis-inducing activity of novel1H-benzo[d]imidazole derivatives of dehydroabietic acid
    Li, A-Liang
    Yang, Ya-Qun
    Wang, Wen-Yan
    Liu, Qing-Song
    Sun, Yue
    Gu, Wen
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2020, 67 (09) : 1668 - 1678
  • [10] Synthesis and Cytotoxic Evaluation of Novel 2-(4-(2,2,2-Trifluoroethoxy)-3-methylpyridin-2-ylthio)-1H-benzo[d]imidazole Derivatives
    Ranganatha, S. R.
    Kavitha, C. V.
    Vinaya, K.
    Prasanna, D. S.
    Chandrappa, S.
    Raghavan, Sathees C.
    Rangappa, K. S.
    ARCHIVES OF PHARMACAL RESEARCH, 2009, 32 (10) : 1335 - 1343