Literature DB >> 33602331

Synthesis and therapeutic potential of imidazole containing compounds.

Ankit Siwach1, Prabhakar Kumar Verma2.   

Abstract

Imidazole is a five-membered heterocyclic moiety that possesses three carbon, two nitrogen, four hydrogen atoms, and two double bonds. It is also known as 1, 3-diazole. It contains two nitrogen atoms, in which one nitrogen bear a hydrogen atom, and the other is called pyrrole type nitrogen. The imidazole name was reported by Arthur Rudolf Hantzsch (1857-1935) in 1887. 1, 3-diazole is an amphoteric in nature i.e. it shows both acidic and basic properties. It is a white or colorless solid that is highly soluble in water and other polar solvents. Due to the presence of a positive charge on either of two nitrogen atom, it shows two equivalent tautomeric forms. Imidazole was first named glyoxaline because the first synthesis has been made by glyoxal and ammonia. It is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. The derivatives of 1, 3-diazole show different biological activities such as antibacterial, antimycobacterial, anti-inflammatory, antitumor, antidiabetic, anti-allergic, antipyretic, antiviral, antioxidant, anti-amoebic, antihelmintic, antifungal and ulcerogenic activities, etc. as reported in the literature. There are different examples of commercially available drugs in the market which contains 1, 3-diazole ring such as clemizole (antihistaminic agent), etonitazene (analgesic), enviroxime (antiviral), astemizole (antihistaminic agent), omeprazole, pantoprazole (antiulcer), thiabendazole (antihelmintic), nocodazole (antinematodal), metronidazole, nitroso-imidazole (bactericidal), megazol (trypanocidal), azathioprine (anti rheumatoid arthritis), dacarbazine (Hodgkin's disease), tinidazole, ornidazole (antiprotozoal and antibacterial), etc. This present review summarized some pharmacological activities and various kinds of synthetic routes for imidazole and their derived products.

Entities:  

Keywords:  1; 3-diazole; Antibacterial; Antioxidant; Antitubercular; Antitumor

Year:  2021        PMID: 33602331      PMCID: PMC7893931          DOI: 10.1186/s13065-020-00730-1

Source DB:  PubMed          Journal:  BMC Chem        ISSN: 2661-801X


  11 in total

1.  Synthesis, vasorelaxant activity and antihypertensive effect of benzo[d]imidazole derivatives.

Authors:  Gabriel Navarrete-Vázquez; Sergio Hidalgo-Figueroa; Mariana Torres-Piedra; Jorge Vergara-Galicia; Julio Cesar Rivera-Leyva; Samuel Estrada-Soto; Ismael León-Rivera; Berenice Aguilar-Guardarrama; Yolanda Rios-Gómez; Rafael Villalobos-Molina; Maximiliano Ibarra-Barajas
Journal:  Bioorg Med Chem       Date:  2010-04-14       Impact factor: 3.641

2.  Synthesis of imidazo[1,2-a]pyridines as antiviral agents.

Authors:  A Gueiffier; S Mavel; M Lhassani; A Elhakmaoui; R Snoeck; G Andrei; O Chavignon; J C Teulade; M Witvrouw; J Balzarini; E De Clercq; J P Chapat
Journal:  J Med Chem       Date:  1998-12-03       Impact factor: 7.446

3.  Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones.

Authors:  Balasubramanian Narasimhan; Deepika Sharma; Pradeep Kumar; Perumal Yogeeswari; Dharmarajan Sriram
Journal:  J Enzyme Inhib Med Chem       Date:  2011-01-21       Impact factor: 5.051

4.  Microwave-assisted, solvent-free and parallel synthesis of some novel substituted imidazoles of biological interest.

Authors:  Gyanendra Kumar Sharma; Devender Pathak
Journal:  Chem Pharm Bull (Tokyo)       Date:  2010-03       Impact factor: 1.645

5.  Trisubstituted imidazoles as Mycobacterium tuberculosis glutamine synthetase inhibitors.

Authors:  Johan Gising; Mikael T Nilsson; Luke R Odell; Samir Yahiaoui; Martin Lindh; Harini Iyer; Achyut M Sinha; Bachally R Srinivasa; Mats Larhed; Sherry L Mowbray; Anders Karlén
Journal:  J Med Chem       Date:  2012-03-08       Impact factor: 7.446

6.  Synthesis, characterization, biological evaluation and molecular docking studies of 2-(1H-benzo[d]imidazol-2-ylthio)-N-(substituted 4-oxothiazolidin-3-yl) acetamides.

Authors:  Snehlata Yadav; Balasubramanian Narasimhan; Siong M Lim; Kalavathy Ramasamy; Mani Vasudevan; Syed Adnan Ali Shah; Manikandan Selvaraj
Journal:  Chem Cent J       Date:  2017-12-22       Impact factor: 4.215

7.  Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of 2-(1-benzoyl-1H-benzo[d]imidazol-2-ylthio)-N-substituted acetamides.

Authors:  Snehlata Yadav; Siong Meng Lim; Kalavathy Ramasamy; Mani Vasudevan; Syed Adnan Ali Shah; Abhishek Mathur; Balasubramanian Narasimhan
Journal:  Chem Cent J       Date:  2018-05-26       Impact factor: 4.215

8.  Design and Synthesis of Some Novel Fluorobenzimidazoles Substituted with Structural Motifs Present in Physiologically Active Natural Products for Antitubercular Activity.

Authors:  Bangalore Nandha; Laxmivenkatesh Gurachar Nargund; Shachindra Laxmivenkatesh Nargund; Kishore Bhat
Journal:  Iran J Pharm Res       Date:  2017       Impact factor: 1.696

9.  Design and Synthesis of Potent in Vitro and in Vivo Anticancer Agents Based on 1-(3',4',5'-Trimethoxyphenyl)-2-Aryl-1H-Imidazole.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Filippo Prencipe; Paola Oliva; Stefania Baraldi; Mojgan Aghazadeh Tabrizi; Luisa Carlota Lopez-Cara; Salvatore Ferla; Andrea Brancale; Ernest Hamel; Roberto Ronca; Roberta Bortolozzi; Elena Mariotto; Giuseppe Basso; Giampietro Viola
Journal:  Sci Rep       Date:  2016-05-24       Impact factor: 4.379

10.  Design and Synthesis of Benzimidazole-Chalcone Derivatives as Potential Anticancer Agents.

Authors:  Cheng-Ying Hsieh; Pi-Wen Ko; Yu-Jui Chang; Mohit Kapoor; Yu-Chuan Liang; Hui-Hsien Lin; Jia-Cherng Horng; Ming-Hua Hsu
Journal:  Molecules       Date:  2019-09-06       Impact factor: 4.411

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  10 in total

1.  Regioselective Synthesis of 2-Aryl-5-cyano-1-(2-hydroxyaryl)-1H-imidazole-4-carboxamides Self-Assisted by a 2-Hydroxyaryl Group.

Authors:  Fábio Pedroso de Lima; Emilio Lence; Pilar Suárez de Cepeda; Carla Correia; M Alice Carvalho; Concepción González-Bello; M Fernanda Proença
Journal:  ACS Omega       Date:  2022-06-24

2.  1-Mesityl-3-(3-Sulfonatopropyl) Imidazolium Protects Against Oxidative Stress and Delays Proteotoxicity in C. elegans.

Authors:  Natalia Andersen; Tania Veuthey; María Gabriela Blanco; Gustavo Fabian Silbestri; Diego Rayes; María José De Rosa
Journal:  Front Pharmacol       Date:  2022-05-24       Impact factor: 5.988

3.  Turn on Fluorescence Sensing of Zn2+ Based on Fused Isoindole-Imidazole Scaffold.

Authors:  Sutapa Sahu; Yeasin Sikdar; Riya Bag; Javier Cerezo; José P Cerón-Carrasco; Sanchita Goswami
Journal:  Molecules       Date:  2022-04-30       Impact factor: 4.927

4.  Viability of Glioblastoma Cells and Fibroblasts in the Presence of Imidazole-Containing Compounds.

Authors:  Elisabeth Christiane Seidel; Claudia Birkemeyer; Rainer Baran-Schmidt; Jürgen Meixensberger; Henry Oppermann; Frank Gaunitz
Journal:  Int J Mol Sci       Date:  2022-05-23       Impact factor: 6.208

5.  Utility of arylglyoxal hydrates in synthesis of 4-aroyl-[1,3,5]triazino[1,2-a]benzimidazol-2(1H)-imines and 5-aryl-2-phenyl-4H-imidazol-4-imines.

Authors:  Bahgat R M Hussein; Amr H Moustafa
Journal:  Mol Divers       Date:  2022-01-21       Impact factor: 2.943

Review 6.  Anticancer Activity of Natural and Synthetic Chalcones.

Authors:  Teodora Constantinescu; Claudiu N Lungu
Journal:  Int J Mol Sci       Date:  2021-10-20       Impact factor: 5.923

7.  Synthesis, Spectroscopic, Thermal, and Catalytic Properties of Eight New Complexes of Metal(II) Formates or Propionates with Imidazole; Relationship between the Carbon Chain Length and Catalytic Activity.

Authors:  Bartłomiej Rogalewicz; Tomasz Maniecki; Radosław Ciesielski; Agnieszka Czylkowska
Journal:  Materials (Basel)       Date:  2021-12-25       Impact factor: 3.623

8.  Design and fabrication of photoactive imidazole-based poly(ether-imide)s and a polyimide/HBP-modified SiO2 composite: toward high heat-resistance, antimicrobial activity and removal of heavy metal ions.

Authors:  Diyari Khaki; Hassan Namazi; S Mojtaba Amininasab
Journal:  RSC Adv       Date:  2021-07-05       Impact factor: 4.036

9.  TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions.

Authors:  Kesatebrhan Haile Asressu; Chieh-Kai Chan; Cheng-Chung Wang
Journal:  RSC Adv       Date:  2021-08-19       Impact factor: 4.036

10.  Tuning Anti-Biofilm Activity of Manganese(II) Complexes: Linking Biological Effectiveness of Heteroaromatic Complexes of Alcohol, Aldehyde, Ketone, and Carboxylic Acid with Structural Effects and Redox Activity.

Authors:  Agnieszka Jabłońska-Wawrzycka; Patrycja Rogala; Grzegorz Czerwonka; Sławomir Michałkiewicz; Maciej Hodorowicz; Katarzyna Gałczyńska; Beata Cieślak; Paweł Kowalczyk
Journal:  Int J Mol Sci       Date:  2021-05-03       Impact factor: 5.923

  10 in total

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