Preferences help
enabled [disable] Abstract
Number of results
2019 | 130 | 42-70
Article title

Novel synthesis of 3-(((E)-benzylidene)amino)-5-((Z)-3,4-dimethoxybenzylidene)-2-phenyl-3,5-dihydro-4H-imidazol-4-one derivatives as potent antimicrobial agents

Title variants
Languages of publication
Novel synthesis of 4H-imidazol-4-one derivative by reaction of (Z)-3-amino-5-(3,4 dimethoxybenzylidene)-2-phenyl-3,5-dihydro-4H-imidazol-4-one with derivative of different aromatic aldehydes and Salicyldehyde. New synthesized compound are thermally stable and neither air-nor moisture sensitive at RT. Successive library of synthesized compound characterized using IR, NMR, Elemental, Mass, and its antimicrobial activity study.
Physical description
  • Chemical Research Laboratory, Department of Chemistry, Saurashtra University, Rajkot - 360005, India
  • Chemical Research Laboratory, Department of Chemistry, Saurashtra University, Rajkot - 360005, India
  • Chemical Research Laboratory, Department of Chemistry, Saurashtra University, Rajkot - 360005, India
  • Chemical Research Laboratory, Department of Chemistry, Saurashtra University, Rajkot - 360005, India
  • Chemical Research Laboratory, Department of Chemistry, Saurashtra University, Rajkot - 360005, India
  • [1] Wail Al Zoubi, Biological Activities of Schiff Bases and Their Complexes: A Review of Recent Works, International Journal of Organic Chemistry, 2013, 3, 73-95
  • [2] Anant Prakash, Devjani Adhikari, Application of Schiff bases and their metal complexes-A Review, Int. J. ChemTech Res. 2011, 3(4).
  • [3] Sunita Bhagat, Nutan Sharma, and Tejpal Singh Chundawat, Synthesis of Some Salicylaldehyde-Based Schiff Bases in Aqueous Media. Journal of Chemistry Volume 2013, Article ID 909217
  • [4] A. Xavier, N. Srividhya, Synthesis and Study of Schiff base Ligands. IOSR Journal of Applied Chemistry Volume 7, Issue 11 Ver.I (Nov. 2014) 06-15
  • [5] Anu Kajal, Suman Bala, Sunil Kamboj, Neha Sharma, and Vipin Saini, Schiff Bases: A Versatile Pharmacophore, Journal of Catalysts, Volume 2013, Article ID 893512.
  • [6] Raghunath B Toche, Prashant Nikam, Synthesis and evaluation of antimicrobial and antitubercular activity of arylidene hydrazines of indenothieno[2,3 d] pyrimidine, Chemistry & Biology Interface, 2015, 5, 4, 246-257
  • [7] Peng-Wu Zheng, Qiao-Mei Qiu, Yu-Yan Linc and Ke-Fan Liud, N,N00-Bis(2,6-dichlo robenzylidene)hydrazine, Acta Cryst. (2006). E62, o1913-o1914
  • [8] Emerson T. da Silva, Adriele da Silva Araújo, Adriana M. Moraes, Leidiane A. de Souza, Maria Cristina Silva Lourenço, Marcus V. N. de Souza, James L. Wardell and Solange M. S. V. Wardell, Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives. Sci. Pharm. 2016, 84, 467-483
  • [9] Sobhi M. Gomha, Magda A. Abdallah, Salim S. Al-Showiman, Mahmoud A. Morad, Yahia N. Mabkhot, Synthesis of new pyridopyrimidinone-based thiadiazoles and pyrazolines aspotential anti-breast cancer agents. Biomedical Research 2017; 28 (22): 9903-9909
  • [10] Nasry Jassim Hussien, Siti Fairus M. Yusoff, Mohamad J. Al-Jeboori, Yang Farina, Hamza M. Abosadiya, Enaam I. Yousif and Riyadh M. Ahmed, Crystal structure of N-phenyl-2-(propan-2-ylidene)hydrazine-1-carbothioamide, Z. Kristallogr. NCS 2019; 234(1): 31-32
  • [11] Osama M. Sayed, Ahmed E.M. Mekky, Ahmad M. Farag and Ahmad H.M. Elwahy, 3,4-Dimethyl-2,5-functionalized thieno[2,3-b]thiophenes: versatile precursors for novel bis-thiazoles. Journal of Sulfur Chemistry, 2015 Vol. 36, No. 2, 124-134
  • [12] Mohanambal D, Sridevi G, Arul Antony S Angayarkani R review: a recent review in applications of heterocyclic compounds as antimicrobial agent, Asian J Pharm Clin Res, Vol. 11, Issue 12, 2018, 66-74
  • [13] Nabil M. Ibrahim, Hisham A. A. Yosef, Ewies F. Ewies, Mohamed R. H. Mahran, Mamdouh M. Alib and Abeer E. Mahmoud, Synthesis and Antitumor Evaluation of New Heterocycles Derived from 3-Methyl-2-benzothiazolinone Hydrazone. J. Braz. Chem. Soc., Vol. 26, No. 6, 1086-1097, 2015
  • [14] Dalia Hussein Soliman, Wagdy Mohamed Eldehn, Hazem Ahmed Ghabbour, Maha Mamdouh Kabil, Marwa Mostafa Abdel-Aziz, and Hatem Abdel-Kader Abdel-Azizh, Novel 6-Phenylnicotinohydrazide Derivatives: Design, Synthesis and Biological Evaluation as a Novel Class of Antitubercular and Antimicrobial Agents, Biol. Pharm. Bull. 40, 1883-1893 (2017)
  • [15] N. M. Goudgaon and Y. Rohini Reddy, Goudgaon and Reddy, Design, synthesis and antimicrobial evaluation of novel 1-(2-(4-fluoro benzylthio)pyrimidin-4-yl-amino)-4-(substituted phenyl)azetidin-2-ones. IJPSR, 2015; Vol. 6(3): 1060-1065
  • [16] Philip A. Conway, Kevin Devine, Francesca Paradisi, A simple and efficient method for the synthesis of Erlenmeyer azlactones, Tetrahedron 65 (2009) 2935-2938
  • [17] Ahmed El-Mekabaty, Erlenmeyer Azlactones Synthesis, Reactions and Biological Activity, International Journal of Modern Organic Chemistry, 2013, 2(1): 40-66
  • [18] Sosale Chandrasekhar and Malempati Srimannarayana, The Erlenmeyer synthesis with a thioazlactone, Arkivoc 2009 (xii) 290-295
  • [19] Ruby Ahmed, Synthesis and biological activity of heterocyclic azlactone and imidazolone derivatives, Indian J. Sci. Res. 13 (1): 126-130, 2017
  • [20] Rakesh N. Mistry and K. R. Desai, Studies on Synthesis of Some Novel Heterocyclic Azlactone Derivatives and Imidazolinone Derivatives and their Antimicrobial Activity, E-Journal of Chemistry, Vol. 2, No. 1, pp 42 -51, January 2005.
  • [21] Sudheer Moorkoth, Srinivasan K.K and Divyashree Bukka, Evaluation of antimicrobial activity of 4-arylidene-2-phenyl oxazol-5-one derivatives against selected skin micro-organisms, Elixir Pharmacy 54 (2013) 12315-12318
  • [22] Muhammad A. Mesaik, Shagufta Rahat, Khalid M. Khan, Zia-Ullah, Muhammad I. Choudhary, Shahnaz Murad, Zakiah Ismail, Atta-ur-Rahmanb and Aqeel Ahmad, Synthesis and immunomodulatory properties of selected oxazolone derivatives, Bioorganic & Medicinal Chemistry 12 (2004) 2049-2057
  • [23] Mehtab Parveen, Akhtar Ali, Sarfaraz Ahmed, Ali Mohammed Malla, Mahboob Alam, P .S. Pereira Silva, Manuela Ramos Silva, Dong-Ung Lee, Synthesis, bioassay, crystal structure and ab initio studies of Erlenmeyer azlactones, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 104 (2013) 538-545
  • [24] Ahmed M. El-Saghier, Embarak F. Alwedi, and Naglaa M. Fawzyc, Synthesis and Antibacterial Activity of Certain Fused Azoles and Oxazinones, J. Heterocyclic Chem. 49, 664 (2012)
  • [25] M. B. Madhusudana Reddy & M. A. Pasha, Molecular Iodine–Catalyzed, Mild, Effective, Ecofriendly, Microwave-Assisted, One-Pot Synthesis of 5-Arylmethylidene-2-phenyloxazol-4-ones (Azalactones) Under Solvent-Free Conditions. Synthetic Communications 1, 40: 1895-1898, 2010
  • [26] Thalita G. Barros, Sergio Pinheiro J. S. Williamson Amılcar Tanuri M. Gomes Jr Helena S. Pereira, R. M. Brindeiro, Jose B. A. Neto, O. A. C. Antunes, Estela M. F. MuriPseudo-peptides derived from isomannide: inhibitors of serine proteases, Amino Acids (2010) 38: 701-709
  • [27] Navin B. Patel and Hemant R. Patel, Design and Synthesis of New Imidazolinone Derivatives as Potential Antifungal Agents, J. Heterocyclic Chem. 48, 373 (2011)
  • [28] Doru Roiban, Elena Serrano, Tatiana Soler, Ion Grosu, Carlos Cativielad and Esteban P. Urriolabeitia, Unexpected [2 + 2] C–C bond coupling due to photocycloaddition on orthopalladated (Z)-2-aryl-4-arylidene-5(4H)-oxazolones, Chem. Commun. 2009, 468104683
  • [29] Khalid Mohammed Khan, Uzma Rasool Mughal, Mahmud Tareq Hassan Khan, Zia-Ullah, Shahnaz Perveenb and Muhammad Iqbal ChoudharyaOxazolones: New tyrosinase inhibitors; synthesis and their structure–activity relationships, Bioorganic & Medicinal Chemistry 14 (2006) 6027-6033
  • [30] Satya Paul,a, Puja Nanda, Rajive Guptaa and Andre Loupyb, Calcium acetate catalyzed synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under solvent-free conditions. Tetrahedron Letters 45 (2004) 425-427
  • [31] B.B.L. Srivastava, Synthesis Of 3-[3-Chloro-4-Hydroxy-2(4-Hydroxy Phenyl)-2h-Azetidene-1-Yl]-5-(4-Hydroxy Benzylidene)-2-Phenyl-3,5-Dihydro-Imidazol-4-One As Possible Antimicrobial Agents, International Journal of ChemTech Research Vol. 5, No. 4, pp 1915-1920, April-June 2013
  • [32] V. O. Topuzyana, L. G. Arutyunyana, A. Oganesyana, and G. Panosyan, Derivatives of α,β-Dehydro Amino Acids: II. New Synthesis of 2,4-Disubstituted 1-Aminoimidazol-5-ones from N-Substituted α,β-Unsaturated α-Amino Acid Hydrazides, Russian Journal of Organic Chemistry, 2007, Vol. 43, No. 6, pp. 936-937
  • [33] N. C. Desai, A. M. Bhavsar and B. B. Baldaniya, Synthesis and Antimicrobial Activity of 5-Imidazolinone Derivatives, Indian J. Pharm. Sci. 2009, 71 (1): 90-94.
  • [34] Magdy M. Hemdana, Ahmed S.A. Youssefa, Fatma A. El-Mariahb and Heba E. Hashemb, Synthesis and antimicrobial assessments of some quinazolines and their annulated systems. Journal of Chemical Research 2017 vol. 41 February, 106-111
  • [35] Maha M. A. Khalifa, Marawan A. Baset, Wafaa El-Eraky, Synthesis and anticonvulsant activity of novel imidazole 5(4H) one and 5-oxo-4,5-dihydroimidazol-1-yl)propanamide derivatives, Med Chem Res (2012) 21: 4447-4454
  • [36] Shital V. Hote , Shital P. Bhoyar, Heterocyclic Compound –A Review, IOSR Journal of Applied Chemistry (IOSR-JAC), 2014, PP 43-46.
  • [37] Ganguly S S, Gami S P, Vilapara K V, Naliapara Y T, Synthesis and Antimicrobial Activities of Some Pyrazoline Derivatives, IJPRS research article V-1, I-4, 2012.
  • [38] Vikas Sharma, Prabodh C. Sharma, Vipin Kumar, A mini review on pyridoacridines: Prospective lead compounds in medicinal chemistry, Journal of Advanced Research (2015) 6, 63-71
  • [39] Murlidhar P. Wadekar, Arun R. Raut, Gopalkrushna H. Murhekar, Synthesis of some novel substituted 5-oxo imidazolines containing azo linkages and their biological screening, Der Pharma Chemica, 2010, 2(1): 76-81
  • [40] N.C. Desai, Dipika Dave, M.D. Shah.and G.D. Vyas, Synthesis and antibacterial activity of some novel 4-Oxo-1,3-Thiazolidines, 2-Oxoazitidenesand 5-oxoimidazolines, Indian Journal of Chemistry Vol. 39B April-2000, pp277-282.
  • [41] Karel Nalepa, Gabriela Zedn Kova, Jarom Marek, and Zdene Tracek, Syntheses of 1-Arylidenamino-2,4-disubstituted-2-imidazoline-5-ones. X-Ray Structure of 1-Benzylidenamino-2-phenyl-4-benzylidene-2-imidazoline-5-one, Monatshefte für Chemie 130, 471-479 (1999)
  • [42] Petr S tepnek, Thomas Y. Cowie, Martin Safark, Jaroslav Sebestik, Radek Pohl, and Petr Bour, Resolving Electronic Transitions in Synthetic Fluorescent Protein Chromophores by Magnetic Circular Dichroism, ChemPhysChem 2016, 17, 1-8
  • [43] Christopher Voosala, Lakshmi Narasimha Murthy Yellajyosula, Viplava Prasad Uppuleti and Padma Suhasini Kilaru, Efficient Synthesis of 5(4H)-Imidazolones and in vitro Antifungal, Asian Journal of Chemistry Vol. 26, No. 10 (2014), 2873-2876
  • [44] Navin B. Patel and Hemant R. Patel, Design and Synthesis of New Imidazolinone Derivatives as Potential Antifungal Agents, J. Heterocyclic Chem. 48, 373 (2011)
  • [45] Khalid Mohammed Khan, Uzma Rasool Mughal, Mahmud Tareq Hassan Khan, Zia-Ullah, Shahnaz Perveenb and Muhammad Iqbal Choudhary, Oxazolones: New tyrosinase inhibitors; synthesis and their structure–activity relationships. Bioorg. Med. Chem. 14 (2006) 6027–6033.
  • [46] Akbar Mobinikhaledi, Hassan Moghanian, Samira Pakdel, Microwave-assisted efficient synthesis of azlactone derivatives using 2-aminopyridine-functionalized sphere SiO2 nanoparticles as a reusable heterogeneous catalyst, Chinese Chemical Letters 26 (2015) 557–563.
  • [47] M. B. Madhusudana Reddy and M. A. Pasha, Molecular iodine–catalyzed, mild, effective, ecofriendly, microwave-assisted, one-pot synthesis of 5-arylmethylidene-2- phenyloxazol-4-ones (azalactones) under solvent-free conditions, Synthetic Communications1, 40: 1895-1898, 2010
  • [48] J. Augusto R. Rodrigues, Rudolph A. Abramovitch, Joana D. F. de Sousa, and Genaro C. Leiva, Diastereoselective Synthesis of Cularine Alkaloids via Enium Ions and an Easy Entry to Isoquinolines by Aza-Wittig Electrocyclic Ring Closure, J. Org. Chem. 2004, 69, 2920-2928
  • [49] T. Maneshwar, N.Vijetha1, V. Balakrishna, Ch. Vijay Kumar, M. Suresh, Synthesis, characterization and anthelmintic activity of novel isatin substituted imidazoline derivatives, Int J Pharm 2014; 4(1): 437-441
  • [50] Mohammad Ali Bodaghifard, Hassan Moghanian, Akbar Mobinikhaledi & Fatemeh Esmaeilzadeh. Microwave-assisted efficient synthesis of azlactones using zeolite NaY as a reusable heterogeneous catalyst, Inorganic and nano-metal chemistry 2017, vol. 47, NO. 6, 845-849
  • [51] Hooshang Hamidian and Ahmad Momeni Tikdari, Novel synthesis of unsaturated 5(4h)-oxazolone derivatives with using palladium(ii) acetate as a catalyst and microvawe irradiation in solvent - free condition, Heterocyclic Communications, Vol. 12, No. 1, 2006.
  • [52] Christopher Voosala, Nagendra Sastry Yarla, Manga Rao Nakka and Siddaiah Vidavaluri, Facile Synthesis of 1-(substituted phenyl)-2-phenyl-4-(substituted benzylidine)-imidazole-5-ones and Antifungal Activity Studies against Phytopathogens, Med Chem. 4(1): 303-305 (2013) -304
  • [53] Johannes S. Buck and Walter S. Ide. Azlactone of α-benzoylamino-β-(3,4-dimethoxyphenyl)-acrylic acid, Organic Syntheses, Coll. Vol. 2, p. 55 (1943);
  • [54] Ahmed M. El-Saghier, Embarak F. Alwedi, and Naglaa M. Fawzyc, Synthesis and Antibacterial Activity of Certain Fused Azoles and Oxazinones, J. Heterocyclic Chem. 49, 664 (2012)
  • [55] I. Ostromistensky ‘Note on Bacteriostatic Azo Compounds. J. Am. Chem. Soc. 1934, 56, 1713-1714
  • [56] D. E. Fink and D. L. Vivian; J. Econ. ‘Entomol.Scintific Notes’ 1936, 29, 804.
  • [57] L. M. Law. The Cancer Producing Properties of Azo Compounds in Mice. Cancer Res. 1941, 1, 397
  • [58] Venkata T, Maruti Kumar, V Prabhakar Reddy and P. HanymanthaRao; Microwave induced solvent-free synthesis of 1-aryl-2-(1E)-aeylvinyl-4-arylmethylene-2-imidazolin—5-one, Indian J. Chem. 2005, 44B, 1931-1932
  • [59] TyagiRashmi, V.K.Tyagi and S. K Pandey, Imidazoline and its derivatives, an overview, J. Oleo .Sci. 2007, 56, 211-222
  • [60] K.M. Khan, U.R. Mughal, N.A. Samreen. J. Enzyme Inhi, Synthesis and leishmanicidal activity of 2,3,4-substituted-5-imidazolones, Med. Chem. 2010, 25(1), 29-37
  • [61] Mohd. Amir, Arun Kumar and IsrarAli, Synthesis and leishmanicidal activity of 2,3,4- substituted-5-imidazolones, Ind. J Chem. 2009, 48B, 1288-1293
  • [62] N.C. Desai, A.M. Bhavsar and B.B. Baldaniya, Synthesis and Antimicrobial Activity of 5-Imidazolinone Derivatives, Ind. J. Pharma Sci. 2009, 71(1), 90-94
  • [63] Anil V. Patel and G.M. Malik, Synthesis and Characterization of Some Novel Biphenyl-4-carboxylic Acid (4-Benzylidene-5-oxo-2-subsituted phenyl-4,5-dihydro-imidazol-1-yl)amide. Asian Journal of Chemistry 21, 7 (2009) 5155-5159
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.