Author(s): G. Muthubhupathi, M. Selvakumar, S. Navi Shree, C. Nisha, P. Sathiya Priya, P. A. Varshini

Email(s): muthubhupathivpcw@gmail.com

DOI: 10.52711/2231-5691.2023.00028   

Address: G. Muthubhupathi*, M. Selvakumar, S. Navi Shree, C. Nisha, P. Sathiya Priya, P. A. Varshini
Department of Pharmaceutical Chemistry, Vivekanandha Pharmacy College for Women, Sankari, Salem - 637303. Tamil Nadu, India.
*Corresponding Author

Published In:   Volume - 13,      Issue - 3,     Year - 2023


ABSTRACT:
An innovative sequence of Oxazolone derivatives were synthesized via chemical reaction including Preparation of benzoyl glycine crystals and Synthesis of oxazolone derivatives. The synthesized compounds such as P- Chlorobenaldehyde, 4-Fluro benaldehyde, Cinnamaldehyde, 2-Chloro benaldehyde, and O- Anisaldehyde were elucidated by Fourier Transform-Infra Red (FT-IR) spectrometer and showed its corresponding peaks. The in- vitro anti-inflammatory activity of synthesized compounds by protein denaturation assay exhibited very good significant anti-inflammatory activity. Additionally, the test compounds 2-Chloro benzaldehyde had nearest IC50 value to the standard diclofenac sodium when compared to all other test compounds, and demonstrated highest zone of inhibition at the low concentration used to exhibit the high potency.


Cite this article:
G. Muthubhupathi, M. Selvakumar, S. Navi Shree, C. Nisha, P. Sathiya Priya, P. A. Varshini. Design, Synthesis, Characterization and Non-steroidal Anti-Inflammatory Activity of Novel Oxazolone Derivatives. Asian Journal of Pharmaceutical Research. 2023; 13(3):145-2. doi: 10.52711/2231-5691.2023.00028

Cite(Electronic):
G. Muthubhupathi, M. Selvakumar, S. Navi Shree, C. Nisha, P. Sathiya Priya, P. A. Varshini. Design, Synthesis, Characterization and Non-steroidal Anti-Inflammatory Activity of Novel Oxazolone Derivatives. Asian Journal of Pharmaceutical Research. 2023; 13(3):145-2. doi: 10.52711/2231-5691.2023.00028   Available on: https://asianjpr.com/AbstractView.aspx?PID=2023-13-3-2


REFERENCES:
1.    Banerjee J, Sharma N. A review on oxazolone, it’s method of synthesis and biological activity. European J. Biomed. Pharm. Sci. 2015; 2(3): 964-987.
2.    Suman B, Minaxi S, Sunil K. Methods for synthesis of oxazolones: A Review. Int. J. Chemtech Res. 2011; 3(3): 1102-1118.
3.    Lamb J, Robson W. The Erlenmeyer synthesis of amino-acids. Biochem J. 1931; 25(4): 1231-6. doi: 10.1042/bj0251231.
4.    Ismail MI.  Physical characteristic polarographic reduction, mechanism of some oxazolones. Can. J. Chem. 1991; 69: 1886-1892.
5.    Park BS, Min oh C, Chun KH, Lee JO. Photoinduced one pot transformation of 2-phenyl-4-ethylidene- 5(4H)-oxazolone and allylic alcohols to γ, δ-unsaturated N-benzoyl amides. Tetrahedron Lett. 1998; 39(52): 9711-9714.
6.    Palcut M. Spectral properties of novel 1, 3-oxazol-5(4H)-ones with substituted benzylidiene and phenyl rings. Acta Chim. Slov. 2009; 56: 362-368.
7.    Seebach D, Jaeschke G, Gottwald K, Matsuda K, Formisano R, Chaplin D, Breuning M, Bringmann G. ChemInform Abstract: Resolution of Racemic Carboxylic Acid Derivatives by Ti-TADDOLate Mediated Esterification Reactions - A General Method for the Preparation of Enantiopure Compounds. Cheminform. 2010; 28. doi: 10.1002/chin.199740043.
8.    Gottwald K, and Seebach D. Ring opening with kinetics resolution of azlactones by Ti- TADDOLates,.Tetrahedron. 1999; 55(3): 723-738.
9.        Matsunaga H, Ishizuka T, Kunieda T. Synthetic utility of five membered heterocycles-chiral functionalization and applications. Tetrahedron. 2005; 61(34): 8073-8094.
10.    Mizoguchi A. Animal Models of Inflammatory Bowel Disease: In Animal Models of Molecular Pathology. Prog. Mol. Biol. Transl. Sci. 2012; 105: 263–320.
11.    Kawkab Y, Saour, Redha I, Al-Bayati, Pharmacist M, Sataar J. (2015). Synthesis of 4-benzylidene-2-(4- nitro-phenyl) - 4H-oxazol-5 -one derivatives with suspected biological activity. Chem. Mater. Res. 2015; 7: 105-109.
12.    Bourotte M, Schmitt M, Wund AF, Pigault C, Haiech J, Bourguignon JJ. Fluorophores related to the green fluorescent protein. Tetrahedron Lett. 2004; 45: 6343-6348.
13.    Jung B, Kim H, Park BS. Photo decarbonylation of 2-phenyl-4alkylidene-5(4H)-oxazolones. Tetrahedron Lett. 1996; 37: 4019-4022.
14.    Ozturk G, Alp S, Ergun Y. Synthesis and spectroscopic properties of new 5-oxazolone derivatives containing an N-phenyl-aza-15-crown-5moiety. Tetrahedron Lett. 2007; 48: 7347-7350.
15.    Ozturk G, Alp S, Ertekin K. Fluorescence emission studies of4-(2furylmethylene)-2-phenyl-5-oxazolone embedded in polymer thin film and detection of Fe 3+ ion. Dyes Pigm. 2007; 72: 150-156.
16.    Murthy YLN, Christophera V, Prasad UV, Bisht PB, Ramanaih DV, Kalanoor BS, Ali SA. Synthesis and study of nonlinear optical properties of 4-substituted benzylidene-2-phenyl oxazol-5-ones by Z-scan technique. Synth. Met. 2010; 160: 535-539.
17.    Tandel RC, Mammen D. Synthesis and study of some compounds containing oxazolone ring showing biological activity. Indian J. Chem. 2008; 47: 932- 937.
18.    Tikdari AM, Fozooni S, Hamidian H. Dodecatungstophosphoric Acid (H3PW12O40), Samarium and Ruthenium (ІІІ) Chloride Catalyzed Synthesis of Unsaturated 2-Phenyl-5(4H)-oxazolone Derivatives under Solvent-free Conditions. Molecules. 2008; 13(12): 3246-3252.
19.    Naganagownda G, Petsom A. Synthesis and Antimicrobial Activity of oxazolone, Imidazolone and Triazine Derivatives Containing Benzothiophene. Bull Korean Chem. Soc. 2011; 32: 11.
20.    Pasha MA, Jayashankara VP, Venugopala KN, Rao KG. Zinc oxide: An efficient catalyst for the synthesis of 4-arylmethylidene-2phenyl5(4H)-oxazolones having Antimicrobial activity. J. Pharmacol. Toxicol. 2007; 2(3): 264-270.
21.    Mariyappan G, Saha BP, Datta S, kumar D, Haldar KP, Design, synthesis and antidiabetic evaluation of oxazolone derivatives. J. Chem. Sci. 2011; 123(3): 335-341.
22.    Pinto IL, West A, Debouckm CM, Dilella G, Gorniak JG, Odonnell KC, Oshannessy DJ, Patel A, Jarvest RL. Novel, selective mechanism- based inhibitors of the herbes proteases. Bioorganic Med. Chem. Let. 1996; 6: 2467-2472.
23.    Bala S, Saini M, Kamboja S, Saini B. Synthesis of 2-[4-(substituted benzylidene)-5-oxo-4,5-dihydro- oxazol-2-ylmethyl]-isoindole-1,3dione derivatives as novel potential anti-microbial agents. Iran. J. Pharmacol. Ther. 2012; 11: 45-52.
24.    Jat RL, Mishra R, Pathak D. Synthesis and anti-cancer activityof4benzylidene-2-phenyloxazol-5(4h)- one derivatives. Int. J. Pharm. Pharm. Sci. 2012; 4; 0975-1491.
25.    Dobhal Y. Rawat R, Parcha D, Sharma R, Chaudhary R. Design, synthesis and evaluation of phenyl oxazolone derivatives as cardioprotective drugs. World J. Pharm. Sci. 2014; 2(12); 1712-1722.
26.    Kupera FC, Radonjica M, Triel VJ, Steruma R, Groota JR, Artsc HEJ. Oxazolone is a respiratory allergent in brown Norway rats. Toxicology. 2011; 59-68.
27.    Akram WAM, Lakshmi S, Shankar B, Gouda TS. Synthesis, characterization and biological evaluation of oxazolone derivatives. Int. J. Pharm. Res. Scholars. 2014; 3: 2.
28.    Witvrouw M, Pannecouque C, Clercq DE, Fernandez-Alvarez E, Marco LJ. Inhibition of human immunodeficiency virus type 1 (HIV-1) replication by some diversely functionalized spirocyclopropyl derivatives. Arch. Pharm. Pharm. Med. Chem. 1999; 332: 163-166.
29.    Sudha BN, Subbaiah NY, Synthesis and Biological Evaluation of Novel N-(2-benzamido-3- phenylacryloyl) Nicotinamide Derivatives. Res. J. Pharm. Biol. Chem. Sci. 2021; 12(5): 8-15.
30.    Madkour HMF. Simple one step synthesis of heterocyclic system from(4z)-2-phenyl-4-(thien-2-ylmethylene)-1,3(4H)-oxazole-5-one. Chem, Pap. 2002; 56: 313-319.
31.    Fareed G, Afza N, Versiani AM, Fareed N, Mughal RU, Kalhoro AM, Iqbal L, Lateef M. Synthesis, spectroscopic characterization and pharmacological evaluation of oxazolone derivatives. J. Serb. Chem. Soc. 2013; 78(8): 1127-1134.
32.    Pinto IL, West A, Debouckm CM, DiLella AG, Gorinak JG, O’Donnell KC, O’Shannessy DJ, Patel A, Jarvest RL. Novel, selective mechanism-based inhibitors of the herpes proteases. Bioorgaic Med. Chem. Lett. 1996; 6: 2467-2472.
33.    Khan KM, Mughal UR, Khan MT, Zia-Ullah, Perveen S, Choudhary MI. Oxazolones: new tyrosinase inhibitors; synthesis and their structure-activity relationships. Bioorg. Med. Chem. 2006; 14(17): 6027- 6033.
34.    Abdel SA. Pesticide effects of imidazolidine and oxazolone derivatives. World J. Agric. Sci. 2009; 5(1): 105-113.
35.    Fozooni S, Tikdari MA, Hamidian H, Khabazzadeha H. A synthesis of some new 4-arylidene-5(4H)- oxazolone azo dyes and an evaluation of their solvato chromic behaviour, Arkivoc. 2008; 42: 3.
36.    Khan KM, Mughal UR, Khan MTH, Ullah Z, Perveen S, Choudhary ML. Oxazolones; new tyrosinase inhibitors; synthesis and their structure-activity relationships. Bioorg. Med. Chem. 2006; 14: 6027-6033.
37.    Towns AD. Development in azo disperse dyes derived from hetero cyclic diazo components. Dyes Pigm. 1992; 42: 3,
38.    Fearnley SP, Market E. Intramolecular Diels-Alder reactions of N-substituted oxazolones. Chem. Commun. 2002; 438-439.
39.    Bourtte M, Schmit M, Wind AF, Pigault C, Haieeh J, Bourguignon JJ. Flourophores realetd to the green fluorscent protein. Tetrahedron Lett. 2004; 45: 6343-6348.
40.    Ozturk G, Alp S, Timur S. Photophysical characterisation of flourscent oxazol-5-one derivatives in PVC and their applications as biosensors in the detection of Ach and AchE inhibitor donepezil. Dyes Pigm. 2008; 76: 792-798.
41.    Pasha MA, Jayashankara VP, Venugopala KN, Rao GK. Zincoxide (ZnO); an efficient catalyst for the synthesis of 4-arylmethylidene2-phenyl-5-(4H)-oxazolones having antimicrobial activity. J. Pharmacol. Toxicol. 2007; 2: 264-270.
42.    Tikdari AM, Fozooni S, Hamidan H. Dodecatungstophosphoric acid (HPW12O21), sumatrium and ruthenium 3 chloride catalyzed synthesis of unsaturated 2-phenyl-5(4H)-Oxazolone derivatives under solvent free conditions. Molecules. 2008; 13: 3246-3252.
43.    Mesaik MA, Rahat S, Khan KM, Ullah Z, Choudhary M, Murad S, Ismail Z, Rahman A, Ahmad A. Synthesis and immunomodulatory properties of selected oxazolone derivatives. Bioorg. Med. Chem. 2004; 12: 2049-2057.
44.    Fareed G, Afza N, Versi Bala S, Saini M, kamboja S, andSaini B. Synthesis of 2-[4-(substituted benzylidene)-5-oxo-4,5-dihydro-oxazol-2ylmethyl]-isoindole-1,3dione derivatives as novel potential anti-microbial agents, Iran. J. Pharmacol. Ther. 2012;11: 45-52.
45.    Bala S, Saini AM, Fareed N, Mughal RU, Kalhoro AM, Iqbal L, Lateef M. Synthesis, spectroscopic characterization and pharmacological evaluation of oxazolone derivatives. J. Serb. Chem. Soc. 2013; 78(8): 1127-1134.
46.    Artis D, Spits H. The biology of innate lymphoid cells. Nature. 2015; 517: 293-301.
47.    Isailovic N, Daigo K, Mantovani A, Selmi C. Interleukin-17 and innate immunity in infections and chronic inflammation. J. Autoimmun. 2015; 60:1-11. doi: 10.1016/j.jaut. 2015.04.006.
48.    Pedraza-Alva G, Perez-Martinez L, Valdez-Hernandez L, Meza-sOSAKF, Ando-Kuri M. Negative regulation of the inflammasome: keeping inflammation under control. Immunol. Rev. 2015; 265: 231- 257.doi: 10. 1111/imr.122294.
49.    Suman B, Minaxi S, Sunil K, Goldie U, Ashok Kumar. Biodiversity of Oxazolone Derivatives in Medicinal Chemistry: A Review. Asian J. Research Chem. 2011; 4(5):685-694.
50.    Vignali DA, Kuchroo VK. IL-12 family cytokines: immunological play makers. Nat Immu. 2012; 13; 722-728. doi :10,1038/ni.2366.
51.    Jennifer F, Revanasiddappa BC, Ishwarbhat K, Vijay Kumar M, Lidwin D’Souza, Shanal Smitha Alva. Synthesis and in-Vitro Anti-Inflammatory Activity of Novel Pyrazoline Derivatives. Research J. Pharm. and Tech. 2017; 10(6): 1679-1682.
52.    Revanasiddappa BC, Vijay Kumar M, Prashanth Nayak, Ajmal Roshan Ali, Jasmine Kalsi. Synthesis and Biological Evaluation of Novel Imidazolinone Derivatives. Research J. Pharm. and Tech. 2017; 10(6): 1726-1729.
53.    Goswami-Giri AS, Neha A. Sawant. Bioactive Molecule of Onion Leaves Act as Inhibitor of PPO. Asian J. Research Chem. 4(11): 2011; 1780-1783.
54.    Vani Mamillapalli, Ratna Harika Chapala, Tejaswi Komal Sai Sareddu, Latha Sri Kondaveeti, Santhi Pattipati, Padmalatha Khantamneni. Evaluation of Phytochemical and in Vitro Anti-Inflammatory activity of Leaf and Fruit Extracts of Casuarina equisetifolia. Asian J. Pharm. Tech. 2020; 10(3):143- 148.
55.    Uma Sankar Gorla, Savithri M, Koteswara Rao GSN, Niharika Y, Devi Sree Sathya P, Harika V. Evaluation of anti-inflammatory activity of Hydroalcoholic extract of Ananas cosmosus fruit peel by HRBC membrane stabilization. Asian J. Pharm. Res. 2018; 8(1):33-35.
56.    Prakash Siju, Rohit Ghetia, Bhavin Vadher, Mital NM. In-Vitro Anti-inflammatory Activity of Fractions of Ailanthus excelsa Roxb. by HRBC Membrane Stabilization. Asian J. Pharm. Tech. 2015; 5(1,) 29-31. doi: 10.5958/2231-5713.2015.0000.
57.    Sureka A, Mary Sharmila C, Chithra Devi R, Muthu Kumar NJ, Banumathi V. Evaluation of In Vitro Anti-inflammatory activity of Kusta Gaja Kesari - A Siddha Herbo Mineral Formulation against Albumin Protein Denaturation. Asian J. Pharm. Res. 2018; 8(3): 145-147.
58.    Sugashini Settu, Sathiavelu Arunachalam. Evaluation of Anti-inflammatory activity of selected medicinal plants of Cucurbitaceae family. Research J. Pharm. Tech. 2023; 16(4):1598.
59.    Mital NM. In-Vitro Anti-inflammatory Activity of Traditionally reported Poly Herbal Combination. Asian J. Pharm. Tech. 2023; 13(1):1-3.

Recomonded Articles:

Author(s): AK Meena, MM Rao, RP Meena, P Panda, Renu

DOI:         Access: Open Access Read More

Author(s): Sonali Syal, Vinay Pandit, M. S Ashawat

DOI: 10.5958/2231-5691.2020.00034.9         Access: Open Access Read More

Author(s): Vani Mamillapalli, Latha Sri Kondaveeti, Ratna Harika Chapala, Tejaswi Komal Sai. Sareddu, Santhi Pattipati, Padmalatha Khantamneni

DOI: 10.52711/2231-5691.2022.00014         Access: Closed Access Read More

Author(s): Binoy Varghese Cheriyan, Sabartina scarlet, Priyadarshini, Shailesh joshi, Santhseelan, Sheik Mohamed

DOI: 10.5958/2231-5691.2019.00032.7         Access: Open Access Read More

Author(s): S.K. Purohit, R. Solanki, V. Mathur, M. Mathur

DOI:         Access: Open Access Read More

Author(s): Prathap Kumar Kothapalli, Jagadeesh. S. Sanganal, N.B. Shridhar

DOI:         Access: Open Access Read More

Author(s): Ghanshyam Dhalendra, Trilochan Satapathy, Amit Roy

DOI:         Access: Open Access Read More

Author(s): Naidu Narapusetty, O. Sivaiah, B. Balanasaraiah, M. Haranadhbabu, B. Prasad, B. Hosanna Crown, Ch. M. M. Prasada Rao

DOI: 10.5958/2231-5691.2017.00015.6         Access: Open Access Read More

Author(s): Venkateshwarlu Goli, Kanakam Vijay Bhaskar, Sravan Prasad Macharla, Jimmidi.Bhaskar, P. Suvarna Devi, T. Ramchander

DOI:         Access: Open Access Read More

Author(s): Debarshi Kar Mahapatra, Ruchi S. Shivhare, Pranesh Kumar

DOI: 10.5958/2231-5691.2018.00002.3         Access: Open Access Read More

Author(s): Kavya V. Reddy, Ashish V. Yachawad, Krushna K. Zambare, Sopan Landge

DOI: 10.5958/2231-5691.2020.00016.7         Access: Open Access Read More

Author(s): P. Lalitha, V. Sachithanandam, N. S. Swarnakumar, R. Sridhar

DOI: 10.5958/2231-5691.2019.00045.5         Access: Open Access Read More

Author(s): Ganesh Akula, Rangu Nirmala, CH. Shanthipriya, S. Rohini Reddy, A. Jaswanth

DOI: 10.5958/2231-5691.2017.00010.7         Access: Open Access Read More

Author(s): Muhammed Shakkeel K.V, Anjan Kumar, Veeresh Babu. D, Narayana Swamy V.B

DOI: 10.5958/2231-5691.2015.00021.0         Access: Open Access Read More

Author(s): Jaseela KP, Anjan Kumar, Veeresh Babu. D, Narayana Swamy V.B

DOI: 10.5958/2231-5691.2016.00014.9         Access: Open Access Read More

Author(s): Rangarajan Narasimhan, Sathiyamoorthy. M

DOI: 10.5958/2231-5691.2016.00001.0         Access: Open Access Read More

Author(s): Muhammad Hamza Ashfaq, Amna Siddique, Sammia Shahid

DOI: 10.52711/2231-5691.2021.00021         Access: Open Access Read More

Asian Journal of Pharmaceutical Research (AJPRes.) is an international, peer-reviewed journal, devoted to pharmaceutical sciences. AJPRes. publishes Original Research Articles, Short Communications..... Read more >>>

RNI: Not Available                     
DOI: 10.5958/2231–5691 


Recent Articles




Tags