A BRIEF REVIEW ON RECENT ADVANCEMENTS AND BIOLOGICAL ACTIVITIES OF ARYL PROPIONIC ACID DERIVATIVES
HTML Full TextA BRIEF REVIEW ON RECENT ADVANCEMENTS AND BIOLOGICAL ACTIVITIES OF ARYL PROPIONIC ACID DERIVATIVES
Punet Kumar * 1, Sangam 2 and Md. Iftekhar Ahmad 1
Department of Pharmaceutical Chemistry 1, Shri Gopichand College of Pharmacy, Baghpat - 250609, Uttar Pradesh, India.
Department of Pharmaceutical Chemistry 2, Oxford College of Pharmacy, Hapur - 201001, Uttar Pradesh, India.
ABSTRACT: Arylpropionic acid derivatives are an important class of NSAIDs. Ibuprofen, 2- (4-isobutylphenyl) propionic acid, is known as NSAIDs. Arylpropionic acid derivatives have a broad biological activity, including antibacterial, anticonvulsant and anticancer activity, analgesic, and anti-inflammatory. In addition to the most powerful ingredients used in analgesic and antipyretic fields, such as ibuprofen, Oxaprozin, Ketoprofen, and Phenoprofen, aryl propionic acid derivatives play an important role in treating other symptoms. The possible improvements in the activity can be further achieved by slight modifications in the substituent on the basic aryl propionic acid. According to Grigoryan et al., 2019 studies reveal that the replacement of the carboxyl group by tetrazole ring, hydroxamate, ester, alcohol, and amide groups forms compound showing lower activity (anti-inflammatory, anti-nociceptive, ulcerogenic activity). The presence of a carboxyl group in the parent molecule of aryl propionic acid is important for broad-spectrum pharmacological activity. This review focused on recent advances and recent research on aryl propionic acid derivatives compared to medicinal chemistry.
Keywords: |
Ulcerogenic activity, Antinociceptive activity, Anti-cancer activity, Anti-convulsant activity, Aryl propionic acid, Anti-inflammatory activity
INTRODUCTION: Medical chemistry is an area that determines the effect of chemical composition on biological activity. Medical chemistry has been expanded with the help of experimental methods for predicting the composition of new compounds that rely heavily on structural changes and the determination of biological properties.
Medical chemistry also provides for the detection, development, explanation, and validation of the mechanism of action of biologically active molecules at the molecular level 1, 2. Arylpropionic acid derivatives are a large and important family of non-steroidal anti-inflammatory drugs (NSAIDs) 2, 5. NSAIDs are often used to treat various arthritis and musculoskeletal disorders 6-9.
The biological response of NSAIDs is the result of inhibition of prostaglandin biosynthesis (PG), where cyclooxygenase enzyme (COX) plays a key role in prostaglandin biosynthesis derived from arachidonic acid 10, 14. In the early 1990s, COX was found to have two forms, namely the COX-1 component, which provides gastrointestinal cyto-protection (GI) and the other inducible COX-2, which mediates inflammation 15, 16. One of the NSAIDs viz. Ibuprofen, a chemical called propionic acid 2- (4-isobutylphenyl), is a popular pain relief 14, 15. This is known for its use in the relief of arthritis pain. Long-term use of NSAIDs leads results in gastrointestinal ulceration, bleeding and nephrotoxicity 18, 20. The gastrointestinal damage is generally associated with two factors which include local irritation by carboxylic acid moiety, which is common in most NSAIDs (topical effect) and decreased the production of tissue prostaglandin (PGs), which minimizes the physiological role of cytoprotective prostaglandins in maintaining GI health and homeostasis 21.
BAYLIS-HILLMAN ADDUCT
TABLE 1: 3-HYDROXY-2-METHYLENE-3PHENYL-PROPIONIC ACID DERIVATIVES
Compounds | R1 | R2 | R3 | R4 |
1 | H | NO2 | H | COOMe |
2 | H | NO2 | H | CN |
3 | NO2 | H | H | COOMe |
4 | NO2 | H | H | CN |
5 | H | CI | H | COOEt |
6 | H | CI | H | CN |
7 | H | F | H | CN |
8 | H | F | H | COOEt |
9 | CI | H | H | CN |
10 | CI | H | H | COOEt |
11 | CI | CI | H | COOEt |
12 | CI | CI | H | CN |
13 | H | H | NO2 | COOEt |
14 | H | H | NO2 | CN |
15 | H | NO2 | H | COOEt |
Studies showed that forming the derivative of the carboxylate function of representative NSAIDs resulted in an enhanced anti-inflammatory activity with reduced ulcerogenic effect. Moreover, certain compounds bearing 1, 3, 4-oxadiazole/thiadiazole and 1, 2, 4-triazole nucleus have been reported to bear significant anti-inflammatory activity 19, 20. In the last two decades, there has been a considerable amount of work in the role of reactive oxygen species in inflammation. Inflammation is one of the manifestations of oxidative stress and the pathways that generate the mediators of inflammation, such as adhesion molecules and interleukins 21.
TABLE 2: DERIVATIVES OF 3- (4, 5-DIPHENYL-1, 3-OXAZOLE-2-YL) PROPIONIC ACID
S. no. | R |
1 | ![]() |
2 | ![]() |
3 | ![]() |
4 | ![]() |
5 | ![]() |
6 | ![]() |
7 | ![]() |
2. Pharmacological Activities:
2.1 Anti-Bacterial Activity: Singh S. A. and Bhat S. V. synthesized twenty Baylis-Hillman adducts (3-hydroxy-2methylene-3-phenyl propionic acid derivatives) from different aromatic aldehydes and activated vinyl derivatives. These were screened for their antimicrobial activity in-vitro by serial dilution method. The synthesized compounds (1-15) showed potent antibacterial activity Table 3 22-25.
TABLE 3: β, β -DIPHENYL PROPIONIC ACID AMIDES
S. no. | R |
1 | H |
2 | C6H4 |
3 | C6H4 |
4 | p.(CH3O)C6H4 |
5 | 2-C5H4N |
6 | 2COOCH3 C6H4 |
7 | SO2NH2 C6H4 |
8 | -NH-CH2-COOH |
TABLE 4: 2-[5, 6-DIPHENYL-3(2H) PYRIDAZINONE-2-YL] ACETIC ACID DERIVATIVES
S. no. | R |
1 | ![]() |
2 | ![]() |
3 | ![]() |
4 | ![]() |
2.2 Anti-Cancer Activity: Rayam P. et al., synthesized a series of acyl hydrazones derivatives of 3-(4, 5-diphenyl-1, 3-oxazole-2-yl) propionic acid. The intermediate N- acyl hydrazine was prepared from NSAID oxaprozin, was coupled with a variety of aromatic aldehydes under conventional as well as microwave irradiation conditions.
The synthesized compounds in Table 2 were further screened for in-vitro anticancer activity. Compounds (1-7) showed potent anticancer activity when the comparison was made with Cisplatin 26-30.
2.3 Anti-convulsant Activity: Semwal A. synthesized a series of b, b- diphenyl propionic acid amides, which were evaluated for anti-convulsant activity using Maximal electroshock seizures (MES) method.
The compounds (1-8) showed mild to moderate anticonvulsant activity ranging from 0.0% to 50% in Table 3. Indomethacin was taken as standard drug 31-33.
TABLE 5: ACYL HYDRAZONE DERIVATIVES OF 3-(4, 5-DIPHENYL-1, 3-OXAZOLE-2-YL) PROPIONIC ACID
S. no. | R |
1 | ![]() |
2 | ![]() |
3 | ![]() |
2.4 Analgesic Activity: Puneet K. et al., synthesized five new β, β-diphenyl propionic acid derivatives. β, β-diphenyl propionyl chloride (Intermediate compound) was prepared by the reaction of β,β-diphenyl propionic acid, and thionyl chloride. β, β-diphenylpropanoyl chloride was reacting to several aromatic amines in the presence of potassium carbonate in acetone. The synthesized compound is characterized by physical properties, IR, 1HNMR, Mass spectral data.
Synthesis derivatives are examined to find out an analgesic activity (the method of working hot plates and tails Flik method) and anti-inflammatory activity (a method induced by Carrageenan induced edema) with Diclofenac and Indomethacin as standard drug. AK-1(diphenylamine derivative) and AK-3 (Morpholine derivative) and are potent analgesics and anti-inflammatory compounds. The derivatives of Arylpropionic acid have pain relief and a great space for further development as a similar and anti-inflammatory agent 30, 34, 35.
Dogruer D. S. et al., synthesized sixteen new amide derivatives by treatment of 2-[5, 6-diphenyl-3(2H)-pyridazinone-2-yl] acetic acid or 3-[5, 6-diphenyl-3(2H)-pyridazinone-2-yl] propionic acid with appropriate amine derivatives in the presence of triethylamine and ethyl chloroformate in dichloro-methane at room temperature Table 4. Out of which, Compounds (1-4) showed higher analgesic activity. Aspirin was taken as standard drug 36-37.
TABLE 6: β, β -DIPHENYL PROPIONIC ACID DERIVATIVES
S. no. | Name | R |
1 | Diphenylamine | ![]() |
2 | Ethyl Piperazine | ![]() |
3 | Morpholine | ![]() |
4 | Piperazine | ![]() |
5 | Pyrrolidine | ![]() |
Rayam P. et al., synthesized a series of acyl hydrazone derivatives of 3-(4, 5-diphenyl-1, 3-oxazole-2-yl) propionic acid. The key intermediate N- acyl hydrazine was prepared in good yield from NSAID oxaprozin, was coupled with a variety of aromatic aldehydes under conventional as well as microwave irradiation conditions. The compounds were screened for in-vivo analgesic activity and compounds (1-3) exhibited significant in-vivo analgesic activity Table 5. Oxaprozin was taken as reference drug 38, 39, 40.
TABLE 7: β, β-DIPHENYL PROPIONIC ACID AMIDES
S. no. | R |
1 | H |
2 | C6H4 |
3 | C6H4 |
4 | p.(CH3O) C6H4 |
5 | 2-C5H4N |
6 | 2COOCH3 C6H4 |
7 | SO2NH2 C6H4 |
8 | -NH-CH2-COOH |
2.5 Anti-inflammatory Activity: Semwal A. synthesized a series of β, β - diphenyl propionic acid amides. The synthesized compounds were evaluated for its anti-inflammatory activity by Carrageenan induced paw edema method.
The compounds (1-8) showed mild to moderate anti-inflammatory activity ranging from 36.13% to 90% after 3 h whereas the standard drug Indo-methacin showed 81.25% inhibition Table 7 40-42. Dogruer D. S. et al., synthesized sixteen new amide derivatives Table 7 by treatment of 2-[5,6diphenyl-3(2H)-pyridazinone-2-yl] acetic acid or 3-[5, 6-diphenyl-3 (2H)-pyridazinone- 2-yl] propionic acid with appropriate amine derivatives in the presence of triethylamine and ethyl chloro-formate in dichloromethane at room temperature. Out of which, compounds (1-3) showed potent anti-inflammatory activity 43, 44.
TABLE 8: 2-[5, 6-DIPHENYL-3(2H) PYRIDAZINONE-2-YL] ACETIC ACID DERIVATIVES
S. no. | R |
1 | ![]() |
2 | ![]() |
3 | ![]() |
Rayam P. et al., synthesized a series of acyl hydrazone derivatives of 3-(4, 5-diphenyl-1, 3-oxazole-2-yl) propionic acid. The key intermediate N- acyl hydrazine was prepared in good yield from NSAID oxaprozin, was coupled with a variety of aromatic aldehydes under conventional as well as microwave irradiation conditions.
The synthesized compounds in Table 9 were screened for in-vivo anti-inflammatory activity, and compounds (1-3) exhibited significant in-vivo anti-inflammatory activity. Oxaprozin was taken as reference compound 45, 46. Dilber S. P. et al., synthesized b-hydroxy-aryl propanoic acids by a two-step process. The first step involves the synthesis of diastereomeric 3-hydroxy-2-methyl-3-(4-biphenylyl) butanoic acids whereas the second step was a modified Reformatsky reaction in presence of Zn in tetra-hydrofuran (THF) at -5 to 10 ºC between the synthesized compound of the first step and 4-acetyl phenyl. The synthesized compounds were screened for anti-inflammatory activity, and only two compounds (1, 2) showed the strongest anti-inflammatory activity 47, 48.
Puneet K. et al., synthesized five new β, β-diphenyl propionic acid derivatives. β, β-diphenyl propionyl chloride (Intermediate compound) was prepared by the reaction of β, β-diphenyl propionic acid, and thionyl chloride. β, β-diphenylpropanoyl chloride was reacting to several aromatic amines in the presence of potassium carbonate in acetone. The synthesized compound is characterized by physical properties, IR, 1HNMR, Mass spectral data. Synthesis derivatives are examined to find out the anti-inflammatory activity (a method induced by Carrageenan induced edema) with Diclofenac and Indomethacin as standard drug.
AK-1(diphenylamine derivative) and AK-3 (Morpholine derivative) and are potent analgesics and anti-inflammatory compounds. The derivatives of Arylpropionic acid have pain relief and a great space for further development as a similar and anti-inflammatory agent 49.
TABLE 9: ACYL HYDRAZONE DERIVATIVES OF 3-(4, 5-DIPHENYL-1, 3-OXAZOL-2-YL) PROPIONIC ACID
S. no. | R |
1 | ![]() |
2 | ![]() |
3 | ![]() |
Gupta R. et al., synthesized 2-(4-secbutyl-phenyl)-propionic acid-pyrrolidin-2-ylcarbamoyl methyl esters by refluxing ibuprofen with 2-aminopyridine in chloroacetyl chloride in presence of glacial acetic acid. The synthesized compounds were evaluated for anti-inflammatory activity. Compounds (1-6) showed potent anti-inflammatory activity Table 10 50, 51.
TABLE 10: 2-(4-SEC-BUTYL-PHENYL) PROPIONIC ACID-PYRROLIDIN -2-YLCARBAMOYL METHYL ESTERS
S. no. | R |
1 | ![]() |
2 | ![]() |
3 | NH2NH2 |
4 | ![]() |
5 | NH(CH3)2 |
6 | NH(C2H5)2 |
2.6 Anti-nociceptive Activity and Ulcerogenic Activity: Grigoryan et al., 2019 synthesized a new method of a non-protein amino acid (NPAA) which showed that this compound injected in a dose of 10 mg/kg (i.p.) inhibited xylene-induced ear edema by about 31.1%, which proved its anti-inflammatory properties. The anti-nociceptive activity of NPAA-36 was assessed in the tail-flick test by the ability to increase the tail cut-off latency by 36.78% within 60 min after injection at the same dose.
Investigation of the ulcerogenic properties of NPAA-36 demonstrated that it exhibited lower gastrointestinal toxicity than a well-known aryl propionic acid derivative NSAID. Results of in-vitro experiments showed the Anti-platelet activity registered not in all (only in 41.2%) cases, which might imply lower bleeding. The obtained data indicate that the new NPAA derivative can be a potential basis for the development of new anti-inflammatory drugs with weak side effects 52.
TABLE 11: POTENT COMPOUNDS AND THEIR PHARMACOLOGICAL SIGNIFICANCE
Studies on the structure-activity relationship (SAR) were conducted on 3-aryl propionic acids as selective agonists by introducing substituents to the chain of propionic acid the adjacent phenyl ring with pyridine chain was replaced to develop a series of containing modified 3-aryl propionic acids with an enhanced half-life in rat 30, 64, 65. The important members of this class, ibuprofen, naproxen, and Ketoprofen are now available as OTC medicines.
However, the indiscriminate use of these drugs without a physician's prescription has resulted in an increased incidence of acute and chronic renal failure in adolescents 70, 57. All compounds belonging to aryl and heteroaryl propionic acids (except Oxaprozin) possess a chiral carbon in the á-position of the acetic acid side chain. Although most of the compounds are marketed as racemates, only the (S)-enantiomer was found to have any inhibitory activity against the COX isoenzymes 72. Therefore, only (S)-enantiomer is believed to be responsible for the observed therapeutic action as well as the drug-induced GI side effects and nephrotoxicity 68, 67.
The details of some potent compounds and their pharmacological activities associated are presented in Table 11.
CONCLUSION: Based on various literature surveys, aryl propionic acid derivatives show broad-spectrum various activities such as anti-bacterial, anti-cancer, anti-Convulsant, analgesic, and anti-inflammatory, antinociceptive activity and ulcerogenic activity. The possible improvements in the activity can be further achieved by slight modifications in the substituent on the basic aryl propionic acid.
ACKNOWLEDGEMENT: I profusely thankful to Prof. Arun Kumar Mishra, Department of Chemistry, IFTM University, Moradabad, for their valuable suggestions and guidance.
CONFLICTS OF INTEREST: The author declares that no conflicts of interest.
REFERENCES:
- Raboisson P, Rognan D, Aldous D and Wermuth CG: The Practice of Medicinal Chemistry. Academic Press. Edition 4th
- Jargalsaikhan BE, Ganbaatar N, Urtnasan M, Uranbileg N and Begzsuren D: Anti-inflammatory effect of polyherbal formulation (PHF) on carrageenan and lipopoly-saccharide-induced acute inflammation in rats. Biomedical and Pharma Journal 2019; 12(04): 1801-9.
- Koparır M, Cansız A and Demirdağ A: Synthesis of some new 4, 5-substituted-4H-1, 2, 4-triazole-3-thiol derivatives. Molecules 2004; 9(4): 204-12.
- Katica C, Vesna D, Vlado K, Dora GM and Aloksandra B: Synthesis, antibacterial and antifungal activity of 4-substituted-5- aryl-1, 2, 4-triazoles. Molecules 2001; 6: 815-24.
- Derek G, Waller, Anthony P and Sampson: Medical Pharmacology and Therapeutics. Elsevier, Edition 5th
- Wong RS: Disease-modifying effects of long-term and continuous use of nonsteroidal anti-inflammatory drugs (NSAIDs) in spondyloarthritis. Advances in Pharmaco-logical Sciences 2019; 1-6.
- Hovsepian TR, Dilanian ER, Engoyan AP and Melik-Ohanjanian RG: Synthesis of Substituted 1, 2, 4-Triazoles and 1, 3, 4-Thiadiazoles. Chemistry of Heterocyclic Compounds 2004; 40(9): 1194-98.
- Goulielmos GN, Zervou MI, Vazgiourakis VM, Ghodke-Puranik Y, Garyfallos A and Niewold TB: The genetics and molecular pathogenesis of systemic lupus erythematosus (SLE) in populations of different ancestry. Gene 2018; 668: 59-72.
- Emanuela R and Garret AF: Prostaglandins and inflammation. Arteriosclerosis, Thrombosis and Vascular Biology 2011; 31(5): 986-1000.
- Attiq A, Jalil J, Husain K and Ahmad W: Raging the war against inflammation with natural products. Frontiers in Pharmacology 2018; 9: 976.
- Dannhardt G and Kiefer W: Cyclooxygenase inhibitors–current status and future prospects. European Journal of Medicinal Chemistry. 2001; 36(2): 109-26.
- Marnett LJ, Rowlinson SW, Goodwin DC, Kalgutkar AS and Lanzo CA: Arachidonic acid oxygenation by COX-1 and COX-2 Mechanisms of catalysis and inhibition. Journal of Biological Chemistry 1999; 274(33): 22903-6.
- Souldozi A and Karami S: One-pot three-component reaction for the synthesis of novel series of fully substituted 1, 3, 4-oxadiazole derivatives bearing pyridine moiety. Phosphorus, Sulfur and Silicon and the Related Elements 2016; 191(6): 867-70.
- Vasincu I, Apotrosoaei M, Tuchilus C, Pânzariu AT, Dragostin O, Lupascu D and Profire L: New derivatives of aryl-propionic acid. Synthesis and biological evaluation. Rev Med Chir Soc Med Nat 2013; 117: 532-37.
- Amir M, Kumar H and Khan SA: Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-inflammatory and analgesic agents. Bioorganic & Medicinal Chemistry Letters 2008; 18(3): 918-22.
- Simon JP and Prince ES: Natural remedies for non‐steroidal anti‐inflammatory drug‐induced toxicity. Journal of Applied Toxicology 2017; 37(1): 71-83.
- Francotte P, Goffin E, Fraikin P, Graindorge E, Lestage P, Danober L, Challal S, Rogez N, Nosjean O, Caignard DH and Pirotte B: Development of thiophenic analogues of benzothiadiazine dioxides as new powerful potentiators of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid (AMPA) receptors. Journal of Medicinal Chemistry. 2013; 56(20): 7838-50.
- Rainsford KD: Ibuprofen: pharmacology, therapeutics and side effects. Springer Science & Business Media, 2013.
- Kapoor S, Nailwal N, Kumar M and Barve K: Recent patents and discovery of anti-inflammatory agents from marine source. Recent Patents on Inflammation & Allergy Drug Discovery 2019; 13(2): 105-14.
- Chaudhary S, Verma HC, Gupta MK, Gupta RK, Kumar A and El-Shorbagi AN: Synthesis and investigation of anthelmintic, antibacterial and antifungal activity of 3, 3-diphenyl propanamide derivatives. Synthesis 2019; 12: 310-05.
- Somani RR and Bhanushali UV: Synthesis and evaluation of anti-inflammatory, analgesic and ulcerogenic potential of NSAIDs bearing 1, 3, 4-oxadiazole scaffold. Indian Journal of Pharmaceutical Sciences 2011; 73 (6): 634.
- Dogruer DS, Unlu S, Kupeli E, Banoglu E and Sahin MF: Synthesis of 2-[5, 6-diphenyl-3 (2H)-pyridazinone-2-yl] acetamide and 3-[5, 6-diphenyl-3 (2H)-pyridazinone-2-yl] propanamide derivatives as analgesic and anti inflamematory agents. Turkish Journal of Pharmaceutical Sciences 2007; 4(2): 57-70.
- Kavitha T and Velraj G: Molecular structure, spectroscopic and docking analysis of 1, 3-diphenylpyrazole-4-propionic acid: A good prostaglandin reductase inhibitor. Journal of Molecular Structure 2018; 1155: 819-30.
- Chaudhari PS, Chitlange SS and Nanda RK: Synthesis and biological evaluation of novel 2-(4-acetyl-3-methyl-5-(arylamino) thiophen-2-yl)-3-arylquinazolin-4 (3h)-one derivatives as potential anti-inflammatory and antioxidant agents. Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry (Formerly Current Medicinal Chemistry-Anti-Inflammatory and Anti-Allergy Agents) 2018; 17(2): 102-14.
- Manjula D, Shabaraya AR and Somashekar S: Topical delivery of fenoprofen proliposomes: preparation, evaluation and in-vitro Int J Pharma Sci Invent 2014; 3(8): 6-12.
- Kovvasu SP, Kunamaneni P, Yeung S, Rueda J and Betageri GV: Formulation of dronedarone hydrochloride-loaded proliposomes: in-vitro and in-vivo evaluation using caco-2 and rat model. AAPS Pharm Sci Tech 2019; 20(6): 226.
- Amnerkar ND and Bhusari KP: Synthesis of some thiazolyl aminobenzothiazole derivatives as potential antibacterial, antifungal and anthelmintic agents. Journal of Enzyme Inhibition and Medicinal Chemistry 2011; 26(1): 22-28.
- Kumar P, Kumar A and Mishra AK: Synthesis and biological evaluation of some bioactive secondary aromatic amine derivatives of 3, 3-diphenyl propionic acid. Current Bioactive Compounds 2018; 14(4): 412-8.
- Dhall H, Kumar A and Mishra AK: Synthesis of some novel substituted phenyl β, β-Diphenyl propanoate with analgesic and anti-inflammatory activity. Current Bioactive Compounds 2018; 14(1): 26-32.
- Eissa SI, Farrag AM and Galeel AA: Non-carboxylic analogues of aryl propionic acid: synthesis, anti-inflammatory, analgesic, antipyretic and ulcerogenic potential. Drug Research 2014; 64(09): 485-92.
- Pilotto A, Sancarlo D, Addante F, Scarcelli C and Franceschi M: Non-steroidal anti-inflammatory drug use in the elderly. Surgical Oncology 2010; 19(3): 167-72.
- Semwal A: A novel β, β- diphenyl propionic acid amide derivatives showing anti-inflammatory and anti-convulsantt activity," International Journal of Medicinal Science and Clinical Invention 2014: l (1): 15-24.
- Singh A and Asif M: Analgesic and anti-inflammatory activities of several 4-substituted-6-(3'-nitrophenyl) pyridazin-(2H)-3-one derivatives. Brazilian Journal of Pharmaceutical Sciences 2013; 49(4): 903-9.
- Manolov S, Ivanov I and Voynikov Y: N-[2-(1H-Indol-3-yl) ethyl]-2-(4-isobutylphenyl) propanamide. Molbank 2018; 2018(4): M1031.
- Tjølsen A, Berge OG, Hunskaar S, Rosland JH and Hole K: The formalin test: an evaluation of the method. Pain 1992; 51(1): 5-17.
- Madhavi S, Sreenivasulu R and Raju RR: Synthesis and biological evaluation of oxadiazole incorporated ellipticine derivatives as anticancer agents. Monatshefte für Chemie-Chemical Monthly 2017; 148(5): 933-8.
- Amdekar S, Roy P, Singh V, Kumar A, Singh R and Sharma P: Anti-inflammatory activity of lactobacillus on Carrageenan-induced paw edema in male wistar rats. International Journal of Inflammation 2012; 1-6.
- Lacroix A, Toussay X, Anenberg E, Lecrux C, Ferreirós N, Karagiannis A, Plaisier F, Chausson P, Jarlier F, Burgess SA and Hillman EM: COX-2-derived prostaglandin E2 produced by pyramidal neurons contributes to neurovascular coupling in the rodent cerebral cortex. Journal of Neuroscience 2015; 35(34): 11791-10.
- Savic J, Dilber S, Milenkovic M, Kotur-Stevuljevic J, Markovic B, Vladimirov S and Brboric J: Docking studies, synthesis and biological evaluation of β-aryl-β-hydroxy propanoic acids for anti-inflammatory activity. Medicinal Chemistry 2017; 13(2): 186-95.
- Palkar MB, Singhai AS, Ronad PM, Vishwanathswamy AH, Boreddy TS, Veerapur VP, Shaikh MS, Rane RA and Karpoormath R: Synthesis, pharmacological screening and in silico studies of new class of Diclofenac analogues as a promising anti-inflammatory agents. Bioorganic & Medicinal Chemistry 2014; 22(10): 2855-66.
- Sabandar CW, Jalil J, Ahmat N and Aladdin NA: Medicinal uses, chemistry and pharmacology of Dillenia species (Dilleniaceae). Phytochemistry 2017; 134: 6-25.
- Aneja DK, Lohan P, Arora S, Sharma C, Aneja KR and Prakash O: Synthesis of new pyrazolyl-2, 4-thia-zolidinediones as antibacterial and antifungal agents. Organic and Medicinal Chemistry Letters 201; 1(1): 15.
- Manjula D, Shabaraya AR and Somashekar S: Topical delivery of fenoprofen proliposomes: preparation, evaluation and in-vitro International Journal of Pharmaceutical Science Invention 2014; 3(8): 6-12.
- Mishra D, Ghosh GO, Kumar PS and Panda PK: An experimental study of analgesic activity of selective COX-2 inhibitor with conventional NSAIDs. Asian Journal of Pharmaceutical and Clinical Research 2011; 4(1): 78-81.
- Dogruer DS, Unlu S, Kupeli E, Banoglu E and Sahin MF: Synthesis of 2-[5, 6-diphenyl-3 (2H)-pyridazinone-2-yl] acetamide and 3-[5, 6-diphenyl-3 (2H)-pyridazinone-2-yl] propanamide derivatives as analgesic and anti inflammatory agents. Turkish Journal of Pharmaceutical Sciences 2007; 4(2): 57-70.
- Patrick GL: An introduction to medicinal chemistry. Oxford University Press 2013.
- Dhall H, Kumar A and Mishra AK: Synthesis of Some Novel Substituted Phenyl β, β-Diphenyl Propanoate with Analgesic and Anti-inflammatory Activity. Current Bioactive Compounds 2018; 14(1):26-32.
- Lee YH, Woo JH, Choi SJ, Ji JD and Song GG: Effect of glucosamine or chondroitin sulfate on the osteoarthritis progression: a meta-analysis. Rheumatology International 2010; 30(3): 357.
- Kumar P, Kumar A and Mishra AK: Synthesis and biological evaluation of some bioactive secondary aromatic amine derivatives of 3, 3-Diphenyl propionic acid. Current Bioactive Compounds 2018; 14(4): 412-8.
- Vasincu IM, Apotrosoaei M, Panzariu AT, Buron F, Routier S and Profire L: Synthesis and biological evaluation of new 1, 3-thiazolidine-4-one derivatives of 2-(4-isobutylphenyl) propionic acid. Molecules 2014; 19(9): 15005-25.
- Portanova JP, Zhang Y, Anderson GD, Hauser SD, Masferrer JL, Seibert K, Gregory SA and Isakson PC: Selective neutralization of prostaglandin E2 blocks inflammation, hyperalgesia and interleukin 6 production in-vivo. The Journal of Experimental Medicine 1996; 184(3): 883-91.
- Steinmeyer J: Pharmacological basis for the therapy of pain and inflammation with nonsteroidal anti-inflammatory drugs. Arthritis Research & Therapy 2000; 2(5): 379.
- Tripathi KD: Essentials of medical pharmacology, Jaypee Brothers. Medical Publishers, New Delhi 2003; 747(150): 391.
- Manjunatha K, Poojary B, Lobo PL, Fernandes J and Kumari NS: Synthesis and biological evaluation of some 1, 3, 4-oxadiazole derivatives. European Journal of Medicinal Chemistry 2010; 45(11): 5225-33.
- Amir M, Kumar S: Synthesis and evaluation of anti-inflammatory, analgesic, ulcerogenic and lipid per-oxidation properties of ibuprofen derivatives. Acta Pharmaceutica 2007; 57(1): 31-45.
- Ymele EV, Dongmo AB and Dimo T: Analgesic and anti-inflammatory effect of aqueous extract of the stem bark of Allanblackia gabonensis (Guttiferae). Inflammo-pharmacology 2013; 21(1): 21-30.
- Abdallah MH, Sammour OA, El-ghamry HA, El-nahas HM and Barakat W: Development and characterization of controlled release ketoprofen microspheres. Journal of Applied Pharmaceutical Science 2012; 2(3): 6.
- Islam M, Siddiqui AA, Rajesh R, Bakht A and Goyal S: Synthesis and antimicrobial activity of some novel oxadiazole derivatives. Acta Pol Pharm 2008; 65: 441-7.
- Mehta N, Aggarwal S, Thareja S, Malla P, Misra M, Bhardwaj TR and Kumar M: Synthesis, pharmacological and toxicological evaluation of amide derivatives of ibuprofen. International Journal of Chem Tech Research 2010; 2(1): 233-8.
- Kumar P, Kumar R and Prasad DN: Synthesis and biological evaluation of new 9-aminoacridine-4-carboxamide derivatives as anticancer agents: 1st Cancer Update. Arabian Journal of Chemistry 20130; 6(1): 59-65.
- Rayama P, Anireddya JS, Polkama N, Allakaa TR, Chepurib K and Nadendlac M: Synthesis and Biological Activity of Novel Acyl Hydrazone Derivatives of 3-(4, 5-diphenyl-1, 3-oxazol-2-yl) propanoic acid as Anticancer, Analgesic and Anti-inflammatory Agents. Journal of Pharmacy Research 2015; 9(2): 157-64.
- Singh S and Bhat S: Antimicrobial potential of 3-hydroxy-2-methylene-3-phenylpropionic acid derivatives. Acta Pharmaceutica 2011; 61(4): 447-55.
- Abramson SB and Weissmann G: The mechanisms of action of non-steroidal anti-inflammatory drugs. Arthritis & Rheumatism: Official Journal of the American College of Rheumatology 1989; 32(1): 1-9.
- Dhall H, Sikka P, Kumar A and Mishra AK: Recent advancements and biological activities of aryl propionic acid derivatives: A review. Oriental Journal of Chemistry 2016; 32(4): 1831-38.
- Lahsasni S, Mohamed SK, Albayati MR and El-Saghier AM: Synthesis of New Potential Chemotherapeutic Agents Incorporating Naproxen Sub-Structure. ANGLISTICUM. Journal of the Association-Institute for English Language and American Studies 2016; 3.
- Kumar S, Kumar P, Marwaha RK and Narasimhan B: Synthesis, antimicrobial evaluation and QSAR studies of propionic acid derivatives. Arabian Journal of Chemistry 2017; 10: S881-93.
- Mahmood S, Ali S, Bhatti MH, Mazhar M, Iqbal R, Khan KM and Maharvi GM: Synthesis, characterization and biological applications of organotin (IV) derivatives of 2-(2-Fluoro-4-biphenyl) propanoic acid. Turkish Journal of Chemistry 2003; 27(5): 657-66.
- Dilber SP, Dobric SL, Juranic ZD, Markovic BD, Vladimirov SM and Juranic IO: Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids. Molecules 2008; 13(3): 603-15.
- Grigoryan SH, Zhamharyan AG, Saghyan AS, Chitchiyan AA, Balyan LS, Poghosyan AS, Topchyan HV and Balasanyan MG: Synthesis and Pharmacological Activity of S (-)-2-Amino-2-Methyl-3-Phenylpropanoic Acid. Pharmaceutical Chemistry Journal 2019; 53(7): 620-3.
- Singh D and Pathak DP: Coumarins: an overview of medicinal chemistry. Potential for new drug molecules. International Journal of Pharmaceutical Sciences and Research 2016; 7(2): 482.
- Raikar P and Shingade S: Synthesis, characterization and screening of pyrazoline derivatives for anti-inflammatory activity. Int J of Pharma Sci and Res 2018; 9(6): 2446-50.
- Singh LP, Tiwari OP and Brijyog: Synthesis and antimicrobial activity of some methyl 4-(1&ITH&IT-BENZO [&ITd&IT] imidazol-2-yl) phenyl carbamodithioate amine derivatives. International Journal of Pharmaceutical Sciences and Research 2018; 9(3): 1194-200.
How to cite this article:
Kumar P, Sangam and Ahmad MI: A brief review on recent advancements and biological activities of aryl propionic acid derivatives. Int J Pharm Sci & Res 2020; 11(9): 4180-88. doi: 10.13040/IJPSR.0975-8232.11(9).4180-88.
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Article Information
11
4180-4188
799
784
English
IJPSR
P. Kumar *, Sangam and M. I. Ahmad
Department of Pharmaceutical Chemistry, Shri Gopichand College of Pharmacy, Baghpat, Uttar Pradesh, India.
punetkumar987@gmail.com
17 October 2019
18 August 2020
23 August 2020
10.13040/IJPSR.0975-8232.11(9).4180-88
01 September 2020