ISSN

0974-4150 (Online)
0974-4169 (Print)


Author(s): S. Bakyalakshmi, CT. Ravichandran

Email(s): ctrchemistry@gmail.com

DOI: 10.52711/0974-4150.2025.00004   

Address: S. Bakyalakshmi, CT. Ravichandran*
PG and Research, Department of Chemistry, Arignar Anna Govt. Arts College, Cheyyar – 604407,
Affiliated to Thiruvalluvar University, Serkkadu, Vellore - 632 115, Tmilnadu, India.
*Corresponding Author

Published In:   Volume - 18,      Issue - 1,     Year - 2025


ABSTRACT:
The synthesis of N-(2-oxo-2-(phenylamino)ethyl) picolinamide derivatives. Reaction between TBTU, triethylamine and amine. Natural chalcones due to various pharmacological activities. Chalcones and antioxidant activities is the attracting areas in medicinal and natural product. The N-(2-oxo-2-(phenylamino)ethyl) picolinamide were evaluated for their anti-inflammatory activity, antidiabetic activity and computational calculations. Molecular docking of synthesized compounds was carried out by using the Auto-Dock software (version 4.2) to evaluate the mode of binding between UDP-N-acetylenol pyruvoyl glucosamine reductase with N-(2-oxo-2-(phenylamino) ethyl) picolinamide (5a-c) derivatives. The synthesized N-(2-oxo-2-(phenylamino) ethyl) picolin amide derivatives (5a-c) were screened for anti-inflammatory activity exhibited madrate activity with diclofenac sodium as a reference drug. The synthesized N-(2-oxo-2-(phenylamino) ethyl) picolinamide derivatives (5a-c) were screened for antidiabetic activity exhibited good activity with acarbose as a standard drug. All the computational calculations representation of HOMO, LUMO, molecular electrostatic potential (MEP). The negative energies of HOMO 5a, 5b and 5c (-5.9863 to -6.2767eV) and LUMO (-1.4743 to -1.5298eV) indicate the stable molecules. The band gap values of the range of 4.456eV - 4.802eV correspondingly. The band gap calculated the compound 5a is higher than more stable 5b and 5c. The suggested the compound 5c exhibited higher electrophilicity index than others. The calculated electrophilicity index is found to be 3.1691eV the highest capacity to accept the electrons. All the N-(2-oxo-2-(phenylamino) ethyl) picolin amide derivatives were thoroughly characterized by 1H - NMR, FT-IR, Mass spectral and CHN analysis.


Cite this article:
S. Bakyalakshmi, CT. Ravichandran. Synthesis, Spectral Characterization, Molecular Docking, DFT Studies and Biological Evaluation of N-(2-Oxo-2-(Phenylamino)Ethyl)Picolinamide Derivatives as Anti-Inflammatory and Antidiabetic Activity. Asian Journal of Research in Chemistry. 2025; 18(1):17-6. doi: 10.52711/0974-4150.2025.00004

Cite(Electronic):
S. Bakyalakshmi, CT. Ravichandran. Synthesis, Spectral Characterization, Molecular Docking, DFT Studies and Biological Evaluation of N-(2-Oxo-2-(Phenylamino)Ethyl)Picolinamide Derivatives as Anti-Inflammatory and Antidiabetic Activity. Asian Journal of Research in Chemistry. 2025; 18(1):17-6. doi: 10.52711/0974-4150.2025.00004   Available on: https://ajrconline.org/AbstractView.aspx?PID=2025-18-1-4


REFERENCES:
1.    Rahman MA. Chalcone: A valuable insight into the recent ad into the recent advances hand potential pharmacological activities. Chem Sci J. 2011.
2.    Henry GD. Palladium-Catalyzed Sonogashira Coupling Reaction of 2-Amino-3-Bromopyridines with Terminal Alkynes. Tetrahedron, 2004; 60: 6043-6061.
3.    Szliszka E, Czuba ZP, Mazur B, Sedek L, Paradysz A, Krol W. Chalcones enhance TRAIL-induced apoptosis in prostate cancer cells. Int J Mol Sci. 2009; 11(1): 1-13.
4.    Hideo K, Tatsurou K, Yoko H. Kojima. Chem. Abstr. 1997; 25: 126.
5.    Abbas A, Naseer MM, Hasan A, Hadda TB. Synthesis and Cytotoxicity Studies of 4-Alkoxychalcones as New Antitumor Agents. J. Mater. Environ. Sci. 2014; 5(1): 281-292.
6.    Grosscurt AC, Van HR, Wellinga K. 1-Phenylcarbamoyl-2-pyrazolines, a new class of insecticides. 3. Synthesis and insecticidal properties of 3,4-diphenyl-1-phenylcarbamoyl-2-pyrazolines. J. Agric. Food Chem. 1979; 27(2): 406-409.
7.    Tanaka H, Nakamura S, Onda K, Tazaki T, Hirano T.Sofalcone, an anti-ulcer chalcone derivative, suppresses inflammatory crosstalk between macrophages and adipocytes and adipocyte differentiation: Implication of heme-oxygenase-1 induction. Biochem. Biophys. Res. Commun. 2009; 381: 566-571.
8.    Takahashi M, Maeda S, Ogura K, Terano A, Omata M. The Possible Role of Vascular Endothelial Growth Factor (VEGF) in Gastric Ulcer Healing Effect of Sofalcone o VEGF Release in Vitro. J. Clin. Gastroenterol. 1998; 27(1): 178-182.
9.    Real L, David C, Francois B. Can J. Pharm. Sci., 1967; 2: 37.
10.    Nitin GG, Rajput PR, Banewar VW, Raut AR. Synthesis and antimicrobial activity of some chalcones and flavones having 2-hydroxy acetophenone moiety. Int. J. Pharm. Bio. Sci. 2012; 3(3): 389-395.
11.    Bowden K, Dal PA, Shah CK. Structure-activity relations, Antibacterial activity of a series of substituted (E)-3-(4-phenylbenzoyl) acrylic acids, -chalcones, -2-hydroxy chalcones and -α-bromochalcones; addition of cysteine to substituted 3-benzoylacrylic acids and related compounds. J. Chem. Res. Synop., 1990; 12: 377.
12.    Marmo E, Caputi AP, Cataldi S. Experimental investigation of 4-(3',4',5'-trimethoxy cinnamoyl)-1-piperaziny l-pyrrolidinyl maleate (67350): effect on the cardiovascular system and on certain smooth muscles. Farmaco Ed. Prat. 1970; 28(3): 132-160.
13.    Ogansyna ET, Khim AH. Farm. 1991; 25(8): 18.
14.    Zongru G, Rui H. Chem. Abstr. 1996; 125: 103768.
15.    De Vincenzo R, Seambla G, Panici P, Benedess Remelletti FO. Anticancer Drug Des. 1995: 481-490.
16.    Hsieh Hasin Kaw, Lee-Tai-Hua Wang, Jih-Pyang Wang. Chem. Abstr. 1998; 128: 225684.
17.    Parmar VS, Jain CS. Indian J. Chem., Sect. B., Org. Chem. Incl Med. Chem. 1998; 37B (7): 628-643.
18.    Nissan Chemical Industries Ltd., Japan Kokai Tokkyo Koho Japan 3808035, 1983.
19.    Gross Curt AC, Van HR, Wellinga K. J. Agric. Food. Chem. 1979; 27(2): 406.
20.    Ur Rashid H, Xu Y, Ahmad N, Muhammad Y, Wang L. Promising anti-inflammatory effects of chalcones via inhibition of cyclooxygenase, prostaglandin E2, inducible NO synthase and nuclear factor κb activities, Bioorganic Chemistry. 2019; 87: 335−365.
21.    Nurkenov O, Ibraev M, Schepetkin I, Khlebnikov A, Seilkhanov T, Arinova A, Isabaeva M. Synthesis, structure, and anti-inflammatory activity of functionally substituted chalcones and their derivatives, Russian Journal of General Chemistry. 2019; 89(7): 1360−1367.
22.    Ibrahim TS, Moustafa AH, Almalki AJ, Allam RM, Althagafi A, Md, S, Mohamed MF. Novel chalcone/aryl carboximidamide hybrids as potent anti-inflammatory via inhibition of prostaglandin E2 and inducible NO synthase activities: design, synthesis, molecular docking studies and ADMET prediction, Journal of Enzyme Inhibition and Medicinal Chemistry. 2021; 36 (1): 1067−1078.
23.    Lakshminarayanan B, Kannappan N, Subburaju T. Synthesis and biological evaluation of novel chalcones with methanesulfonyl end as potent analgesic and anti-inflammatory agents, Int. J. Pharmaceutical Res. Biosci. 2020; 11(10): 4974−4981.
24.    Higgs J, Wasowski C, Marcos A, Jukic M, Pavan CH, Gobec S, de Tezanos Pinto F, Colettis N, Marder M. Chalcone derivatives: synthesis, in vitro and in vivo evaluation of their antianxiety, anti-depression and analgesic effects, Heliyon. 2019; 5(3): e01376.
25.    Bale AT, Salar U, Khan KM, Chigurupati S, Fasina T, Ali F, Ali M, Nanda SS, Taha M, Perveen S. Chalcones and Bis-Chalcones Analogs as DPPH and ABTS Radical Scavengers, Letters in Drug Design & Discovery. 2021; 18(3): 249−257.
26.    Al Zahrani NA, El-Shishtawy RM, Elaasser MM, Asiri AM. Synthesis of novel chalcone -based phenothiazine derivatives as antioxidant and anticancer agents. Molecules. 2020; 25(19): 4566.
27.    Qin HL, Zhang ZW, Lekkala R, Alsulami H, Rakesh K. Chalcone hybrids as privileged scaffolds in antimalarial drug discovery: a key review. European Journal of Medicinal Chemistry. 2020; 193: 112215.
28.    Fu Y, Liu D, Zeng H, Ren X, Song BHD, Gan X. New chalcone derivatives: Synthesis, antiviral activity and mechanism of action. RSC Advances. 2020; 10(41): 24483−24490.
29.    Alsafi MA, Hughes DL, Said MA, First COVID-19 molecular docking with a chalcone-based compound: synthesis, single-crystal structure and Hirshfeld surface analysis study. Acta Crystallogr, Sect. C: Structural Chemistry. 2020; 76(12): 1043−1050.
30.    Duran N, Polat MF, Aktas DA, Alagoz MA, Ay E, Cimen F, Tek E, Anil B, Burmaoglu S, Algul O. New chalcone derivatives as effective against SARS-CoV-2 agent. Int. J. Clin. Pract. 2021: e14846.
31.    Kalirajan R. Activity of some novel chalcone substituted 9-anilinoacridines against coronavirus (COVID-19): a computational approach. Corona viruses. 2020: 13−22.
32.    Welday Kahssay S, Hailu GS, Taye Desta K, Design, Synthesis, Characterization and in vivo Antidiabetic Activity Evaluation of Some Chalcone Derivatives. Drug Design, Development and Therapy. 2022; 15: 3119.
33.    Jain A, Jain D. Synthesis, characterization and biologicalevaluation of some new heterocyclic derivatives of chalcone as antihyperglycemic agents. Int. J. Pharmaceutical Sci. Res. 2019; 59: 5700−5706.
34.    Kozłowska J, Potaniec B, Baczyńska D, Żarowska B, Anioł M. Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents. Molecules. 2019; 24(22): 4129; doi: 10.3390/molecules24224129.
35.    Rioux B, Pinon A, Gamond A, Martin F, Laurent A, Champavier Y, Barette C, Liagre B, Fagnère C, Sol V, Pouget C. Synthesis and biological evaluation of chalcone-polyamine conjugates as novel vectorized agents in colorectal and prostate cancer chemotherapy. European Journal of Medicinal Chemistry. 2021; 222: 113586; doi: 10.1016/j.ejmech.2021.113586.
36.    Lu CF, Wang SH, Pang XJ, Zhu T, Li HL, Li QR, Li QY, Gu YF, Mu ZY, Jin MJ, Li YR, Hu YY, Zhang YB, Song J, Zhang SY, Synthesis and Biological Evaluation of Amino Chalcone Derivatives as Antiproliferative Agents. Molecules. 2020; 25(23): 5530; doi: 10.3390/molecules25235530.
37.    Modi SR, Naik HB. Orient J. Chem., 1994; 10(1): 85-86.
38.    Siger A, Czubinski J, Kachlicki P, Dwiecki K, Lampart-Szczapa E, Nogala-Kalucka AM.  Antioxidant activity and phenolic content in three lupin species. J Food Compos A al. 2012; 25(2): 190-7.
39.    Echeverria C, Santibanez JF, Donoso-Tauda O, Escobar CA, Ramirez-Tagle R. Structural antitumoral activity relationships of synthetic chalcones. I t J Mol Sci. 2009; 221-31.
40.    Rahman MA. Chalcone: A valuable insight into the recent advances and potential pharmacological activities. Chem Sci J. 2011.
41.    Selvakumar N, Kumar GS, Azhagan AM, Rajulu GG, Sharma S, Kumar MS. Synthesis, SAR and antibacterial studies on novel chalcone oxazolidinone hybrids. Eur J Med Chem. 2007; 42(4): 538-43.
42.    Sribalan R, Banuppriya G, Kirubavathi M, Jayachitra A, Padmini V. Multiple biological activities and molecular docking studies of newly synthesized 3-(pyridin-4-yl)-1H-pyrazole-5-carboxamide chalcone, Bioorg. Med. Chem. Lett. 2016; 26: 5624-5630.
43.    Sarojinidevi K, Subramani P, Jeeva M, Sundaraganesan N, Boobalan MS, Prabhu GV. Synthesis, molecular structure, quantum chemical analysis, spectroscopic and molecular docking studies of N-(Morpholinomethyl) succinimide using DFT method. J. Mol. Struct. 2018; 1175: 609-623.
44.    Shafieyoon P, Mehdipour E, Mary YS. Synthesis, characterization and Biological Investigation of glycine- based sulfonamide derivative and its complex: vibration assignment, HOMO and LUMO analysis, MEP and molecular docking. J. Mol. Struct. 2019; 1181: 244-252.

Recomonded Articles:

Author(s): Kateryna Taran, Ayaou Abderrahim, Vera Kravchenko, Olena Novosel, Svitlana Taran

DOI: 10.5958/0974-4150.2020.00034.6         Access: Open Access Read More

Author(s): Ravi N. Patel, Urviben Y. Patel, Kiran M. Patel, Jimit S. Patel, Ankit D. Patel, Dhrubo Jyoti Sen

DOI:         Access: Open Access Read More

Author(s): Arun Kumar, Vinita Gupta, Sanchita Singh, Y.K. Gupta

DOI: 10.5958/0974-4150.2017.00038.4         Access: Open Access Read More

Author(s): Shravani S. Pawar, Sachin H. Rohane

DOI: 10.5958/0974-4150.2021.00014.6         Access: Open Access Read More

Author(s): Anshul Sinha, A. K. Meena, P. Panda, Bhavana Srivastava, M. D. Gupta, M. M. Padhi

DOI:         Access: Open Access Read More

Author(s): Maddineni Aruna Kumari, Chunduri Venkatarao

DOI: 10.5958/0974-4150.2020.00072.3         Access: Open Access Read More

Author(s): Hunasnalkar Shivraj G, Shaikh Gazi, Patil SM, Surwase Ulhas S

DOI:         Access: Open Access Read More

Author(s): K.P. Beena, G. Sathya Pooja

DOI: 10.52711/0974-4150.2022.00030         Access: Open Access Read More

Author(s): SR Pattan, NS Dighe, SA Nirmal, AN Merekar, RB Laware, HV Shinde, DS Musmade

DOI:         Access: Open Access Read More

Author(s): Sindhu. T. J, Akhilesh K. J, Anju. Jose, Binsiya K. P, Blessy Thomas, Elizabeth Wilson

DOI: 10.5958/0974-4150.2020.00026.7         Access: Open Access Read More

Author(s): Shashi Ravi Suman Rudrangi, Vijaya Kumar Bontha, Venkata Reddy Manda, Srinivas Bethi

DOI:         Access: Open Access Read More

Author(s): Pankaj Baboo, Girendra Gautam, S.K. Gupta

DOI: 10.5958/0974-4150.2017.00039.6         Access: Open Access Read More

Author(s): K. Kishore Kumar, R.S.K. Sharma, P. Chanti Babu, M. Sreenivasa Rao, K. Durga Prasadu, D. Ravi Kumar

DOI: 10.5958/0974-4150.2017.00067.0         Access: Open Access Read More

Author(s): Bhagyashree L. Jejurikar, Sachin H. Rohane

DOI: 10.5958/0974-4150.2021.00025.0         Access: Open Access Read More

Author(s): Gupta Akhilesh, Rawat Swati

DOI:         Access: Open Access Read More

Author(s): Sabale Prafulla, Potey Lata, Rahangdale Priya, Sabale Vidya

DOI: 10.5958/0974-4150.2019.00011.7         Access: Open Access Read More

Author(s): Kishore Kumar Valluri, Tejeswara Rao Allaka, I V Kasi Viswanath, Nagaraju PVVS

DOI: 10.5958/0974-4150.2018.00111.6         Access: Open Access Read More

Asian Journal of Research in Chemistry (AJRC) is an international, peer-reviewed journal devoted to pure and applied chemistry..... Read more >>>

RNI: Not Available                     
DOI: 10.5958/0974-4150 


Recent Articles




Tags