Author(s): Mayur S. Bhosale, K. Sarvanan, N. S. Dighe

Email(s): mayur.bhosale@pravara.in

DOI: 10.52711/2349-2988.2021.00035   

Address: Mayur S. Bhosale*, Dr. K. Sarvanan, Dr. N. S. Dighe
Department of Pharmaceutical Chemistry, Pravara Rural College of Pharmacy, Pravaranagar, 413736 Dist- Ahmednagar (M.S.) India.
*Corresponding Author

Published In:   Volume - 13,      Issue - 3,     Year - 2021


ABSTRACT:
This review covers up synthesis, characterization and Pharmacological activities of various derivatives of 1,2,3,4-Tetrahydropyrimidine-2-one, including recent mechanistic advances, new building blocks and new pharmacological disclosures. Tetrahydropyrimidines (THPs) are one of the most important systems among the heterocycles. These compounds reported to have less toxicity to human and animals. Various synthesis strategies have been reported for different derivatives of Tetrahydropyrimidines, mainly these involves Biginelli reaction (condensation) consisting of one pot synthesis of 1,2,3,4-Tetrahydropyrimidine derivatives using urea, ß-keto ester and aldehyde. These derivatives also forms important part as intermediate in the manufacture of various Pharmaceuticals. Techniques such as infrared spectroscopy, liquid chromatography-mass spectrometry, 1H NMR and 13C NMR spectrometry along with single crystal X-ray diffraction has been reported for structural characterization of these derivatives. U.S. National Library of Medicines, NIH and European PMC have reported many these derivatives. Some of derivatives have reported to have promising anti-bacterial, cytotoxic, antifungal, anti-inflammatory activities. Recently Ultrasound and Microwave promoted synthesis has shown promising results in synthesis of these derivatives. Many exciting prospects await for its exploitation in this fields.


Cite this article:
Mayur S. Bhosale, K. Sarvanan, N. S. Dighe. Recent Progress on Synthesis and Bio-activities of Tetrahydropyrimidine-2-one derivatives. Research Journal of Science and Technology. 2021; 13(3):221-8. doi: 10.52711/2349-2988.2021.00035

Cite(Electronic):
Mayur S. Bhosale, K. Sarvanan, N. S. Dighe. Recent Progress on Synthesis and Bio-activities of Tetrahydropyrimidine-2-one derivatives. Research Journal of Science and Technology. 2021; 13(3):221-8. doi: 10.52711/2349-2988.2021.00035   Available on: https://rjstonline.com/AbstractView.aspx?PID=2021-13-3-11


REFERENCES:
1.    C, Oliver Kappe, Tetrahedron report number 336, Tetrahedron 1993; 49 (32): 6937-6963.
2.    Atul D. Baldev, Kartik B, Vyas, Ketan B, Patel, Synthesis of 1,2,3,4-tetrahydro pyrimidine derivatives as an antimicrobial agent, Journal of Chemical and Pharmaceutical Research, 2012; 4(6): 2972-2978.
3.    Hamid Reza Memarian, Mahnaz Ranjbar, Hassan Sabzyan, Molecular structure and conformational analysis of two 2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-esters, Journal of Molecular Structure, 1048, 2013; 196 – 201.
4.    Anatoly D, Shutalev, Ekaterina K, Natalie V. Sivova, A New Synthesis of Biginelli Compounds, Molecules, 1998; 3: 100–106.
5.    Hamid B, Reza A, and Zahra K, Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives, Advances in Chemistry, 2014; 1-4.
6.    Anatoly D, Shutalev, Ekaterina A, Kishko, Natalie V Sivova, A New Convenient Synthesis of 5-Acyl-1,2,3,4-tetrahydropyrimidine-2-thiones/ones, Molecules, 1998; 3: 100–106.
7.    Sangram G, Sundarababu B, and Burkhard K, A highly efficient and green synthesis of 3,4-dihydropyrimidin-2-ones in low melting mixtures, Supplementary Material (ESI) for Green Chemistry, The Royal Society of Chemistry, 2011; S2-S71.
8.    Ctirad Podesva; Jose Maria Do Nascimento, United States Patent, 1974; 3.
9.    Radhika C, Venkatesham A, Anantha D, Synthesis and Biological activity of new 5-Methyl-3-Oxo-N2 [5’-Carbonyl-(4’-Aryl-6’methyl)-1’,2’,3’,4’–Tetrahydropyrimidine-2’-One] Pyrazolidines, Journal of Advanced Pharmacy Education & Research, 2014; 4(1): 1-5.
10.    Razzaghi-Asl O, Kamrani-M, Farhangi B. Vahabpour R, Zabihollahi R, Sepehri S, Design, synthesis and evaluation of cytotoxic, antimicrobial and anti-HIV-1 activities of new 1,2,3,4-tetrahydropyrimidinederivatives, 2019, 14(2): 155-166.
11.    Manish M, A K Gupta, S Negi, Meenakshi B, synthesis of some new oxadiazole with antimicrobial activity, International Journal of Pharmaceutical Sciences and Research, 2010; 1(3): 172-177.
12.    JN Vishwakarma, MC Dutta K, Chanda, Bhaskar D, MA Laskar, and RL Nongkhlawc, Synthesis and anti-bacterial activities of novel 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidines and bis-(5-isonicotinoyl-1,2,3,4-tetrahydropyrimidines), Arkive For Organic Chemistry, 2009; (xiii): 131-141.
13.    Katharigatta V, GB Dharma Rao., Subhrajyoti B, Melendhran P, Deepak C, Bandar A, Mahesh A, Osama A, Sree H, Koleka M, Drug Design, Design, synthesis, and characterization of (1-(4-aryl)-1H-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against Mycobacterium tuberculosis, Development and Therapy 2016;10: 2681–2690.
14.    JD Akbari, PK Kachhadia, SD Tala, AH Bapodra, MF Dhaduk, HS Joshi, KB Mehta, SJ Pathak, Synthesis of Some New 1,2,3,4-Tetrahydropyrimidine-2-thiones and Their Thiazolo[3,2-a]pyrimidine Derivatives as Potential Biological Agents ,Taylor & Francis Group, 2008; 1911–1922.
15.    Santosh N, Sandeep S, Rupali E, Jaiprakash S, Devanand S, Synthesis and anti-inflammatory activity of some 3-(4,6-disubtituted-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl) propanoic acid derivatives, Bioorganic & Medicinal Chemistry Letters, 2010; 20: 4424–4426.
16.    Ashoka S, Mamatha P, and Santhosh M, Synthesis, antimicrobial and electrochemical study with SnO2 Nano particle modified carbon paste electrode of ethyl L 6 methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5 carboxylate derivatives, Research Journal of Life Sciences, Bioinformatics, Pharmaceutical and Chemical Sciences, 2018; 4(1): 78.
17.    SS Kshirsagar, BV Dhokchawle, SS Shinde, C Thakare, H Shewale and VR Shinde, Synthesis and pharmacological screening of novel 6-methyl-2-oxo-4-substituted-5-(5-phenyl-1,3,4-oxadiazole-2yl)-1,2, 3,4-tetrahydropyrimidine, Biosciences, Biotechnology Research Asia, 2008; 5(1): 319-324.
18.    Ramesh S, and Varsha S, Synthesis, Spectral Characterization and Analgesic Activity of 2-Methylthio-1,4-Dihydropyrimidines, Services Iranian Journal of Pharmaceutical Research 2011; 10(4): 733-739.
19.    Olayinka A, Fisayo O, Emmanuel J, Oluwatosin A, and Olatunde O, Facile synthesis of N’-(anthracen-9(10H)-ylidene)-4-(4-hydrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carbohydrazide and other derivatives, Journal of Physics: Conference Series, 2019; 1742-6596.
20.    Ramesh S, Supriya R, and Jyoti W, Synthesis, QSAR and docking studies of 5HT2A receptor antagonizing thiazolo[3,2-a] pyrimidines as antipsychotic agents, Marmara Pharmaceutical Journal, 2014; 18: 109-119.
21.    Hamid B, Reza A, and Zahra K, Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives, Hindawi Publishing Corporation, 2014; 1-4.
22.    Haitham S, and Hasmukh P, Synthesis, spectral investigation and biological evaluation of novel hydrazones derivative of substituted 1,2-dihydropyrimidine ring, Der Pharmacia Sinica, 2012; 3(3): 305-311.
23.    Hery S, Salma Z, Kautsar U, Alfinda K and Indriani I, Ethyl 4-[5-(methoxymethyl) furan-2-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, Molbank, 2017; 1-5.
24.    Marwa S, Mahmoud F, Asma E, and Hassan M, Antioxidant Activity of Novel Fused Heterocyclic Compounds Derived from Tetrahydropyrimidine Derivative, Chemical and Pharmaceutical Bulletin, 2015; 63(11): 866–872.
25.    Atul B, Kartik V, Ketan P, and Kiran N, Synthesis of 1,2,3,4-tetrahydro pyrimidine derivatives as an antimicrobial agent, Journal of Chemical and Pharmaceutical Research, 2012; 4(6): 2972-2978.
26.    Ambareen S, and Jyotsna M, Synthesis and pharmacological activity evaluation of oxadiazoles containing substituted dihydropyrimidinone and chloroquinoline moities, International Journal of Pharmaceutical Sciences and Research, 2013; 4(12): 4607-4614.
27.    Mariana M., Gonçalo., Adriana S., Amílcar F.,Samuel S.and Gilberto A., Potential antitumoral 3,4-dihydropyrimidin-2-(1H)-ones: synthesis, in vitro biological evaluation and QSAR studies, The Royal Society of Chemistry, 2013; 00: 1-3.
28.    Narkhede I, Nevagi J, Kumbhare M, and Kaur P, Synthesis and in-vitro screening of novel dihydropyrimidine derivatives as potential calcium channel blockers, Der Pharma Chemica, 2014; 6(2): 221-227.
29.    VV Kastron, RO Vitolin, EL Kanina, G Ya Dubur, and AA, Kimenis, Synthesis and pharmacological activity of fluorine-containing derivatives of 1,2,3,4-tetrahydropyrimidine, Plenum Publishing Corporation, 1988; 571-574.
30.    Naglaa M. and Eman G., Synthesis of Novel Substituted Tetrahydropyrimidine Derivatives and Evaluation of Their Pharmacological and Antimicrobial Activities, J. Heterocyclic Chem., 2019; 56: 81-91.
31.    RW Brimblecombe, RR Hunt, RL Rickard, Joan T, The synthesis and pharmacology of some 1,4,5,6-tetrahydropyrimidines, British Journal of Pharmacology, 1969; 37: 425-435.
32.    Naser Somayeh B., Hoda P, and Masoumeh S, Synthesis of Some New Tetrahydropyrimidine Derivatives as Possible Antibacterial Agents, Iranian Journal of Pharmaceutical Research 2017; 16 (2): 596-601.
33.    ME Monteiro, G Lechuga, LS Lara, BA, Synthesis, structure-activity relationship and trypanocidal activity of pyrazole-imidazoline and new pyrazole-tetrahydropyrimidine hybrids as promising chemotherapeutic agents for Chagas disease, European Journal of Medicinal Chemistry, 2019; 182: 1-13.
34.    Jimish P, Laxman P, Predictive QSAR modeling on tetrahydropyrimidine-2-onederivatives as HIV-1 protease enzyme inhibitors, Medicinal chemistry research, 2012; 1-7.
35.    Tomoko O, Nobutaka H, Yoshikuni M, Satoshi M, Sakan M, Toshihiko O, and Koji U, Methylglyoxal Modification of Protein, The journal of biological chemistry, 1999; 274(26): 18492–18502.
36.    Fan-Jie Meng, Lei Shi, Guang-Shou Feng, Lei Sun and Yong-Gui Zhou, Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)‑ones through Organocatalytic Transfer Hydrogenation of 2-Hydroxypyrimidines, The Journal of Organic Chemistry. 2019; 84: 4435-4442.
37.    Shubhangi W and Pravina P., Novel synthesis of oxadiazole derivatives with pyrimidine moiety, International Journal of Pharmaceutical Sciences and Research, 2013; 4(11): 4416-4421.
38.    Aniket S, Mohan J, Mujahed A, and Mrudula W, Maleic acid as a versatile catalyst for one pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and their thione analogues, 2016; 8(2): 204-209.
39.    Sara R, Lotfollah, Afshin F, Conformational Properties of Novel 1,2,3,4-Tetrahydropyrimidinone (thione) Derivatives: A DFT study, Journal of Reports in Pharmaceutical Sciences, 2012; 1(2), 118‐126.
40.    Parthiv C, Ajay P and V.H. Shah, Synthesis and biological studies of 1, 2, 3, 4-tetrahydro pyrimidine derivatives, Oriental Journal of Chemistry, 2010; 26(4): 1377-1383.
41.    Sandip K, P. Shanmugasundaram, Synthesis and Calcium Channel Blocking Activity of 1, 2, 3, 4,-Tetrahydropyrimidine Derivatives Containing Carbamates and Carbamides, International Journal of Chemical and Technical Research, 2013; 5(6): 2899-2912.
42.    Niharika S, Sandip K, Hemlata N, Praful C, Jayendrasing B, Rajesh O, Microwave assisted synthesis of 4 substituted 1,2,3,4 Tetrahydropyrimidines derivatives, International Journal of Pharmacy and Pharmaceutical Sciences, 2011; 3(1): 1-3.
43.    Behzad G, Hamid B, Hadi H, Study of Antibacterial Effect of Novel Thiazole, Imidazole, and Tetrahydropyrimidine Derivatives against Listeria Monocytogenes, Annals of Military & Health Sciences Research, 2015; 13: 103-107.
44.    Balaswamy P, Battu S, and Seema A, Synthesis of Pyrrolidines and Tetrahydropyrimidines via one-pot and three component cascade coupling strategy in water, January – March 2017; 10 (1), 6-12.
45.    Marwa S, Mahmoud F, Asma E, and Hassan M, Antioxidant Activity of Novel Fused Heterocyclic Compounds Derived from Tetrahydropyrimidine Derivative, Chemical and Pharmaceutical Bulletin, 2015; 63: 866–872.
46.    Saurabh P., Balbir K., Anupama P. and Harish K., Ultrasound Promoted Cu (ClO4)2 Catalyzed Rapid Synthesis of Substituted l,2,3,4-Tetrahydropyrimidine-2-Ones and Hantzsch 1,4-Dihydropyridines in dry media, 2009; 15(1), 51-55.

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