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Newer chalcone scaffolds with reactive functional groups: Process, spectral and single crystal XRD studies
Niteen Borane (1) , Amar Ghanshyam Deshmukh (2) , Nidhi Harnesh Oza (3) , Rajamouli Boddula (4) , Paresh Narayan Patel (5,*)
(1) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(2) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(3) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(4) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(5) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(*) Corresponding Author
Received: 25 Dec 2022 | Revised: 25 Mar 2023 | Accepted: 30 Mar 2023 | Published: 30 Jun 2023 | Issue Date: June 2023
Chalcones are versatile scaffolds for the synthesis of various heterocyclic systems with commercial utility. This work describes the synthesis of five novel chalcone derivatives. Syntheses were performed by a simple one-pot, straightforward Claisen-Schmidt condensation catalyzed with pyrrolidine and KOH. The chalcones were prepared by condensation of 4-formylbenzonitrile with different aromatic ketones at room temperature. The structures of all compounds have been investigated by FT-IR, NMR, and HR-MS spectroscopy. In addition, one chalcone structure was characterized by single-crystal XRD study. Crystal data for C21H15NO2 (Ch2): monoclinic, space group P21/c (no. 14), a = 6.5694(3) Å, b = 33.2697(15) Å, c = 7.4516(4) Å, β = 97.563(2)°, V = 1614.47(14) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.083 mm-1, Dcalc = 1.289 g/cm3, 16000 reflections measured (4.898° ≤ 2Θ ≤ 49.99°), 2822 unique (Rint = 0.0249, Rsigma = 0.0196) which were used in all calculations. The final R1 was 0.0484 (I > 2σ(I)) and wR2 was 0.1257 (all data). The absorption maxima of all novel products were evaluated by UV-visible spectroscopy. These well-established structures of all newly prepared chalcone scaffolds with reactive functional groups (i.e. nitrile and 2-propenone) can be exploited as a crucial intermediate in the synthesis of new heterocyclic scaffolds with fluorescence and other applications.
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The work was financially supported by the GUJCOST, Government of India (Project No. GUJCOST/2020-21/2012).
. Dong, F.; Jian, C.; Zhenghao, F.; Kai, G.; Zuliang, L. Synthesis of chalcones via Claisen-Schmidt condensation reaction catalyzed by acyclic acidic ionic liquids. Catal. Commun. 2008, 9, 1924-1927.
. Durairaj, M.; Sivakumar, S.; Gnanendra, S. Chemical synthesis of chalcones by claisen-Schmidt condensation reaction and its characterization. Int. J. Res. Appl. Sci. Eng. Technol. 2018, 6, 2311-2315.
. Bohm, B. A. Introduction to flavonoids; CRC Press: Boca Raton, FL, 1999.
. Gao, F.; Huang, G.; Xiao, J. Chalcone hybrids as potential anticancer agents: Current development, mechanism of action, and structure-activity relationship. Med. Res. Rev. 2020, 40, 2049-2084.
. Mahapatra, D. K.; Bharti, S. K.; Asati, V. Chalcone derivatives: Anti-inflammatory potential and molecular targets perspectives. Curr. Top. Med. Chem. 2017, 17, 3146-3169.
. Rocha, S.; Ribeiro, D.; Fernandes, E.; Freitas, M. A systematic review on anti-diabetic properties of chalcones. Curr. Med. Chem. 2020, 27, 2257-2321.
. Xu, S.; Chen, M.; Chen, W.; Hui, J.; Ji, J.; Hu, S.; Zhou, J.; Wang, Y.; Liang, G. Chemopreventive effect of chalcone derivative, L2H17, in colon cancer development. BMC Cancer 2015, 15, 870.
. Lin, Y.; Zhang, M.; Lu, Q.; Xie, J.; Wu, J.; Chen, C. A novel chalcone derivative exerts anti-inflammatory and anti-oxidant effects after acute lung injury. Aging (Albany NY) 2019, 11, 7805-7816.
. Henry, E. J.; Bird, S. J.; Gowland, P.; Collins, M.; Cassella, J. P. Ferrocenyl chalcone derivatives as possible antimicrobial agents. J. Antibiot. (Tokyo) 2020, 73, 299-308.
. de Mello, M. V. P.; Abrahim-Vieira, B. de A.; Domingos, T. F. S.; de Jesus, J. B.; de Sousa, A. C. C.; Rodrigues, C. R.; Souza, A. M. T. de A comprehensive review of chalcone derivatives as antileishmanial agents. Eur. J. Med. Chem. 2018, 150, 920-929.
. Cheng, P.; Yang, L.; Huang, X.; Wang, X.; Gong, M. Chalcone hybrids and their antimalarial activity. Arch. Pharm. (Weinheim) 2020, 353, e1900350.
. Rajesh Kumar, P. C.; Ravindrachary, V.; Janardhana, K.; Poojary, B. Structural and optical properties of a new chalcone single crystal. J. Cryst. Growth 2012, 354, 182-187.
. Anuradha, G.; Vasuki, G.; Khan, I. A.; Kulkarni, M. V. Crystal and Molecular Structure of N-[2-(6-Methoxy-2-oxo-2H-Chromen-4-yl-Benzofuran-3-yl]- Benzamide. Cryst. Struct. Theory Appl. 2012, 01, 107-113.
. Xie, Z.; Chen, C.; Xu, S.; Li, J.; Zhang, Y.; Liu, S.; Xu, J.; Chi, Z. White-light emission strategy of a single organic compound with aggregation-induced emission and delayed fluorescence properties. Angew. Chem. Int. Ed Engl. 2015, 54, 7181-7184.
. Tandel, S. N.; Deshmukh, A. G.; Rana, B. U.; Patel, P. N. Studies of novel benzofuran based chalcone scaffolds: A dual spectroscopic approach as selective hydrazine sensor. Chem. Phys. Lett. 2023, 817, 140426.
. Ali, M. K. M.; Elzupir, A. O.; Ibrahem, M. A.; Suliman, I. I.; Modwi, A.; Idriss, H.; Ibnaouf, K. H. Characterization of optical and morphological properties of chalcone thin films for optoelectronics applications. Optik (Stuttg.) 2017, 145, 529-533.
. Dhanaraj, P. V.; Rajesh, N. P.; Vinitha, G.; Bhagavannarayana, G. Crystal structure and characterization of a novel organic optical crystal: 2-Aminopyridinium trichloroacetate. Mater. Res. Bull. 2011, 46, 726-731.
. STOE IPDS diffractometer control software, version 2.87. Stoe & Cie GmbH Darmstadt, Germany.
. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. SIR2004: an improved tool for crystal structure determination and refinement. J. Appl. Crystallogr. 2005, 38, 381-388.
. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. C Struct. Chem. 2015, 71, 3-8.
. Bruker (2012). APEX. Bruker AXS Inc., Madison, Wisconsin, USA.
. Bruker (2012). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
. Bruker (2012). XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
. Farrugia, L. J. WinGXandORTEP for Windows: an update. J. Appl. Crystallogr. 2012, 45, 849-854.
. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. Mercury: visualization and analysis of crystal structures. J. Appl. Crystallogr. 2006, 39, 453-457.
. Spek, A. L. Structure validation in chemical crystallography. Acta Crystallogr. D Biol. Crystallogr. 2009, 65, 148-155.
. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. A 2008, 64, 112-122.
. Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. CRYSTALS version 12: software for guided crystal structure analysis. J. Appl. Crystallogr. 2003, 36, 1487-1487.
. Patel, P. N.; Chadha, A. Synthesis, single crystal structure and spectroscopic aspects of Benzo[b]thiophene-3-carbaldehyde based chalcones. J. Chem. Crystallogr. 2016, 46, 245-251.
. Rai, S.; Patel, P. N.; Chadha, A. Preparation, characterisation, and crystal structure analysis of (2E,2′E)-3,3′-(1,4-phenylene)bis(1-(2-aminophenyl)prop-2-en-1-one. Crystallogr. Rep. 2016, 61, 1086-1089.
. Patel, P. N.; Chadha, A. A simple metal free highly diastereoselective synthesis of heteroaryl substituted (±) cyclohexanols by a branched domino reaction. Tetrahedron 2018, 74, 204-216.
. Tandel, S.; Patel, N. C.; Kanvah, S.; Patel, P. N. An efficient protocol for the synthesis of novel hetero-aryl chalcone: A versatile synthon for several heterocyclic scaffolds and sensors. J. Mol. Struct. 2022, 1269, 133808.
. Patel, P. N.; Desai, D. H.; Patel, N. C.; Deshmukh, A. G. Efficient multicomponent processes for synthesis of novel poly-nuclear hetero aryl substituted terpyridine scaffolds: Single crystal XRD study. J. Mol. Struct. 2022, 1250, 131737.
. Patel, P. N.; Desai, D. H.; Patel, N. C. Synthesis, spectral, and single crystal XRD studies of novel terpyridine derivatives of benzofuran-2-carbaldehyde and their Cu(II) complex. Russ. J. Coord. Chem. 2021, 47, 909-914.
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DOI Link: https://doi.org/10.5155/eurjchem.14.2.297-302.2405
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