Vibrational spectral analysis, XRD-structure, computation, exo⇔endo isomerization and non-linear optical crystal of 5-((5-chloro-1H-indol-2-yl)methylene)-1,3-diethyl-2-thioxodihy-dropyrimidine-4,6 (1H,5H)-dione
Tóm tắt
This work deals with the synthesis and characterization of the novel 5-((5-chloro-1H-indol-2-yl)methylene)-1,3-diethyl-2-thioxodihydro-pyrimidine-4,6(1H,5H)-dione π-bridge (D–A–D) donor–acceptor–donor compound. Its exo-isomer structure has been proven by XRD-single-crystal analysis for the first time. The IR, UV–Vis., MS, CHN-, 1H and 13C NMR analysis were also carried out. The DFT-optimized structural-parameters were matched with the XRD-crystallographic data. The experimental-XRD-interactions in the lattice were compared to the computed Hirshfeld analysis (HSA), MEP map and Mulliken charge population. The DFT/6-311G(d) calculations like IR/B3LYP, TD-SCF, HOMO–LUMO, GRD and GIAO-NMR have been compared to their corresponding experimental parameters. Non-linear optical (NLO) crystal theoretical-analysis was carried out then compared to urea reference. The compound thermal activity was evaluated in an open-atmosphere by TG/DTG analysis.
Tài liệu tham khảo
Barakat A, Soliman SM, Ghabbour HA, Ali M, Al-Majid AM, Zarrouk A, Warad I (2017) Intermolecular interactions in crystal structure, Hirshfeld surface, characterization, DFT and thermal analysis of 5-((5-bromo-1H-indol-3-yl) methylene)-1, 3-dimethylpyrimidine-2, 4, 6 (1H, 3H, 5H)-trione indole. J Mol Struct 1137:354–361
Serrano JL, Cavalheiro E, Barroso S, Romão MJ, Silvestre S, Almeida P (2017) A synthetic route to novel 3-substituted-2, 1-benzisoxazoles from 5-(2-nitrobenzylidene)(thio) barbiturates. C R Chim 20(11–12):990–995
Ziarani GM, Aleali F, Lashgari N (2016) Recent applications of barbituric acid in multicomponent reactions. RSC Adv 6(56):50895–50922
Mahmudov KT, Kopylovich MN, Maharramov AM, Kurbanova MM, Gurbanov AV, Pombeiro AJ (2014) Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds. Coord Chem Rev 265:1–37
Nikoofar K, Khademi Z (2017) Barbituric acids in organic transformations, an outlook to the reaction media. Mini Rev Org Chem 14(2):143–173
Laxmi SV, Reddy YT, Kuarm BS, Reddy PN, Crooks PA, Rajitha B (2011) Synthesis and evaluation of chromenyl barbiturates and thiobarbiturates as potential antitubercular agents. Bioorg Med Chem Lett 21(14):4329–4331
Kenchappa R, Bodke YD, Asha B, Telkar S, Sindhe MA (2014) Synthesis, antimicrobial, and antioxidant activity of benzofuran barbitone and benzofuran thiobarbitone derivatives. Med Chem Res 23(6):3065–3081
Biradar JS, Sasidhar BS, Parveen R (2010) Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. Eur J Med Chem 45(9):4074–4078
Dhorajiya BD, Bhakhar BS, Dholakiya BZ (2012) Synthesis, characterization, solvatochromic properties, and antimicrobial evaluation of 5-acetyl-2-thioxo-dihydro-pyrimidine-4, 6-dione-based chalcones. Med Chem Res 22(9):4075–4086
Singh P, Kaur M, Design Verma P (2009) synthesis and anticancer activities of hybrids of indole and barbituric acids—identification of highly promising leads. Bioorg Med Chem Lett 19(11):3054–3058
Radwan MA, Ragab EA, Sabry NM, El-Shenawy SM (2007) Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents. Bioorg Med Chem 15(11):3832–3841
Johnson SR, Zheng W (2006) Recent progress in the computational prediction of aqueous solubility and absorption. AAPS J 8(1):E27–E40
Ulrich CM, Bigler J, Potter JD (2006) Non-steroidal anti-inflammatory drugs for cancer prevention: promise, perils and pharmacogenetics. Nat Rev Cancer 6(2):130–140
Penthala NR, Ponugoti PR, Kasam V, Crooks PA (2013) 5-((1-Aroyl-1H-indol-3-yl) methylene)-2-thioxodihydro-pyrimidine-4, 6 (1H, 5H)-diones as potential anticancer agents with anti-inflammatory properties. Bioorg Med Chem Lett 23(5):1442–1446
Figueiredo J, Serrano JL, Cavalheiro E, Keurulainen L, Yli-Kauhaluoma J, Moreira VM, Ferreira S, Domingues FC, Silvestre S, Almeida P (2018) Trisubstituted barbiturates and thiobarbiturates: synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents. Eur J Med Chem 143:829–842
Harriman GC, Brewer M, Bennett R, Kuhn C, Bazin M, Larosa G, Skerker P, Cochran N, Gallant D, Baxter D, Picarella D (2008) Selective cell adhesion inhibitors: barbituric acid based α4β7—MAdCAM inhibitors. Bioorg Med Chem Lett 18(7):2509–2512
Wang J, Radomski MW, Medina C, Gilmer JF (2013) MMP inhibition by barbiturate homodimers. Bioorg Med Chem Lett 23(2):444–447
Di Bella S, Fragalà I, Ledoux I, Diaz-Garcia MA, Marks TJ (1997) Synthesis, characterization, optical spectroscopic, electronic structure, and second-order nonlinear optical (NLO) properties of a novel class of donor–acceptor bis (salicylaldiminato) nickel (II) Schiff base NLO chromophores. J Am Chem Soc 119(40):9550–9557
Lacroix PG (2001) Second-order optical nonlinearities in coordination chemistry: the case of bis (salicylaldiminato) metal Schiff base complexes. Eur J Inorg Chem 2:339–348
Spek AL (2009) Structure validation in chemical crystallography. Acta Cryst 65:148–155
Barakat A, Islam MS, Al-Majid AM, Ghabbour HA, Atef S, Zarrouk A, Warad I (2018) Quantum chemical insight into the molecular structure of l-chemosensor 1, 3-dimethyl-5-(thien-2-ylmethylene)-pyrimidine-2, 4, 6-(1 H, 3 H, 5 H)-trione: naked-eye colorimetric detection of copper (II) anions. J Theor Comp Chem 17(01):1850005
Warad I, Barakat A (2017) Synthesis, physicochemical analysis of two new hemilabile ether-phosphine ligands and their first stable bis-ether-phosphine/cobalt (II) tetrahedral complexes. J Mol Struct 1134:17–24
Asadi Z, Esrafili MD, Vessally E, Asnaashariisfahani M, Yahyaei S, Khani A (2017) A structural study of fentanyl by DFT calculations, NMR and IR spectroscopy. J Mol Struct 1128:552–562
Tarı GÖ, Ceylan Ü, Uzun S, Ağar E, Büyükgüngör O (2018) Synthesis, spectroscopic (FT-IR, UV–Vis), experimental (X-Ray) and theoretical (HF/DFT) study of:(E)-2-Chloro-N-((4-nitrocyclopenta-1, 3-dienyl) methylene) benzenamine. J Mol Struct 1156:74–82
Ahmed NH, Yasin Kh, Ayub Kh, Mahmood T, Tahir NM, Khan AB, Hafeez M, Ahmed M, Ul-Haq I (2016) Click one pot synthesis, spectral analyses, crystal structures, DFT studies and brine shrimp cytotoxicity assay of two newly synthesized, 4,5-trisubstituted 1,2,3-triazoles. J Mol Struct 1106:430–439
Sherzaman S, Rehman S, Ahmed M, Khan B, Mahmood T, Ayub Kh, Tahir M (2017) Thiobiuret based Ni(II) and Co(III) complexes: synthesis, molecular structures and DFT studies. J Mol Struct 1148:388–396
Ahmed M, Yasin Kh, Khan R, Mahmood T, Ayub Kh, Malik D, Hafeez M, Khan A, Tahir M (2017) Synthesis, crystal structure, spectral analysis, DFT studies and antimicrobial activity of ethyl 6-(4-(ethoxycarbonyl)-1H-1,2,3-triazol-1-yl)pyridine-3-carboxylate. J Chem Soc Pak 39:640–649
Thorat KG, Sekar N (2017) Pyrrole-thiazole based push-pull chromophores: an experimental and theoretical approach to structural, spectroscopic and NLO properties of the novel styryl dyes. J Photochem Photobiol A Chem 333:1–7
Wolff SK, Grimwood DJ, McKinnon JJ, Jayatilaka D, Spackman MA (2007) Crystal explorer 2.1. University of Western Australia, Perth
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA et al (2010) Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford
Mahmood T, Kosar N, Ayub K (2017) DFT study of acceleration of electrocyclization in photochromes under radical cationic conditions: comparison with recent experimental data. Tetrahedron 73:3521–3528