Abstract
We report the characterization of novel derivatives of bis-1,3,4-thiadiazoles. The investigated derivatives were characterized using UV‒Vis and FTIR spectroscopic techniques. In addition to spectroscopic analyses, DFT calculations were utilized to predict the chemical and drug-like properties of the compounds under investigation. According to the obtained results, the bis-1,3,4-thiadiazole derivatives under study were found to have high electrophilicity indices (> 2.5). Moreover, the experimentally investigated electronic transitions in the UV‒Vis region of the electromagnetic spectrum were studied by theoretical means through the visualization of HOMO and LUMO molecular orbitals (ΔE ~ 7 eV) and TDDFT calculations. It was found that the compounds maximally absorb the electromagnetic radiation at wavelengths of about 350 nm (in chloroform) in addition to some absorption shoulders which may be due to π‒π* and/or n‒π* electronic transitions. Electrostatic potential maps were used to visualize the sites of high and low electrostatic potential which give information about the possible sites of electrophilic and nucleophilic reactions.
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References
Ahmad Yahia H, Hassan Walid MI (2012) Corrosion inhibition of steel in hydrochloric acid solution using a triazole derivative: electrochemical and computational studies. Int J Electrochem Sci 7(12):12456–12469
Chandra S, Gautam S, Kumar A, Madan M (2015) Coordination mode of pentadentate ligand derivative of 5-amino-1,3,4-thiadiazole-2-thiol with nickel(II) and copper(II) metal ions: synthesis, spectroscopic characterization, molecular modeling and fungicidal study. Spectrochim Acta Part A Mol Biomol Spectrosc 136:672–681. https://doi.org/10.1016/j.saa.2014.09.081
Chemcraft - graphical software for visualization of quantum chemistry computations. https://www.chemcraftprog.com
Dena Abo, Ahmed S (2014) To the memory of Hugo Schiff: applications of Schiff bases in potentiometric sensors. Russ J Appl Chem 87(3):383–396. https://doi.org/10.1134/S1070427214030227
Dena Abo, Ahmed S, Hassan Walid M I (2016) Spectrochimica acta part a : molecular and biomolecular spectroscopy experimental and quantum mechanical studies on the ion-pair of levocetirizine and bromocresol green in aqueous solutions. Spectrochem Acta Part A 163:108–114. https://doi.org/10.1016/j.saa.2016.03.030
Dena Abo, Ahmed S, Gaber SAA (2017) In vitro drug interaction of levocetirizine and diclofenac: theoretical and spectroscopic studies. Spectrochim Acta Part A Mol Biomol Spectrosc 181:239–248. https://doi.org/10.1016/j.saa.2017.03.043
Dennington Roy, Keith Todd, Millam John (2009) Gauss view version 05. Semichem Inc., Shawnee Mission
Dong Wei-Li, Liu Zheng-Xiao, Liu Xing-Hai, Li Zheng-Ming, Zhao Wei-Guang (2010) Synthesis and antiviral activity of new acrylamide derivatives containing 1,2,3-thiadiazole as inhibitors of hepatitis B virus replication. Eur J Med Chem 45(5):1919–1926. https://doi.org/10.1016/j.ejmech.2010.01.032
El-Shazly TS, Hassan Walid MI, Abdel Sayed T, Rahim A, Allam NK (2015) Unravelling the interplay of dopant concentration and band structure engineering of monoclinic niobium pentoxide: a model photoanode for water splitting. Int J Hydrogen Energy 40(40):13867–13875. https://doi.org/10.1016/j.ijhydene.2015.08.056
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G et al (2009) Gaussian 09, Revision B.01. Gaussian Inc., Wallingford
Gomha Sobhi M, Marwa S, Muhammad EZA, Abdelhamid AO, Abdel-Aziz MM (2018) Utility of bis-hydrazonoyl chlorides as precursors for synthesis of new functionalized bis-thiadiazoles as potent antimicrobial agents. J Heterocycl Chem 55:844–851. https://doi.org/10.1002/jhet.3108
Hassan Walid M I, Dena ASA (2014) Unraveling the nature of interaction between substituted phenol and amiodarone. Anal Chem 86(3):1881–1886. https://doi.org/10.1021/ac403964b
Hu Yang, Li Cui-yun, Wang Xiao-ming, Yang Yong-hua, Zhu Hai-liang (2014) 1,3,4-Thiadiazole: synthesis, reactions, and applications in medicinal, agricultural, and materials chemistry. Chem Rev 114:5572–5610. https://doi.org/10.1021/cr400131u
Issa Yousry Moustafa, Sherif Omaima Elsayed, Dena Ahmed Saeed Abo (2013) Spectral studies on the ion-pairs of levocetirizine dihydrochloride and some triphenylsulphonephthaleines. Egypt J Anal Chem 83(2013):67–83
Jakovljević K, Matić IZ, Stanojković T, Krivokuća A, Marković V, Joksović MD, Mihailović N, Nićiforović M, Joksović L (2017) Synthesis, antioxidant and antiproliferative activities of 1,3,4-thiadiazoles derived from phenolic acids. Bioorg Med Chem Lett 27(2017):3709–3715. https://doi.org/10.1016/j.bmcl.2017.07.003
James BF, Frisch A (2015) Exploring chemistry with electronic structure methods, 3rd edn. Gaussian Inc, Pittsburgh
John EM (2011) Organic Chemistry, 8th edn. 20 Davis Drive, Belmont. https://www.amazon.com/Organic-Chemistry-John-McMurry/dp/0840054440. Accessed 31 May 2019
Jorgensen William L (2004) The many roles of computation in drug discovery. Science 303(5665):1813–1818. https://doi.org/10.1126/science.1096361
Karabasanagouda T, Adhikari AV, Shetty NS (2007) Synthesis and antimicrobial activities of some novel 1,2,4-triazolo[3,4-B]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-B]-1,3,4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moieties. Eur J Med Chem 42(4):521–529. https://doi.org/10.1016/j.ejmech.2006.10.010
Karcz Dariusz, Matwijczuk Arkadiusz, Boroń Bożena, Creaven Bernadette, Fiedor Leszek, Niewiadomy Andrzej, Gagoś Mariusz (2017) Isolation and spectroscopic characterization of Zn(II), Cu(II), and Pd(II) complexes of 1,3,4-thiadiazole-derived ligand. J Mol Struct 1128(2017):44–50. https://doi.org/10.1016/j.molstruc.2016.08.042
Kumar D, Kumar NM, Chang K-H, Shah K (2010) Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles. Eur J Med Chem 45(10):4664–4668. https://doi.org/10.1016/j.ejmech.2010.07.023
Li Z, Zhan P, Liu X (2011) 1,3,4-Oxadiazole: a privileged structure in antiviral agents. Mini Rev Med Chem 11(13):1130–1142
Li Qing, Ren Jianming, Dong Fang, Feng Yan, Guodong Gu, Guo Zhanyong (2013) Synthesis and antifungal activity of thiadiazole-functionalized chitosan derivatives. Carbohydr Res 373(May):103–107. https://doi.org/10.1016/j.carres.2013.03.001
Lin You Sheng, De Li Guan, Mao Shan Ping, Da Chai Jeng (2013) Long-range corrected hybrid density functionals with improved dispersion corrections. J Chem Theory Comput 9(1):263–272. https://doi.org/10.1021/ct300715s
Lipinski Christopher A, Lombardo Franco, Dominy Beryl W, Feeney Paul J (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 64:4–17. https://doi.org/10.1016/j.addr.2012.09.019
Mansour Ahmed M, Hassaneen Hamdi M, Mohammed Yasmin Sh, Ghani NTA (2013) Single crystal, spectral, computational studies and in vitro cytotoxicity of 2-chloro-3-formylpyrido[2,1-a]isoquinoline-1-carbonitrile derivative. J Mol Struct 1045:180–190. https://doi.org/10.1016/j.molstruc.2013.04.032
Mathew V, Keshavayya J, Vaidya VP, Giles D (2007) Studies on synthesis and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo[3,4-B]-1,3,4-thiadiazoles and their dihydro analogues. Eur J Med Chem 42(6):823–840. https://doi.org/10.1016/j.ejmech.2006.12.010
Nasiri Rasoul, Zahedi Mansour, Jamet H, Moosavi-Movahedi AA (2012) Theoretical studies on models of lysine-arginine cross-links derived from α-oxoaldehydes: a new mechanism for glucosepane formation. J Mol Model 18(4):1645–1659. https://doi.org/10.1007/s00894-011-1161-x
Ningegowda Raghu, Shivananju Nanjunda Swamy, Rajendran Peramiyan, Basappa Kanchugarakoppal S, Rangappa Arunachalam Chinnathambi, Li Feng et al (2017) A novel 4,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole derivative inhibits tumor cell invasion and potentiates the apoptotic effect of TNFα by abrogating NF-κB activation cascade. Apoptosis 22(1):145–157. https://doi.org/10.1007/s10495-016-1312-8
Othman AA, Kihel M, Amara S (2014) 1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents. Arab J Chem. https://doi.org/10.1016/j.arabjc.2014.09.003
Rajak Harish, Kharya Murli Dhar, Mishra Pradeep (2007) Synthesis of some novel oxadiazole and oxadiazoline analogues for their antiinflammatory activity. Yakugaku Zasshi 127(10):1757–1764
Sadek Bassem, Fahelelbom Khairi Mustafa Salem (2011) Synthesis, characterization, and antimicrobial evaluation of oxadiazole congeners. Molecules 16(6):4339–4347. https://doi.org/10.3390/molecules16064339 (Basel, Switzerland)
Sharmoukh W, Hassan Walid MI, Gros Philippe C, Allam Nageh K (2016) Design and synthesis of new Ru-complexes as potential photo-sensitizers: experimental and TD-DFT insights. RSC Adv 6(73):69647–69657. https://doi.org/10.1039/c6ra16458g
Tan SY, Tatsumura Y (2015) Alexander Fleming (1881–1955): discoverer of Penicillin Siang. Singapore Med J 56(7):366–367. https://doi.org/10.11622/smedj.2015105
Zarei Maaroof (2017) One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent. Tetrahedron 73(14):1867–1872. https://doi.org/10.1016/j.tet.2017.02.042
Zou Y, Zhao Q, Liao J, Hu H, Yu S, Chai X, Xu M, Wu Q (2012) New triazole derivatives as antifungal agents: synthesis via click reaction, in vitro evaluation and molecular docking studies. Bioorg Med Chem Lett 22(8):2959–2962. https://doi.org/10.1016/j.bmcl.2012.02.042
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The authors are grateful to the National Organization for Drug Control and Research (NODCAR) for providing the chemicals and the instruments needed to accomplish this work.
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Abo Dena, A.S., Muhammad, Z.A. & Hassan, W.M.I. Spectroscopic, DFT studies and electronic properties of novel functionalized bis-1,3,4-thiadiazoles. Chem. Pap. 73, 2803–2812 (2019). https://doi.org/10.1007/s11696-019-00833-7
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DOI: https://doi.org/10.1007/s11696-019-00833-7