Structural study and thermal behavior of novel interaction product of 4-amino-5-(furan-2-yl)-4H-1,2,4-triazole-3-thione with molecular iodine

References

• Kumar, P.; Udupi, R.; Dubey, P. Synthesis and Biological Study of Substituted 1,3,4-Oxadiazoles and 1,2,4-Triazoles. Int. J. Pharm. Tech. Res. 2009, 4, 1654–1662.
   Google Scholar
• Pibiri, I.; Buscemi, S. A Recent Portrait of Bioactive Triazoles. CBC. 2010, 6, 208–242. DOI: 10.2174/157340710793237281.
   Google Scholar
• Pehere, A. D.; Pietsch, M.; Gütschow, M.; Neilsen, P. M.; Pedersen, D. S.; Nguyen, S.; Zvarec, O.; Sykes, M. J.; Callen, D. F.; Abell, A. D.; et al. Synthesis and Extended Activity of Triazole-Containing Macrocyclic Protease Inhibitors. Chem. Eur. J. 2013, 19, 7975–7981. DOI: 10.1002/chem.201204260.
   PubMed Web of Science ®Google Scholar
• Serbest, K.; Özen, A.; Ünver, Y.; Er, M.; Değirmencioğlu, İ.; Sancak, K. Spectroscopic and Theoretical Study of 1,2,4-Triazole-3-One Based Salicylaldimine Complexes and Evaluation of Superoxide-Scavenging Properties. J. Mol. Struct. 2009, 922, 1–10. DOI: 10.1016/j.molstruc.2009.02.001.
   Web of Science ®Google Scholar
• Patil, S. A.; Kamble, U. V.; Badami, P. S. Antimicrobial and DNA-Cleavage Studies of 22-Membered N4 Tetraaza Macrocyclic Triazoles: Template Synthesis and Physicochemical Characterization. Nucleos. Nucleot. Nucl. 2010, 29, 658–675. DOI: 10.1080/15257770.2010.504600.
   PubMed Web of Science ®Google Scholar
• Lo Conte, M.; Marra, A.; Chambery, A.; Gurcha, S. S.; Besra, G. S.; Dondoni, A. Modular Approach to Triazole-Linked 1,6-α-D-Oligomannosides to the Discovery of Inhibitors of Mycobacterium Tuberculosis Cell Wall Synthetase. J. Org. Chem. 2010, 75, 6326–6336. DOI: 10.1021/jo100928g.
   PubMed Web of Science ®Google Scholar
• Tong, W.; Wu, J.-C.; Sandstrom, A.; Chattopadhyaya, J. Synthesis of New 20,30-Dideoxy-20,30-α-Fusedheterocyclic Uridines, & Some 20,3 0-Ene-20-Substituted Uridines From Easily Accessible 20,30ene-30phenylselenonyl Uridine. Tetrahedron 1990, 46, 3037–3060. DOI: 10.1016/S0040-4020(01)88395-2.
   Web of Science ®Google Scholar
• Monceaux, C. J.; Hirata-Fukae, C.; Lam, P. C.-H.; Totrov, M. M.; Matsuoka, Y.; Carlier, P. R. Triazole-Linked Reduced Amide Isosteres: An Approach for the Fragment-Based Drug Discovery of Anti-Alzheimer s BACE1 Inhibitors. Bioorg. Med. Chem. Lett. 2011, 21, 3992–3996. DOI: 10.1016/j.bmcl.2011.05.007.
   PubMed Web of Science ®Google Scholar
• Borgati, T. F.; Alves, R. B.; Teixeira, R. R.; de Freitas, R. P.; Perdigão, T. G.; et al. Synthesis and Phytotoxic Activity of 1,2,3triazole Derivatives. J. Braz. Chem. Soc. 2013, 24, 953–961. DOI: 10.5935.0103.5053.20130121.
   Web of Science ®Google Scholar
• Mandal, S. K.; Saha, D.; Jain, V. K.; Jain, B. Sythesis and Antitubercular Activity of Some Triazole Derivatives of Propyl Gallate. Int. J. Pharm. Sci. Res. 2010, 1, 465–472.
   Google Scholar
• Cunha, A. C.; Figueiredo, J. M.; Tributino, J. L. M.; Miranda, A. L. P.; Castro, H. C.; Zingali, R. B.; Fraga, C. A. M.; de Souza, M. C. B. V.; Ferreira, V. F.; Barreiro, E. J.; et al. Antiplatelet Properties of Novel Nsubstituted-Phenyl-1,2,3-Triazole-4-Acylhydrazone Derivatives. Bioorg. Med. Chem. 2003, 11, 2051–2059. DOI: 10.1016/S0968-0896(03)00055-5.
   PubMed Web of Science ®Google Scholar
• Jordão, A. K.; Ferreira, V. F.; Lima, E. S.; de Souza, M. C. B. V.; Carlos, E. C. L.; Castro, H. C.; Geraldo, R. B.; Rodrigues, C. R.; Almeida, M. C. B.; Cunha, A. C.; et al. Synthesis, Antiplatelet and in Silico Evaluations of Novel N-Substituted-Phenylamino-5-Methyl-1H-1,2,3-Triazole-4-Carbohydrazides. Bioorg. Med. Chem. 2009, 17, 3713–3719. DOI: 10.1016/j.bmc.2009.03.053.
   PubMed Web of Science ®Google Scholar
• Menegatti, R.; Cunha, A. C.; Ferreira, V. F.; Perreira, E. F. R.; El-Nabawi, A.; Eldefrawi, A. T.; Albuquerque, E. X.; Neves, G.; Rates, S. M. K.; Fraga, C. A. M.; et al. Design, Synthesis and Pharmacological Profile of Novel Dopamine D2 Receptor Ligands. Bioorg. Med. Chem. 2003, 11, 4807–4813. DOI: 10.1016/S0968-0896(03)00487-5.
   PubMed Web of Science ®Google Scholar
• Sidwell, R. W.; Revankar, G. R.; Robins, R. K. Ribavirin: Review of a Broad-Spectrum Antiviral Agent. Viral Chemother. 1985, 2, 49–108.
   Google Scholar
• de Carvalho da Silva, F.; Do Carmo Cardoso, M. F.; Ferreira, G. P.; Ferreira, V. F. Biological Properties of 1H-1,2,3 and 2H-1,2,3-Triazoles. Top. Heterocycl. Chem. 2014, 40, 117–165. DOI: 10.1007/7081_2014_124.
   Google Scholar
• Foroumadi, A.; Mansouri, S.; Kiani, Z.; Rahmani, A. Synthesis and in Vitro Antibacterial Evaluation of N-[5-(5-Nitro-2-Thienyl)-1,3,4-Thiadiazole-2-yl] Piperazinyl Quinolones. Eur. J. Med. Chem. 2003, 38, 851–854. DOI: 10.1002/chin.200407144.
   PubMed Web of Science ®Google Scholar
• Ram, V. J.; Mishra, L.; Pandey, N. H.; Kushwaha, D. S.; Pieters, L. A. C.; Vlietinck, A. J. Bis Heterocycles as Potential Chemotherapeutic Agents. X. Synthesis of Bis(4‐Arylthiosemicarbazido)‐, Bis(2‐Arylamino‐1,3,4‐Thiadiazol‐5‐yl) and Bis(4‐Aryl‐1,2,4‐Triazolin‐3‐Thione‐5‐yl)Pentanes and Related Compounds. J. Heterocycl. Chem. 1990, 27, 351–355. DOI: 10.1002/chin.199034154.
   Web of Science ®Google Scholar
• Ergenc, N.; Ilhan, E.; G. Pharmazie, Ö. Synthese Und Biologische Wirkung Einiger 1,4-Disubstituierter Thiosemicarbazide Und Deren 1,2,4-Triazol-5-thion-Derivate. Pharmazie 1992, 47, 59–60.
   PubMed Web of Science ®Google Scholar
• Kalyoncuoğlu, N.; Rollas, S.; Sür-Altiner, D.; Yegenoğlu, Y.; Anğ, Ö. 1-(p-Benzoylamino) Benzoyl)-4-Substituted Thisemicarbazides: Synthesis and Antibacterial and Antifungal Activities. Pharmazie 1992, 47, 796–797.
   PubMed Web of Science ®Google Scholar
• Rollas, S.; Kalyoncuoğlu, N.; Sur-Altiner, D.; Yeğenoğlu, Y. 5-(4-Aminophenyl)-4-Substituted-2,4-Dihydro-3H-1,2,4-Triazole-3-Thiones: Synthesis and Antibacterial and Antifungal Activities. Pharmazie 1993, 48, 308–309. DOI: 10.1016/S0223-5234(99)80048-8.
   PubMed Web of Science ®Google Scholar
• Mir, I.; Siddiqui, M. T.; Comrie, A. Antituberculosis Agents-I: α-[5-(2-Furyl)-1,2,4-Triazol-3-Ylthio] Acethydrazide and Related Compounds. Tetrahedron 1970, 26, 5235–5238.
   PubMed Web of Science ®Google Scholar
• Rudnicka, W.; Foks, H.; Janowiec, M.; Zwolska-Kwiek, Z. Studies of pyrazine derivatives. XXI. Synthesis and Tuberculostatic Activity of 4-Aryl-1-Pyrazinoylthiosemicarbazides and the Products of Their Cyclization to 1,2,4-Triazole-3-Thione Derivatives. Acta Pol. Pharm. 1986, 43, 523–843.
   PubMedGoogle Scholar
• Holla, B. S.; Veerendra, B.; Shivananda, M. K.; Poojary, B. Synthesis Characterization and Anticancer Activity Studies on Some Mannich Bases Derived From 1,2,4-Triazoles. Eur. J. Med. Chem. 2003, 38, 759–767. DOI: 10.1016/S0223-5234(03)00128-4.
   PubMed Web of Science ®Google Scholar
• Duran, A.; Dogan, H. N.; Rollas, S. Synthesis and Preliminary Anticancer Activity of New l,4-Dihydro-3-(3-Hydroxy-2-Naphthyl)-4-Substituted-5H-l,2,4-Triazoline-5-Thiones. Farmaco 2002, 57, 559–564. DOI: 10.1016/S0014-827X(02)01248-X.
   PubMedGoogle Scholar
• Yale, H. L.; Piala, J. J. Substituted s-Triazoles and Related Compounds. J. Med. Chem. 1966, 9, 42–46. DOI: 10.1021/jm00319a010.
   PubMed Web of Science ®Google Scholar
• Mhasalkar, M. Y.; Shah, M. H.; Nikam, S. T.; Anantanarayanan, K. G.; Deliwala, C. V. 4-alkyl-5-Aryl-4H-1,2,4-Triazole-3thiols as Hypoglycemic Agents. J. Med. Chem. 1970, 13, 672–674. DOI: 10.1021/jm00298a021.
   PubMed Web of Science ®Google Scholar
• Chernovyants, M. S.; Aleshina, N. V.; Shcherbakov, I. N.; Starikova, Z. A. Spectroscopic Study of Interaction of 1H-1,2,4-Triazoline-3-Thione With Molecular Iodine. Russ. J. Gen. Chem. 2013, 83, 986–988. DOI: 10.1134/S1070363213050186.
   Web of Science ®Google Scholar
• Liu, D.; Xu, Y.; Li, X.; Ying, S.; Chen, W. Bis (4H-1, 2, 4-Triazol-3-yl) Disulfane. Acta Crystallogr. E Struct. Rep. Online 2008, 64, 247. DOI: 10.1107/S1600536807065452.
   Google Scholar
• Vorontsov, A. V. Photocatalytic Transformations of Organic Sulfur Compounds and H2S. Russ. Chem. Rev. 2008, 77, 909–926. DOI: 10.1070/RC2008v077n10ABEH003805.
   Google Scholar
• Koparir, M.; Orek, C.; Parlak, A. E.; Söylemez, A.; Koparir, P.; Karatepe, M.; Dastan, S. D. Synthesis and Biological Activities of Some Novel Aminomethyl Derivatives of 4-Substituted-5-(2- Thienyl)-2,4-Dihydro-3H-1,2,4-Triazole-3-Thiones. Eur. J. Med. Chem. 2013, 63, 340–346. DOI: 10.1016/j.ejmech.2013.02.025.
   PubMed Web of Science ®Google Scholar
• Madhu Sekhar, M.; Nagarjuna, U.; Padmavathi, V.; Padmaja, A.; Reddy, N. V.; Vijaya, T. Synthesis and Antimicrobial Activity of Pyrimidinyl 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles and 1,2,4-Triazoles. Eur. J. Med. Chem. 2018, 145, 1–10. DOI: 10.1016/j.ejmech.2017.12.067.
   PubMed Web of Science ®Google Scholar
• Koparir, P. Synthesis, Antioxidant and Antitumor Activities of Some of New Cyclobutane Containing Triazoles Derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2019, 194, 1–7. DOI: 10.1080/10426507.2019.1597363.
   Web of Science ®Google Scholar
• Khan, I.; Hameed, S.; Al-Masoudi, N. A.; Abdul-Reda, N. A.; Simpson, J. New Triazolothiadiazole and Triazolothiadiazine Derivatives as Kinesin Eg5 and HIV Inhibitors: Synthesis, QSAR and Modeling Studies. Z. Naturforsch. B: Chem. Sci. 2015, 70, 47–58. DOI: 10.1515/znb-2014-0162.
   Google Scholar
• Tamilselvi, A.; Mugesh, G. Inhibition of Peroxidase-Catalyzed Iodination by Cephalosporins: Metallo-β-Lactamase-Induced Antithyroid Activity of Antibiotics. ChemMedChem 2009, 4, 512–516. DOI: 10.1002/cmdc.200800371.
   PubMed Web of Science ®Google Scholar
• Ivolgina, V. A.; Chernov'yants, M. S.; Popov, L. D.; Suslonov, V. V.; Borodkin, G. S.; Luanguzov, N. V.; Avtushenko, N. A. Perspective anti-Thyroid Drug 2-Thioxo-5-(3,4,5-Trimethoxybenzylidene) Thiazolidin-4-One: X-Ray and Thermogravimetric Characterization of Two Novel Molecular Adducts, Obtained by Interaction With I2. J. Mol. Struct. 2019, 1180, 629–635. DOI: 10.1016/j.molstruc.2018.12.043.
   Web of Science ®Google Scholar
• Aragoni, M. C.; Arca, M.; Demartin, F.; Devillanova, F. A.; Garau, A.; Isaia, F.; Lippolis, V.; Verani, G. Anti-Thyroid Drug Methimazole: X-Ray Characterization of Two Novel Ionic Disulfides Obtained From Its Chemical Oxidation by I2. J. Am. Chem. Soc. 2002, 124, 4538–4539. DOI: 10.1021/ja012731k.
   PubMed Web of Science ®Google Scholar
• Chernov’yants, M. S.; Burykin, I. V.; Starikova, Z. A.; Tereznikov, A. Y.; Kolesnikova, T. S. Spectroscopic and Structural Study of Novel Interaction Product of Pyrrolidine-2-Thione With Molecular Iodine. Presumable Mechanisms of Oxidation. J. Mol. Struct. 2013, 1047, 204–208. DOI: 10.1016/j.molstruc.2013.04.062.
   Web of Science ®Google Scholar
• Bartashevich, E.; Yushina, I.; Kropotina, K.; Muhitdinova, S.; Tsirelsonb, V. Testing the Tools for Revealing and Characterizing the Iodine–Iodine Halogen Bond in Crystals. Acta Crystallogr. B Struct. Sci. Cryst. Eng. Mater. 2017, 73, 217–226. DOI: 10.1107/S2052520617002931.
   PubMedGoogle Scholar
• Yushina, I. D.; Rudakov, B. V.; Stash, A. I.; Bartashevich, E. Comparison of Non-Covalent Interactions and Spectral Properties in 1-Methyl-3-Methylthio-5-Phenyl-1,2,4-Triazinium Mono- and Tetraiodide Crystals. Struct. Chem. 2019, 30, 1981–1991. DOI: 10.1007/s11224-019-01372-3.
   Web of Science ®Google Scholar
• Deplano, P.; Ferraro, J. R.; Mercuri, M. L.; Trogu, E. F. Structural and Raman Spectroscopic Studies as Complementary Tools in Elucidating the Nature of the Bonding in Polyiodides and in donor-I2 Adducts. Coord. Chem. Rev. 1999, 188, 71–95. DOI: 10.1016/S0010-8545(98)00238-0.
   Web of Science ®Google Scholar
• Karle, I. L. Anomalous Electron Scattering From Iodine Vapor. J. Chem. Phys. 1955, 23, 1739. DOI: 10.1063/1.1742448.
   Web of Science ®Google Scholar
• Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, NY, 1960.
   Google Scholar
• Chernov’yants, M. S.; Kolesnikova, T. S.; Suponitsky, K. Y. Study of the Interaction of Imidazolidine-2-Thione With Molecular Iodine. Russ. Chem. Bull. 2016, 65, 811–815. DOI: 10.1007/s11172-016-1379-y.
   Web of Science ®Google Scholar
• Aragoni, M. C.; Arca, M.; Devillanova, F. A.; Garau, A.; Isaia, F.; Lippolis, V.; Verani, G. Charge-Transfer Adducts Between Donors Containing Chalcogens (S and Se) and Di-Iodine: Solution Studies. Coord. Chem. Rev. 1999, 184, 271–290. DOI: 10.1016/S0010-8545(98)00259-8.
   Web of Science ®Google Scholar
• Wang, C.; Luo, Y.-H.; He, X.-T.; Hong, D.-L.; Wang, J.-Y.; Chen, F.-H.; Chen, C.; Sun, B.-W. Porous High-Valence Metal − Organic Framework Featuring Open Coordination Sites for Effective Water Adsorption. Inorg. Chem. 2019, 58, 3058–3064. DOI: 10.1021/acs.inorgchem.8b03042.
   PubMed Web of Science ®Google Scholar
• He, X.-T.; Hong, D.-L.; Chen, C.; Chen, F.-H.; Zhai, L.-H.; Guo, L.-H.; Luo, Y.-H.; Sun, B.-W. Comparison Between the Acidification of Acidic and Alkalic Groups. Cryst. Growth Des. 2019, 19, 437–443. DOI: 10.1021/acs.cgd.8b01532.
   Web of Science ®Google Scholar
• Yushina, I. D.; Kolesov, B. A.; Bartashevich, E. V. Raman Spectroscopy Study of New Thia- and Oxazinoquinolinium Triiodides. New J. Chem. 2015, 39, 6163–6170. DOI: 10.1039/C5NJ00497G.
   Web of Science ®Google Scholar
• Chernov’yants, M. S.; Khokhlov, E. V.; Lykova, E. O.; Kazheva, O. N.; Aleksandrov, G. G. Investigation of the Reaction of 1-Methylimidazoline-2-Thione With Molecular Iodine. Russ. Chem. Bull. 2008, 57, 1239–1243. DOI: 10.1007/s11172-008-0157-x.
   Web of Science ®Google Scholar
• Chernov’yants, M. S.; Starikova, Z. A.; Kolesnikova, T. S.; Karginova, A. O.; Lyangusov, N. V. Synthesis and Structure of Interaction Product of Quinoline-2(1H)-Thione With Molecular Iodine. Spectrochim. Acta A 2015, 139, 533–538. DOI: 10.1016/j.saa.2014.12.075.
   Web of Science ®Google Scholar
• Ivolgina, V. A.; Chernov'yants, M. S. Spectroscopic and Structural Investigation of Interaction of 5-Mercapto-3-Phenyl-1,3,4-Thiadiazole-2-Thione Potassium Salt With Molecular Iodine. Spectrochim. Acta A 2018, 199, 315–321. DOI: 10.1016/j.saa.2018.03.069.
   Web of Science ®Google Scholar
• Tatucu, M.; Rotaru, P.; Rau, I.; Spinu, C.; Kriza, A. Thermal Behavior and Spectroscopic Investigation of Some Methyl 2-Pyridyl Ketone Complexes. J. Therm. Anal. Calorim. 2010, 100, 1107–1114. DOI: 10.1007/s10973-009-0276-0.
   Web of Science ®Google Scholar
• Zianna, A.; Vecchio, S.; Gdaniec, M.; Czapik, A.; Hatzidimitriou, A.; Lalia-Kantouri, M. Synthesis, Thermal Analysis, and Spectroscopic and Structural Characterizations of Zinc(II) Complexes With Salicylaldehydes. J. Therm. Anal. Calorim. 2013, 112, 455–464.2. DOI: 10.1007/s10973-012-2719-.
   Web of Science ®Google Scholar
• Antniadis, C. D.; Corban, G. J.; Hadjikakou, S. K.; Hadjiliadis, N.; Kubicki, M.; et. al. Synthesis and Characterization of (PTU)I2 (PTU = 6-n-Propyl-2-Thiouracil) and (CMBZT = 5-Chloro-2-Mercaptobenzothiazole) and Possible Implications for the Mechanism of Action of Anti-Thyroid Drugs. Eur. J. Inorg. Chem. 2003, 8, 1635–1640. DOI: 10.1002/ejic.200390215.
   Google Scholar
• Cansiz, A.; Koparir, M.; Demirdağ, A. Synthesis of Some New 4,5-Substituted-4H-1,2,4-Triazole-3-Thiol Derivatives. Molecules 2004, 9, 204–212. DOI: 10.3390/90400204.
   PubMed Web of Science ®Google Scholar
• Gordon, A.; Ford, R. A Handbook of Practical Data. The Chemist Companion; Wiley: New York, 1972.
   Google Scholar
• Spec, A. I. Single-Crystal Structure Validation With the Program PLATON. J. Appl. Cryst. 2003, 36, 7–13. DOI: 10.1107/S0021889802022112.
   Web of Science ®Google Scholar
• 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. DOI: 10.1107/S002188980600731X.
   Web of Science ®Google Scholar
• Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. K.; Puschmann, H. A. Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, 339–341. DOI: 10.1107/S0021889808042726.
   Web of Science ®Google Scholar
• Palatinus, L.; Chapuis, G. SUPERFLIP—A Computer Program for the Solution of Crystal Structures by Charge Flipping in Arbitrary Dimensions. J. Appl. Crystallogr. 2007, 40, 786–790. DOI: 10.1107/S0021889807029238.
   Web of Science ®Google Scholar
• Palatinus, L.; Lee, A. Symmetry Determination Following Structure Solution in P1. J. Appl. Crystallogr. 2008, 41, 975–984. DOI: 10.1107/S0021889808028185.
   Web of Science ®Google Scholar
• Palatinus, L.; Prathapa, S. J.; Smaalen, S. EDMA: A Computer Program for Topological Analysis of Discrete Electron Densities. J. Appl. Crystallogr. 2012, 45, 575–580. DOI: 10.1107/S0021889812016068.
   Web of Science ®Google Scholar
• Sheldrick, G. M. Crystal Structure Refinement With SHELXL. Acta Crystallogr. C Struct. Chem. 2015, 71, 3–8. DOI: 10.1107/S2053229614024218.
   PubMed Web of Science ®Google Scholar