Abstract
In this study, two novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives, 3-[2-(4-methoxyphenyl)ethyl]-6-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine (compound 1) and 3-[2-(3,4,5-trimethoxyphenyl)ethyl]-6-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine (compound 2), having analgesic–anti-inflammatory activity were synthesized and characterized by IR, 1H-NMR, and mass spectroscopic techniques besides elementary analysis. Additionally, the structures and molecular packings of the mentioned compounds have been investigated by X-ray single crystal diffraction. The six-membered thiadiazine ring adopts the screw boat conformation in both the compounds. In the crystal packings of the compounds 1 and 2, C–H···N and C–H···O interactions link the molecules into a two-dimensional network and generate infinite chains. Furthermore, C–H···π intermolecular interactions provide further stability to the molecular packing in both the molecules. The conformers have been predicted by the potential energy surface scan employing the AM1 method. Geometry optimizations and electrostatic properties have been obtained using AM1 and ab initio quantum methods.
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References
Tozkoparan B, Ayhan-Kılcıgil G, Ertan R, Ertan M, Kelicen P, Demirdamar R (1999) Arzneimittel-Forschung 49(12):1006–1016
Tozkoparan B, Gökhan N, Aktay G, Yeşilada E, Ertan M (2000) Eur J Med Chem 35(7):743–750
Tozkoparan B, Aktay G, Yeşilada E, Ertan M (2001) Arzneimittel-Forschung 51(6):470–477
Tozkoparan B, Aktay G, Yeşilada E (2002) Il Farmaco 57(2):145–152
Tozkoparan B, Gökhan N, Küpeli E, Yeşilada E, Ertan M (2004) Arzneimittel-Forschung 54(1):35–41
Tozkoparan B, Küpeli E, Yeşilada E, Ertan M (2007) Bioorg Med Chem 15(4):1808–1821
Doğdaş E, Tozkoparan B, Kaynak FB, Eriksson L, Küpeli E, Yeşilada E, Ertan M (2007) Arzneimittel-Forschung 57(4):196–202
Tozkoparan B, Aytaç SP, Aktay G (2009) Arch Pharm 342:291–298
Aytaç SP, Tozkoparan B, Kaynak FB, Aktay G, Göktaş Ö, Ünüvar S (2009) Eur J Med Chem 44(11):4528–4538
Prasad AR, Ramalingam T, Rao AB, Diwan PV, Sattur PB (1989) Eur J Med Chem 24:199–201
Karegoudar P, Prasad DJ, Ashok M, Mahalinga M, Poojary B, Holla BS (2008) Eur J Med Chem 43(4):808–822
Enraf-Nonius (1994) CAD-4 Express Software. Enraf-Nonius, Delft, The Netherlands
Altomare A, Cascarano G, Giacovazzo C, Guagliardi A, Burla MC, Polidori G, Camalli M (1994) SIR92—a program for automatic solution of crystal structures by direct methods. J Appl Cryst 27:435
Sheldrick GM (1997) SHELXS97. Program for the solution of crystal structure. University of Göttingen, Germany
Sheldrick GM (1997) SHELXL97. Program for the refinement of crystal structures. University of Göttingen, Germany
Nardelli MJ (1995) Appl Cryst 28:659
Farrugia LJ (1997) ORTEP-3 for Windows. J Appl Cryst 30:565
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE Jr, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (2003) GAUSSIAN 03. Gaussian Inc., Pittsburgh, PA
Walters P, Stahl M (1994) Babel, version 1.1. Department of Chemistry, University of Arizona, Tucson, AZ
Zhang L-X, Zhou S-N, Zhang A-J, Lei X-X, Cai C-X (2005) Acta Cryst E61:o4058–o4059
Jin J-Y, Zhang L-X, Zhou S-N, Xiao H-P, Zhang A-J (2006) Acta Cryst E62:o713–o714
Cremer D, Pople JAJ (1975) Am Chem Soc 97:1354–1358
Zhang L-X, Zhang Z-Y, Zeng F-L (1990) Chem J Chin Univ 11:148–151
Zou K-H, Cai L-Q, Chen J-X, Zhang L-X, Zhang A-J, Hu ML (2004) Acta Cryst E60:o1736–o1738
HyperChem 7.5 (2003), Hypercube Inc
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The authors would like to acknowledge the support of Hacettepe University Research Fund (project no: 0302602001 and 0701301001).
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Kaynak, F.B., Aytaç, S.P. & Tozkoparan, B. A joint theoretical and experimental structural study of two novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives. Struct Chem 21, 795–802 (2010). https://doi.org/10.1007/s11224-010-9613-y
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DOI: https://doi.org/10.1007/s11224-010-9613-y