4-(3-metil-3-fenilsiklobütil)-2-(2-(piridin-4-ylmetilen)hidrazinil) tiyazol’un Sentezi, Karakterizasyonu, Kristalografik Yapısı ve Hirshfeld Yüzeyinin İncelenmesi

Abstract

Bu çalışmada, 4-(3-metil-3-fenilsiklobütil)-2-(2-(piridin-4-ylmetilen)hidrazinil)tiyazol [C20H20N4S] molekülü sentezlendi ve IR, 1H NMR 13C NMR spektroskopileri ile karakterize edildi. Kristalografik ve moleküler yapısı tek kristal X−ışınları kırınımı tekniği ile belirlenmiştir. Bileşik ortorombik P 212121 uzay grubu ile kristalleşmiştir ve birim hücre parametreleri a=6.208(5) Å, b=15.938(5) Å, c=19.573(5) Å ve α=β=γ=90.00°’dır.Bileşiğin moleküller yapısındaki önemli etkileşimleri belirleyebilmek için PLATON ve Crystal Explorer programları kullanılmış ve kristal örgüsündeki moleküllerin paketlenmesinin doğası anlaşılmaya çalışılmıştır.

Keywords

• Hirshfeld yüzeyi
• siklobütan
• x-ışını kırınımı

Synthesis, characterization, crystallographic structure and investigation of Hirshfeld surface of 4-(3-methyl-3- phenylcyclobutyl)-2-(2-(pyridin-4-ylmethylene)hydrazinyl)thiazole

Abstract

In this study, the title compound 4-(3-methyl-3-phenylcyclobutyl)-2-(2-(pyridin-4-ylmethylene) hydrazinyl)thiazole [C20H20N4S] was synthesized, characterized with IR, 1H NMR 13C NMR. Crystallographic and molecular structure determined by single-crystal X-ray diffraction techniques. The compound was crystallized in the orthorhombic space group P 212121 with a = 6.208(5) Å, b = 15.938(5) Å, c = 19.573(5) Å, and α=β=γ=90.00°. PLATON and Crystal Explorer programs were used to determine the remarkable interactions between the molecules and the nature of packing the molecules in the crystal has been tried to be understood.

Keywords

• Cyclobutane
• Hirshfeld surface
• x-ray diffraction

References

1. Abbas I, Gomha S, Elaasser M, Bauomi M, 2015. Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents. Turkish Journal of Chemistry, 39: 334-346.
2. Bachir M, Riffaud J, Lacolle J, Lemoine J, Almeida AD, Houziaux P, Danrée B, 1990. Synthesis and anticonvulsant activity of some 2-(N-substituted glycylamino)-4-methyl thiazoles. European Journal of Medicinal Chemistry, 25 (1):71-74.
3. Bhardwaj V, Noolvi MN, Jalhan S, Patel HM, 2012. Synthesis, and antimicrobial evaluation of new pyridine imidazo [2,1b]-1,3,4-thiadiazole derivatives. Journal of Saudi Chemical Society, 20: S406-S410.
4. Cankılıç MY, Yurttaş L, 2017. Study on the Antimicrobial Effects of Novel Thiazole Derivatives. Marmara Pharmaceutical Journal, 21(3): 654-659.
5. Chimenti F, Bizzarri B, Maccioni E, Secci D, Bolasco A, Fioravanti R, Chimenti P, Granese A, Carradori S, Rivanera D, Lilli D, Zicari A, Distinto S, 2007. Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp. Bioorganic & Medicinal Chemistry Letters, 17: 4635-4640.
6. Dehmlow EV, Schmidt S, 1990. Synthese von stereoisomeren 3-substituierten Cyclobutancarbonsäure-Derivaten. Liebigs Annalen der Chemie, 5: 411-414.
7. Farrugia LJ, 2012. WinGX and ORTEP for Windows: an update. Journal of Applied Crystallography, 30: 837–838.
8. Ghasemi B, Sanjarani G, Sanjarani Z, Majidiani H, 2015. Evaluation of anti-bacterial effects of some novel thiazole and imidazole derivatives against some pathogenic bacteria. Iranian Journal of Microbiology, 7(5):281-286.

9. Gueiffier A, Mavel S, Lhassani M, Elhakmaoui A, Snoeck R, Andrei G, Chavignon O, Teulade J, Witvrouw M, Balzarini J, Clercq E, Chapat J, 1998. Synthesis of Imidazo[1,2-a]pyridines as Antiviral Agents. Journal of Medical Chemistry, 41 (25): 5108–5112.
10. Hassan FA, 2012. Synthesis, Characterization, Anti-inflammatory, and Antioxidant Activities of Some New Thiazole Derivatives. International Journal of Applied Science and Technology, 2 (7): 180-187.
11. Inkaya E, Dinçer M, Ekici Ö, Cukurovali A, 2013. 1-(3-Methyl-3-mesityl)-cyclobutyl-2-(5-pyridin-4-yl-2H-[1,2,4]triazol-3-ylsulfanyl)-ethanone: X-ray structure, spectroscopic characterization and DFT studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 101:218-227.
12. Jaishree V, Ramdas N, Sachin J, Ramesh B, 2012. In vitro antioxidant properties of new thiazole derivatives. Journal of Saudi Chemical Society, 16: 371–376.
13. Joseyphus RS, Nair MS, 2008. Antibacterial and Antifungal Studies on Some Schiff Base Complexes of Zinc(II). Mycobiology, 36(2): 93–98.
14. Karegoudar P, Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumari NS, 2008. Synthesis of some novel 2,4-disubstituted thiazoles as possible antimicrobial agents. European Journal of Medicinal Chemistry, 43: 261-267.
15. Lesyk R, Vladzimirska O, Holota S, Zaprutko L, Gzella A, 2007. New 5-substituted thiazolo[3,2-b][1,2,4]triazol-6-ones: Synthesis and anticancer evaluation. European Journal of Medicinal Chemistry, 42: 641-648.
16. Lesyk R, Zimenkovsky B, Atamanyuk D, Jensen F, Kieć-Kononowicz K, Gzella A, 2006. Anticancer thiopyrano[2,3-d][1,3]thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies. Bioorganic & Medicinal Chemistry, 14: 5230–5240.
17. Liaras K, Geronikaki A, Glamočlija J, Ćirić A, Soković M, 2011. Thiazole-based chalcones as potent antimicrobial agents. Synthesis and biological evaluation. Bioorganic & Medicinal Chemistry, 19: 3135–3140. Lu X, Liu X, Wan B, Franzblau SG, Chen L, Zhou C, You Q, 2012. Synthesis and evaluation of anti-tubercular and antibacterial activities of new 4-(2,6-dichlorobenzyloxy)phenyl thiazole, oxazole and imidazole derivatives. Part 2. European Journal of Medicinal Chemistry, 49: 164-171.
18. Mohamed MS, Awad YEE, El-Hallouty SM, El-Araby M, Design, 2012. Synthesis and Cancer Cell Line Activities of Pyrazolo[3,4-b]pyridine Derivatives. Open Journal of Medicinal Chemistry, 2: 78-88.
19. Narayana B, Vijaya Raj KK, Ashalatha BV, Kumari NS, Sarojini BK, 2004. Synthesis of some new 5-(2-substituted-1,3-thiazol-5-yl)-2-hydroxy benzamides and their 2-alkoxy derivatives as possible antifungal agents. European Journal of Medicinal Chemistry, 39: 867–872.
20. Nardelli M, 1995. PARST95 - an update to PARST: a system of Fortran routines for calculating molecular structure parameters from the results of crystal structure analyses. Journal of Applied Crystallography, 28:659.
21. Pradhan J, Goyal A, 2016. Synthesis, anticonvulsant activity and QSAR studies of some new pyrazolyl pyridines. Medical Chemistry Research, 25(8): 1639-1656.
22. Prasad AVGS, Trinagaraju K, Rao BG, Usha Y, Reddy PS, Rao PV, 2013. Synthesis and Biological Activity Of Aniline Derivative Schiff Bases. International Journal of Innovative Research & Development, 2(10): 97-102.
23. Rajput CS, Sharma S, Yashovardhan, 2011. Synthesis of New Pyridine Derivatives as potent antifungal agents. International Journal of Pharma and Bio Sciences. 2(3): 200-209.
24. Salam OIA, Al-Omar MA, Khalifa NM, Amr AEE, Abdallah MM, 2013. Analgesic and Anticonvulsant Activities of Some Newly Synthesized Trisubstituted Pyridine Derivatives. Zeitschrift für Naturforschung, 68:264-268.
25. Saravanan G, Alagarsamy V, Prakash C R, Kumar PD, Selvam TP, 2011. Synthesis of Novel Thiazole Derivatives as Analgesic Agents. Asian Journal of Research in Pharmaceutical Sciences, 1(4): 134-138. Şen F, Dinçer M, Cukurovali A, 2015. Structural and spectroscopic characterization of 4-(3-methyl-3-phenylcyclobutyl)-2-(2-propylidenehydrazinyl)thiazole: A combined experimental and DFT analysis. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 150: 257-267.
26. Şen F, Efil K, Bekdemir Y, Dinçer M, 2017. Structural, spectroscopic characterization of (E)-4-chloro-2-((4-methoxybenzylidene)amino)phenol as potential antioxidant compound. Journal of Molecular Structure, 1127: 645-652.
27. Sheldrick GM, 1997. SHELXL-97; Program for Crystal Structures Refinement, University of Gottingen.
28. Sheldrick GM, 1997. SHELXS-97; Program for the Solution of Crystal Structures, University of Gottingen.
29. Silva MC, Silva LD, Modolo LV, Alves RB, Resende AM, Martins VBC, Fátima A, 2011. Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research, 2 (1): 1-8.
30. Solomons G, Fryhle C, 2000. Organic Chemistry (Seventh Edition), John Wiley & Sons, Inc., New York.
31. Spackman M, Jayatilaka D, 2009. Hirshfeld surface analysis. Crystal Engineering Communication, 11: 19-32.
32. Spackman M, McKinnona JJ, 2002. Fingerprinting intermolecular interactions in molecular crystals. Crystal Engineering Communication, 4: 378-392.
33. Spek AL, 2009. Structure validation in chemical crystallography. Acta Crystallographica Section D: Bıologıcal Crystallography, D65: 148-155.
34. Stoe & Cie, X-AREA (Version 1.18) X-RED32 (Version 1.04), Stoe & Cie, Darmstadt, Germany, 2002.
35. Thore SN, Gupta SV, Baheti KG, 2013. Docking, synthesis, and pharmacological investigation of novel substituted thiazole derivatives as non-carboxylic, anti-inflammatory, and analgesic agents. Medicinal Chemistry Research, 22: 3802–3811.
36. Turner M J, McKinnon J J, Wolff S K, Grimwood D J, Spackman P R, Jayatilaka D, Spackman M A, 2017. CrystalExplorer17. University of Western Australia.
37. Utreja D, Vibha, Singh S, Kaur M, 2015. Schiff Bases and their Metal Complexes as Anti-Cancer Agents: A Review. Current Bioactive Compounds, 11(4): 215-230.
38. Zhou X, Shao L, Jin Z, Liu J, Dai H, Fang J, 2007. Synthesis and Antitumor Activity Evaluation of Some Schiff Bases Derived from 2-Aminothiazole Derivatives. Heteroatom Chemistry, 18(1): 55-59.