N-(4-metilfenil)-N-(5-(3-hidroksinaftil-2-il)-1,3,4-oksadiazol-2-il) amin’in Sentezi Karakterizasyonu ve Gaussian Hesaplamaları

Yıl 2018, Cilt: 8 Sayı: 1, 169 - 177, 31.03.2018

Murat Genç

https://doi.org/10.21597/jist.407866

Cited By: 1

Öz

Bu çalışmada ilk olarak 3-hidroksi-2-naftoikhidrazit bileşiği kullanılarak 3-hidroksinaftil-2-il-N- (4-Metilfenil) hidrazinkarbotiyoamid bileşiği sentezlendi. Elde edilen bileşiğin civa(II)asetat bileşiği ile reaksiyonundan N-(4-metilfenil)-N-(5-(3-hidroksinaftil-2-il)-1,3,4-oksadiazol-2-il) amin sentezlendi. Bileşiklerin yapıları NMR, FT-IR, elementel analiz ile karakterize edildi. Çalışmanın ikinci etabında ise; Gaussian 09 hesaplamaları kullanılarak HOMO ve LUMO orbital enerjileri, atomların mulliken yükleri, molekülün aktivitesini belirlemek için HOMO-1 ve LUMO+1 orbital enerjileri araştırıldı. Teorik NMR ve FT-IR hesaplamalarının deneysel değerlerle uyumu araştırıldı.

Anahtar Kelimeler

1, 3, 4-oksadiazol, DFT

The Synthesis, Characterization and Gaussian Calculations of N-(4-methylphenyl)-N-(5-(3-hydroxynahptyl-2-yl)-1,3,4-oxadiazol2-yl)amine

Öz

In this study; firstly, 3-hydroxynahptyl-2-yl-N-(4-Methylphenyl) hydrazincarbotihioamide compound was synthesized by using 3-hydroxy-2-nahptonoic hydrazide compound. N-(4-methylphenyl)-N-(5-(3- hydroxynahptyl-2-yl)-1,3,4-oxadiazol-2-yl)amine compound was synthesized by the reaction mercury(II)acetate with the obtained compound. The structures of the compounds were characterized by using NMR, FT-IR, elemental analysis. In the second part of the study; HOMO- LUMO orbital energies, atoms’ mulliken charges and HOMO-1 and LUMO+1 orbital energies for molecular activity were investigated by using Gaussian 09. The compatibility of the theoretical NMR and FT-IR with experimental values were investigated. 

Anahtar Kelimeler

1, 3, 4-oxadiazole, DFT

Kaynakça

• Akhtar T, Hameed S, Al-Masoudi NA, Loddo R, Colla, PL, 2010. In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2- thione derivatives. Acta Pharmazie, 58: 135-49.
• Akhter M, Husain A, Azad B, Ajmal M, 2009. Aroylpropionic acid based 2,5- disubstituted-1,3,4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities. European Journal of Medicinal Chemistry , 44: 2372–8.
• Bahgat K, Fraihat S, 2015. Normal coordinate analysis, molecular structure, vibrational, electronic spectra and NMR investigation of 4-Amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione by ab initio HF and DFT method. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,135: 1145-1155.
• Bharathi D, Hemalatha S, Devadass G, Kumar PR, Shanmugasundaram P, Aanandhi MV, 2010, Synthesis, Characterisation and in-vitro Antiinflammatory and Anthelmintic activities of 1,3,4-Oxadiazole derivatives. International Journal of Chem Tech Research, 2(4): 1867-70.
• James ND, Growcott JW, 2009. Zibotentan. Drugs Future, 34: 624–633. Dogan HN, Duran A,Yemni E, 1999. Synthesis and antibacterial activity of 1-(3-hydroxy-2-naphthoyl)-4-substituted thiosemicarbazides. Drug Metabolism and Drug Interactions, 15: 187-195
• Jayashankar B, Rai KML, Baskaran N, Sathish H.S, 2009. Synthesis and pharmacological evaluation of 1,3,4- oxadiazole bearing bis(heterocycle) derivatives as anti-inflammatory and analgesic agents. European Journal of Medicinal Chemistry , 44: 3898–902.
• Kanthiah S, Kalusalingam A, Velayutham R, Vimala AT, and Beyatricks J, 2011. 5-(2-aminophenyl)-1,3,4- oxadiazole-2(3H)-thione derivatives Synthesis, characterization and antimicrobial evaluation. International Journal of Pharmaceutical Sciences Review and Research, 6(1): 64-7. Naveena CS, Boja P, Kumari NS, 2010. Synthesis, characterization and antimicrobial activity of some disubstituted 1,3,4-oxadiazoles carrying 2-(aryloxymethyl)phenyl moiety. European Journal of Medicinal Chemistry ,45:4708-19.
• Oliveira C, Lira B, Barbosa-Filho J, Lorenzo JGF. and Athayde-Filho P, 2012. Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012. Molecules,17: 10192-10291.
• Rostom SAF, Shalaby MA, ElDemellawy MA, 2003. Synthesis of new 1-(4- chlorophenyl)-4-hydroxy-1H-pyrazole- 3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. European Journal of Medicinal Chemistry .38: 959-74.
• Sridhara AM, Reddy KRV, Keshavayya J, Goud PSK, Somashekar BC, Bose P, 2010. Synthesis and antimicrobial activity of 2-substituted [4-(1,3,4-oxadiazol-2-yl methyl)] phthalazin-1(2H)-one derivatives. European Journal of Medicinal Chemistry, 45: 4983-9.
• Shyma PC, Balakrishna K, Peethambar SK, Vijesh AM, 2015. Synthesis, characterization, antidiabetic and antioxidant activity of 1,3,4-oxadiazole derivatives bearing 6-methyl pyridine moiety, Der Pharma Chemica, 7(12): 137-145
• Savarino A, 2006, A historical sketch of the discovery and development of HIV-1 integrase inhibitors. Expert Opinion on Investigational Drugs, 15: 1507–1522. Bouabdallah I, Rahal M, Harit T, El Hajbi A, Malek F, Eddike D, Tillard M, Ramdani A, 2013. Hartree-Fock and density functional theory studies on tautomerism of 5,5-diisopropyl-3,3-bipyrazole in gas phase and solution. Chemical Physics Letters, 588: 208-214
• Moser A, Range K, York DM, 2010. Accurate Proton Affinity and Gas-Phase Basicity Values for Molecules Important in Biocatalysis. The Journal of Physical Chemistry B, 114: 13911-13921.