Research Article
BibTex RIS Cite

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

Year 2018, , 169 - 177, 31.03.2018
https://doi.org/10.21597/jist.407866

Abstract

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.

References

  • 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.

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

Year 2018, , 169 - 177, 31.03.2018
https://doi.org/10.21597/jist.407866

Abstract

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. 

References

  • 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.
There are 13 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Kimya / Chemistry
Authors

Murat Genç 0000-0003-1224-4128

Publication Date March 31, 2018
Submission Date July 25, 2017
Acceptance Date October 2, 2017
Published in Issue Year 2018

Cite

APA Genç, M. (2018). N-(4-metilfenil)-N-(5-(3-hidroksinaftil-2-il)-1,3,4-oksadiazol-2-il) amin’in Sentezi Karakterizasyonu ve Gaussian Hesaplamaları. Journal of the Institute of Science and Technology, 8(1), 169-177. https://doi.org/10.21597/jist.407866
AMA Genç M. N-(4-metilfenil)-N-(5-(3-hidroksinaftil-2-il)-1,3,4-oksadiazol-2-il) amin’in Sentezi Karakterizasyonu ve Gaussian Hesaplamaları. Iğdır Üniv. Fen Bil Enst. Der. March 2018;8(1):169-177. doi:10.21597/jist.407866
Chicago Genç, Murat. “N-(4-Metilfenil)-N-(5-(3-Hidroksinaftil-2-Il)-1,3,4-Oksadiazol-2-Il) amin’in Sentezi Karakterizasyonu Ve Gaussian Hesaplamaları”. Journal of the Institute of Science and Technology 8, no. 1 (March 2018): 169-77. https://doi.org/10.21597/jist.407866.
EndNote Genç M (March 1, 2018) N-(4-metilfenil)-N-(5-(3-hidroksinaftil-2-il)-1,3,4-oksadiazol-2-il) amin’in Sentezi Karakterizasyonu ve Gaussian Hesaplamaları. Journal of the Institute of Science and Technology 8 1 169–177.
IEEE M. Genç, “N-(4-metilfenil)-N-(5-(3-hidroksinaftil-2-il)-1,3,4-oksadiazol-2-il) amin’in Sentezi Karakterizasyonu ve Gaussian Hesaplamaları”, Iğdır Üniv. Fen Bil Enst. Der., vol. 8, no. 1, pp. 169–177, 2018, doi: 10.21597/jist.407866.
ISNAD Genç, Murat. “N-(4-Metilfenil)-N-(5-(3-Hidroksinaftil-2-Il)-1,3,4-Oksadiazol-2-Il) amin’in Sentezi Karakterizasyonu Ve Gaussian Hesaplamaları”. Journal of the Institute of Science and Technology 8/1 (March 2018), 169-177. https://doi.org/10.21597/jist.407866.
JAMA Genç M. N-(4-metilfenil)-N-(5-(3-hidroksinaftil-2-il)-1,3,4-oksadiazol-2-il) amin’in Sentezi Karakterizasyonu ve Gaussian Hesaplamaları. Iğdır Üniv. Fen Bil Enst. Der. 2018;8:169–177.
MLA Genç, Murat. “N-(4-Metilfenil)-N-(5-(3-Hidroksinaftil-2-Il)-1,3,4-Oksadiazol-2-Il) amin’in Sentezi Karakterizasyonu Ve Gaussian Hesaplamaları”. Journal of the Institute of Science and Technology, vol. 8, no. 1, 2018, pp. 169-77, doi:10.21597/jist.407866.
Vancouver Genç M. N-(4-metilfenil)-N-(5-(3-hidroksinaftil-2-il)-1,3,4-oksadiazol-2-il) amin’in Sentezi Karakterizasyonu ve Gaussian Hesaplamaları. Iğdır Üniv. Fen Bil Enst. Der. 2018;8(1):169-77.