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7-Etil-6-klor-2-metilkromon ve 7-Etil-6-klorflavonun Sentezi ve Teorik Hesaplamaları

Year 2020, , 26 - 35, 13.03.2020
https://doi.org/10.17798/bitlisfen.556653

Abstract

Bu
çalışmada, 7-Etil-6-klor-2-metil kroman ve 7-Etil-6-klorflavon bileşikleri
sentezlenip, teorik spektroskopik özellikleri B3LYP/6-31G (d,p) temel seti ile
araştırılmıştır. Sentezlenen bileşiklerin ilk olarak DFT yöntemi ve 6-31G (d,p)
temel setinden faydalanılarak optimizasyonları yapılmıştır. H-NMR, kimyasal
kayma değerleri hesaplanmış, teorik olarak hesaplanan değerlerin elde edilen
deneysel verilerle uyum içinde oldukları görülmüştür. Deneysel ve teorik
kimyasal kayma değerleri için korelasyon grafiği ile regrasyon analizleri
yapılmıştır. Bunlara ilaveten çalışılan bileşiklerin en yüksek dolu moleküler
orbital enerjisi (HOMO) ve en düşük boş moleküler orbital enerjisi (LUMO), bağ
uzunlukları, bağ açıları ve mulliken atomik yük değerleri hesaplanmıştır. HOMO
ve LUMO enerji değerlerinden yararlanılarak iyonizasyon potansiyeli elektron
ilgisi, elektronegatiflik,  kimyasal
sertlik, kimyasal yumuşaklık gibi parametrelerin hesaplamaları bir tablo
halinde sunulmuştur. 

References

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  • 2. Chetan B., Nımesh M. S., Manısh P. P. and Ranjan G. P. 2012. Microwave-assisted synthesis of novel 4H-chromene derivatives bearing phenoxypyrazole and their antimicrobial activity assessment, Journal of the Serbian Chemical Society, 77 (9) 1165–1174
  • 3. Milan M., Mirjana M., Desanka B., Sanja M., Neda N., Vladimir M., Nenad V., Slobodan S., and Slavica S. 2011. In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives SAR, QSAR and DFT Studies, International Journal of Molecular Sciences, 12, 2822-2841
  • 4. Jie-Fei C., Akira I., Yoshinori O., Thomas A. and Alex N. 2003. Novel Chromene Derivatives as TNF-α Inhibitors, Bioorganic&Medicinal Chemistry Letters, 13:3647–3650
  • 5. Suresh T., Arunıma V., Atın K., Sandeep G., Prarthana V. Rewatkar and Ganesh R. K. 2010. Novel Chromeneımıdazole Derıvatıves As Antıfungal Compounds: Synthesıs and In Vitro Evaluation Acta Poloniae Pharmaceutica Drug Research, Vol. 67 No. 4 pp. 423-427
  • 6. Nareshkumar J., Jiayi X., Ramesh M. Kanojia F. D., Guo J., Emmanuel P., Muh-Tsann L., Amy M., George A., Michael R., Xun L., DoWon H., Martin C., Sean P., David R., Ronald R., Scott L., and Zhihua S. 2009. Identification and Structure-Activity Relationships of Chromene-Derived Selective Estrogen Receptor Modulators for Treatment of Postmenopausal Symptoms, Journal of Medicinal Chemistry, 52, 7544–7569
  • 7. Jun M.,Makoto I.,Makoto T., and Haruo S. 2006. A Synthetic Study on Antiviral and Antioxidative Chromene Derivative, Chemical and Pharmaceutical Bulletin, 54(3) 391—396
  • 8. Aliaa M.K., Manal M.K., Eman K., Abd El-all and Heba A., Elshemy H. 2012 Design and synthesis of substituted chromenes as potential anticancer agents, International Journal of Pharmaceutical Research & Development, 4(3):310-322.
  • 9. Denish C.K., Hetal K.P., Nilesh K.G. 2012. Synthesis, characterization & anti-HIV activity of 4-Hydroxy-3-(5-methylisoxazol-3- yl)pyrano(3,2-C)chromene-2,5-dione, Asian Journal of Biochemical and Pharmaceutical Research, 2(2):126-130.
  • 10. Nimesh R.K., Dhaval D.H., Prashant T.M., Saurabh K.P. 2011. Synthesis and evaluation of in vitro antitubercular activity and antimicrobial activity of some novel 4H-chromeno[2,3-d]pyrimidine via 2- amino-4-phenyl-4H-chromene-3-carbonitriles, Medicinal Chemistry Research, 20(7);854-864.
  • 11. Nitin K., Sushil K., Himanshu G., Sharma P.K. 2012. 3-Hydroxy-2-(substituted phenyl) -4H-chromen-4-one derivatives- synthesis, spectral characterization and pharmacological screening, World Research Journal of Biochemistry, 1(1): 1-5.
  • 12. Bhat M.A., Siddiqui N., Khan S.A. 2008. Synthesis of novel 3-(4-acetyl-5H/methyl-5-substituted phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones as potential anticonvulsant agents, Acta Poloniae Pharmaceutica, 65(2):235-39.
  • 13. Thompson L. A., Ellman J. A. 1996. Synthesis and Applications of Small Molecule Libraries, Chemical Reviews, 96, 555-600.
  • 14. Hester L. V. L.,Wei Z.,Tore H., Floris P. J. T., Rutjes and Karl A.J. 2003. Formation of optically active chromanes by catalytic asymmetric tandem oxa-Michael addition–Friedel–Crafts alkylation reactions, Organic and Biomolecular Chemistry, 1, 1953–1958
  • 15. Nianhuan Y., Aiming S., Xiaobing W., Seth D., and Kit S. L. 2007. Synthesis of Flavonoid Analogues as Scaffolds for Natural Product-Based Combinatorial Libraries, American Chemical Society, 9, 668-676
  • 16. Atohoun Y. G. S., Chabi D. R., Kpota Houngue M. T. A., Urbain K. A., Gaston A. K., et Jean-Baptiste M. 2016. Theoretical Study of antioxidant properties of three isomers flavonoids: kaempferol, luteolin and fisetin, American Journal Of Scientific And Industrial Research, 7(6):145-152
  • 17. Frisch M.J., Trucks H.B., Schlegel G.E., Scuseria M., Robb J.R., Cheeseman G., Scalmani V., Barone B., Mennucci G.A., Petersson H., Nakatsuji M., Caricato X., Li H.P., Hratchian A.F., Izmaylov J., Bloino G., Zheng J.L, Sonnenberg M., Hada M., Ehara K, Toyota R, Fukuda J, Hasegawa M., Ishida T., Nakajima Y., Honda O., Kitao H., Nakai T., Vreven A., Montgomery J., Peralta F., Ogliaro M., Bearpark J.J., Heyd E., Brothers K.N., Kudin V.N., Staroverov R., Kobayashi J., Normand K., Raghavachari A., Rendell J.C., Burant S.S., Iyengar J., Tomasi M., Cossi N., Rega J.M., Millam M. 2009. Gaussian Inc. Wallingford CT.
  • 18. Lee C., Yang W., and Parr R. 1988. Development of the Colle- Salvetti correlation energy formula into a functional of the electron density, Physical Review B, 37, 785–789,
  • 19. Wolinski K., Hinton J. F., and Pulay P. 1990. Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations, Journal of the American Chemical Society, 112, 8251
  • 20. Erdoğdu Y., Ünsalan O. and Güllüoğlu M. T. 2009. Vibrational analysis of flavone, Turkish Journal Of Physics, 33 , 249 – 259.
  • 21. Günay N., Pir H. ve Atalay Y. 2011. L-Asparaginyum Pikrat Molekülünün Spektroskopik Özelliklerinin Teorik Olarak İncelenmesi, Sakarya Üniversitesi Fen Edebiyat Dergisi, 15-32
  • 22. Boopathi M., Udhayakala P., Ramkumaar G. R. 2016. Vibrational spectroscopic (FT-IR, FT-Raman), NMR and electronic structure calculations of metaxalone, Der Pharma Chemica, 8(7):161-172
Year 2020, , 26 - 35, 13.03.2020
https://doi.org/10.17798/bitlisfen.556653

Abstract

References

  • 1. Henriette G., Lorraine L., Bettina H., Clemence D., Kelly D., Irenej K., Dominique C., Chantal B., Lilianne G., Sui-Xiong C., John D., Denis L., Shailaja K., and Ben T. 2004. Antivascular and antitumor evaluation of 2-amino-4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-chromenes, a novel series of anticancer agents, Molecular Cancer Therapeutics, 3(11).
  • 2. Chetan B., Nımesh M. S., Manısh P. P. and Ranjan G. P. 2012. Microwave-assisted synthesis of novel 4H-chromene derivatives bearing phenoxypyrazole and their antimicrobial activity assessment, Journal of the Serbian Chemical Society, 77 (9) 1165–1174
  • 3. Milan M., Mirjana M., Desanka B., Sanja M., Neda N., Vladimir M., Nenad V., Slobodan S., and Slavica S. 2011. In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives SAR, QSAR and DFT Studies, International Journal of Molecular Sciences, 12, 2822-2841
  • 4. Jie-Fei C., Akira I., Yoshinori O., Thomas A. and Alex N. 2003. Novel Chromene Derivatives as TNF-α Inhibitors, Bioorganic&Medicinal Chemistry Letters, 13:3647–3650
  • 5. Suresh T., Arunıma V., Atın K., Sandeep G., Prarthana V. Rewatkar and Ganesh R. K. 2010. Novel Chromeneımıdazole Derıvatıves As Antıfungal Compounds: Synthesıs and In Vitro Evaluation Acta Poloniae Pharmaceutica Drug Research, Vol. 67 No. 4 pp. 423-427
  • 6. Nareshkumar J., Jiayi X., Ramesh M. Kanojia F. D., Guo J., Emmanuel P., Muh-Tsann L., Amy M., George A., Michael R., Xun L., DoWon H., Martin C., Sean P., David R., Ronald R., Scott L., and Zhihua S. 2009. Identification and Structure-Activity Relationships of Chromene-Derived Selective Estrogen Receptor Modulators for Treatment of Postmenopausal Symptoms, Journal of Medicinal Chemistry, 52, 7544–7569
  • 7. Jun M.,Makoto I.,Makoto T., and Haruo S. 2006. A Synthetic Study on Antiviral and Antioxidative Chromene Derivative, Chemical and Pharmaceutical Bulletin, 54(3) 391—396
  • 8. Aliaa M.K., Manal M.K., Eman K., Abd El-all and Heba A., Elshemy H. 2012 Design and synthesis of substituted chromenes as potential anticancer agents, International Journal of Pharmaceutical Research & Development, 4(3):310-322.
  • 9. Denish C.K., Hetal K.P., Nilesh K.G. 2012. Synthesis, characterization & anti-HIV activity of 4-Hydroxy-3-(5-methylisoxazol-3- yl)pyrano(3,2-C)chromene-2,5-dione, Asian Journal of Biochemical and Pharmaceutical Research, 2(2):126-130.
  • 10. Nimesh R.K., Dhaval D.H., Prashant T.M., Saurabh K.P. 2011. Synthesis and evaluation of in vitro antitubercular activity and antimicrobial activity of some novel 4H-chromeno[2,3-d]pyrimidine via 2- amino-4-phenyl-4H-chromene-3-carbonitriles, Medicinal Chemistry Research, 20(7);854-864.
  • 11. Nitin K., Sushil K., Himanshu G., Sharma P.K. 2012. 3-Hydroxy-2-(substituted phenyl) -4H-chromen-4-one derivatives- synthesis, spectral characterization and pharmacological screening, World Research Journal of Biochemistry, 1(1): 1-5.
  • 12. Bhat M.A., Siddiqui N., Khan S.A. 2008. Synthesis of novel 3-(4-acetyl-5H/methyl-5-substituted phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones as potential anticonvulsant agents, Acta Poloniae Pharmaceutica, 65(2):235-39.
  • 13. Thompson L. A., Ellman J. A. 1996. Synthesis and Applications of Small Molecule Libraries, Chemical Reviews, 96, 555-600.
  • 14. Hester L. V. L.,Wei Z.,Tore H., Floris P. J. T., Rutjes and Karl A.J. 2003. Formation of optically active chromanes by catalytic asymmetric tandem oxa-Michael addition–Friedel–Crafts alkylation reactions, Organic and Biomolecular Chemistry, 1, 1953–1958
  • 15. Nianhuan Y., Aiming S., Xiaobing W., Seth D., and Kit S. L. 2007. Synthesis of Flavonoid Analogues as Scaffolds for Natural Product-Based Combinatorial Libraries, American Chemical Society, 9, 668-676
  • 16. Atohoun Y. G. S., Chabi D. R., Kpota Houngue M. T. A., Urbain K. A., Gaston A. K., et Jean-Baptiste M. 2016. Theoretical Study of antioxidant properties of three isomers flavonoids: kaempferol, luteolin and fisetin, American Journal Of Scientific And Industrial Research, 7(6):145-152
  • 17. Frisch M.J., Trucks H.B., Schlegel G.E., Scuseria M., Robb J.R., Cheeseman G., Scalmani V., Barone B., Mennucci G.A., Petersson H., Nakatsuji M., Caricato X., Li H.P., Hratchian A.F., Izmaylov J., Bloino G., Zheng J.L, Sonnenberg M., Hada M., Ehara K, Toyota R, Fukuda J, Hasegawa M., Ishida T., Nakajima Y., Honda O., Kitao H., Nakai T., Vreven A., Montgomery J., Peralta F., Ogliaro M., Bearpark J.J., Heyd E., Brothers K.N., Kudin V.N., Staroverov R., Kobayashi J., Normand K., Raghavachari A., Rendell J.C., Burant S.S., Iyengar J., Tomasi M., Cossi N., Rega J.M., Millam M. 2009. Gaussian Inc. Wallingford CT.
  • 18. Lee C., Yang W., and Parr R. 1988. Development of the Colle- Salvetti correlation energy formula into a functional of the electron density, Physical Review B, 37, 785–789,
  • 19. Wolinski K., Hinton J. F., and Pulay P. 1990. Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations, Journal of the American Chemical Society, 112, 8251
  • 20. Erdoğdu Y., Ünsalan O. and Güllüoğlu M. T. 2009. Vibrational analysis of flavone, Turkish Journal Of Physics, 33 , 249 – 259.
  • 21. Günay N., Pir H. ve Atalay Y. 2011. L-Asparaginyum Pikrat Molekülünün Spektroskopik Özelliklerinin Teorik Olarak İncelenmesi, Sakarya Üniversitesi Fen Edebiyat Dergisi, 15-32
  • 22. Boopathi M., Udhayakala P., Ramkumaar G. R. 2016. Vibrational spectroscopic (FT-IR, FT-Raman), NMR and electronic structure calculations of metaxalone, Der Pharma Chemica, 8(7):161-172
There are 22 citations in total.

Details

Primary Language Turkish
Journal Section Araştırma Makalesi
Authors

Bayhan Karabulut 0000-0002-6677-5023

Publication Date March 13, 2020
Submission Date April 22, 2019
Acceptance Date August 1, 2019
Published in Issue Year 2020

Cite

IEEE B. Karabulut, “7-Etil-6-klor-2-metilkromon ve 7-Etil-6-klorflavonun Sentezi ve Teorik Hesaplamaları”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 9, no. 1, pp. 26–35, 2020, doi: 10.17798/bitlisfen.556653.



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