Research Article
BibTex RIS Cite

Synthesis and Spectroscopic Characterization of Novel Pyridine-based N-acyl Hydrazone Derivatives and Molecular Docking Studies on Glucosamine-6-Phosphate

Year 2023, Volume: 13 Issue: 1, 135 - 152, 15.03.2023

Derya Vural Selbi Keskin

https://doi.org/10.31466/kfbd.1184337

Abstract

Antimicrobial resistance in infectious diseases caused by organisms such as bacteria, fungi, viruses, and parasites has led to an increase in studies and demands for new antimicrobial drug development. The compounds including pyridine and N-acylhydrazone skeletons in their structures have a large application area in drug discovery due to their anticancer, anti-tubercular, anti-bacterial and anti-fungal activities. Here, the novel N-acyl-hydrazone derivatives, (E)-2-oxo-N'-(2,3,4-trimethoxybenzylidene)-1,2-dihydropyridine-3-carbohydrazide and (E)-N'-(1-(4-bromophenyl) ethylidene)-2-oxo-1,2-dihydropyridine-3-carbohydrazide were synthesized through a multistep reaction sequence. The structures of newly synthesized compounds were established on the basis of IR, 1D and 2D NMR spectra and mass spectral data. The theoretical electronic structure analysis was performed by density functional theory (DFT) at the B3LYP level with the 6-311++G(d,p) basis set in the gas phase of synthesized compounds. The newly synthesized compounds were docked on glucosamine-6 phosphate synthase to determine potential interactions between the analyzed compounds and its active site due to its role in microbial cell wall synthesis. The possibilities of these compounds to being active for antimycobacterial and antituberculosis have been found as quite high, and their interactions in the binding site have been determined with the range of binding affinity, [-7.1, -7.3] kcal/mol, respectively.

Keywords

N-acylhydrazone nitrogen containing heterocycles molecular docking glucosamine-6 phosphate

Supporting Institution

the Scientific Research Project Found of Giresun Üniversitesi

Project Number

FEN-BAP-A-250-221-26

References

  • Referans1 Ali, I., Burki, S., El-Haj, B. M., Shafiullah, Parveen, S., Nadeem, H. Ş., Nadeem, S., & Shah, M. R. (2020). Synthesis and characterization of pyridine-based organic salts: Their antibacterial, antibiofilm and wound healing activities. Bioorganic Chemistry, 100, 103937. doi: 10.1016/j.bioorg.2020.103937
  • Referans2 Ali, M. T., Blicharska, N., Shilpi, J. A., & Seidel, V. (2018). Investigation of the anti-TB potential of selected propolis constituents using a molecular docking approach. Scientific Reports, 8:12238, 1–8. doi: 10.1038/s41598-018-30209-y
  • Referans3 Almutairi, M. S., Zakaria, A. S., Ignasius, P. P., Al-Wabli, R. I., Joe, I. H., & Attia, M. I. (2018). Synthesis, spectroscopic investigations, DFT studies, molecular docking and antimicrobial potential of certain new indole-isatin molecular hybrids: Experimental and theoretical approaches. Journal of Molecular Structure, 1153, 333–345. doi: 10.1016/j.molstruc.2017.10.025
  • Referans4 Askri, S., Dbeibia, A., McHiri, C., Boudriga, S., Knorr, M., Roulland, E., Laprévote, O., Saffon-merceron, N., & Gharbi, R. (2022). Antimicrobial activity and in silico molecular docking studies of pentacyclic spiro[oxindole-2,3′-pyrrolidines] tethered with succinimide scaffolds. Applied Sciences, 12(1), 360. doi: 10.3390/app12010360
  • Referans5 Backes, G. L., Jursic, B. S., & Neumann, D. M. (2015). Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs. Bioorganic and Medicinal Chemistry, 23(13), 3397–3407. doi: 10.1016/j.bmc.2015.04.040
  • Referans6 Banerjee, K., Gupta, U., Gupta, S., Wadhwa, G., Gabrani, R., Sharma, S. K., & Jain, C. K. (2011). Molecular docking of glucosamine-6-phosphate synthase in Rhizopus oryzae. Bioinformation, 7(6), 285–290. doi: 10.6026/007/97320630007285
  • Referans7 Becke, A. D. (1993). Density-functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98(7), 5648–5652. doi: 10.1063/1.464913
  • Referans8 Bedia, K. K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R., & Dimoglo, A. (2006). Synthesis and characterization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. European Journal of Medicinal Chemistry, 41(11), 1253–1261. doi: 10.1016/j.ejmech.2006.06.009
  • Referans9 BIOVIA, Dassault Systemes, Discovery Studio Modeling Environment, Release 2017, San Diego, Dassault Systemes ___ (2016).
  • Referans10 Cai, Y., Wang, Z., Li, Z., Zhang, M., & Wu, J. (2011). (E)-1-(4-Methoxyphenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one. Acta Crystallographica Section, E67, o1432. doi: 10.1107/S1600536811017788
  • Referans11 Cancès, E., Mennucci, B., & Tomasi, J. (1997). A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to Isotropic and anisotropic dielectrics. Journal of Chemical Physics, 107(8), 3032–3041. doi: 10.1063/1.474659
  • Referans12 Chmara, H., & Borowski, E. (1986). Bacteriolytic effect of cessation of glucosamine supply, induced by specific inhibition of glucosamine-6-phosphate synthetase. Acta Microbiologica Polonica, 35(1–2), 15–27.
  • Referans13 David, K., Munoz-Muriedas, J., Sime, M., Steadman, J. G. A., Thewlis, R. E. A., Trani, G., & Walter, D. S. (2010). 5,6,7,8-TetrahvdroM.2,41triazolor4,3-alpvrazine derivatives as P2X7 modulators. WO 2010/125102 Al.
  • Referans14 Demurtas, M., Baldisserotto, A., Lampronti, I., Moi, D., Balboni, G., Pacifico, S., Vertuani, S., Manfredini, S., & Onnis, V. (2019). Indole derivatives as multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity of indole hydrazones. Bioorganic Chemistry, 85, 568–576. doi: 10.1016/j.bioorg.2019.02.007
  • Referans15 Dennington, R., Keith, T., & Millam, J. (2009). GaussView, Version 5. Semichem Inc., Shawnee Mission. Shawnee Mission KS, Semichem Inc.
  • Referans16 Ditchfield, R. (1974). Self-consistent perturbation theory of diamagnetism. Molecular Physics: An International Journal at the Interface Between Chemistry and Physics, 27(4), 789–807. doi: 10.1080/00268977400100711
  • Referans17 El Sayed, M. T., El-Sharief, M. A. M. S., Zarie, E. S., Morsy, N. M., Elsheakh, A. R., Nayel, M., Voronkov, A., Berishvili, V., Sabry, N. M., Hassan, G. S., & Abdel-Aziz, H. A. (2018). Design, synthesis, anti-inflammatory antitumor activities, molecular modeling and molecular dynamics simulations of potential naprosyn® analogs as COX-1 and/or COX-2 inhibitors. Bioorganic Chemistry, 76, 188–201. doi: 10.1016/j.bioorg.2017.11.002
  • Referans18 Fikrika, H., Ambarsari, L., & Sumaryada, T. (2016). Molecular Docking Studies of Catechin and Its Derivatives as Anti-bacterial Inhibitor for Glucosamine-6-Phosphate Synthase. IOP Conference Series: Earth and Environmental Science, 31(1), 012009. doi: 10.1088/1755-1315/31/1/012009
  • Referans19 Filimonov, D. A., Lagunin, A. A., Gloriozova, T. A., Rudik, A. V., Druzhilovskii, D. S., Pogodin, P. V., & Poroikov, V. V. (2014). Prediction of the biological activity spectra of organic compounds using the pass online web resource. Chemistry of Heterocyclic Compounds, 50(3), 444–457. doi: 10.1007/s10593-014-1496-1
  • Referans20 Frisch, M. J., Trucks, G. W., Schlegel, H. B., & G. E. Scuseria, et al. (2009). Gaussian 09, Revision C.01. Gaussian Inc. Wallingford, CT.
  • Referans21 Fun, H. K., Chantrapromma, S., & Suwunwong, T. (2011). (2E)-1-(Pyridin-2-yl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one. Acta Crystallographica Section, E67, o2789. doi: 10.1107/S1600536811039110
  • Referans22 He, W. W., Yang, J., Ma, J. F., & Song, S. Y. (2012). Metal-dependent assemblies of an unusual pentanuclear cadmium cluster and a fascinating 3D 4-connected lead-containing framework. Inorganic Chemistry Communications, 24, 63–66. doi: 10.1016/j.inoche.2012.07.044
  • Referans23 Kandasamy, M., Mak, K.-K., Devadoss, T., Thanikachalam, P. V., Sakirolla, R., Choudhury, H., & Pichika, M. R. (2019). Construction of a novel quinoxaline as a new class of Nrf2 activator. BMC Chemistry, 13(1), 1–10. doi: 10.1186/s13065-019-0633-4
  • Referans24 Khalil, N. A., Ahmed, E. M., Mohamed, K. O., & Zaitone, S. A. B. (2013). Synthesis of new nicotinic acid derivatives and their evaluation as analgesic and anti-inflammatory agents. Chemical and Pharmaceutical Bulletin, 61(9), 933–940. doi: 10.1248/cpb.c13-00261
  • Referans25 Kotb, E. R., Soliman, H. A., Morsy, E. M. H., & Abdelwahed, N. A. M. (2017). New pyridine and triazolopyridine derivatives: Synthesis, antimicrobial and antioxidant evaluation. Acta Poloniae Pharmaceutica - Drug Research, 74(3), 861–872.
  • Referans26 Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785–789.
  • Referans27 More, U. A., Joshi, S. D., Aminabhavi, T. M., Gadad, A. K., Nadagouda, M. N., & Kulkarni, V. H. (2014). Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents. European Journal of Medicinal Chemistry, 71, 199–218. doi: 10.1016/j.ejmech.2013.11.004
  • Referans28 Morjan, R. Y., Mkadmh, A. M., Beadham, I., Elmanama, A. A., Mattar, M. R., Raftery, J., Pritchard, R. G., Awadallah, A. M., & Gardiner, J. M. (2014). Antibacterial activities of novel nicotinic acid hydrazides and their conversion into N -acetyl-1,3,4-oxadiazoles. Bioorganic & Medicinal Chemistry Letters, 24, 5796–5800. doi: 10.1016/j.bmcl.2014.10.029
  • Referans29 Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. doi: 10.1002/jcc.21256
  • Referans30 Mouilleron, S., Badet-Denisot, M. A., & Golinelli-Pimpaneau, B. (2008). Ordering of C-terminal Loop and Glutaminase Domains of Glucosamine-6-Phosphate Synthase Promotes Sugar Ring Opening and Formation of the Ammonia Channel. Journal of Molecular Biology, 377(4), 1174–1185. doi: 10.1016/j.jmb.2008.01.077
  • Referans31 Muluk, M. B., Dhumal, S. T., Rehman, N. N. M. A., Dixit, P. P., Kharat, K. R., & Haval, K. P. (2019). Synthesis, Anticancer and Antimicrobial Evaluation of New (E)-N′-Benzylidene-2-(2-ethylpyridin-4-yl)-4-methylthiazole-5-carbohydrazides. ChemistrySelect, 4(31), 8993–8997. doi: 10.1002/slct.201902030
  • Referans32 Narang, R., Narasimhan, B., Sharma, S., Sriram, D., Yogeeswari, P., Clercq, E. De, Pannecouque, C., & Balzarini, J. (2011). Nicotinic Acid Benzylidene/Phenyl-Ethylidene Hydrazides: Synthesis, Antimicrobial Evaluation and QSAR Studies. Letters in Drug Design & Discovery, 8(8), 733–749. doi: 10.2174/157018011796575999
  • Referans33 Narang, R., Narasimhan, B., Sharma, S., Sriram, D., Yogeeswari, P., De Clercq, E., Pannecouque, C., & Balzarini, J. (2012). Synthesis, antimycobacterial, antiviral, antimicrobial activities, and QSAR studies of nicotinic acid benzylidene hydrazide derivatives. Medicinal Chemistry Research, 21(8), 1557–1576. doi: 10.1007/s00044-011-9664-7
  • Referans34 Neuman, D. M. (2018). Antimicrobial pyridinohydrazide and hydrazomethylpyridine-based agents (US 2018/0072672 A1).
  • Referans35 Pomarnacka, E., Bednarski, P. J., Reszka, P., Dziemidowicz-Borys, E., Bieńczak, A., Werel, W., & Hałasa, R. (2006). Synthesis and biological activity of new 2-amino-8-chloro-5,5-dioxo[1,2,4]triazolo[2,3-b][1,4,2]benzodithiazines. European Journal of Medicinal Chemistry, 41(5), 633–639. doi: 10.1016/j.ejmech.2005.11.009
  • Referans36 Ragavendran, J. V., Sriram, D., Patel, S. K., Reddy, I. V., Bharathwajan, N., Stables, J., & Yogeeswari, P. (2007). Design and synthesis of anticonvulsants from a combined phthalimide-GABA-anilide and hydrazone pharmacophore. European Journal of Medicinal Chemistry, 42(2), 146–151. doi: 10.1016/j.ejmech.2006.08.010
  • Referans37 Shah, N., & Soman, S. (2018). Design , synthesis and evaluation of antimicrobial and anticancer activity of novel 3-aminomethyl pyridin derivatives. European Journal of Pharmaceutical and Medical Research, 5(10), 229–241.
  • Referans38 Shyma, P. C., Kalluraya, B., Peethambar, S. K., Telkar, S., & Arulmoli, T. (2013). Synthesis, characterization and molecular docking studies of some new 1,3,4-oxadiazolines bearing 6-methylpyridine moiety for antimicrobial property. European Journal of Medicinal Chemistry, 68, 394–404. doi: 10.1016/j.ejmech.2013.07.019
  • Referans39 Soujanya, M., & Rajitha, G. (2017). CODEN ( USA ): PCHHAX Synthesis , Characterization , Molecular Docking and Antimicrobial Activity of Nicotinic Acid Derived N-acylhydrazones. Der Pharma Chemica, 9(17), 10–15.
  • Referans40 Tok, F., Uğraş, Z., Sağlık, B. N., Özkay, Y., Kaplancıklı, Z. A., & Koçyiğit-Kaymakçıoğlu, B. (2021). Novel 2,5-disubstituted-1,3,4-oxadiazole derivatives as MAO-B inhibitors: Synthesis, biological evaluation and molecular modeling studies. Bioorganic Chemistry, 112, 104917. doi: 10.1016/j.bioorg.2021.104917
  • Referans41 Trott, O., & Olson, A. J. (2010). AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading. Journal of Computational Chemistry, 31, 455–461. doi: 10.1002/jcc.21334
  • Referans42 Ukrainets, I. V., Sidorenko, L. V., & Golovchenko, O. S. (2007). 4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides. Chemistry of Heterocyclic Compounds, 43(11), 1434–1439. doi: 10.1007/s10593-007-0221-8
  • Referans43 Wang, S., Liu, H. Y., Xu, R. F., & Sun, J. (2017). Synthesis, biological evaluation, and molecular docking studies of diacylhydrazine derivatives possessing 1,4-benzodioxan moiety as potential anticancer agents. Russian Journal of General Chemistry, 87(11), 2671–2677. doi: 10.1134/S1070363217110238
  • Referans44 Wolinski, K., Hinton, J. F., & Pulay, P. (1990). Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations. Journal of the American Chemical Society, 112(23), 8251–8260. doi: 10.1021/ja00179a005
  • Referans45 World Health Organization WHO. (2021). Retrieved from https://www.who.int/news-room/fact-sheets/detail/antimicrobial-resistance
  • Referans46 Wu, J., Zhang, L., Wang, J., Yang, S., & Li, X. (2009). 1-Phenyl-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one. Acta Crystallographica Section, E65, o2805. doi: 10.1107/S1600536809041877

Yeni Piridin Bazlı N-Açil Hidrazon Türevlerinin Sentezi ve Spektroskopik Karakterizasyonu ve Glukozamin-6-Fosfat Üzerine Moleküler Yerleştirme Çalışmaları

Year 2023, Volume: 13 Issue: 1, 135 - 152, 15.03.2023

Derya Vural Selbi Keskin

https://doi.org/10.31466/kfbd.1184337

Abstract

Bakteri, mantar, virüs ve parazit gibi organizmaların neden olduğu bulaşıcı hastalıklardaki antimikrobiyal direnç yeni antimikrobiyal ilaç geliştirmeye yönelik çalışmaların ve taleplerin artmasına neden olmuştur. Temel yapısında piridin ve N-açilhidrazon içeren bileşikler, antikanser, tüberküloz, anti-bakteriyel ve anti-fungal aktivitelerinden dolayı ilaç tasarımında geniş bir uygulama alanına sahiptir. Bu çalışmada, yeni N-açil-hidrazon türevleri, (E)-2-okso-N'-(2,3,4-trimetoksibenziliden)-1,2-dihidropiridin-3-karbohidrazid ve (E)-N'-(1-(4-bromofenil)etiliden)-2-okso-1,2-dihidropiridin-3-karbohidrazid, çok aşamalı bir reaksiyon dizisi yoluyla sentezlenmiştir. Yeni sentezlenen bileşiklerin yapıları IR, 1D ve 2D NMR spektrumları ve kütle spektral verileri kullanılarak belirlenmiştir. Teorik elektronik yapı analizleri ise 6-311++G(d,p) baz setine sahip B3LYP seviyesinde yoğunluk fonksiyonel teorisi kullanılarak gaz fazında gerçekleştirilmiştir. Glukozamin-6 fosfat sentaz proteininin mikrobiyal hücre duvarı sentezindeki rolü nedeniyle, yeni sentezlenen bileşiklerin bu moleküller aralarında gerçekleşebilecek etkileşimlerini belirlemek için moleküler yerleştirme analizi yapılmıştır. Bu bileşiklerin antimikobakteriyel ve antitüberküloz aktivitelerinin oldukça yüksek olduğu belirlenerek bağlanma bölgesindeki etkileşimleri de sırasıyla [-7.1, -7.3] kcal/mol bağlanma afinititesi olarak belirlenmiştir.

Keywords

N-açil hidrazon azot içeren heterohalkalı bileşikler moleküler yerleştirme glukozamin-6 fosfat

Project Number

FEN-BAP-A-250-221-26

References

  • Referans1 Ali, I., Burki, S., El-Haj, B. M., Shafiullah, Parveen, S., Nadeem, H. Ş., Nadeem, S., & Shah, M. R. (2020). Synthesis and characterization of pyridine-based organic salts: Their antibacterial, antibiofilm and wound healing activities. Bioorganic Chemistry, 100, 103937. doi: 10.1016/j.bioorg.2020.103937
  • Referans2 Ali, M. T., Blicharska, N., Shilpi, J. A., & Seidel, V. (2018). Investigation of the anti-TB potential of selected propolis constituents using a molecular docking approach. Scientific Reports, 8:12238, 1–8. doi: 10.1038/s41598-018-30209-y
  • Referans3 Almutairi, M. S., Zakaria, A. S., Ignasius, P. P., Al-Wabli, R. I., Joe, I. H., & Attia, M. I. (2018). Synthesis, spectroscopic investigations, DFT studies, molecular docking and antimicrobial potential of certain new indole-isatin molecular hybrids: Experimental and theoretical approaches. Journal of Molecular Structure, 1153, 333–345. doi: 10.1016/j.molstruc.2017.10.025
  • Referans4 Askri, S., Dbeibia, A., McHiri, C., Boudriga, S., Knorr, M., Roulland, E., Laprévote, O., Saffon-merceron, N., & Gharbi, R. (2022). Antimicrobial activity and in silico molecular docking studies of pentacyclic spiro[oxindole-2,3′-pyrrolidines] tethered with succinimide scaffolds. Applied Sciences, 12(1), 360. doi: 10.3390/app12010360
  • Referans5 Backes, G. L., Jursic, B. S., & Neumann, D. M. (2015). Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs. Bioorganic and Medicinal Chemistry, 23(13), 3397–3407. doi: 10.1016/j.bmc.2015.04.040
  • Referans6 Banerjee, K., Gupta, U., Gupta, S., Wadhwa, G., Gabrani, R., Sharma, S. K., & Jain, C. K. (2011). Molecular docking of glucosamine-6-phosphate synthase in Rhizopus oryzae. Bioinformation, 7(6), 285–290. doi: 10.6026/007/97320630007285
  • Referans7 Becke, A. D. (1993). Density-functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98(7), 5648–5652. doi: 10.1063/1.464913
  • Referans8 Bedia, K. K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R., & Dimoglo, A. (2006). Synthesis and characterization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. European Journal of Medicinal Chemistry, 41(11), 1253–1261. doi: 10.1016/j.ejmech.2006.06.009
  • Referans9 BIOVIA, Dassault Systemes, Discovery Studio Modeling Environment, Release 2017, San Diego, Dassault Systemes ___ (2016).
  • Referans10 Cai, Y., Wang, Z., Li, Z., Zhang, M., & Wu, J. (2011). (E)-1-(4-Methoxyphenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one. Acta Crystallographica Section, E67, o1432. doi: 10.1107/S1600536811017788
  • Referans11 Cancès, E., Mennucci, B., & Tomasi, J. (1997). A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to Isotropic and anisotropic dielectrics. Journal of Chemical Physics, 107(8), 3032–3041. doi: 10.1063/1.474659
  • Referans12 Chmara, H., & Borowski, E. (1986). Bacteriolytic effect of cessation of glucosamine supply, induced by specific inhibition of glucosamine-6-phosphate synthetase. Acta Microbiologica Polonica, 35(1–2), 15–27.
  • Referans13 David, K., Munoz-Muriedas, J., Sime, M., Steadman, J. G. A., Thewlis, R. E. A., Trani, G., & Walter, D. S. (2010). 5,6,7,8-TetrahvdroM.2,41triazolor4,3-alpvrazine derivatives as P2X7 modulators. WO 2010/125102 Al.
  • Referans14 Demurtas, M., Baldisserotto, A., Lampronti, I., Moi, D., Balboni, G., Pacifico, S., Vertuani, S., Manfredini, S., & Onnis, V. (2019). Indole derivatives as multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity of indole hydrazones. Bioorganic Chemistry, 85, 568–576. doi: 10.1016/j.bioorg.2019.02.007
  • Referans15 Dennington, R., Keith, T., & Millam, J. (2009). GaussView, Version 5. Semichem Inc., Shawnee Mission. Shawnee Mission KS, Semichem Inc.
  • Referans16 Ditchfield, R. (1974). Self-consistent perturbation theory of diamagnetism. Molecular Physics: An International Journal at the Interface Between Chemistry and Physics, 27(4), 789–807. doi: 10.1080/00268977400100711
  • Referans17 El Sayed, M. T., El-Sharief, M. A. M. S., Zarie, E. S., Morsy, N. M., Elsheakh, A. R., Nayel, M., Voronkov, A., Berishvili, V., Sabry, N. M., Hassan, G. S., & Abdel-Aziz, H. A. (2018). Design, synthesis, anti-inflammatory antitumor activities, molecular modeling and molecular dynamics simulations of potential naprosyn® analogs as COX-1 and/or COX-2 inhibitors. Bioorganic Chemistry, 76, 188–201. doi: 10.1016/j.bioorg.2017.11.002
  • Referans18 Fikrika, H., Ambarsari, L., & Sumaryada, T. (2016). Molecular Docking Studies of Catechin and Its Derivatives as Anti-bacterial Inhibitor for Glucosamine-6-Phosphate Synthase. IOP Conference Series: Earth and Environmental Science, 31(1), 012009. doi: 10.1088/1755-1315/31/1/012009
  • Referans19 Filimonov, D. A., Lagunin, A. A., Gloriozova, T. A., Rudik, A. V., Druzhilovskii, D. S., Pogodin, P. V., & Poroikov, V. V. (2014). Prediction of the biological activity spectra of organic compounds using the pass online web resource. Chemistry of Heterocyclic Compounds, 50(3), 444–457. doi: 10.1007/s10593-014-1496-1
  • Referans20 Frisch, M. J., Trucks, G. W., Schlegel, H. B., & G. E. Scuseria, et al. (2009). Gaussian 09, Revision C.01. Gaussian Inc. Wallingford, CT.
  • Referans21 Fun, H. K., Chantrapromma, S., & Suwunwong, T. (2011). (2E)-1-(Pyridin-2-yl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one. Acta Crystallographica Section, E67, o2789. doi: 10.1107/S1600536811039110
  • Referans22 He, W. W., Yang, J., Ma, J. F., & Song, S. Y. (2012). Metal-dependent assemblies of an unusual pentanuclear cadmium cluster and a fascinating 3D 4-connected lead-containing framework. Inorganic Chemistry Communications, 24, 63–66. doi: 10.1016/j.inoche.2012.07.044
  • Referans23 Kandasamy, M., Mak, K.-K., Devadoss, T., Thanikachalam, P. V., Sakirolla, R., Choudhury, H., & Pichika, M. R. (2019). Construction of a novel quinoxaline as a new class of Nrf2 activator. BMC Chemistry, 13(1), 1–10. doi: 10.1186/s13065-019-0633-4
  • Referans24 Khalil, N. A., Ahmed, E. M., Mohamed, K. O., & Zaitone, S. A. B. (2013). Synthesis of new nicotinic acid derivatives and their evaluation as analgesic and anti-inflammatory agents. Chemical and Pharmaceutical Bulletin, 61(9), 933–940. doi: 10.1248/cpb.c13-00261
  • Referans25 Kotb, E. R., Soliman, H. A., Morsy, E. M. H., & Abdelwahed, N. A. M. (2017). New pyridine and triazolopyridine derivatives: Synthesis, antimicrobial and antioxidant evaluation. Acta Poloniae Pharmaceutica - Drug Research, 74(3), 861–872.
  • Referans26 Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785–789.
  • Referans27 More, U. A., Joshi, S. D., Aminabhavi, T. M., Gadad, A. K., Nadagouda, M. N., & Kulkarni, V. H. (2014). Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents. European Journal of Medicinal Chemistry, 71, 199–218. doi: 10.1016/j.ejmech.2013.11.004
  • Referans28 Morjan, R. Y., Mkadmh, A. M., Beadham, I., Elmanama, A. A., Mattar, M. R., Raftery, J., Pritchard, R. G., Awadallah, A. M., & Gardiner, J. M. (2014). Antibacterial activities of novel nicotinic acid hydrazides and their conversion into N -acetyl-1,3,4-oxadiazoles. Bioorganic & Medicinal Chemistry Letters, 24, 5796–5800. doi: 10.1016/j.bmcl.2014.10.029
  • Referans29 Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. doi: 10.1002/jcc.21256
  • Referans30 Mouilleron, S., Badet-Denisot, M. A., & Golinelli-Pimpaneau, B. (2008). Ordering of C-terminal Loop and Glutaminase Domains of Glucosamine-6-Phosphate Synthase Promotes Sugar Ring Opening and Formation of the Ammonia Channel. Journal of Molecular Biology, 377(4), 1174–1185. doi: 10.1016/j.jmb.2008.01.077
  • Referans31 Muluk, M. B., Dhumal, S. T., Rehman, N. N. M. A., Dixit, P. P., Kharat, K. R., & Haval, K. P. (2019). Synthesis, Anticancer and Antimicrobial Evaluation of New (E)-N′-Benzylidene-2-(2-ethylpyridin-4-yl)-4-methylthiazole-5-carbohydrazides. ChemistrySelect, 4(31), 8993–8997. doi: 10.1002/slct.201902030
  • Referans32 Narang, R., Narasimhan, B., Sharma, S., Sriram, D., Yogeeswari, P., Clercq, E. De, Pannecouque, C., & Balzarini, J. (2011). Nicotinic Acid Benzylidene/Phenyl-Ethylidene Hydrazides: Synthesis, Antimicrobial Evaluation and QSAR Studies. Letters in Drug Design & Discovery, 8(8), 733–749. doi: 10.2174/157018011796575999
  • Referans33 Narang, R., Narasimhan, B., Sharma, S., Sriram, D., Yogeeswari, P., De Clercq, E., Pannecouque, C., & Balzarini, J. (2012). Synthesis, antimycobacterial, antiviral, antimicrobial activities, and QSAR studies of nicotinic acid benzylidene hydrazide derivatives. Medicinal Chemistry Research, 21(8), 1557–1576. doi: 10.1007/s00044-011-9664-7
  • Referans34 Neuman, D. M. (2018). Antimicrobial pyridinohydrazide and hydrazomethylpyridine-based agents (US 2018/0072672 A1).
  • Referans35 Pomarnacka, E., Bednarski, P. J., Reszka, P., Dziemidowicz-Borys, E., Bieńczak, A., Werel, W., & Hałasa, R. (2006). Synthesis and biological activity of new 2-amino-8-chloro-5,5-dioxo[1,2,4]triazolo[2,3-b][1,4,2]benzodithiazines. European Journal of Medicinal Chemistry, 41(5), 633–639. doi: 10.1016/j.ejmech.2005.11.009
  • Referans36 Ragavendran, J. V., Sriram, D., Patel, S. K., Reddy, I. V., Bharathwajan, N., Stables, J., & Yogeeswari, P. (2007). Design and synthesis of anticonvulsants from a combined phthalimide-GABA-anilide and hydrazone pharmacophore. European Journal of Medicinal Chemistry, 42(2), 146–151. doi: 10.1016/j.ejmech.2006.08.010
  • Referans37 Shah, N., & Soman, S. (2018). Design , synthesis and evaluation of antimicrobial and anticancer activity of novel 3-aminomethyl pyridin derivatives. European Journal of Pharmaceutical and Medical Research, 5(10), 229–241.
  • Referans38 Shyma, P. C., Kalluraya, B., Peethambar, S. K., Telkar, S., & Arulmoli, T. (2013). Synthesis, characterization and molecular docking studies of some new 1,3,4-oxadiazolines bearing 6-methylpyridine moiety for antimicrobial property. European Journal of Medicinal Chemistry, 68, 394–404. doi: 10.1016/j.ejmech.2013.07.019
  • Referans39 Soujanya, M., & Rajitha, G. (2017). CODEN ( USA ): PCHHAX Synthesis , Characterization , Molecular Docking and Antimicrobial Activity of Nicotinic Acid Derived N-acylhydrazones. Der Pharma Chemica, 9(17), 10–15.
  • Referans40 Tok, F., Uğraş, Z., Sağlık, B. N., Özkay, Y., Kaplancıklı, Z. A., & Koçyiğit-Kaymakçıoğlu, B. (2021). Novel 2,5-disubstituted-1,3,4-oxadiazole derivatives as MAO-B inhibitors: Synthesis, biological evaluation and molecular modeling studies. Bioorganic Chemistry, 112, 104917. doi: 10.1016/j.bioorg.2021.104917
  • Referans41 Trott, O., & Olson, A. J. (2010). AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading. Journal of Computational Chemistry, 31, 455–461. doi: 10.1002/jcc.21334
  • Referans42 Ukrainets, I. V., Sidorenko, L. V., & Golovchenko, O. S. (2007). 4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides. Chemistry of Heterocyclic Compounds, 43(11), 1434–1439. doi: 10.1007/s10593-007-0221-8
  • Referans43 Wang, S., Liu, H. Y., Xu, R. F., & Sun, J. (2017). Synthesis, biological evaluation, and molecular docking studies of diacylhydrazine derivatives possessing 1,4-benzodioxan moiety as potential anticancer agents. Russian Journal of General Chemistry, 87(11), 2671–2677. doi: 10.1134/S1070363217110238
  • Referans44 Wolinski, K., Hinton, J. F., & Pulay, P. (1990). Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations. Journal of the American Chemical Society, 112(23), 8251–8260. doi: 10.1021/ja00179a005
  • Referans45 World Health Organization WHO. (2021). Retrieved from https://www.who.int/news-room/fact-sheets/detail/antimicrobial-resistance
  • Referans46 Wu, J., Zhang, L., Wang, J., Yang, S., & Li, X. (2009). 1-Phenyl-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one. Acta Crystallographica Section, E65, o2805. doi: 10.1107/S1600536809041877
There are 46 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Derya Vural 0000-0002-0120-3024

Selbi Keskin 0000-0003-0664-9903

Project Number FEN-BAP-A-250-221-26
Publication Date March 15, 2023
Published in Issue Year 2023 Volume: 13 Issue: 1

Cite

APA Vural, D., & Keskin, S. (2023). Synthesis and Spectroscopic Characterization of Novel Pyridine-based N-acyl Hydrazone Derivatives and Molecular Docking Studies on Glucosamine-6-Phosphate. Karadeniz Fen Bilimleri Dergisi, 13(1), 135-152. https://doi.org/10.31466/kfbd.1184337
 Download Cover Image

by-nc-sa.png

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.