СИНТЕЗ ПИРИДИН- И ПИПЕРИДИНСОДЕРЖАЩИХ ПОЛИЦИКЛИЧЕСКИХ СОЕДИНЕНИЙ НА ОСНОВЕ 2,6-ДИНИТРОГАЛОГЕНБЕНЗОЛОВ
Аннотация и ключевые слова
Аннотация (русский):
Исследовано нитрование 4-хлор-3-нитробензойной кислоты. Субстрат является сильно дезактивированным для реакций SEAr, и требуются жесткие условия для их проведения (безводный KNO3 в концентрированной H2SO4 при 165 °С в течение 10 часов). Разработаны методики превращения 4-хлор-3,5-динитробензойной кислоты и её сложного эфира в новые полициклические системы, содержащие пиридиновый или пиперидиновый фрагменты в реакциях кватернизации и восстановления.

Ключевые слова:
4-хлор-3-нитробензойная кислота, соли N-(2,6-динитроарил)-пиридиния, N-(2,6-динитроарил)-пиперидины, нитрование, кватернизация пиридина
Текст
Текст произведения (PDF): Читать Скачать
Список литературы

1. Rehman A., Hussain M., Rehman Z., Ali S., Rauf A., Nasim F.H., Helliwell M. Self-assembled pentagonal bipyramidal and skew trapezoidal organotin(IV) complexes of substituted benzoic acids: Their antibacterial, antifungal, cytotoxic, insecticidal and urease inhibition activities // Inorg. Chim. Acta. 2011. Vol. 370. P. 27-35. DOI:https://doi.org/10.1016/j.ica.2011.01.007. URL: https://www.sciencedirect.com/science/article/pii/S0020169311000144

2. Gautam N., Goyal K., Saini O., Kumar A., Gautam D.C. Synthesis and biological activity of substituted 3 fluoro/3-trifluoromethyl 10H-phenothiazines, its ribofuranosides and sulfones // J. Fluor. Chem. 2011. Vol. 132. P. 420-426. DOI:https://doi.org/10.1016/j.jfluchem.2011.04.012. URL: https://www.sciencedirect.com/science/article/pii/S0022113911001230

3. Remes C., Paun A., Zarafu I., Tudose M., Caproiu M.T., Ionita G., Bleotu C., Matei L., Ionita P. Chemical and biological evaluation of some new antipyrine derivatives with particular properties // Bioorg. Chem. 2012. Vol. 41-42. P. 6-12. DOI:https://doi.org/10.1016/j.bioorg.2011.12.003. URL: https://www.sciencedirect.com/science/article/pii/S0045206811001064

4. Jangid D.K., Guleria A., Gautam D.C., Yadav H., Mathur M., Swami A.K. Antimicrobial studies, synthesis and characterization of novel 1-nitro-10H-phenothiazine bearing sulfone/nucleoside moieties // Nucleosides, Nucleotides and Nucleic Acids. 2019. Vol. 38. P. 533-549. DOI:https://doi.org/10.1080/15257770.2019.1576879. URL: https://www.tandfonline.com/doi/abs/10.1080/15257770.2019.1576879

5. Al-Hiari M., Qaisi A.M., El-Abadelah M.M., Voelter W. Synthesis and Antibacterial Activity of Some Substituted 3-(Aryl)- and 3-(Heteroaryl)indoles // Monatshefte für Chemie. 2006. Vol. 137. P. 243–248. DOI:https://doi.org/10.1007/s00706-005-0424-6. URL: https://link.springer.com/article/10.1007/s00706-005-0424-6

6. Gautam N., Gupta S., Ajmera N., Gautam D.C. Synthesis, Characterization, and Biological Evaluation of 10H-Phenothiazines, Their Sulfones and Ribofuranosides // J. Heterocycl. Chem. 2012. Vol. 49. P. 710-715. DOI: https:https://doi.org/10.1002/jhet.771. URL: https://onlinelibrary.wiley.com/doi/full/10.1002/jhet.771

7. Zhang B., Pang L., Nautiyal M., Graef S.D., Gadakh B., Lescrinier E., Rozenski J., Strelkov S.V., Weeks S.D., Aerschot A.V. Synthesis and Biological Evaluation of 1,3-Dideazapurine-Like 7-Amino-5-HydroxymethylBenzimidazole Ribonucleoside Analogues as Aminoacyl-tRNA Synthetase Inhibitors // Molecules. 2020. Vol. 25. P. 1-24. DOI:https://doi.org/10.3390/molecules25204751. URL: https://www.mdpi.com/1420-3049/25/20/4751

8. Sykes B.M., Atwell G.J., Hogg A., Wilson W.R., O’Connor C.J., Denny W.A. N-Substituted 2-(2,6-Dinitrophenylamino)propanamides: Novel Prodrugs That Release a Primary Amine via Nitroreduction and Intramolecular Cyclization // J. Med. Chem. 1999. Vol. 42. P. 346-355. DOI:https://doi.org/10.1021/jm960783s. URL: https://pubs.acs.org/doi/10.1021/jm960783s

9. Baguley T.D., Nairn A.C., Lombroso P.J., Ellman J.A. Synthesis of benzopentathiepin analogs and their evaluation as inhibitors of the phosphatase STEP // Bioorg. Med. Chem. Lett. 2015. Vol. 25. P. 1044-1046. DOI:https://doi.org/10.1016/j.bmcl.2015.01.020. URL: https://www.sciencedirect.com/science/article/pii/S0960894X15000323

10. Molteni V., He X., Nabakka J., Yang K., Kreusch A., Gordon P., Bursulaya B., Warner I., Shin T., Biorac T., Ryder N.S., Goldberg R., Doughtyc J., He Y. Identification of novel potent bicyclic peptide deformylase inhibitors // Bioorg. Med. Chem. Lett. 2004. Vol. 14. P. 1477–1481. DOI:https://doi.org/10.1016/j.bmcl.2004.01.014. URL: https://www.sciencedirect.com/science/article/pii/S0960894X04000502

11. Kojima T., Mochizuki M., Takai T., Hoashi Y., Morimoto S., Seto M., Nakamura M., Kobayashi K., Sako Y., Tanaka M., Kanzaki N., Kosugi Y., Yano T., Aso K. Discovery of 1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazoles as novel class of corticotropin releasing factor 1 receptor antagonists // Bioorg. Med. Chem. 2018. Vol. 26. P. 2229-2250. DOI:https://doi.org/10.1016/j.bmc.2018.01.020. URL: https://www.sciencedirect.com/science/article/pii/S0968089617323374

12. Mochizuki M., Kori M., Kobayashi K., Yano T., Sako Y., Tanaka M., Kanzaki N., Gyorkos A.C., Corrette C.P., Cho S.Y., Pratt S.A., Aso K. Design and synthesis of benzimidazoles as novel corticotropin-releasing factor 1 receptor antagonists // J. Med. Chem. 2016. Vol. 59(6). P. 2551–2566. DOI:https://doi.org/10.1021/acs.jmedchem.5b01715. URL: https://pubs.acs.org/doi/10.1021/acs.jmedchem.5b01715

13. Zheng Z., Bhatia P., Daanen J., Kolasa T., Patel M., Latshaw S., Kouhen O.F.E., Chang R., Uchic M.E., Miller L. , Nakane M., Lehto S.G., Honore M.P., Moreland R.B., Brioni J.D., Stewart A.O. Structure-Activity Relationship of Triazafluorenone Derivatives as Potent and Selective mGluR1 Antagonists // J. Med. Chem. 2005. Vol. 48. P. 7374-7388. DOI:https://doi.org/10.1021/jm0504407. URL: https://pubs.acs.org/doi/10.1021/jm0504407

14. Filimonov S.I., Makarova E.S., Chirkova J.V., Kabanova M.V. Diastereomeric composition of the reaction of the formation of hexahydro-5h-chromeno[4,3-d]pyrimidin-5-ones // From Chemistry Towards Technology Step-By-Step. 2022. Vol. 3, iss. 1. P. 131-138. DOI:https://doi.org/10.52957/27821900_2022_01_131. URL: http://chemintech.ru/index.php/tor/2022tom3no1

15. Kotov A.D., Kunichkina A.S., Peoskurina I.K. Transformation of 5-halogen-3-aryl-2,1-benzisooxazoles into quinazolines // From Chemistry Towards Technology Step-By-Step. 2022. Vol. 2, iss. 4. P. 81-84. DOI:https://doi.org/10.52957/27821900_2021_04_81. URL: http://chemintech.ru/index.php/tor/2021-2-4

16. Begunov R.S., Sokolov A.A. One-pot Reduction and Halogenation of N-(2,4-dinitrophenyl)piperidine // From chemistry towards technology. Step-by-step. 2022. Vol. 3, iss. 2. P. 92-97. DOI:https://doi.org/10.52957/27821900_2022_02_92. URL: http://chemintech.ru/index.php/tor/2022tom3no2

17. Vitaku E., Smith D.T., Njardarson J.T. Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals // J. Med. Chem. 2014. Vol. 57, iss. 24. P. 10257-10274. DOI:https://doi.org/10.1021/jm501100b. URL: https://pubs.acs.org/doi/10.1021/jm501100b

18. Van Duin H. The separation and identification of normal aliphatic alcohols // Recueil des Travaux Chimiques des Pays-Bas. 1954. Vol. 73. P. 68-77. DOI:https://doi.org/10.1002/recl.19540730111. URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/recl.19540730111.

Войти или Создать
* Забыли пароль?