СИНТЕЗ ПРОИЗВОДНЫХ АМИНОФЕНОЛА И ОЦЕНКА ИХ БИОЛОГИЧЕСКОЙ АКТИВНОСТИ. ОБЗОР
Аннотация
Производные аминфенолов в последние годы привлекают все большее внимание благодаря их широкому биологическому потенциалу и синтетической универсальности. В литературе описаны синтез и исследование значительного числа соединений этого класса, главным образом, из-за разнообразия их биологической активности, включающей выраженную антимикробную, противоопухолевую и антиоксидантную активность. Также, аминофенолы могут рассматриваться как важные прекурсоры для построения биологически активных гетероциклических каркасов, что значительно повышает их значимость в медицинской химии и фармацевтическом дизайне. Современные достижения органического синтеза позволили получать производные аминфенолов с высокими выходами, зачастую превышающими 90%, с использованием различных стратегий. Среди наиболее широко применяемых следует отметить однофазные (one-pot) методики, обеспечивающие прямое замещение фенольной гидроксильной группы в гидрохиноне аминогруппами, а также классические восстановительные превращения нитрофенольных производных с применением специфических восстановителей. Параллельно были предложены и альтернативные синтетические подходы, отличающиеся сокращенными синтетическими последовательностями, применением дешевых реагентов и простыми экспериментальными условиями, что облегчает доступность и снижает стоимость процесса. Антиоксидантные свойства аминофенолов являются уникальными несмотря на сохраняющиеся ограничения в их противоопухолевой и антимикробной эффективности. Практически все производные аминфенолов демонстрируют сильную способность к улавливанию свободных радикалов, зачастую сопоставимую или превосходящую активность стандартных антиоксидантов, таких как аскорбиновая кислота (AA) и бутилгидроксианизол (BHA). В совокупности эти данные подчеркивают значимость производных аминфенолов как перспективных терапевтических агентов и универсальных промежуточных соединений в органическом, медицинском и фармацевтическом синтезе.
Для цитирования:
Нго Лан Ань, Нгуен Ван Дат Синтез производных аминофенола и оценка их биологической активности. Обзор. Изв. вузов. Химия и хим. технология. 2026. Т. 69. Вып. 5. С. 6-22. DOI: 10.6060/ivkkt.20266905.6756.
Литература
Toshihiro O., Takayasu Y., Kimio H., Noriko T. Potent anticancer activities of novel aminophenol analogues against varioys cancer cell lines. Bioorg. Med. Chem. 2007. V. 16. N 2. P. 847 – 853. DOI: 10.1016/j.bmc.2006.10.042.
Noriko T., Toshihiro O., Takayasu Y., Kimio H. Antioxidant and anticancer activities of novel p-alkylaminophenols and p-acylaminophenols (aminophenol analogues). Bioorg. Med. Chem. 2006. V. 14. N 17. P. 6089 – 6096. DOI: 10.1016/j.bmc.2006.05.013.
Saba Z., Muhammad H., Mirza W.B., Muhammad T., Zahoor A., Muhammad N.T., Tashfeen A. Synthesis, crystal structure, anti-cancer, antiflammatory, antioxidant and quantum chemical studies of 4-(pyrrolidine-2,5-dione-1-yl)phenol. J. Molec. Struct. 2021. V. 1221. P. 129267. DOI: 10.1016/j.molstruc.2020.129267.
Aihua M., Tingwei H., Shaoyun S., Hongying S., Shisheng W., Qingming J. Morphologies and antibacterial properties of poly(o-aminophenol). Polymer Adv. Technol. 2014. V. 25. N 5. P. 575 – 580. DOI: 10.1002/pat.3283.
Mary B., Haslewood G.A.D. The Antibacterial Activity of Simple Derivatives of 2-Aminophenol. Biochem. J. 1945. V. 39. N 4. P. 285 – 297. DOI: 10.1042/bj0390285.
Shahzad M., Jamshaid A. Synthesis, Antioxidant and Antimicrobial Activity of 4-Aminophenol and 2-Aminobenzoic Acid Based Novel Azo Compounds. Asian J. Chem. 2015. V. 27. N 10. P. 3651-3654. DOI: 10.14233/ajchem.2015.18816.
Naoki S., Fumihiko A., Shigeki K., Masahiko K., Yoshiko S., Haruko Y., Masanori S., Chikara F. Synthesis and Topical Antiinflammatory and Antiallergic Activities of Antioxidant o-Aminophenol Derivatives. J. Med. Chem. 1994. V. 37. N 13. P. 1977 – 1982. DOI: 10.1021/jm00039a010.
Stephen C.M., Paul C., Rosemary W. Aminophenols. Kirk-Othmer Encyclopedia of Chemical Technology. 2000. DOI: 10.1002/0471238961.0113091413092003.a01.pub2.
Bel’kov M.V., Ksendzova G.A., Kuzovkov P.V. Polozov G.I., Skornyakov I.V., Sorokin V.L., Tolstorozhev G.B., Shadyro O.I. Intramolecular hydrogen bonds and antioxidant activity of aminophenol. J. Appl. Spectrosc. 2007. V. 74. P. 635 – 641. DOI: 10.1007/s10812-007-0103-y.
Loginova N.V., Koval’chuk’ T.V., Zheldakova R.A., Osi-povich N.P., Sorokin V.L., Polozov G.I., Ksendzova G.A., Glushonok G.K., Chernyavskaya A.A., Shadyro O.I. Synthesis and biological evaluation of copper (II) complexes of sterically hindered o-aminophenol derivatives as antimicrobial agents. Bioorg. Med. Chem. Lett. 2006. V. 16. N 20. P. 5403 – 5407. DOI: 10.1016/j.bmcl.2006.07.065.
Laxmi K., Pranya V.J., Tapan K.D., Sanjima P., Milind N., Thomas W., Vedabati G.P., Konkimalla V.B., Sunita S.-G. Reaction between lawsone and aminophenol derivatives: Synthesis, characterization, molecular structures and antipro-liferative activity. J. Molec. Struct. 2014. V. 1075. P. 297 – 405. DOI: 10.1016/j.molstruc.2014.07.007.
Mukovoz P.P., Slepulkhin P.A., Danilova E.A., Aysuvakova O.P., Glinushkin A.P. Synthesis, Structure, and Biological Activity of Products of Reactions of 3,4-Dioxohexane-1,6-dioic Esters with 2-Aminophenol. Russ. J. Chem. 2018. V. 88. N 7. P. 1363 – 1368. DOI: 10.1134/S0044460X18070028.
Nuaman F.A. Synthesis, Characterization and Antimicrobial Activity Study of Some New Substituted Benzoxazole Derivatives. Baghdad Sci. J. 2019. V. 16. N 3. P. 616 – 625. DOI: 10.21123/bsj.2019.16.3.0616.
Pakpour F., Safaei E., Azami S.M., Wojtczak A., Kaldun-ska S. The role of a redoxactive non-innocent ligand in addi-tive-free C–C Glaser–Hay and Suzuki coupling reactions by an o-aminophenol palladium(II) complex. RCS Adv. 2023. V. 13. N 5. P. 3278 – 3289. DOI: 10.1039/D2RA07252A.
Maryna L., Olga A.A., Irina P.Z., Alexander M. Synthesis and Physiological effects of new 4-aminophenol derivatives as paracetamol analogues. Bioorg. Med. Chem. Lett. 2025. V. 117. P. 130080. DOI: 10.1016/j.bmcl.2024.130080.
Shadyro O., Ksendzova G., Polozov G., Sorokin V., Bore-ko E., Savinova O., Dubovik B., Bizunok N. Synthesis and study of antiviral and antiradical properties of aminophenol derivatives. Bioorg. Med. Chem. Lett. 2008. V. 18. N 7. P. 2420 – 2423. DOI: 10.1016/j.bmcl.2008.02.055.
Ananta K.D., Islam A.F.M.M., Rouf M.A., Paul P., Hassan M.J., Roy S., Esha E.J, Hossain M.S., Hossain M.M., Hossain M.E., Saha K. Synthesis and Biological Evaluation of p-Aminophenol Derivatives Applying In Vivo, Ex Vivo, and In Silico Approach. ChemistrySelect. 2024. V. 9. N 46. P. e202404333. DOI: 10.1002/slct.202404333.
Sheng X.-H., Han L.-C., Gong A., Meng X.-S., Wang X.-H., Teng L.-S., Sun X.-H., Xu K.-C., Liu Z.-H., Wang T., Ma J.-P., Zhang L. Discovery of Novel Ortho-Aminophenol Derivatives Targeting Lipid Peroxidation with Potent Antifer-roptotic Activities. J. Med. Chem. 2024. V. 67. N 11. P. 9536 – 9551. DOI: 10.1021/acs.jmedchem.4c00600.
Largeron M., Neudorffer A., Fleury M.-B. A Simple One-Pot Electrochemical Procedure for the Preparation of Novel 3,4-aminophenol Derivatives Possessing Anti-stress Oxidative Properties. Tetrahed. Lett. 1998. V. 28. N 9. P. 5035 – 5038. DOI: 10.1016/S0040-4039(98)00995-2.
Wakamatsu K., Tanaka H., Tabuchi K., Ojika M., Zucca F.A., Zecca L., Ito S. Reduction of the Nitro Group to Amine by Hydroiodic Acid to Synthesize o-Aminophenol Derivatives as Putative Degradative Markers of Neuromelanin. Molecules. 2014. V. 19. N 6. P. 8039 – 8050. DOI: 10.3390/molecules19068039.
Gillespie R.J., Millen D.J. Aromatic nitration. Chem. Soc. Rev. 1948. V. 2. N 4. P. 277 – 392. DOI: 10.1039/QR9480200277.
Belson D.J., Strachan A.N. Aromatic nitration in aqueous nitric acid. J. Chem. Soc. Perkin Trans. 2. 1989. V. 2. N 1. P. 15 – 19. DOI: 10.1039/P29890000015.
Smith K., Musson A., DeBoos G.A. A Novel Method for the Nitration of Simple Aromatic Compounds. J. Org. Chem. 1998. V. 63. N 23. P. 8448 – 8454. DOI: 10.1021/jo981557o.
Albright L.F. Nitration. Kirk‐Othmer Encyclopedia of Chem-ical Technology. 2000. DOI: 10.1002/0471238961. 1409201801120218.a01.
Cartolano A.R., Vedage G.A. Amines by Redution. Kirk‐Othmer Encyclopedia of Chemical Technology. 2004. DOI: 0471238961.0113091419030809.a01.pub2.
Scheme B.G.R. Béchamp Reduction. In: Comprehensive Organic Name Reactions and Reagents. 2010. P. 284 – 287. DOI: 10.1002/9780470638859.conrr063.
Sajilo H., Hattori K., Hirota K. The Formation of a Novel Pd/C−Ethylenediamine Complex Catalyst: Chemoselective Hydrogenation without Deprotection of the O-Benzyl and N-Cbz Groups. J. Org. Chem. 1998. V. 63. N 22. P. 7990 – 7992. DOI: 10.1021/jo9814694.
Shafiee A., Parang K., Khazan M., Ghasemian F. Nitroimidazoles X. Syntheses of substituted 2-(1-methyl-5-nitro-2-imidazolyl)quinolines. J. Heterocycl. Chem. 1992. V. 29. N 7. P. 1859 – 1861. DOI: 10.1002/jhet.5570290732.
Begunov R.S., Khlopotinin A.I., Lobanova L.V., Vorontsov S.M., Savina L.I., Danilova A.S. New UV Absorbers Based On N-(2-Aminoaryl)Benzotriazoles. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2024. V. 67. N 11. P. 86 – 94 (in Russian). DOI: 10.6060/ivkkt.20246711.7070.
Jouncour R., Duguet N., Métay E., Ferreira A., Lemaire M. Amidation of phenol derivatives: a direct synthesis of paracetamol (acetaminophen) from hydroquinone. Green Chem. 2014. V. 16. N 6. P. 2997 – 3002. DOI: 10.1039/ C4GC00166D.
Liang J., Tang Y.-X., Tang X.-Z., Liang H.-J., Gao Y., Fang C., Zhang T.-Y., Yan M. Discovery of meta-Amido Bromophenols as New Antitubercular Agents. Chem. Pharm. Bull. 2019. V. 67. N 4. P. 372 – 381. DOI: 10.1248/cpb.c18-00917.
McOmie J.F.W., Watts M.L., West D.E. Demethylation of aryl methyl ethers by boron tribromide. Tetrahedron. 1968. V. 24. N 5. P. 2289 – 2292. DOI: 10.1016/0040-4020(68)88130-X.
Jeffery B.P. Deethylation of Aryl Ethyl Ethers by Boron Tribromide. Synth. Commun. 1979. V. 9. N 5. P. 407 – 410. DOI: 10.1080/00397917908064169.
Brindaban C.R., Sanjay B. Dealkylation of Ethers. A Review. Org. Prep. Proced. Int. 1996. V. 28. N 4. P. 371 – 409. DOI: 10.1080/00304949609356549.
Li X., He J., Zhang Y. BBr3-Assisted Preparation of Aro-matic Alkyl Bromides from Lignin and Lignin Model Compounds. J. Org. Chem. 2018. V. 83. N 18. P. 11019 – 11027. DOI: 10.1021/acs.joc.8b01628.
Quentin E.T. The Diacylation of Amides by Acyl Chloride – Pyridine Compounds. J. Am. Chem. Soc. 1951. V. 73. N 12. P. 5841 – 5846. DOI: 10.1021/ja01156a115.
Tso W.-W., Snyder C.H., Powell H.B. Amidehydrogen halide adducts from the reaction of acyl halides and amines. J. Org. Chem. 1970. V. 35. N 3. P. 849 – 850. DOI: 10.1021/jo00828a079.
Montalbetti C.A., Falque V. Amide bond formation and peptide coupling. Tetrahedron. V. 61. N 46. P. 10827 – 10852. DOI: 10.1016/j.tet.2005.08.031.
Albeiicio F., Chinchilla R., Dodsworth D.J., Nájera C. New Trends in Peptide Coupling Reagents. Org. Prep. Pro-ced. Int. 2001. V. 33. N 3. P. 203 – 303. DOI: 10.1080/ 00304940109356592.
Albericio F. Developments in peptide and amide synthesis. Curr. Opin. Chem. Biol. 2004. V. 8. N 3. P. 211 – 221. DOI: 10.1016/j.cbpa.2004.03.002.
Gai K., Liu B., Zhang Y. Identification of unexpected unlabeled N,N-dimethylamide formation in the synthesis of deuterated fragment of ribociclib by a HATU-mediated coupling reaction. J. Label. Compd. Radiopharm 2018. V. 62. N. 2. P. 62 – 66. DOI: 10.1002/jlcr.3690.
Du N.D., Dien P.H., Thao N.T.T., Mai N.T.N, Dat N.V., Hoan D.Q. Synthesis and Biological Activities of Some Benzo[d]thiazole Derivatives Containing An Amide Bond. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2025. V. 68. N 10. P. 19 – 25. DOI: 10.6060/ivkkt.20256810.7227.
Dhanalakshmi B., Kumar B.M.A.K., Srinivasa S.M., Vivek H.K., Sennappan M., Rangappa S., Murthy V.S. Design and synthesis of 4-aminophenol-1,3,4-oxadiazole derivative potentiates apotosis by targeting MAP kinase in triple negative breast cancer cells. J. Biomolec. Struct. Dynam. 2023. V. 42. N. 23. P. 13114 – 13129. DOI: 10.1080/ 07391102.2023.2274973.
Himo F., Demko Z.P., Noodleman L., Sharpless K.B. Mechanisms of Tetrazole Formation by Addition of Azide to Nitriles. J. Am. Chem. Soc. 2002. V. 124. N 41. P. 12210 – 12216. DOI: 10.1021/ja0206644.
Kaushik N., Kumar N., Kumar A., Singh U.K. Tetrazoles: Synthesis and Biological Activity. Immunol. Endocr. Metab. Agent Med. Chem. 2018. V. 18. N 1. P. 3 – 21. DOI: 10.2174/ 1871522218666180525100850.
Vishwakarma R., Gadipelly C., Mannepalli L.K. Advances in Tetrazole Synthesis – An Overview. Chem. Select. 2022. V. 29. N 7. e202200706. DOI: 10.1002/slct.202200706.
Shagalov E.V., Pogonin A.E., Kiselev A.N., Syrbu S.A., Maizlish V.E. New dinitrile: synthesis, structure, and spectra. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2023. V. 66. N 8. P. 22 – 32 (in Russian). DOI: 10.6060/ivkkt.20236608.6809.
Baranov A.B., Tsypin V.G., Malin A.S. Synthesis of 2-Chloromethyl-5-aryl-, 2-Chloromethyl-5-(5-methyl-2-furyl)-, and 2-Chloromethyl-5-(1,5-dimethyl-2-pyrrolyl)-1,3,4-oxadiazoles from Tetrazole Derivatives. Russ. J. Appl. Chem. 2005. V. 78. P. 773 – 775. DOI: 10.1007/s11167-005-0389-6.
Gao X.-H., Liu L.-B., Liu H.-R., Tang J.-J., Kang L., Wu H., Cui P., Yan J. Structure–activity relationship investigation of benzamide and picolinamide derivatives containing di-methylamine side chain as acetylcholinesterase inhibitors. J. Enzym. Inhib. Med. Chem. 2018. V. 33. N 1. P. 110 – 114. DOI: 10.1080/14756366.2017.1399885.
Garg A., Borah D., Trivedi P., Gogoi D., Chaliha A.K., Ali A.A., Chetia D., Chaturvedi V., Sarma D. A Simple Work-Upfree, Solventfree Approach to Novel Amino Acid Linked 1,4-Disubstituted 1,2,3-Triazoles as Potent Antituber-culosis Agents. ACS Omega. 2020. V. 5. N 46. P. 29830 – 29837. DOI: 10.1021/acsomega.0c03862.
Du N.D., Dat N.V., Mai N.T.N., Anh N.L., Anh D.Q., Phuong N.T., Lan B.N., Dien P.H., Hoan D.Q. Design and Synthesis of Some Novel Amino Acid Derivatives Containing Benzo[d]thiazole. J. Chem. Appl. 2024. V. 71. N 3B. P. 3 – 11.
Mai N.T.N., Hoan D.Q., Tuyet V.T.A., Trang T.T.T., Linh D.K., Huan T.T. An Effective Assembling of Novel Derivatives Containing Both Benzo[d]thiazole and Benzo[d]oxazole Rings. Lett. Org. Chem. 2020. V. 17. N 11. P. 815 – 822. DOI: 10.2174/1570178617666200207104912.
Grenier J.L., Cotelle N., Catteau J.P., Cotelle P. Synthesis and physico-chemical properties of nitrocaffeic acids. J. Phys. Org. Chem. 2000. V. 13. N 9. P. 511 – 517. DOI: 10.1002/1099-1395(200009)13:9<511::AID-POC283>3.0.CO;2-8.
Hoan D.Q., Linh N.M., Hoa P.T., Quynh H.T.N., Tuyet V.T.A. Using a domestic microwave oven for synthesis of benzo[d]thiazole derivatives. J. Sci. HNUE. 2018. V. 63. N 6. P. 127 – 135.
Hoan D.Q., Tuyet V.T.A., Duong L.T., Hien N. Preparation of some new benzo[d]thiazole derivatives. Vietnam J. Chem., Int. Ed. 2017. V. 55. N 4. P. 433 – 437. DOI: 10.15625/2525-2321.2017-00486.
Sahoo S.S., Shukla S., Nandy S., Sahoo H.B. Synthesis of novel coumarin derivatives and its biological evaluations. Eur. J. Experim. Biol. 2012. V. 2. N 4. P. 899 – 908.
Mai N.T.N., Huan T.T., Thanh L.V., Huan N.V., Hoan D.Q. Synthesis and antimicrobial activities of hydrazones de-rived from 4-hydroxy-3-nitrobenzaldehyde. Vietnam J. Sci.Technol. 2023. V. 63. N 3. P. 373 – 381. DOI: 10.15625/ 2525-2518/17073.
Guo Z., Tellew J.E., Gross R.S., Dyck B., Grey J., Had-dach M., Kiankarimi M., Lanier M., Li B.-F., Luo Z., McCarthy J.R., Moorjani M., Saunders J., Sullivan R., Zhang X., Zamani-Kord S., Grigoriadis D.E., Crowe P.D., Chen T.K., Williams J.P. Design and Synthesis of Tricyclic Imidazo[4,5-b]pyridin-2-ones as Corticotropin-Releasing Factor-1 Antagonists. J. Med. Chem. 2005. V. 48. N 16. P. 5104 – 5107. DOI: 10.1021/jm050384.
Du N.D., Dat N.V., Hue N.V., Giang V.T.H., Ha N.X., Hai L.T.H., Dien P.H., Trang N.T.H., Tai T.M., Nga N.T., Hue N.T.M., Hoan D.Q. Synthesis, Formation Mechanisms, and Molecular Dynamics Simulation of Novel Benzothiazole and Benzo[1,4]oxazin-3(4H)-one as Potential Acetylcholines-terase Inhibitors. ACS Omega. 2025. V. 10. N 11. P. 10835 – 10851. DOI: 10.1021/acsomega.4c06760.
Mai N.T.N., Huan T.T., Tuan P.V., Trang T.T.T., Hien H.T. Synthesis of Some o-Aminophenol Derivatives and Antioxidants Activities. Hong Duc University J. Sci. 2023. V. 13. N E8. P. 84 – 91.
Bekdemir Y., Efil K. Microwave Assisted Solvent-Free Synthesis of Some Imine Derivatives. Org. Chem. Int. 2014. P. 816487. DOI: 10.1155/2014/816487.
Cho B.T., Kang S.K. Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions. Tetrahedron. 2005. V. 61. N 24. P. 5725 – 5734. DOI: 10.1016/j.tet.2005.04.039.
Massah A.R., Toghyani M., Najafabadi B.H. Green and efficient method for the acylation of amines and phenols inthe presence of hydrotalcite in water. J. Chem. Res. 2012. V. 36. N 10. P. 603 – 605. DOI: 10.3184/174751912X13460810792101.
Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 1999. DOI: 10.1002/0471220574.
Dat N.V., Ly T.D., Phuong V.N.U., Luc M.V., Mai N.T.N., Anh N.L., Hoan D.Q. Design, Synthesis, and Bio-logical Evaluation of Some Novel o-aminophenol Derivatives. Curr. Org. Synth. 2025. V. 22. N 6. P. 754 – 768. DOI: 10.2174/0115701794360303250109065121.
Venkateswarlu K., Lloyd J.N., Jim C.S. Construction of Escherichia coli Strains for Conversion of Nitroacetophenones to ortho-Aminophenols. Appl. Environ. Microbiol. 2003. V. 69. N 11. P. 6520 – 6526. DOI: 10.1128/AEM. 69.11.6520–6526.2003.
Yongjun M., Long Z., Wenxin C., Pengfei W., Lehao B., Jingli X. A Practical, Wastewater-free Synthesis of m-Aminophenol and 3-(Dibutylamino)phenol. Org. Prepar. Proced. Int. 2020. V. 52. N 3. P. 226 – 231. DOI: 10.1080/00304948.2020.1743117.
Hang Q., Cui -C.W., Zi -C.S., Ming -X.S., Hong -C.Z., Shiming F., Juan F., Shouxin L. and Zhi -W.Z. Catalyst- and additive-free [3 + 3] cyclization–aromatization of β,γ-dioxobutanoate with amines for synthesis of p-aminophenols. Green Chem. 2022. N 24. P. 9690 - 9696. DOI: 10.1039/ D2GC03936B.
Bo L., Alessandro R., and Daniele L. A Photochemical Strategy for ortho-Aminophenol Synthesis via Dearomative-Rearomative Coupling Between Aryl Azides and Alcohols. Angew. Chem. Int. Ed. 2023. V. 62. N 52. e202310540. DOI: 10.1002/anie.202310540.
Ramesh M.C., Masahiko I., Sarah A., Daisuke S., Noriko T., Terrence R.B. Examination of aminophenol-containing compounds designed as antiproliferative agents and potential atypical retinoids. Bioorg. Med. Chem. 2023. V. 82. P. 117214. DOI: 10.1016/j.bmc.2023.117214.
Biping X., Xiaojie L., Lei D., Yaping S., Xiaoming J., Weiping S. Dehydrogenative synthesis of N-functionalized 2-aminophenols from cyclohexanones and amines: Molecular complexities via one-shot assembly. Sci. Adv. 2024. V. 10. N 18. P. eadn7656. DOI: 10.1126/sciadv.adn7656.
Wang K., Wang C., Sun C. The Antibacterial Activity, Acute Toxicity, and Antibacterial Mechanism of 2,6-Dimethyl-4-aminophenol Hydrochloride. Russ. J. Bioorg. Chem. 2025. V. 51. P. 2142 – 2151. DOI: 10.1134/S1068162024606499.
Shahidi F., Janitha P.K., Wanasundara P.D. Phenolic antioxidants. Crit. Rev. Food Sci. Nutr. 1992. V. 32. N 1. P. 67 – 103. DOI: 10.1080/10408399209527581.
Vorobyev S.V., Primerova O.V., Ivanova L.V., Ryabov V.D., Koshelev V.N. Facile synthesis of phenolic derivatives, containig lactamomethyl substituents. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2019. V. 62. N 10. P. 40 – 48 (in Russian). DOI: 10.6060/ivkkt. 20196210.5930.
Rasulov Ch.K., Aghamaliyev Z.Z., Nagiyeva M.V., Gasanova G.D., Gasimova F.I. Synthesis and Properties of 2-Hydroxy-5[1(3)-Methylcycloalkyl]-Benzylaminoethylnonylimidazolines. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2021. V. 64. N 4. P. 79 – 84 (in Russian). DOI: 10.6060/ivkkt.20216404.6265.
Kumar H.V., Naik N. Synthesis and antioxidant properties of some novel 5H-dibenz[b,f]azepine derivatives in different in vitro model systems. Eur. J. Med. Chem. 2010. V. 45. N 1. P. 2 – 10. DOI: 10.1016/j.ejmech.2009.09.016.
Aslam M., Anis I., Mehmood R., Iqbal L., Iqbal S., Khan I., Chishti M.S., Perveen S. Synthesis and biological activi-ties of 2-aminophenol-based Schiff bases and their structure–activity relationship. Med. Chem. Res. 2016. V. 25. P. 109 – 115. DOI: 10.1007/s00044-015-1468-8.
