Amidoalkyl Naphthols as Important Bioactive Substances and Building Blocks: A Review on the Current Catalytic Mannich-Type Synthetic Approaches
Source abstract
Abstract
Currently, 1-amidoalkyl-2-naphthol derivatives are of increasing interest due to their biological activities and further use in the preparation of other important bioactive molecules, such as aminoalkyl naphthols and oxazines. The synthesis of 1-amidoalkyl-2-naphthol moiety is usually achieved by employing one-pot multicomponent Mannich reactions. This review covers the recent reports on 1-amidoalkyl-2-naphthols’ preparation with the use of different catalysts and summarizes the available published data for the period of the last 3 years. It also puts emphasis on the structure, synthetic transformation and biological importance of this class of products.
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Research context
OpenAlex topics: Multicomponent Synthesis of Heterocycles · Synthesis and biological activity · Synthesis of Indole Derivatives
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev St., Bl. 9, 1113 Sofia, Bulgaria
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, 1649-003 Lisbon, Portugal
Funding
VIHREN · European Union’s Horizon
References (96)
Show source-provided references
1. Strategies for the Asymmetric Construction of Pelletierine and its Use in the Synthesis of Sedridine, Myrtine, and Lasubine10.1002/ejoc.201900477 ↗
2. Larwood, D.J. (2020). Nikkomycin Z—Ready to Meet the Promise?. J. Fungi, 6.10.3390/jof6040261 ↗
3. Stoffwechselprodukte von Mikroorganismen. 154. Mitteilung. Nikkomycin, ein neuer hemmstoff der chitinsynthese bei pilzen
4. A new antibiotic, negamycin10.7164/antibiotics.23.170 ↗
5. Lopinavir/ritonavir in the treatment of HIV-1 infection: A review10.2147/TCRM.S3285 ↗
6. Pharmacological and therapeutic properties of ritonavir-boosted protease inhibitor therapy in HIV-infected patients10.1093/jac/dkh029 ↗
7. The Haloperidol Story10.1080/10401230591002048 ↗
8. Schatzberg, A.F., and Nemeroff, C.B. (2017). The American Psychiatric Association Publishing Textbook of Psychopharmacology, American Psychiatric Association Publishing.10.1176/appi.books.9781615371624 ↗
9. Sonia, T.A., and Sharma, C.P. (2014). Oral Delivery of Insulin, Elsevier.
10. Tramadol as an analgesic for mild to moderate cancer pain10.1016/S1734-1140(09)70159-8 ↗
11. Biological study of naphthalene derivatives with antiinflammatory activities10.1002/ddr.10327 ↗
12. El-Wahab, A.H.F.A. (2012). Synthesis, Reactions and Evaluation of the Antimicrobial Activity of Some 4-(p-Halophenyl)-4H-naphthopyran, Pyranopyrimidine and Pyranotriazolopyrimidine Derivatives. Pharmaceuticals, 5.10.3390/ph5070745 ↗
13. A Concise Synthesis and the Antibacterial Activity of 5,6-Dimethoxynaphthalene-2-carboxylic Acid
14. Synthesis and antibacterial activity of 2-amino chromenes arising cyanoiminocoumarins and β-naphthol10.25135/acg.oc.6.16.11.442 ↗
15. Effects of 1-pyrrolidinylmethyl-2-naphthol on contractile force and ionic current in cardiac and vascular smooth myocytes10.1002/(SICI)1098-2299(199806/07)44:2/3<87::AID-DDR6>3.0.CO;2-6 ↗
16. Synthesis of a Resveratrol Analogue with High Ceramide-Mediated Proapoptotic Activity on Human Breast Cancer Cells10.1021/jm050528k ↗
17. Inactivation of enveloped viruses by singlet oxygen thermally generated from a polymeric naphthalene derivative10.1016/S0166-3542(98)00007-2 ↗
18. Synthesis of 1-amidoalkyl-2-naphthols and oxazine derivatives with study of their antibacterial and antiviral activities10.1007/s00044-012-0205-9 ↗
19. Synthesis of novel amidoalkyl naphthol-based azo dyes and evaluation of their antimicrobial activities10.1007/s13738-018-1563-0 ↗
20. Green and one-pot synthesis of novel amidoalkyl naphthols using triethanolammonium acetate [(OHCH2CH2)3NH][OAc]) ionic liquid and their anti-H.pylori activity10.1007/s11164-022-04803-9 ↗
21. Design and synthesis of some new biologically active amidoalkyl naphthols in the presence of sulfonic acid functionalized silica-coated Fe3O4 nanoparticles10.1007/s11164-021-04610-8 ↗
22. Synthesis, anti-leishmanial screening, molecular docking, and ADME study of 1-amidoalkyl 2-naphthol derivatives catalyzed by amino acid ionic liquid10.1007/s11164-022-04723-8 ↗
23. Synthesis, Docking Study and Biological Activities Evaluation of 1-Amidoalkyl-2-naphthol Derivatives as Dual Inhibitors of Cholinesterase and α-Glucosidase10.1002/slct.202000558 ↗
24. Synthesis, crystal structure, biological evaluation, docking study, and DFT calculations of 1-amidoalkyl-2-naphthol derivative10.1016/j.molstruc.2020.128179 ↗
25. Free radical scavenging activity and mechanisms of amidoalkyl-2-naphthol derivative: A joint experimental and theoretical study10.1007/s11696-021-01827-0 ↗
26. Recent perspectives concerning the mechanism of H3O+- and hydroxide-promoted amide hydrolysis10.1021/ar00023a001 ↗
27. A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles10.3998/ark.5550190.p009.205 ↗
28. Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance10.1021/ja910083q ↗
29. Simple, versatile, and chemoselective reduction of secondary amides and lactams to amines with the Tf2O–NaBH4 or Cp2ZrHCl–NaBH4 system10.1039/C4QO00317A ↗
30. In vitro and in vivo multidrug resistance reversal activity by a Betti-base derivative of tylosin10.1038/sj.bjc.6605716 ↗
31. Synthesis and cardiovascular evaluation of N-substituted 1-aminomethyl-2-naphthols10.1016/S0223-5234(99)00204-4 ↗
32. Use of readily available chiral compounds related to the betti base in the enantioselective addition of diethylzinc to aryl aldehydes10.1016/S0040-4020(99)00914-X ↗
33. New 1,3-amino alcohols derived from ketopinic acid and their application in catalytic enantioselective reduction of prochiral ketones10.1016/S0957-4166(99)00043-9 ↗
34. Synthesis of a new chiral amino phosphine ligand and its application in the asymmetric allylic alkylation (AAA) reaction10.1016/j.tetasy.2007.05.005 ↗
35. Synthesis of highly functionalized oxazines by Vilsmeier cyclization of amidoalkyl naphthols10.1016/j.tetlet.2009.07.051 ↗
36. Recent advances in one-pot multicomponent catalytic synthesis of amidoalkyl naphthols
37. Current Progress in the Multicomponent Catalytic Synthesis of Amidoalkyl-Naphthols: An Update10.2174/1385272822666200217100344 ↗
38. Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols10.1021/jacs.7b06785 ↗
39. Cu-Catalyzed Cross-Dehydrogenative ortho-Aminomethylation of Phenols10.1002/anie.201804829 ↗
40. Ruthenium-Catalyzed Hydrogen Evolution o-Aminoalkylation of Phenols with Cyclic Amines10.1021/acs.orglett.0c01580 ↗
41. Brønsted acid catalysed chemo- and ortho-selective aminomethylation of phenol10.1039/D1OB00820J ↗
42. Multicomponent Reactions with Isocyanides10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U ↗
43. Green organic synthesis via multicomponent reactions
44. Ganta, R.K., Kerru, N., Maddila, S., and Jonnalagadda, S.B. (2021). Advances in Pyranopyrazole Scaffolds’ Syntheses Using Sustainable Catalysts—A Review. Molecules, 26.10.3390/molecules26113270 ↗
45. Multicomponent reactions: Advanced tools for sustainable organic synthesis10.1039/C4GC00013G ↗
46. Green chemistry for chemical synthesis10.1073/pnas.0804348105 ↗
47. Synthesis and Structures of Air-Stable Binuclear Hafnocene Perfluorobutanesulfonate and Perfluorobenzenesulfonate and their Catalytic Application in C-C Bond-Forming Reactions10.1002/adsc.201300439 ↗
48. Saccharin Sulfonic Acid (SASA) as a Highly Efficient Catalyst for the Condensation of 2-Naphthol with Arylaldehydes and Amides (Thioamides or Alkyl Carbamates) Under Green, Mild, and Solvent-Free Conditions10.1080/10426507.2012.692131 ↗
49. Efficient one-pot synthesis of 1-carbamatoalkyl-2-naphthols using aluminum methanesulfonate as a reusable catalyst10.1007/s11164-012-0744-1 ↗
50. Graphene oxide supported dicationic ionic liquid: An efficient catalyst for the synthesis of 1-carbamatoalkyl-2-naphthols10.1007/s11164-019-03922-0 ↗
51. Magnetically retrievable magnetite (Fe3O4) immobilized ionic liquid: An efficient catalyst for the preparation of 1-carbamatoalkyl-2-naphthols10.1039/C5CY00849B ↗
52. Zwitterionic-type molten salt: An efficient mild organocatalyst for synthesis of 2-amidoalkyl and 2-carbamatoalkyl naphthols10.1016/j.catcom.2010.06.001 ↗
53. Evaluation of catalytic activity of two newly prepared functionalized sulfonic acids ionic liquids in the synthesis of carbamatoalkyl naphthols under mild conditions10.1134/S1070363217020268 ↗
54. N, N, N′, N′-tetramethylethylene-diaminium-N, N′-disulfonic acid chloride as a highly effective catalyst for the synthesis of 4H-pyrano [2, 3-c]pyrazoles, α-carbamatoalkyl-β-naphthols and α-amidoalkyl-β-naphthols
55. Varga, V., Ábrányi-Balogh, P., and Milen, M. (2020). Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®). Chemistry, 2.10.3390/chemistry2020037 ↗
56. A Green Protocol for One-Pot Three-Component Synthesis of Amidoalkyl Naphthols Catalyzed by Succinic Acid
57. Environment-friendly green chemistry approaches for an efficient synthesis of 1-amidoalkyl-2-naphthols catalyzed by tannic acid10.1016/j.arabjc.2014.08.022 ↗
58. The generation and reactions of quinone methides
59. Miao, J. (2018). Brønsted Acid Catalyzed Carbon-Carbon Bond Forming Reactions. [Ph.D. Thesis, University of Denver].
60. Adipic Acid as a Biodegradable Solid Acid Catalyst for One-Pot, Three Component Synthesis of 1-Amidoalkyl-2-naphthols10.2174/2213337206666190515091358 ↗
61. Solvent free synthesis of amidoalkyl derivatives under green and convenient conditions10.1002/jhet.4409 ↗
62. 2,6-Pyridinedicarboxylic Acid (PDCA) Catalyzed Improved Synthetic Approach for 1-Amidoalkyl Naphthols, Dihydropyrimidin-2(1H)-ones and Bis-indoles10.1002/slct.202102445 ↗
63. Synthesis of amidoalkyl naphthols in PEG-400 as a green and efficient solvent and theoretical study of their spectroscopic properties10.2174/1570178618666210610170234 ↗
64. Ionic Liquids: Synthesis and Applications in Catalysis10.1155/2014/729842 ↗
65. Use of deep eutectic solvents as catalyst: A mini-review10.1515/gps-2019-0003 ↗
66. Facile, efficient and one-pot access to diverse new functionalized aminoalkyl and amidoalkyl naphthol scaffolds via green multicomponent reaction using triethylammonium hydrogen sulfate ([Et3NH][HSO4]) as an acidic ionic liquid under solvent-free conditions10.1007/s11030-019-09945-4 ↗
67. Magnetic phosphonium ionic liquid: Application as a novel dual role acidic catalyst for synthesis of 2′-aminobenzothiazolomethylnaphthols and amidoalkyl naphthols10.1007/s11164-019-03996-w ↗
68. Magnetic Ionic Liquid Functionalized Sulfonic Acid: A Green and Efficient Catalyst for the One-pot Synthesis of 1-Amidoalkyl-2-Naphthols
69. New Tetradentate Acidic Catalyst for Solvent-Free Synthesis of 1- Amidoalkyl-2-Naphthols and 4,4′-(Arylmethylene)-Bis(3-Methyl-1-Phenyl-1H-Pyrazol-5-ol)s10.1080/10406638.2019.1678180 ↗
70. One-pot three-component synthesis of 1-amidoalkyl naphthols and polyhydroquinolines using a deep eutectic solvent: A green method and mechanistic insight10.1039/D0NJ05687A ↗
71. Cetrimonium Bromide Promoted Efficient Multi-component Protocol for Synthesis of 1-Amidoalkyl-2-naphthols in Aqueous Medium10.14233/ajchem.2021.23251 ↗
72. Complex Nanomaterials in Catalysis for Chemically Significant Applications: From Synthesis and Hydrocarbon Processing to Renewable Energy Applications10.1155/2022/1552334 ↗
73. Preparation and characterization of nano-Co-[4-chlorophenyl-salicylaldimine-methyl pyranopyrazole]Cl2as a new Schiff base complex and catalyst for the solvent-free synthesis of 1-amidoalkyl-2-naphthols10.1002/aoc.5252 ↗
74. Solvent-free synthesis of 1-amidoalkyl-2-naphthols using magnetic nanoparticle-supported 2-(((4-(1-iminoethyl)phenyl)imino)methyl)phenol Cu (II) or Zn (II) Schiff base complexes10.1007/s11164-020-04142-7 ↗
75. A new application of nickel nanoparticles as a heterogeneous catalyst for synthesis of 1-amidoalkyl-2-naphthols according to green chemistry principles
76. Phosphotungstic acid supported on functionalized graphene oxide nanosheets (GO-SiC3-NH3-H2PW): Preparation, characterization, and first catalytic application in the synthesis of amidoalkyl naphthols10.33945/SAMI/ECC.2020.3.10 ↗
77. Catalytic evaluation of newly prepared GO-SB-H2PMo as an efficient and reusable nanocatalyst for the neat synthesis of amidoalkyl naphthols10.33945/SAMI/ECC.2020.3.4 ↗
78. Rostami, E., Nejad, M.S.G., Saberi, A., and Haghayeghi, S.M. (Iran. J. Chem. Chem. Eng., 2022). An efficient and sustainable procedure for the synthesis of amidoalkyl naphthols under solvent-free conditions using a novel graphene oxide based catalyst functionalized with 2-aminobenzothiazole and phosphoric acid, Iran. J. Chem. Chem. Eng., in press.
79. A Novel Hybrid Organic-Inorganic Nanomaterial: Preparation, Characterization and Application in Synthesis of Diverse Heterocycles10.1080/10406638.2020.1776346 ↗
80. Solvent-free synthesis of 1-amidoalkyl-2-naphthol and 3-amino-1-phenyl-1H benzo[f]chromene-2-carbonitrile derivatives by Fe3O4@enamine-B(OSO3H)2 as an efficient and novel heterogeneous magnetic nanostructure catalyst10.2478/pjct-2020-0012 ↗
81. Magnetite (Fe3O4) nanoparticles-supported dodecylbenzenesulfonic acid as a highly efficient and green heterogeneous catalyst for the synthesis of substituted quinolines and 1-amidoalkyl-2-naphthol derivatives10.1007/s13738-020-02069-9 ↗
82. Nano-[Fe3O4@SiO2@RNHMe2][HSO4]: An effectual catalyst for the production of 1-amidoalkyl-2-naphthols
83. Pistachio peel biomass derived magnetic nanoparticles Fe3O4@C-SO3H: A highly efficient catalyst for the synthesis of isoxazole-5(4H)-one, 1-amido alkyl-2-naphthol, pyrano[2,3-c]pyrazole and 2,3-dihydro quinazoline-4(1H)-one derivatives
84. Synthesis of 1-amidoalkyl-2-naphthol derivatives using a magnetic nano-Fe3O4@SiO2@Hexamethylenetetramine-supported ionic liquid as a catalyst under solvent-free conditions10.1002/jccs.201900234 ↗
85. One-pot Synthesis of Amidoalkyl Naphthol Derivatives as Potential Nucleoside Antibiotics and HIV Protease Inhibitors using Nano-SnO2 as an Efficient Catalyst
86. Synthesis of 1-amidoalkyl-2-naphthol derivatives using Supported sulfonic acid on silica coated cobalt ferrite nanoparticles as a catalyst under solvent free conditions
87. Synthesis of Bis (Benzoyl Acetone Ethylene Diimine) Schiff Base Complex of Nickel (II) Supported on Magnetite Silica Nanoparticles (Fe3O4@SiO2/Schiff-Base of Ni(II)) and Using It as an Efficient Catalyst for Green Synthesis of 1-Amidoalkyl-2-Naphthols10.1007/s10904-021-02119-6 ↗
88. Synthesis of the acid–base bifunctional hybrid catalyst via covalently anchored organomoieties on to the SBA-15: A recyclable catalyst for the one-pot preparation of 1-amidoalkyl-2-naphthols10.1007/s11164-022-04802-w ↗
89. Immobilization of CdCl2 on filamentous silica nanoparticles as an efficient catalyst for the solvent free synthesis of some amidoalkyl derivatives10.1080/10406638.2022.2039239 ↗
90. CuFe2O4/KCC-1/PMA as an efficient and recyclable nanocatalyst for the synthesis of amidoalkyl derivatives under solvent-free condition10.1016/j.jorganchem.2022.122530 ↗
91. The phenyltetrazolethiol-based nickel complex: A versatile catalyst for the synthesis of diverse amidoalkyl naphthols and chromenes10.1007/s11164-021-04617-1 ↗
92. Synthesis and Characterization of Pine-cone Derived Carbon-based Solid Acid: A Green and Recoverable Catalyst for the Synthesis of Pyrano_ pyrazole, Amino-benzochromene, Amidoalkyl Naphthol and Thiazolidinedione Derivatives10.2174/1570178617666200210105635 ↗
93. Chitosan-SO3H (CTSA) an efficient and biodegradable polymeric catalyst for the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) and α-amidoalkyl-β-naphthol’s10.1080/00397911.2020.1753078 ↗
94. Bovine bone-derived natural hydroxyapatite-supported ZnCl2 as a sustainable high efficiency heterogeneous biocatalyst for synthesizing amidoalkyl naphthols10.1016/j.jpcs.2021.110533 ↗
95. Synthetic Strategy to Amido Alkyl Naphthols from Pyrazole Aldehydes using Silica Supported NaHSO4.SiO2 as an efficient Heterogeneous Catalyst10.13005/ojc/380426 ↗
96. ZS-1 Zeolite as a Highly Efficient and Reusable Catalyst for Facile Synthesis of 1-amidoalkyl-2-naphthols Under Solvent-Free Conditions10.1007/s10562-021-03684-8 ↗