Synthesis, structural investigation and molecular docking studies of pyridinyl tetrahydroisoquinoline, morpholine and piperidine containing schiff's bases
Keywords:
Schiff's bases, pyridinyl tetrahydroisoquinoline, morpholine, piperidine, aromatic amines, aminobenzaldehydeAbstract
The present work was conducted to synthesize some Schiff's bases derived from pyridinyl tetrahydroisoquinoline, morpholine and piperidine moieties by the condensation reaction of aminobenzaldehyde with various aromatic amines in good to excellent yield. The structures of synthesized compounds were confirmed by 1H NMR, 13C NMR and mass spectra (ESI-MS) data. These compounds also evaluated for their in silico anti-microbial properties by molecular docking studies. Docking studies were carried out by using Argus Lab 4.0.1 software.
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Ahirwar J, Ahirwar D, Lanjhiyana S, Jha AK, Dewangan D, Badwaik H. Analgesic and Anti‐inflammatory Potential of Merged Pharmacophore Containing 1,2,4‐triazoles and Substituted Benzyl Groups via Thio Linkage. J Heterocycl Chem. 2018a;55(9):2130-2141.
Ahirwar J, Ahirwar D, Lanjhiyana S, Jha AK, Dewangan D, Badwaik H. Synthesis, Characterization, Molecular Modeling, and Biological Evaluation of 1, 2, 4‐Triazole‐pyridine Hybrids as Potential Antimicrobial Agents.J Heterocycl Chem. 2018b;55(11):2598-609.
Kumar, S. (2022). A quest for sustainium (sustainability Premium): review of sustainable bonds. Academy of Accounting and Financial Studies Journal, Vol. 26, no.2, pp. 1-18
Allugunti V.R (2022). A machine learning model for skin disease classification using convolution neural network. International Journal of Computing, Programming and Database Management 3(1), 141-147
Allugunti V.R (2022). Breast cancer detection based on thermographic images using machine learning and deep learning algorithms. International Journal of Engineering in Computer Science 4(1), 49-56
Bentley K. W. β-Phenylethylamines and the isoquinoline alkaloids. Nat. Prod. Rep. 2005; 22: 249–268.
Cai HY, Luo W. Preparation of Schiff Base Derived from 3, 4-Dimethoxybenzaldehyde and p-Aminobenzoic Acid by Supersonic Speed Gas Impacting Method. 2014; 218376:5.
Castillo JC, Jiménez E, Portilla J, Insuasty B, Quiroga J, Moreno-Fuquen R, Kennedy A R, Abonia R. Application of a catalyst-free Domino Mannich/Friedel-Crafts alkylation reaction for the synthesis of novel tetrahydroquinolines of potential antitumor activity. Tetrahedron. 2018; 74: 932–947.
Dewangan D, Nakhate KT, Verma VS, Nagori K, Badwaik H, Nair N, et al. Synthesis and Molecular Docking Study of Novel Hybrids of 1, 3, 4‐Oxadiazoles and Quinoxaline as a Potential Analgesic and Anti‐Inflammatory Agents. J Heterocycl Chem. 2018;55(12):2901-10.
Dewangan D, Vaishnav Y, Mishra A, Jha AK, Verma S, Badwaik H. Synthesis, molecular docking, and biological evaluation of Schiff base hybrids of 1, 2, 4-triazole-pyridine as dihydrofolate reductase inhibitors. Curr Res Pharmacol Drug discov. 2021;2:100024.
Dhar DN, Taploo CL. Schiff bases and their applications. J Sci Ind Res. 1982; 41:501-506.
Fodale V, Santamaria LB. Obstetric Anesthesia Handbook. Eur. J. Anaesthesiol, 5th ed.; Datta S, Kodali BS, Segal S, Academic Press: New York, 2002; 466–473.
Gao M, Kong D, Clearfield A, Zheng Q.-H. Synthesis of carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives as new potential PET AMPA receptor ligands. Bioorg. Med. Chem. Lett. 2006; 16: 2229–2233.
Guo Z, Xing R, Liu S, Zhong Z, Ji X, Wang L. Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan. Carbohydr Res. 2007; 342 (10):1329-1332.
Gupta RR, Gupta VK. Heterocyclic Chemistry Three- and Four-Membered Heterocycles I. Pub. By: Springer Berlin Heidelberg. 1998.
Kamdi SP, Badwaik HR, Raval A, Nakhate KT. Ameliorative potential of phloridzin in type 2 diabetes-induced memory deficits in rats. Eur J pharmacol. 2021;913:174645.
Karthik CS, Mallesha L, Santhosh MV, Nagashree S, Mallu P. Synthesis, Characterization, Antimicrobial Activity, and Optical Properties of Schiff Bases Derived from 4 (Aminomethyl) Piperidine. Indian Journal of Advances in Chemical Science. S1 2016; 206-212.
Kenchappa R, Bodke YD, Chandrashekar A, Telkar S, Manjunatha SK, Sindhe MA. Synthesis of some 2,6-bis(1-coumarin-2-yl)-4-(4-substituted phenyl)pyridine derivatives as potent biological agents. Arab J Chem.2017; 10:S1336–S1344.
Ko YS, Park EJ, Kim YM, Kim HJ, Yun-Choi H, Lee DH, Chang KC. A limited series of synthetic tetrahydroisoquinoline alkaloids reduce inflammatory gene iNOS via inhibition of p-STAT-1 and suppress HMGB1 secretion in LPS-treated mice lung tissue. Int. Immunopharmacol. 2017; 52: 297–304.
Pastine SJ, McQuid KM, Sames D. Room Temperature Hydroalkylation of Electron-Deficient Olefins: sp3 C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event J. Am. Chem. Soc.2005; 127: 12180.
Pingaew R, Mandi P, Nantasenamat C, Prachayasittikul S, Ruchirawat S. Prachayasittikul V. Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity. Eur. J. Med. Chem. 2014; 81: 192–203.
Sadia M, Khan J, Naz R et al., Schiff base ligand L synthesis and its evaluation as anticancer and antidepressant agent, Journal of King Saud University- Science. 2021; 33 (2): 101331.
Sakthikumar K, Raja JD, Sankarganesh M and Rajesh J. Antimicrobial, Antioxidant and DNA Interaction Studies of Water-soluble Complexes of Schiff Base Bearing Morpholine Moiety. Indian J Pharm Sci. 2018; 80(4):727-738.
Sano T, Shinohara T, Takeda A, Toda J, Terasawa N. A highly efficient synthesis of 1-methyl-, 1-benzyl-, and 1-phenyl-1, 2, 3, 4-tetrahydroisoquinolines by a modified pummerer reaction. Heterocycles 1997; 46: 555–565.
Santos FL, Moragues ME, Climent E, Agostini A, Martínez-Máñez R, F. Sancenón Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the years 2010–2011. Chem. Soc. Rev.2013; 42 (8): 3489.
Scott JD, Williams RM. Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. Chem. Rev. 2002; 102: 1669-1730.
Siegfried L, Helmut V, Guenther W, Thomas S, Eckart S, Dieter L, Gunter L. Ger (East) DD. 1988; 258: 013; Appl. 1987, 300, 312; 5. Chem. Abstr. 1989; 110.
Takada K, Uehara T, Nakao Y, Matsunaga S, van Soest RWM. Fusetani N. Schulzeines A–C, New α-Glucosidase Inhibitors from the Marine Sponge Penares schulzei1. J. Am. Chem. Soc. 2004; 126: 187–193.
Zaman K, Rahim F, Taha M. et al., Synthesis of new isoquinoline-base-oxadiazole derivatives as potent inhibitors of thymidine phosphorylase and molecular docking study. Sci Rep. 2019; 9: 16015.
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