Synthesis and in Vitro Biological Activity Study of Novel Phenol Mannich Base Analogs Containing Spiroheterocycle as Core Compound
Article Main Content
The condensation reactions between Gabapentin lactam and phenols have been carried out in the presence of formaldehyde for the synthesis of various mannich base series. To confirm the formation of these series of newly prepared mannich bases thus synthesized, various characterization techniques have been used, such as, GC-MS, 1H-NMR, 13C-NMR and FT-IR. Further their antibacterial and antifungal activities against pathogenic bacteria have been evaluated. These compounds show promising activities against the pathogenic bacteria, hence are useful as antibacterial and antifungal active compounds.
References
-
Tramontini M, Angiolini L. Mannich Bases: Chemistry and Uses. CRC Press, Boca Raton; 1994.
Google Scholar
1
-
Saab AN, Sloan KB, Beall HD, Villaneuva R. Effect of Aminomethyl (N-Mannich Base) Derivatization on the Ability of S6Acetyloxymethyl-S-Mercaptopurine Prodrug to Deliver 6-Mercaptopurine through Hairless Mouse Skin. J. Pharm. Sci. 1990; 79(12): 1099.
Google Scholar
2
-
Us D, Berk B, Gürdal E, Aytekin N, Kocagöz T, Çağlayan B, Aksan Kurnaz I, Demir Erol D, Mannich base derivMannich base derivatives of 3-hy es of 3-hydroxy-6- methyl-4H-p xy-6- methyl-4H-pyran-4-one an-4-one with antimicrobial activity, Turk. J. Chem. 2010; 34: 447.
Google Scholar
3
-
Aytemir MD, Özçelik B. Synthesis and biological activities of new Mannich bases of chlorokojic acid derivatives, Med. Chem. Res. 20; 443(2011).
Google Scholar
4
-
Sriram D, Yogeeswari P, Madhu K. Synthesis and in vitro and in vivo antimycobacterial activity of isonicotinoyl hydrazones, Bioorg Med. Chem. Lett. 15; 4502(2005).
Google Scholar
5
-
Us D, Gürdal E, Berk B, Öktem S, Kocagöz T, Çağlayan B, Kurnaz IA, Erol DD, 4H-Pyran-4-one deriv an-4-one derivatives:; leading molecule for pr es:; leading molecule for preparation of ation of compounds with antimycobacterial potential,Turk. J. Chem. 33; 803(2009).
Google Scholar
6
-
Bhaskar Reddy MV, Chen SS, Lin ML, Chan HH, Kuo PC, Wu TS, Preparation of a Series of Novel Bichalcones Linked with a 1,4-Dimethylenepiperazine Moiety and Examination of Their Cytotoxicity, Chem. Pharm. Bull. 2011; 59: 1549.
Google Scholar
7
-
Chen HL, Chang CY, Lee HT, Lin HH, Lu PJ, Yang CN, Shiau CW, Shaw AY. Synthesis and pharmacological exploitation of clioquinol-derived copper-binding apoptosis inducers triggering reactive oxygen species generation and MAPK pathway activation, Bioorg. Med. Chem. 17; 7239(2009).
Google Scholar
8
-
Lan W, Wei J, Qiu J, Yang Z, Su G, Dai Z. Synthesis and biological evaluation mannich bases, Lett. Drug Des. Discov. 2013; 10: 689.
Google Scholar
9
-
Chukicheva IY, Fedorova IV, Buravlev EV, Lumpov AE, Vikharev YB, Anikina LV, Grishko VV, Kuchin AV. The first tetra(meso-aryl)porphyrin bearing isobornyl substituents was synthesized by tetrapyrrole condensation from 4-hydroxy-3,5-diisobornylbenzaldehyde and pyrrole,Chem. Nat. Compd. 46, 478 (2010)
Google Scholar
10
-
Bandgar BP, Patil SA, Totre JV, Korbad BL, Gacche RN, Hote BS, Jalde SS, Chavan SS. Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-α and IL-6 inhibitors with antioxidant activity, Bioorg. Med. Chem. Lett. 2010; 20: 2292-2296.
Google Scholar
11
-
Malhotra M, Sharma R, Sanduja M, Kumar R, Jain J, Deep A. Synthesis of Mannich base derivatives of berberine and evaluation of their anticancer and antioxidant effects Acta Pol. Pharm. 2012; 69: 355.
Google Scholar
12
-
Lal B, Gund VG, Bhise NB, Gangopadhyay AK. Mannich reaction: A versatile and convenient approach to bioactive skeletons Bioorg. Med. Chem. 2004; 12: 1751.
Google Scholar
13
-
Chai H, Zhao Y, Zhao C, Gong P. One-pot synthesis of 1-arylindole-3-carboxylates from 2-(2-isocyanophenyl)acetates. Bioorg. Med. Chem. 2006; 14: 911.
Google Scholar
14
-
Zhao Y, Feng R, Liu Y, Zhang Y, Gong P. Synthesis and in vitro anti-hepatitis B virus activity of some ethyl 5-hydroxy-4-substituted aminomethyl-2-sulfinylmethyl-1H-indole-3-carboxylates Chem. Res. Chin. Univ. 2010; 26: 272.
Google Scholar
15
-
Trofimov FA, Tsyshkova NG, Bogdanova NS, Nikolaeva IS, Zotova SA, Sakhaschik ZM, Padeiskaya EN, et al. US Patent. 1993; 5(198):552.
Google Scholar
16
-
Boriskin, Y S, Leneva, IA, Pecheur, EI, Polyak SJ. Rbidol: A Broad-Spectrum Antiviral Compound that Blocks Viral Fusion. Curr. Med. Chem. 2008; 15: 997.
Google Scholar
17
-
Teissier E, Loquet A, Lavillette D, Lavergne JP, Montserret R, Cosset FL, Böckmann A, et al. The broad-spectrum antiviral arbidol (Arb) inhibits cell entry of enveloped viruses by blocking viral fusion with host cell membrane. PLoS ONE 2011; 6: 15874.
Google Scholar
18
-
Zhao Q, Liu X, Zhang L, Shen X, Qi J, Wang J, Qian N, Deng L. Bone selective protective effect of a novel bone-seeking estrogen on trabecular bone in ovariectomized ratsCalcif. Tissue Int. 2013; 93: 172.
Google Scholar
19
-
Aytemir MD, Septioglu E, Çalis U. Synthesis and anticonvulsant activity of new kojic acid derivatives, Arzneimittelforschung 2010; 60: 22.
Google Scholar
20
-
Chukicheva IY, Fedorova IV, Buravlev EV, Lumpov AE, Vikharev YB, Anikina LV, Grishko VV, Kuchin AV. Anti-inflammatory activity of isobornylphenol derivatives chem. Nat. Compd. 2010; 46: 478.
Google Scholar
21
-
Shen AY, Huang, MH,Liao LF, Wang TS. Thymol analogues with antioxidant and L-type calcium current inhibitory activity. Drug Dev. Res. 2005; 64: 195.
Google Scholar
22
-
Fernandez-Bachiller MI, Perez C, Gonzalez-Munoz GC, Conde S, Lopez MG, Villarroya M, García AG, et al. Novel Tacrine−8-Hydroxyquinoline Hybrids as Multifunctional Agents for the Treatment of Alzheimer’s Disease, with Neuroprotective, Cholinergic, Antioxidant, and Copper-Complexing Properties, J. Med. Chem. 2010; 53: 4927.
Google Scholar
23
-
Bandgar BP, Patil SA, Gacche RN, Korbad BL, Hote BS, Kinkar SN, Jalde SS. Synthesis and biological evaluation of nitrogen-containing chalcones as possible anti-inflammatory and antioxidant agents, Bioorg. Med. Chem. Lett. 2010; 20: 730.
Google Scholar
24
-
Velazquez AM, Martínez V, Abrego V, Balboa MA, Toreres LA, Camacho B, Díaz-Barriga S, et al. The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates, Eur. J. Med. Chem. 2008; 43: 486.
Google Scholar
25
-
Abrego VH, Martínez-Perez B, Torres LA, Angeles E, Martínez L, Marroquín-Pascual JL, Moya-Hernandez R, et al. Antihypertensive and antiarrhythmic properties of a para-hydroxy[bis(ortho-morpholinylmethyl)]phenyl-1,4-DHP compound: Comparison with other compounds of the same kind and relationship with logP values, Eur. J. Med. Chem. 2010; 45: 4622.
Google Scholar
26
-
Reddy MV, Tsai WJ, Qian K, Lee KH, Wu TS. Structure–activity relationships of chalcone analogs as potential inhibitors of ADP- and collagen-induced platelet aggregation. Bioorg. Med. Chem. 2011, 19, 7711.
Google Scholar
27
-
Akkoç S, Tüzün B, İlhan OI, Akkurt M. Investigation of structural, spectral, electronic, and biological properties of 1,3-disubstituted benzimidazole derivatives, J. Mol. Struct, 2020; 128582.
Google Scholar
28
-
Douche D, Elmsellem H, Guo L, Hafez B, Tüzün B, El Louzi A, Bougrina K, et al. Examination of anti-oxidant properties and molecular docking parameters of some compounds in human body, J. Mol. Liq, 2020, 113042.
Google Scholar
29
-
Tüzün B, Saripinar E. J. Iran. Chem. Soc, 2020; 17: 985.
Google Scholar
30
-
Singh R, Bhardwaj D, Saini MR. RSC Adv., 2021; 11: 4760-4804.
Google Scholar
31
-
Morjan RY, Ghonium FJ, Abu-Teim OS, Awadallah AM, Al-Reefi MR, Elmanama A, et al. IUG J.Nat. Stud, 2022; 30(02): 38-46.
Google Scholar
32
-
Manika M, Chanotiya C, Darokar M, Singh S, Bagchi G. Rec. Nat. Prod., 2016; 10: 40-46.
Google Scholar
33
-
Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria grow aerobically. Approved Standard M7-A4. Wayne, Pa, USA, 2005.
Google Scholar
34
-
Collins CH, Lyne PM. Microbiology methods, 1970.
Google Scholar
35
-
Atlad RM. Principles of microbiology, 1987; 10: 356.
Google Scholar
36