Open Access
Subscription or Fee Access
Review Paper on Mannich Bases for Heterocyclic Compound Synthesis
Abstract
Mannich bases are the Lewis bases which are β-amino carbonyl compounds synthesized as the end
products of well known condensation reaction known as Mannich reaction. These are the
aminoalkylation reactions involving the formation of carbon-carbon, carbon-Nitrogen, carbonsulphur
bonds. Mannich bases of 2-furylmethylketone, catechol, 4-chlorophenol, derivative of
berberine, lawsone, anisaldehyde, benzaldehyde show diversity of biological activities. Mannich
reaction is a carbon-carbon bond forming nucleophilic addition reaction and is a key step in synthesis
of a widespread variety of natural products and pharmaceuticals. Mannich reaction is important for
the construction of nitrogen comprising compounds. There are number of aminoalkyl chain bearing a
Mannich bases connected to the fluoxetine, atropine, ethacrynic acid and so forth with high curative
value. Literature studies informed that the Mannich bases are very reactive and predictable to possess
the potent diverse activities like anti-inflammatory, anticancer, antifilarial, antibacterial, antifungal,
analgesic, anti-HIV, antimalarial, antipsychotic, antiviral activities and so forth. Biological activity of
the Mannich bases are largely accredited to α, β-unsaturated ketone which can be made by the
deamination of hydrogen atom of the amine group.
Keywords: Mannich reaction, Carbonyl compound, Metal complexes, Biological activity.
References
Livingstone SE. Metal Chelates As Anti-Cancer Agents. Coordination Chemistry–XX. 1980; 141-148.
Collma JP, Gagne RR, Reed C, et al. Picket fence porphyrins. Synthetic models for oxygen binding hemoproteins. Journal of the American Chemical Society. 1975; 97(6): 1427-1439.
Thomson AJ. Proteins containing nickel. Nature. 1982; 298(5875): 602-603.
Hay RW. A two site mechanism for carbonic anhydrase B. Inorganica Chimica Acta, 46. (1980); L115-L117.
Spik CG, Parry RW. Thermodynamics of Chelation. I. The Statistical Factor in Chelate Ring Formation1. Journal of the American Chemical Society. 1953; 75(11): 2726-2729.
Rao J, Srimal RC, Audry E, et al. Synthesis and QSAR studies on hypotensive N-< 3-aryl (thio/sulfono) propyl> piperazines/piperidines. Indian J Chem. 1987; 26: 761-768.
Kasim ANM, Venkatesa PG. Synthesis, characterisation and antimicrobial screening of aminobenzylated Mannich bases of acetamide and urea. Asian Journal of Chemistry. 2000; 12(2): 385.
Desai PS, Desai KR. Synthesis and Antibacterial Activity of 2‐(6′‐Chlorobenzothiazol‐2′‐ylamino)‐4‐(N4‐(N1‐(n‐butyl) sulfanilamido))‐6‐(arylthioureido)‐s‐triazine Derivatives. ChemInform. 1994; 25(24).
Paul RC, Bedi As. Compounds of Transition Metal Tetrafluoroborates With Oxygen And Nitrogen Bases. 1976.
Sigel H, Martin RB. Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands. Chemical Reviews. 1982; 82(4): 385-426.
Gerrard W, Lappert MF, Wallis JW. 432. Interaction of boron trichloride and amides or oximes, and allied reactions. Journal of the Chemical Society (Resumed). 1960; 2141-2144.
Werner K, Mecke R. Spektroskopische Untersuchungen an organischen Ionen—V Die Struktur der Salze des Acetamids. Spectrochimica Acta. 1962; 18(4): 549-560.
Kerridge DH. The chemistry of molten acetamide and acetamide complexes. Chemical Society Reviews. 1988; 17: 181-227.
Srivastava TN, Tandon SK, Bajpai B. Co-ordination compounds of acetamide and its substituted derivatives with diphenyltin dihalides. Inorganica Chimica Acta. 1975; 13: 109-112.
Cunningham WK, Stephens RS, Ragsdale RO. Nickel (II) and cobalt (II) complexes of primary alkyl amides. Journal of Inorganic and Nuclear Chemistry. 1969; 31(11): 3579-3584.
Paul RC, Bedi AS. Compounds of transition metal tetrafluoroborates with oxygen and nitrogen bases. 1976.
Paul RC, Dev R. Acetamide as a polar solvent. i. formation of solvates and study of nature of solutions of lewis acids in acetamide. Indian journal of chemistry. 1967; 5(6): 267.
Kravchenko VV. Magnetochemical and spectroscopic investigation of some carbamide and acetamide derivatives of manganese (ii), cobalt (ii) and nickel (ii) derivatives. Zhurnal neorganicheskoi khimii. 1990; 35(2): 419-423.
Venkatesa PG, Mohamed Kasim AN. Synthesis, characterisation and biological activity of oxovanadium (IV), thorium (IV) and dioxouranium (VI) complexes of N-(1-piperidinobenzyl) urea and N, N'-bis (N-morpholinobenzyl) urea. Asian Journal of Chemistry. 2000; 12(2): 379-384.
Venkatesa PG, Venkappayya D. Metal Complexes of Piperidinobenzylurea. Journal of the Indian Chemical Society. 1995; 72(8): 511-514.
Penland RB, Yamaguchi A, Lane J, et al. Infrared Absorption Spectra of Inorganic Coördination Complexes. X. Studies of Some Metal-Urea Complexes1a, b. Journal of the American Chemical
Toscano PJ, Fordon KJ, Liu S, et al. Novel square pyramidal copper (II) complexes of the stereospecific linear NSNN tetradentate ligand, N-[(2-pyridyl) methyl]-2-[(2-aminoethyl) thio] acetamide (pygeH). The crystal structures of [Cu (pyge) X](X= Br, N3). Polyhedron. 1990; 9(19): 2375-2383.
Kasim ANM, Venkappayya D, Prabhu GV. Synthesis, characterisation and antimicrobial activity of metal complexes of N-(1-piperidinobenzyl) acetamide. Journal of the indian chemical society. 1999; 76(2): 67-69.
Anion, Copper. Sabastiyan & vbnkappayya: copper (h) complexes of morpholino methyl urea etc. Journal of the Indian Chemical Society. 1984; 61: 16-19.
Viswanathan M, Krishnan G. Synthesis and Characterization of Mixed Ligand Complexes of Praseodymium (III), Neodymium (III), Samarium (III), Gadolinium (III) and Dysprosium (III) with Piperidinobenzylurea. Asian Journal of Chemistry. 2004; 16(1): 156.
Bruckner R. Advanced organic chemistry: reaction mechanisms. Elsevier. 2001.
Belinelo VJ, Reis GT, Stefani GM, et al. Synthesis of 6α, 7β-di-hydroxy-vouacapan-17β-oic acid derivatives. XXIII: obtention and characterization of N-ethyl-N-methyl-6α, 7β-dimethoxy-vouacapan-17β-amide. Journal of Brazilian chemical society. 2002; 13.
Joshi S, Khosla N, Tiwari P. In vitro study of some medicinally important Mannich bases derived from antitubercular agent. Bioorganic & medicinal chemistry. 2004; 12(3): 571-576.
Racane L, Kulenovic VT, Jakic LF. Synthesis of bis-substituted amidinobenzothiazoles as potential anti-HIV agents. Heterocycles. 2001; 55(11): 2085-2098.
Kashiyama E, Chua MS, Phillips LR, et al. Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C-and N-oxidation products of antitumor 2-(4-aminophenyl) benzothiazoles. Journal of medicinal chemistry. 1999; 42(20): 4172-4184.
Bhusare SR, Pawar RP, Vibhute YB. Synthesis and antibacterial activity of some new 2-(substituted phenyl sulfonamido)-6-substituted benzothiazoles. Indian Journal of Heterocyclic Chemistry. 2001; 11(1): 79-80.
Ivanova Y, Momekov G, Petrov O, et al. Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2 (3H)-benzoxazolones. European journal of medicinal chemistry. 2007; 42(11-12): 1382-1387.
Gul HI, Gul M, erciyas E, et al. Cytotoxic activities of mono and bis Mannich bases derived from acetophenone against Renca and Jurkat cells. Pharmaceutica Acta Helvetiae. 2000; 74(4): 393-398.
Köksal M, Gokhan N, Kupeli E, et al. Analgesic and antiinflammatory activities of some new Mannich bases of 5-nitro-2-benzoxazolinones. Archives of pharmacal research. 2007; 30(4): 419-424.
Pandeya SN, Sriram D, Nath G, et al. Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin Mannich bases. European journal of medicinal chemistry. 2000; 35(2): 249-255.
Edwards ML, Ritter HW, Stewart KT, et al. Mannich bases of 4-phenyl-3-buten-2-one. A new class of antiherpes agent. Journal of medicinal chemistry. 1983; 26(3): 431-436.
Bala S, Sharma N, Saini V, et al. Mannich bases: an important pharmacophore in present scenario. International journal of medicinal chemistry. 2014.
Barlin GB, Jiravinyu C. Potential antimalarials. X. Di-Mannich Bases of 4-(7'-Trifluoromethyl-1', 5'-naphthyridin-4'-ylamino) phenol and N-(4'-Diethylamino-1'-methylbutyl)-7-trifluoromethyl-1, 5-naphthyridin-4-amine. Australian Journal of chemistry. 1990; 43(7): 1175-1181.
Mithun A, Holla BS, Poojary B. Convenient one pot synthesis and antimicrobial evaluation of some new Mannich bases carrying 4-methylthiobenzyl moiety. European journal of medicinal chemistry. 2007; 42(8): 1095-1101.
Kalluraya B, Chimbalkar RM, Hegde JC. Anticonvulsant activity of nicotinyl∖isonicotinyl substituted 1,2,4-triazol-5-thione Mannich bases. Indian Journal of Heterocyclic Chemistry. 2005; 15(1): 15–18.
Eva BJ, Bryant C. Novel sources of anthelmintics. International Journal for Parasitology. 1996; 26(8-9): 937-947.
Tang M, Li J, Li Z, et al. Mannich base as corrosion inhibitors for N80 steel in a CO2 saturated solution containing 3 wt% NaCl. Materials. 2019; 12(3): 449.
Korpman R. Absorbent products, process and compositions for immobilization of particulate absorbents. U.S. Patent No. 4,410,571. 1983.
Kannan SS, Basha F, Padusha MSA. Effect of metal complexes of 1-[morpholino (4-nitrophenyl) methyl]-3-phenylurea on viability of dpph free radical scavenging and anti-inflammatory activities. Research Journal of Life sciences, Bioinformatics, Pharmaceutical and Chemical Sciences. 2018; 4(6): 531.
Anusuya AM, Krishna BS. Synthesis Characterization and biological applications of some Heterocyclic molecules of Transition metal complexes. Synthesis. 2019; 7(5).
Padusha MSA, Krishnaveni G. Synthesis, Spectral Characterisation and Antibacterial Activity of metal complexes derived from the mannich base, n-(3-(furan-2-yl)-3-oxo-1-phenylpropyl) acetamide. International Journal of Creative Reasearch Thoughts. 2018; 6(1): 801-807.
Ayeni A, Oyerinde M, Emmanuel A. Synthesis, Characterisation and Antimicrobial Activity of Mannich base Transition Metal Complexes derived from 3-(diethanolamin-1-ylmethyl) benzene-1, 2-diol. Journal of Chemical and Pharmaceutical Research. 2016; 8(7): 171-175.
Chen G, Yuan W, Jeje A, et al. Methanol enhanced catalytic viscosity-reduction of heavy oil by transition metal-Mannich base complex under low temperature. Russian Journal of Applied Chemistry. 2016; 89(11): 1853-1860.
Mistry B, Keum YS, Kim DH, et al. Synthesis of piperazine based N-Mannich bases of berberine and their antioxidant and anticancer evaluations. Journal of the Iranian Chemical Society. 2016; 13(3): 531-539.
Ahmad A, Mahal K, Padhye S, et al. New ferrocene modified lawsone Mannich bases with anti-proliferative activity against tumor cells. Journal of Saudi Chemical Society. 2017; 21(1): 105-110.
Petchiammal M., Ravichandran S. Synthesis, Spectral Characterisation And Antibacterial Activity Of Metal Complexes Derived From The Mannich Base, N-[1-Piperidino (4-Methoxybenzyl)] Acetamide. International Journal of Chemical Technology. 2017; 4(5): 229-232.
Liaqat M, Mahmud T, Imran M, et al. Synthesis, characterization and biological activities of a novel Mannich base 2-[(3, 4-dimethoxyphenyl)(pyrrolidin-1-yl) methyl] cyclopentanone and its complexes with Cu (II), Co (II), Ni (II) and Fe (II) ions. BULGARIAN CHEMICAL COMMUNICATIONS. 2018; 50(1): 37-43.
Mohammed A, Ryan N, Lewis D, et al. Tripodal O‐N‐O Bis‐Phenolato Amine Titanium (IV) Complexes Show High in vitro Anti‐Cancer Activity. European Journal of Inorganic Chemistry. 2019; 219(22): 2774-2780.
Muruganandam L, Krishnakumar K. Synthesis, characterization and antimicrobial studies of a new mannich base n-[morpholino (phenyl) methyl] acetamide and its cobalt (ii), nickel (ii) and copper (ii) metal complexes. Journal of Chemistry. 2012; 9(2): 875-882.
Refbacks
- There are currently no refbacks.