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Review of Literature Chapter 3 Review of Literature Sunil G. Sanghani et al have investigated a series of Mannich bases were prepared by the reaction of 7-methyl-2-(p-methyl phenyl)imidazo[1,2-a]pyridine with secondary amines and p-formaldehyde in appropriate solvent. The newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR and mass spectra. All the synthesized compounds were tested for their antibacterial activities against Gram positive and Gram negative bacteria and antifungal activities [1]. 2-(p-methylphenyl)-7-methyl imidazo[1,2-a]pyridine Lingappa et al has prepared the new series of 3-(4,6-disubstituted-2- thiomethylpyrimidyl)-4-amino-5-mecapto-1,2,4-triazoles have been synthesized. These triazoles on reaction with aldehyde in the presence of acid catalyst forms Schiff’s base. These Schiff’s bases can exist both in the thiol as well as in the thione tautomeric form. However when these compounds are subjected to Mannich reaction, Mannich base are obtained rather than the S-Mannich bases. The structures of the new compounds have been confirmed by spectral and analytical data. Few of these Mannich base have been evaluated for their possible antifungal and antibacterial activity. Most of the test compounds show significant antifungal and antibacterial activity [2]. Huseyin Istanbullu et al have studied the design, synthesis, characterization, and cytotoxic activity of a series of uracil C-Mannich bases. Among them, one hybrid compound (1), a molecular combination of the potential antimetabolite substituted uracil and nitrogen mustard, having potential alkylating capability was prepared as a Mannich base. The other compound was synthesized with the replacement of chlorines in the ethyl chains with hydroxyl groups for testing for anticancer activity. Some of Mannich bases having several amino groups with different pKa values were also synthesized and investigated in terms of cytotoxic activity. Their chemical structures were confirmed by means of their UV, IR, 1H NMR, 13C-NMR, and MS data. © IOR INTERNATIONAL PRESS 2019 P.Sounthari and P.R. Sivakumar, Synthesis and Characterization of Some Novel Mannich Base Compounds, https://doi.org/10.34256/ioriip1983 38 Review of Literature Compounds 6 with diethylamine and 8 with piperazine are reported for the first time in the literature and compounds 1, 4, and 5 containing nitrogen mustard, pyrolidine, and diethanolamine, respectively, as amine function are reported for first time with detailed spectral data herein. Morpholine, piperidine, and dimethylamine were used in Mannich reactions for the synthesis of compounds 2, 3 and 7. The biological activities using MTT assays on 3 human cell lines: HeLa (cervix adenocarcinoma), MCF7 (breast adenocarcinoma), and A431 (skin epidermoid carcinoma). While compounds 2-8 have the potential to deaminate, forming ortho-quinone methides, which would be capable of alkylating cellular thiols, compound 1 has the potential to give aziridinium ion for nucleophilic alkylation. Our results are discussed in terms of the significance of these compounds in pharmaceutical use [3]. Compound R Groups Compound R Groups 1 R1=R2= -CH2CH2Cl 5 R1=R2= -CH2CH2OH 2 R1=R2= -C2H4OC2H4 6 R1=R2= -CH2CH3 3 R1=R2= -C5H10 7 R1=R2= -CH3 4 R1=R2= -C4H8 8 R1=R2= -C2H4NHC2H4 Shaker Youssifa et al have synthesized several 6-substitued-1-methyl- 2,5,7,8-tetrahydro-2-thiopyrimido[4,5-d]pyrimidine-4-ones and ethyl-7-amino-5- aryl-1-methyl-4-oxo-1,2,3,4-tetrahydro-2-thiopyrido[2,3-d]pyrimidines-6- carboxylates were synthesized by treatment of 6-amino-1-methyl-2-thiouracil with primary amines and formalin (40%) and with ethyl 3-aryl-2-cyanoacrylate respectively. 8-Substituted-7-hydroxy-3-methyl-2-thioxanthines were synthesized by the treatment of 6-amino-1-methyl-5-nitroso-2-thiouracil with benzylidene-anilines. Elemental and spectral analyses were performed for the new compounds [4]. 6-amino-1-methyl-2-thiouracil R=-C6H5, -C6H4-4-CH3, -C6H4-4-NO2, -C6H4-4-OCH3, -naphthyl-2, -C2H5, -C6H4-3-OCH3, -C6H4-3-Cl 39 Review of Literature Haiffaa Y. Hussin have been prepared some acetylenic amine derivatives containing nitrogen bases (cytosine, uracil) were synthesized through Mannich reaction which involved reaction of N-propargyl cytosine or uracil with paraformaldehyde and secondary amines. The structures of synthesized compounds have been confirmed depending on the physical and spectral data [5]. Synthesized acetylenic amines derivatives Tomasz Pospieszny et al have synthesized six new 2-o-(m- and p-) chlorobenzylthio-6-methyl-5-piperidino-(or morpholino-) methyluracils. The structures of these compounds were confirmed by spectroscopic (FT-IR, UV-Vis, 1H NMR, 13C NMR, and HMBC) and elemental analyses. Estimation of pharmacotherapeutic potential has been made for synthesized compounds on the basis of prediction of activity spectra for substances (PASS) [6]. X = CH2, o-C X = O, o-Cl X = CH2, m-CI X = O, m-CI X = CH2, m-CI X = O, m-CI X = CH2, p-CI X = O, p-CI Govindu et al have been prepared the synthesis, as well as spectroscopic characterization, biological evaluation and docking studies of a novel class of N'-((1- (piperidin/morpholin/ thiomorpholin/ methylpiperazine)-1H-imidazol-4-yl) methylene)-3-(4-substituted phenyl-[1,2,4] triazolo [4,3-c] pyrimidine-8- carbohydrazide derivatives are described. All the synthesized compounds were characterized by elemental analysis FTIR, 1H-NMR, 13C NMR, and Mass spectral data. All the synthesized compounds were exhibits antimicrobial activities. Further the docking studies were carried out based on mycobacterial studies for the model 40 Review of Literature compounds against Transaminase BioA enzyme and the results found are moderate [7]. X= CH2, O, S, NCH3 R= H, CH3, OCH3, NO2, CF3 pyrimidines containing imidazole Mannich bases derivatives Hironao Sajiki et al have been reported the reaction of 5-halogenouracil and uridine derivatives with active methylene compounds under basic conditions produced diverse and selective C-C bond formation products by virtue of the nature of the carbanions. Three different types of reactions such as the regioselective C-C bond formation at the 5 and 6-positions of uracil and uridine derivatives and the formation of fused heterocycle derivatives 2,4-diazabicyclo[4.1.0]heptane and 2,4-diazabicyclo- [4.1.0]nonane via dual C-C bond formations at both the 5- and 6-positions were due to the different active methylene compounds used as reagents [8] R=CO2Et, CN 2,4-diazabicyclo[4.1.0]heptane 2,4-diazabicyclo[4.1.0]nonane (cyclopropane) (cyclopentane) Navgeet Kaur et al have investigated a series of pyrimidines bearing a pyronyl side chain in the 4-position is described. These unreported compounds are obtained starting from commercially available dehydro acetic acid (DHA), aromatic aldehydes and S-benzylisothiouronium chloride (SBT). A series of compounds were 41 Review of Literature prepared and tested for their antimicrobial activity. These synthesized compounds showed mild activity against gram +ve bacteria and very less activity against gram - ve bacteria. Compounds 6-(4-Fluorophenyl)-4-(4-hydroxy-6-methyl-2-oxo-2H- pyran-3-yl)-2-S-benzylthio pyrimidine, 6-(2-Thiophene)-4-(4-hydroxy-6-methyl-2- oxo-2H-pyran-3-yl)-2-S-benzylthiopyrimidine, 6-(4-Pyridyl)-4-(4-hydroxy-6- methyl-2-oxo-2H-pyran-3-yl)-2-S-benzylthio pyrimidine showed mild activity against gram +ve Bacillus subtilis bacteria while against gram -ve Pseudomonas aeruginosa compound 6-(2-Thiophene)-4-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3- yl)-2-S-benzylthiopyrimidine showed minor activity [9]. Ar = Ph, 4-FC6H4, 3-ClC6H4, 4-BrC6H4, 4-OH-3-Et- C6H3, 3-OCH3-4-OH- C6H3, (CH3)2NC6H4, (C2H5)2NC6H4, 2-Thienyl, 4-Pyridyl Caurino Cesar Bombardieri et al have synthesized some new Mannich bases was accomplished by the condensation of secondary amines and formaldehyde with the following compounds: (1) 2-pyrrolidone, (2) 2,4-thiazolidinedione, (3) hydantoin, (4) 5,5-dimethylhydantoin, (5) uracil, (6) ethylnitramine, and (7) n- butylnitramine [10]. Firouzeh Nematia et al have prepared Three-component Mannich-type reaction of acetophenon, aromatic aldehydes, and aromatic amines is catalyzed by 2,4,6-trichloro[1,3,5]triazine at ambient temperature in EtOH and solvent-free conditions to give various β-amino ketones in high yields [11]. The Mannich reaction using TCT. Desai Sweta D et al have prepared ten compound which were synthesized in a series of 2,4,6-trichloro-1,3,5-s-triazine analogues which in substitution with 42 Review of Literature anisole, 4-hydroxy coumarin and different N-substituted piperazine derivatives on the C-6 position of s-triazine ring. The title compounds were screened for their in vitro antimicrobial activity against two gram negative bacteria (E. coli, K. pneumoniae), two gram-positive bacteria (S. aureus, B. subtilis) and two fungal species (C. albicans and S. cerevisiae) using the disc diffusion method. Most of the synthesized compounds appeared with promising antimicrobial activity. The structure of the novel compounds were elucidated on the basis of IR, 1H NMR and elemental analysis [12]. Marwa F. Balaha et al have investigated that dihydrofolate reductase (DHFR) is the primary target enzyme for antifolate drugs and 1,3,5-triazine derivatives containing various amino groups at position 2, 4 or 6 have been known as potent anticancer drugs, two series of tri-amino-substituted 1,3,5-triazine derivatives were designed, synthesized and evaluated as cytotoxic agent against non-small cell lung cancer(A549). The first series are N2-(4-phenylthiazol-2-yl)-1,3,5-triazine-2,4,6- triamine analogs and the second series are 4-((4,6-Diamino-1,3,5-triazin-2-yl)amino)- 4H-1,2,4-triazole-3-thiol analogs. Out of twenty two synthesized compounds there were thirteen compounds showed a higher cytotoxic activity against A549 cell line than methotrexate and four compounds were equipotent to methotrexate.
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