Thiadiazine Derivatives as Antiprotozoal New Drugs (original) (raw)
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2012
The 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thione scaffold has found many applications in recent years. This review is aimed at highlighting the most important aspects of these compounds: Synthesis, spectroscopic characterization and biological activities. How the chemical nature of N-substituents influences the overall activity and cytotoxicity profile will also be discussed.
Thiadiazines, N,N-heterocycles of biological relevance
Molecules (Basel, Switzerland), 2012
The 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thione scaffold has found many applications in recent years. This review is aimed at highlighting the most important aspects of these compounds: Synthesis, spectroscopic characterization and biological activities. How the chemical nature of N-substituents influences the overall activity and cytotoxicity profile will also be discussed.
Synthesis and antimicrobial activity of novel 1,3,4-thiadiazine derivatives
2013
Compound (1) was treated with phenacyl bromide to yield compound (3), which was brominated to yield compound (4) and Further condensed with piperazine ester to obtained compound (6). Compound (6) was treated with hydrazine hydrate to obtained compound (7), which on further treatment with aromatic aldehydes which yielded corresponding Schiff base compound (8). Compound (8) in acidic medium undergoes cyclization to yield respective novels thiadiazine derivatives(9). The structures of the newly synthesized compounds were confirmed by IR, 1H NMR and mass spectroscopic analysis.
2017
were screened for their antibacterial and antifungal activities against some selected pathogenic organisms like Escherichia coli, Proteus vulgaris, Staphylococcus aureus, Salmonella typhimurium, Klebsiella pneumonie, Psudomonas aeruginosa, Aspergillus Niger and Candida albicance. These compounds show appreciable activity towards these microorganisms. The identities of these newly synthesized-1,3,5-thiadiazines have been established on the basis of elemental analysis, IR, 1 HNMR and MASS spectral studies. The literature survey reveals that the heterocyclic compounds having 1, 3, 5-thiadiazines nucleus enhanced pharmaceutical, medicinal, agricultural and industrial values. The high synthetic versatility exhibited by the isothiocyanate moiety has allowed its use as a building block in the preparation of a variety of derivatives. In carbohydrates, the strong electrophilicity shown by isothiocyanates, together with the possibility of undergoing cyclization reaction has made it possible t...
Synthesis and transformations of 2-amino-1,3,4-thiadiazines
Chemistry of Heterocyclic Compounds, 1991
Depending on the reaction conditions, 2-amino-l,3,4-thiadiazine and 2.hydrazinothiazole derivatives were obtained by cyclization of thiosemicarbazide with ethyl bromopyruvate in concentrated hydrochloric acid. The rearrangements of 5-carbonyl-substituted 2.amino.l,3,4-thiadiazines to thiazole derivatives in an acidic medium were studied.
Sciprints, 2016
A novel series of thiazole based-1,3,4-thiadiazoles were designed and prepared via the reaction of the 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbothioamide with the appropriate hydrazonoyl chlorides. The structures of the newly synthesized compounds were established based on spectroscopic evidences and their alternative syntheses. Thirteen new 1,3,4-thiadiazoles have been evaluated for their anticancer activity against liver carcinoma cell line (HepG2). Also, their structure activity relationship (SAR) was studied. The 1,3,4-thiadiazoles 12d, 12c, 6g,18b, 6c, and 6f(IC50 = 0.82, 0.91, 1.06, 1.25, 1.29 and 1.88 µM, respectively) have promising antitumor activity against liver carcinoma cell line (HepG2).
Asian Journal of Chemistry, 2014
Cancer is a major public health concern worldwide. Transcending heart disease, cancer disease is the second leading cause of death due to different worldwide factors 1-4. Cell division includes two following processes, mainly involves DNA copying and discrimination of replicated chromosomes into two separate cells. Initially, two stages are considered in cell division: mitosis (M), i.e. the process of nuclear split up and interphase i.e., the interval period between two M phases. The interphase stage constitutes G1, S and G2 phases through which the cells simply grow in size 5. In the interphase stage, replication of DNA takes place in the S phase which is preceded by G1 phase; a gap during which the cell prepares for DNA synthesis. Another, gap called G2 come after G1, during which the cell gets ready for mitosis. G1, S, G2 and M phases are the main parts of the standard cell cycle. Before involvement in DNA replication, cells in G1 enter a resting state called G0. Cells in G0 account for the major part of the non-growing, non-proliferating cells in the human body. In cancer, cell proliferation results mainly from alterations in the genetic control of cell division. Two classes of genes are involved in this mutation including protooncogenes and tumour suppressor genes. In normal cells, the products of Synthesis and Characterization of bis-3,5-Disubstituted Thiadiazine-2-thione Derivatives as Anticancer Agents
A facile synthesis and anticancer activity of some novel thiazoles carrying 1,3,4-thiadiazole moiety
Chemistry Central Journal
Background: Thiazoles and 1,3,4-thiadiazoles have been reported to possess various pharmacological activities. Results: A novel series of thiazoles carrying 1,3,4-thiadiazole core were designed and prepared via the reaction of the 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbo-thioamide with the appropriate hydrazonoyl chlorides. The structures of the newly synthesized compounds were confirmed based on elemental and spectral analysis as well as their alternative syntheses. The cytotoxic potency of the newly synthesized thiadiazoles was evaluated by their growth inhibitory potency in liver HepG2 cancer cell line. Also, the structure activity relationship was studied. Conclusions: All the newly synthesized compounds were evaluated for their anticancer activity against liver carcinoma cell line (HepG2) using MTT assay. The results revealed that the compounds 12d, 12c, 6g, 18b, 6c, and 6f (IC50 = 0.82, 0.91, 1.06, 1.25, 1.29 and 1.88 µM, respectively) had good antitumor activity against liver carcinoma cell line (HepG2) when compared with the standard drug Doxorubicin (IC 50 = 0.72 µM).
SYNTHESIS, ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES OF 1,3,5-THIADIAZINE DERIVATIVES
A series of N-(4-(benzyloxy)benzylidene)-2-(arylimino)-6-(phenylimino)-3,6-dihydro-2H-1,3,5-thiadiazin-4-amine derivatives (4a-d) have been synthesized by condensation of 1-(N-4-(benzyloxy) benzylidenecarbamimidoyl)-3-arylthiourea (3a-d) with phenyl isocyanodichloride. Interaction of 1-carbamimidoyl-3-arylthiourea (2a-d) and p-benzyloxy benzaldehyde yielded (3a-d). Monoacetyl (5b) and mononitroso (6b) derivatives were also synthesised by substitution of hydrogen atom of cyclic –NH-of 4b on treatment with acetic anhydride and sodium nitrite respectively. Further, 4b upon boiling with 5% aqueous ethanolic (1:1) sodium hydroxide solution underwent isomerisation into corresponding 4-(4-(benzyloxy)benzylideneamino)-6-(4-chlorophenylimino)-1-phenyl-5,6-dihydro-1,3,5-triazine-2(1H)-thione (7b). The structures of the newly synthesized 1,3,5-thiadiazine derivatives have been established on the basis of chemical transformations, elemental analysis and IR, 1 H NMR, and Mass spectral studies. The zone of inhibition for some of the title compounds synthesized were determined against E. coli, S. aureus, B. thurengienesis and E. aerogenes and compared with Chloramphenicol as a reference drug. Some of the newly synthesized compounds showed moderate to high antimicrobial activity. Antioxidant activities of all the compounds were also determined. 4a, 4c and 4d were found to possess significant antioxidant activity.