Synthesis and Tuberculostatic Activity of Some 2-Piperazinmethylene Derivatives 1,2,4-Triazole-3-Thiones

Foks, Henryk; Janowiec, M; Zwolska, Zofia; Augustynowicz–Kopeć, Ewa

doi:10.1080/104265090517280

Cited by 31 publications

(8 citation statements)

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“…The calculated 1 H and 13 C chemical shifts for 9e , f , and also for the previously reported 9a – d [ 15 , 27 , 28 ], were correlated with the experimental values. In all cases, linear correlations were found as depicted in Figure 3 for the 13 C-NMR data.…”

Section: Resultssupporting

confidence: 76%

“…The structures and identities of the four new acylthiosemicarbazides 3e – h were proven by 1 H- and 13 C-NMR and quantum chemical calculations ( 3a – d have been previously reported [ 14 , 15 , 16 ]). A linear correlation (1) between the experimental (δ exp ) and calculated (δ calc , details provided further on) 13 C- NMR chemical shifts was obtained [ 12 ]: δ exp 13 C = 1.12 × δ calc 13 C − 20.58 R = 0.99 …”

Section: Resultssupporting

confidence: 56%

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Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Tomascikova¹,

Imrich²,

Danihel³

et al. 2008

Molecules

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A series of 1-acyl-4-phenyl/(acridin-9-yl)thiosemicarbazides 3, including four new compounds, were prepared in order to study substituent effects on cyclization reactions with oxalyl chloride (producing imidazolidine-4,5-diones 4), dimethyl acetylenedicarboxylate (to give thiazolidin-4-ones 7 and 8) and autocondensation under alkaline conditions (to yield 1,2,4-triazoles 9). A positional isomer, 10 of compound 3f was also prepared. Altogether, twenty new compounds characterized and identified by IR, UV, 1H, 13C and 2D NMR and quantum chemical calculations are described. The tautomerism of the products and regioselectivity of the reactions were evaluated. Compounds 3f–h, 3h∙2HCl, 7b,d and 10 were screened for cytotoxic activity against the L1210 leukemia cell line and all compounds, except for 3f, exhibited promising inhibitions of cell growth.

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Section: Resultssupporting

confidence: 76%

Section: Resultssupporting

confidence: 56%

Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Tomascikova¹,

Imrich²,

Danihel³

et al. 2008

Molecules

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“…On the other hand, Mannich bases 187 (R 1 ¼ H, OH; R 2 ¼ C 2 H 5 , CH 2 CH]CH 2 , C 6 H 5 , 4-BrC 6 H 4 ; R 3 ¼ CH 2 C 6 H 5 , C 6 H 5 , substituted phenyl, 2-pyrimidinyl) derived from 1,2,4-triazole-3thiones ( Fig. 33) had low antimycobacterial activity (MIC values between 25 and 100 mg/mL) [283]. The majority of Mannich bases derived from either 2,3-dihydro-1,2,4-triazole-3-thione or 2,3dihydro-1,2,4-triazole-3-one having a 3-pyridinyl moiety at position 5 of the triazole ring were more potent antimycobacterials (MIC between 16 and 32 mg/mL) than reference drug streptomycin against M. smegmatis [175].…”

Section: Antimycobacterial Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

271

110

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The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates through the introduction of an aminomethyl function by means of the Mannich reaction, is surveyed, with emphasis on the relationship between structure and biological activity. The review covers extensively the literature reports that have disclosed Mannich bases as anticancer and cytotoxic agents, or compounds with potential antibacterial and antifungal activity in the last decade. The most relevant studies on the activity of Mannich bases as antimycobacterial agents, antimalarials, or antiviral candidates have been included as well. The review contains also a thorough coverage of anticonvulsant, anti-inflammatory, analgesic and antioxidant activities of Mannich bases. In addition, several minor biological activities of Mannich bases, such as their ability to regulate blood pressure or inhibit platelet aggregation, their antiparasitic and anti-ulcer effects, as well as their use as agents for the treatment of mental disorders have been presented. The review gives in the end a brief overview of the potential of Mannich bases as inhibitors of various enzymes or ligands for several receptors.

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“…In view of the resourceful importance of both coumarins and 1,2,4‐triazoles thione in antimicrobial and antitubercular activity, it is beneficial to combine these two heterocyclic systems in a single hybrid compound via a synthetic methodology and enhancing the antimicrobial and antitubercular activity. The structurally related some 1,2,4‐triazoles thione (A, B, C and D Figure ) and coumarin derivatives (E and F Figure ), with interesting antibacterial and antitubercular activity is presented in Figure .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antitubercular and Antimicrobial Activity of 1,2,4‐Triazolidine‐3‐thione Functionalized Coumarin and Phenyl Derivatives and Molecular Docking Studies

et al. 2019

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Tuberculosis (TB) is still a demanding worldwide health problem and mycobacterium tuberculosis (MTB) remains one of the most toxic human pathogens. In pursuit of searching new antitubercular and antimicrobial agents, substituted coumarin and phenyl‐1,2,4‐triazolidine‐3‐thiones 4a‐i and 5a‐e have been synthesized and evaluated for their antitubercular and antimicrobial activities. Most of the Substituted coumarin and phenyl‐1,2,4‐triazolidine‐3‐thiones showed promising activity against Mycobacterium tuberculosis (H37Rv). The title compounds have exhibited excellent in vitro antibacterial activity against the S.aureus, Bacillus sps and E.coli with the values of low MIC ranging from of 0.4 to 1.6 μg/mL. In vitro antifungal activity shown that the compounds 4a‐i and 5a‐e are excellent antifungal agents against Candida albicans, Aspergillus flavus, Aspergillus niger and Aspergillus fumigate fungal stains with the values of low minimum inhibitory concentrations (MIC) ranging from 0.4 to 6.25 μg/mL. Molecular docking study was performed for all the synthesized compounds with E.coli as antibacterial and Mycobacterium tuberculosis DprE1 as antituberculosis.

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Synthesis and Tuberculostatic Activity of Some 2-Piperazinmethylene Derivatives 1,2,4-Triazole-3-Thiones

Cited by 31 publications

References 1 publication

Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Mannich bases in medicinal chemistry and drug design

Synthesis, Antitubercular and Antimicrobial Activity of 1,2,4‐Triazolidine‐3‐thione Functionalized Coumarin and Phenyl Derivatives and Molecular Docking Studies

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