Synthesis, Antimicrobial Evaluation of 4-[(arylimino) methyl-5-(4-[(aryl) methylidene] amino) Phenyl)-4H-1, 2, 4-triazole-3-thiol Derivatives

Rajurkar, Vikas G.; Deshmukh, Vinayak; Sonawane, Manisha

doi:10.1080/22297928.2016.1214081

Cited by 2 publications

(7 citation statements)

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“…The coordination of these compounds often lead to enhanced biological activity in several pathogenic fungi [3,[19][20][21]. Some of these metal complexes have been known to accelerate drug action and the efficacy of a therapeutic agent [1][2][3][4][5][6][19][20][21].The Schiff bases synthesized in this study are the di-2-pyridylketone Schiff bases of isomeric dithiocarbazates, S-2-methylbenzyldithiocarbazate, S-3-methylbenzyl dithiocarbazate and S-4-methylbenzyldithiocarbazate (Fig. 1).…”

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confidence: 99%

Synthesis, characterisation and biological activities of S-2- or S-4-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate and Cu(II), Ni(II), Zn(II) and Cd(II) complexes

et al. 2017

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Metal complexes of general formula, [M(NNS)2] (M = Cu(II), Ni(II), Zn(II) and Cd(II); NNS'= S-2-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate (1), NNS''= S-3-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate (2) and NNS'''= S-4-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate (3) have been synthesized by reacting the respective metal acetates with the Schiff bases in an ethanol/acetonitrile mixture. negative estrogen receptor) cell lines. Only 9 was active against MCF-7 whereas 10 and 13were active against the MDA-MB-231 cell line. Cytotoxic activity was observed to be enhanced upon complexation particularly for the Ni(II) complexes.Keywords: biological activities, S-R-methylbenzyldithiocarbazate, di-2-pyridylketone, Schiff bases IntroductionDithiocarbazate Schiff bases and their transition metal complexes [1-10] have been of considerable interest to scientists for many years as they show a wide range of therapeutic properties against various diseases, with different anti-bacterial, anti-malarial, anti-viral and anti-tumour properties [1][2][3][4][5][6][7][8][9][10]. In recent years, heterocyclic thiosemicarbazones and Schiff bases derived from S-alkyl dithiocarbazates have been considered as useful model compounds for sulphur-containing analogues of purine and pyrimidine bases [11][12][13]. The π-delocalisation of charge and the configurational flexibility of their molecular chain give rise to a great variety of coordination modes [14][15][16][17][18]. Their chemistry and pharmacological applications have been widely investigated as well [1][2][3][4][5][6][15][16][17][18].Coordination compounds, especially those that contain nitrogen-sulphur ligands are synthesized via relatively simple, cost-effective procedures and it has been observed that small changes in their structure, such as change of substituents and their chelation to different metal ions cause great changes in their bioactivities. The coordination of these compounds often lead to enhanced biological activity in several pathogenic fungi [3,[19][20][21]. Some of these metal complexes have been known to accelerate drug action and the efficacy of a therapeutic agent [1][2][3][4][5][6][19][20][21].The Schiff bases synthesized in this study are the di-2-pyridylketone Schiff bases of isomeric dithiocarbazates, S-2-methylbenzyldithiocarbazate, S-3-methylbenzyl dithiocarbazate and S-4-methylbenzyldithiocarbazate (Fig. 1). Investigations have shown that di-2-pyridylketone thiosemicarbazone and an analogue, 2-benzoylpyridine thiosemicarbazone, demonstrated marked and selective antitumour activity in vitro and also in vivo against many tumours. Di-2-pyridylketone thiosemicarbazone has also been found to possess several structural characteristics important for iron chelating efficacy and potent anti-proliferative activity, and can be further modified as anti-neoplastic agents. Iron has a crucial role in the active site of ribonuclease reductase which is the rate-limiting step of DNA synthesis. This Schiff base and other similar compounds h...

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Synthesis, characterisation and biological activities of S-2- or S-4-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate and Cu(II), Ni(II), Zn(II) and Cd(II) complexes

et al. 2017

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“…The preparation of triazole-3-thiol moieties from PABA was carried out using green synthesis methodology. 4-amino benzohydrazide undergoes reflux with carbon disulfide in the presence of alcoholic potassium hydroxide to synthesize oxadiazole-2-thiol derivatives [57] as presented in Scheme 2A. Novel pyrimidines were also synthesized through the microwave assistance method.…”

Section: Synthesis Of Antimicrobial Agentsmentioning

confidence: 99%

“…The synthesized moiety was further refluxed in alcoholic KOH with CS 2 to form diazolethiol derivatives as shown in Scheme 2B. Further refluxing this compound with amine in ethanol gave triazolethiol as the end product [57]. Scheme 2A,B represented the protocols for the synthesis of derivatives of PABA having antimicrobial potential.…”

Section: Synthesis Of Antimicrobial Agentsmentioning

confidence: 99%

“…(A): Synthetic routes for derivatives of p-aminobenzoic acid having antimicrobial potential (adapted from refs. [30,31,38,[57][58][59][60][61][62][63]65,66]). (B): Synthetic routes of derivatives of p-aminobenzoic acid having antimicrobial potential (adapted from refs.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…These compounds were screened for antimicrobial activity against E. coli, S. aureus, B. subtilis, K. pneumonia, and fungi, i.e., S. cerevisiae and A. niger. The antimicrobial evaluation identified that 4-chloro-6-nitro-, 6-chloro-, and 4-nitro-substituted benzothiazoletriazolethiol derivatives have significant potential as compared to Ketoconazole and Norfloxacin (standard drugs) [57]. Thienopyrimidinylamino-N-phenylbenzamide and its N-(4-chlorophenyl)-substituted compounds possess significant inhibitory potencies against P. aeruginosa, S. aureus, B. subtilis, and E. coli, with effective MICs (2-10 µg/mL) [58].…”

Section: Antimicrobial Activitymentioning

confidence: 99%

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Novel Para-Aminobenzoic Acid Analogs and Their Potential Therapeutic Applications

Haroon,

Farwa,

Arif

et al. 2023

Biomedicines

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A “building block” is a key component that plays a substantial and critical function in the pharmaceutical research and development industry. Given its structural versatility and ability to undergo substitutions at both the amino and carboxyl groups, para-aminobenzoic acid (PABA) is a commonly used building block in pharmaceuticals. Therefore, it is great for the development of a wide range of novel molecules with potential medical applications. Anticancer, anti-Alzheimer’s, antibacterial, antiviral, antioxidant, and anti-inflammatory properties have been observed in PABA compounds, suggesting their potential as therapeutic agents in future clinical trials. PABA-based therapeutic chemicals as molecular targets and their usage in biological processes are the primary focus of this review study. PABA’s unique features make it a strong candidate for inclusion in a massive chemical database of molecules having drug-like effects. Based on the current literature, further investigation is needed to evaluate the safety and efficacy of PABA derivatives in clinical investigations and better understand the specific mechanism of action revealed by these compounds.

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Synthesis, Antimicrobial Evaluation of 4-[(arylimino) methyl-5-(4-[(aryl) methylidene] amino) Phenyl)-4H-1, 2, 4-triazole-3-thiol Derivatives

Cited by 2 publications

References 11 publications

Synthesis, characterisation and biological activities of S-2- or S-4-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate and Cu(II), Ni(II), Zn(II) and Cd(II) complexes

Synthesis, characterisation and biological activities of S-2- or S-4-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate and Cu(II), Ni(II), Zn(II) and Cd(II) complexes

Novel Para-Aminobenzoic Acid Analogs and Their Potential Therapeutic Applications

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