Synthesis and Antitumor Activity of the Thiazoline and Thiazine Multithioether

Wang, Wei; Zhao, Bing; Xu, Chao; Wu, Weitai

doi:10.4236/ijoc.2012.22018

Cited by 35 publications

(14 citation statements)

References 12 publications

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“…As second moiety in this introduction, thiazole has a great component impact of the pharmacophores of a wide number of medicinal significance molecules such as antibacterial [22], antiprotozoal [23], and antifungal activities [24,25]. Moreover, synthetic thiazoles were widely studied and documented as antiproliferative agents [26][27][28], and apoptosis-inducing [29] and cell divisioninhibiting abilities were reported as anticancer activity mechanism [30].…”

Section: Introductionmentioning

confidence: 99%

Pyrazole‐1‐carbothioamide as a Potent Precursor for Synthesis of Some New N‐heterocycles of Potential Biological Activity

Azab

Ali

El‐Zahrani

et al. 2018

Journal of Heterocyclic Chem

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Herein, we reported the efficient synthesis of new azoles as bio‐functional analogs, employing the easily obtainable N‐acetyl‐3,5‐diphenyl‐4,5‐dihydro‐1H‐pyrazole‐1‐carbothioamide (1), as a versatile precursor. The structures of the newly synthesized compounds were elucidated based on their IR, 1H NMR, and 13C NMR mass spectral and elemental analysis. Furthermore, some selected compounds were evaluated in vitro for their antimicrobial activities. The preliminary bioassay results indicate that the majority of the tested compounds exhibited significant antimicrobial activity. Compounds 12, 11, 18, 30, 22, 3, and 2 were found to be the most potent against the tested microorganisms with minimum inhibitory concentration ≤ (12.25 μg/mL), indicating that conjugates bearing thiazole moiety, as well as those with N‐substituted electron‐withdrawing groups, exhibited higher potency than the rest of other compounds.

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Section: Introductionmentioning

confidence: 99%

Pyrazole‐1‐carbothioamide as a Potent Precursor for Synthesis of Some New N‐heterocycles of Potential Biological Activity

Azab

Ali

El‐Zahrani

et al. 2018

Journal of Heterocyclic Chem

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“…Furthermore, bacterial isolates ulbactin F, G, aerugine and pyochelin, which possess tandemly connected thiazoline and thiazolidine ring systems, were declared with tumor cell migration inhibitory activity ( Figure 1 ) [ 12 ]. Therewithal, synthetic thiazoline derivatives exhibiting antiproliferative activity were widely studied and well documented in literature [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Apoptosis inducing [ 23 ] and cell division inhibiting [ 24 ] abilities were reported as anticancer activity mechanism.…”

Section: Introductionmentioning

confidence: 99%

New Thiazoline-Tetralin Derivatives and Biological Activity Evaluation

et al. 2018

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In this study, novel N′-(3-cyclohexyl/phenyl-4-(substituted phenyl)thiazole-2(3H)-ylidene)-2-[(5,6,7,8-tetrahydronaphthalen-2-yl)oxy]acetohydrazide (4a–4k) derivatives were synthesized and their anticancer potency were evaluated on human breast adenocarcinoma cell line (MCF-7), human lung carcinoma cell line (A549) and mouse embryoblast cell line (NIH/3T3) using the MTT method, DNA synthesis inhibition and flow cytometric analysis. Compound 4e bearing 4-methoxyphenyl moiety exhibited the highest antitumor efficiency against MCF-7 cell line with higher DNA synthesis inhibition and apoptotic cell percentages (ealy+late apoptotic cell). On the other hand, compounds 4f, 4g, and 4h bearing 4-bromo, 4-chloro and 4-florophenyl moieties, respectively caused excellent apoptosis levels against A549 cell line when treated with lower concentration even than cisplatin. Anticholinesterase activity of the compounds were also tested, compound 4h showed 49.92% inhibition of acetylcholinesterase (AChE).

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“…1, 3-thiazines which contain nitrogen and sulfur in their sixmember heterocyclic ring system (N-C-S), as a pharmacophore and it was found to be fairly stable, also in some other medicinally important compounds like xylazine (agonist at the α2-adrenergic receptor is used for sedation, anesthesia, muscle relaxation, and analgesia in animals) [2], and chlormezanone (used as an anxiolytic and a muscle relaxant) [3]. Thiazine derivative moiety results has shown diverse biological and pharmaceutical profiles such as anticonvulsant [4], antimicrobial [5][6][7][8][9][10], analgesic, antiinflammatory and ulcerogenic [11][12][13], anticancer [14][15][16][17][18], antidiabetic [19], immunotropic [20], antianxiety [21], insecticidal and pesticidal [22], antitubercular [23], anthelmintic [24], anesthetic [25], antiviral [26] activities etc. The treatment for bacterial infection currently represents a significant therapeutic challenge throughout the world.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Biological Evaluation and Docking of Some Novel Substituted 1, 3-Thiazine Derivatives

Bairam

Muppavarapu²,

Sivan

2017

Int J Pharm Pharm Sci

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Objective: Chalcones and their heterocyclic analogs represent an important class of small molecules which have a wide range of pharmacological activities. Therefore, in this study, synthesis and anticonvulsant and antimicrobial activities of some new 1, 3-thiazines have been extensively discussed.Methods: The reaction mixture of 4-tert-butylcyclohexanone on Claisen-Schmidt condensation with various aromatic aldehydes in the presence of dilute sodium hydroxide afforded the corresponding chalcones. Further, these compounds were subjected to cocondensation with thiourea, in the presence of isopropanol, catalyzed by aqueous potassium hydroxide to form 4-aryl 8-arylidene-5, 6-dihydro-2-imino-6-methyl-4H, 7H-(1, 3) benzothiazines. The structures of the newly synthesized compounds have been established on the basis of their spectral analysis. The newly synthesized compounds have been tested for their biological screening. Antimicrobial activity by cup plate agar diffusion method and antiepileptic activity by pentylenetetrazole (PTZ) induced seizures model, using diphenyl hydantain as standard, and also they are subjected to molecular properties prediction, toxicity, drug-likeness, lipophilicity and solubility parameters determination were done by using Osiris program, Molsoft, Prototox and ALOGPS 2.1 software. The binding mode of the synthesized compounds with active protein site has been predicted using docking method.Results: Most of the compounds have shown good anticonvulsant as well as antimicrobial activities, but it is less than the standard drugs. 1, 3-thiazines derivatives were more potent, and among them, compounds TB5 andTB7 were the most active compounds in these series; TB5 whichcontains isopropyl phenyl moiety, was shown moderate potent activity with onset of convulsion at 14.1 min and TB7 containing 3, 4, 5-trimethoxyphenyl substituents on the thiazine moiety was more potent as it has prolonged the onset of convulsions by 18.7 min. Whereas in the case of antimicrobial activity of the compounds, from the results we have observed that TB5 have been shown greatest antimicrobial activity in all the bacterial and fungal strains, TB2 also shown superior activity, the others have been shown good antimicrobial activity.Conclusion: According to the activity studies, it is observed that the synthesis and antimicrobial as well as anticonvulsant activities of novel 1, 3-thiazine derivatives have been shown better activity. Moreover molecular docking results give an insight into how further modification of the lead compound can be carried out for higher inhibitory activity. In particular, compounds with electron withdrawing substituents along with lipophilic methoxyl and isopropyl groups were more potent.

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Synthesis and Antitumor Activity of the Thiazoline and Thiazine Multithioether

Abstract: A series of novel multithioether derivatives were synthesized by the combination of thiazoline and thiazine with dibromides and their structures were characterized by IR, 1 H NMR, MS and elemental analysis. The synthesized derivatives were tested for antitumor activity.

Cited by 35 publications

References 12 publications

Pyrazole‐1‐carbothioamide as a Potent Precursor for Synthesis of Some New N‐heterocycles of Potential Biological Activity

Pyrazole‐1‐carbothioamide as a Potent Precursor for Synthesis of Some New N‐heterocycles of Potential Biological Activity

New Thiazoline-Tetralin Derivatives and Biological Activity Evaluation

Synthesis, Characterization, Biological Evaluation and Docking of Some Novel Substituted 1, 3-Thiazine Derivatives

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