Synthesis of 5‐(6‐Pyridazinone‐3‐yl)‐2‐glycosylamino‐1,3,4‐thiadiazoles

Tao, Jing; Wang, Duo-Zhi; Cao, Liping

doi:10.1002/jccs.201000151

Cited by 3 publications

(2 citation statements)

References 16 publications

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“…9 Due to this bioactivity and pharmacological impact of the compound and in the persistence of our ongoing study on heterocyclic compounds, we decided to synthesize a novel series of thiazolidin-4-one" derivatives, in which 1,3,4-Thiadiazole nucleus was added as intermediate. Writing demonstrates that a molecule having 1,3,4-Thiadiazole core has a wide scope of pharmacological exercises that incorporate antifungal, 10 antibacterial, 11 antiviral, anti-inflammatory, 12 antitubercular, 13,14 painrelieving, antileishmanial, antiepileptic, CNS depressant, anticancer, 15 anticonvulsant, cell reinforcement, diuretic, 16 molluscicidal, antidiabetic, 17 and antihypertensive. 18 From the scientific works, both the nucleus was found to be active as anticancer, antimicrobials and antiinflammatory agents.…”

Section: Introductionmentioning

confidence: 99%

1,3,4-thiadiazole Attached 2, 3- disubstituted Thiazolidinones Derivatives: Synthesis and Biological Evaluation

Garg¹,

Garg²

2021

IJPER

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Background: Thiazolidinone derivatives are the subject of prominent importance since they have been seen as valuable intermediates for the formulating/synthesize of different heterocyclic derivatives and it gives various subsidiaries with every extraordinary kind of exercise. What're more, researches show that derivatives having 1,3,4-Thiadiazole core/ nucleus have a wide scope of pharmacological potential that incorporates antifungal, antibacterial, antiviral, anticancer, antitubercular, anticonvulsant, antidiabetic and antioxidant. From the literature reviewed, both the nucleus was found to be active as antimicrobials, anti-inflammatory as well as anticancer agents. Materials and Methods: It has been planned to synthesize "1,3,4-thiadiazolyl-thiazolidin-4-one" derivatives and evaluate their biological activities. The novel subordinates (4a-4j) of 2, 3-disubstituted Thiazolidinones were integrated into acceptable yield by the synthesis of benzaldehyde with thiosemicarbazide to provide thiosemicarbazones, 1,3,4-thiadiazoles is then produced by thiosemicarbazone cyclized by involving ferric chloride. By the reaction of various aromatic aldehyde with 1,3,4-thiadiazoles yielded different Schiff bases. The final derivative 2-aryl-3-(5-aryl-1,3,4-thiadiazol-2-yl)-1,3-thiazolidine-4-one was obtained by the reaction between the schiff base with thioglycolic acid. All subordinates/ derivatives were portrayed by spectral analysis examination (IR, 1H NMR) and elemental analysis and then screened for biological activities (in-vitro anticancer, antimicrobial, anti-inflammatory). Results and Conclusion: The analysis reveals that synthesized derivatives of thiazolidinone possessing methyl, hydro, nitro, hydroxyl, flouro, chloro, methoxy, dimethoxy and amino substitution through phenyl ring. All these groups help pharmacophore, to increase their pharmacological activities. However, the substituted phenyl ring in the side chain also facilitates the biological action of the molecules. The increased activity of the new derivatives explains that they act as a more powerful and potent bioactive molecule when compare with the standard drug. This significant activity may be due to the substitution in the 2 nd position of thiazolidinone nucleus. As result, all the tested compounds exhibit good activity and compounds 4i, 4b, 4f and 4a were established more noteworthy and outstanding as of all the derivatives.

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Section: Introductionmentioning

confidence: 99%

1,3,4-thiadiazole Attached 2, 3- disubstituted Thiazolidinones Derivatives: Synthesis and Biological Evaluation

Garg¹,

Garg²

2021

IJPER

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“…Derivatives of 1,3,4-thiadiazole have been found to possess a wide spectrum of activities (1,2) , thiadiazole were studied for anumber of pathological conditions including inflammation (3) or hypertension (4) . The synthesis of substituted 1,3,4-thiadiazole has attracted attention due to their application as anti-inflammatory (5,7) , analgesic (8,9) , antimicrobial antibacterial (10)(11)(12) , anticonvulsant (13,14) , anticancer (15) , antifungal (16,17) and plant growth regulating effect (18) . Substituted 1,3,4-thiadiazoles were synthesis from thiosemicarbazide with carboxylic acid in concentrated sulfuric acid (19) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2- alkyl/phenyl -5-Substituted 1,3,4- Thiadiazoles

Daoud¹,

Ismaeel²,

Mohamad³

2014

J.Edu.Sci.

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A new synthetic access to 2-N-(glycosyl)thiosemicarbazides from 3-N-(glycosyl)oxadiazolinethiones and the regioselectivity of the glycosylation of their oxadiazolinethione precursors

Ashry¹,

Tamany²,

Fattah³

et al. 2013

Beilstein J. Org. Chem.

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SummaryGlycosylations of 5-(1H-indol-2-yl)-1,3,4-oxadiazoline-2(3H)-thione delivered various degrees of S- and/or N-glycosides depending on the reaction conditions. S-Glycosides were obtained regiospecifically by grinding oxadiazolinethiones with acylated α-D-glycosyl halides in basic alumina, whereas 3-N-(glycosyl)oxadiazolinethiones were selectively obtained by reaction with HgCl2 followed by heating the resultant chloromercuric salt with α-D-glycosyl halides in toluene under reflux. On using Et3N or K2CO3 as a base, mixtures of S- (major degree) and N-glycosides (minor degree) were obtained. Pure 3-N-(glycosyl)oxadiazolinethiones can also be selectively obtained from glycosylsulfanyloxadiazoles by the thermal S→N migration of the glycosyl moiety, which is proposed to occur by a tight-ion-pair mechanism. Thermal S→N migration of the glycosyl moiety can be used for purification of mixtures of S- or N-glycosides to obtain the pure N-glycosides. The aminolysis of the respective S- or N-glycosides with ammonia in aqueous methanol served as further confirmation of their structures. While in S-glycosides the glycosyl moiety was cleaved off again, 3-N-(glycosyl)oxadiazolinethiones showed a ring opening of the oxadiazoline ring (without affecting the glycosyl moiety) to give N-(glycosyl)thiosemicarbazides. Herewith, a new synthetic access to one of the four classes of glycosylthiosemicarbazides was found. The ultimate confirmation of new structures was achieved by X-ray crystallography. Finally, action of ammonia on benzylated 3-N-(galactosyl)oxadiazolinethione unexpectedly yielded 3-N-(galactosyl)triazolinethione. This represents a new path to the conversion of glycosyloxadiazolinethiones to new glycosyltriazolinethione nucleosides, which was until now unknown.

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Synthesis of 5‐(6‐Pyridazinone‐3‐yl)‐2‐glycosylamino‐1,3,4‐thiadiazoles

Cited by 3 publications

References 16 publications

1,3,4-thiadiazole Attached 2, 3- disubstituted Thiazolidinones Derivatives: Synthesis and Biological Evaluation

1,3,4-thiadiazole Attached 2, 3- disubstituted Thiazolidinones Derivatives: Synthesis and Biological Evaluation

Synthesis of 2- alkyl/phenyl -5-Substituted 1,3,4- Thiadiazoles

A new synthetic access to 2-N-(glycosyl)thiosemicarbazides from 3-N-(glycosyl)oxadiazolinethiones and the regioselectivity of the glycosylation of their oxadiazolinethione precursors

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