Synthesis and evaluation of anti-inflammatory and analgesic activity of some substituted thiazolyl and thaizolidinonyl tetrahydronapthalene derivatives

Haiba, Mogedda E.; El-Karim, Somaia S. Abd; Gouhar, Rasha S.; El-Zahar, Magdy I.; Awdan, Sally A. El

doi:10.1007/s00044-014-0926-z

Cited by 17 publications

(8 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In comparison to the standard drug indomethacin, the derivative 76 displayed higher anti-inflammatory and analgesic activity. The high activity might be attributed to the presence of 4H-chromen-4-one-3-yl)methylene)hydrazine [115]. In a separate study, sulfonamide-substituted coumarinylthiazoles were synthesized and tested for anti-inflammatory activity in vivo.…”

Section: Thiazoles As Anti-inflammatory Agentsmentioning

confidence: 99%

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Arshad¹,

Alam

Alshammari

et al. 2022

Molecules

View full text Add to dashboard Cite

For many decades, the thiazole moiety has been an important heterocycle in the world of chemistry. The thiazole ring consists of sulfur and nitrogen in such a fashion that the pi (π) electrons are free to move from one bond to other bonds rendering aromatic ring properties. On account of its aromaticity, the ring has many reactive positions where donor–acceptor, nucleophilic, oxidation reactions, etc., may take place. Molecules containing a thiazole ring, when entering physiological systems, behave unpredictably and reset the system differently. These molecules may activate/stop the biochemical pathways and enzymes or stimulate/block the receptors in the biological systems. Therefore, medicinal chemists have been focusing their efforts on thiazole-bearing compounds in order to develop novel therapeutic agents for a variety of pathological conditions. This review attempts to inform the readers on three major classes of thiazole-bearing molecules: Thiazoles as treatment drugs, thiazoles in clinical trials, and thiazoles in preclinical and developmental stages. A compilation of preclinical and developmental thiazole-bearing molecules is presented, focusing on their brief synthetic description and preclinical studies relating to structure-based activity analysis. The authors expect that the current review may succeed in drawing the attention of medicinal chemists to finding new leads, which may later be translated into new drugs.

show abstract

Section: Thiazoles As Anti-inflammatory Agentsmentioning

confidence: 99%

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Arshad¹,

Alam

Alshammari

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

“…All the tested compounds and indomethacin were orally administered 1 h before induction of inflammation. The right hind paw volume was measured immediately before carrageenan injection and at selected times (1, 2, 3, and 4 h) thereafter by planimeter [33].…”

Section: Pharmacologymentioning

confidence: 99%

Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

et al. 2018

View full text Add to dashboard Cite

not only essential for survival but also at the same time is one of the major causes of human mortality [25,26]. It's known that, non-steroidal anti-inflammatory drugs (NSAIDs) are used to treat a wide variety of illnesses and diseases, such as inflammation [24], cancers [25] and the peripheral and central nervous system diseases [26]. The anti-inflammatory effect of NSAIDs arises from their ability to inhibit both COX-1 and COX-2 isoforms of cyclooxygenase (COX) enzyme [27]. Literature survey revealed that some of the synthesized derivatives having quinoline ring or bearing thiazole ring have significant antiinflammatory and analgesic activity [31-33, 20, 21]. In the light of above mentioned facts and our interest in designing new biologically active molecules, our efforts were directed towards I N this paper we report the synthesis of some quinoline based thiazolidinone derivatives (13-22) in a three-step process. Condensation of 2-hydrazinylquinoline 2 with different aromatic aldehydes gave the corresponding Schiff bases 3-10 which in turn were reacted with thioglycolic acid to furnish the corresponding thiazolidinone derivatives 13-20. Reaction of compound 2 with isatin or methyl isatin gave 1-sustituted-3-(2-(quinolin-2-yl)hydrazono) indolin-2-ones 11 and 12, which were converted to 1-substituted 3'-(quinolin-2-ylamino) spiro[indoline-3,2'-thiazolidine]-2,4'-dione 21 and 22 by cyclocondensation with thioglycolic acid. All newly synthesized compounds have been characterized by means of elemental analyses, IR, 1 H NMR and MS. Furthermore, all new thiazolidinone derivatives were evaluated for their anti-inflammatory and analgesic activity. The Study results revealed that the highest anti-inflammatory potency was gained by 6 derivatives according to the following order 22 > 17 >13 > 14 > 21 > 15, showing a good edema inhibition compared to the reference drug indomethacin. Compound 22 carrying indole ring system inhibited the edema volume significantly at the 1 st h post administration, and the activity was enhanced up to the 4 th h giving a promising edema volume inhibition compared to that produced by indomethacin. The longest duration of analgesic action up to 90 min post compounds administration was obtained by the compounds 13, 17 and 22, they exhibited potent analgesia compared to that obtained by aspirin.

show abstract

“…After analysing the binding modes of known MDM2 inhibitors and CDK4 inhibitors, we speculated that fusion of the planar tetrahydronaphthalene (THN) ring at the C3-position of oxindole might generate a scaffold that could bind at the P53-binding site in MDM2 as well as at the allosteric site in CDK4. We started with THN 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 and spirooxindole derivatives 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 because they are privileged drug-like architectures, so the resulting THN-fused C3-spirooxindoles should possess good druglikeness ( Fig. 2 C).…”

Section: Introductionmentioning

confidence: 99%

Rational drug design, synthesis, and biological evaluation of novel chiral tetrahydronaphthalene-fused spirooxindole as MDM2-CDK4 dual inhibitor against glioblastoma

Wang

Huang

et al. 2020

Acta Pharmaceutica Sinica B

View full text Add to dashboard Cite

Simultaneous inhibition of MDM2 and CDK4 may be an effective treatment against glioblastoma. A collection of chiral spirocyclic tetrahydronaphthalene (THN)-oxindole hybrids for this purpose have been developed. Appropriate stereochemistry in THN-fused spirooxindole compounds is key to their inhibitory activity: selectivity differed by over 40-fold between the least and most potent stereoisomers in time-resolved FRET and KINOMEscan® in vitro assays. Studies in glioblastoma cell lines showed that the most active compound ent- 4g induced apoptosis and cell cycle arrest by interfering with MDM2 -P53 interaction and CDK4 activation. Cells treated with ent- 4g showed up-regulation of proteins involved in P53 and cell cycle pathways. The compound showed good anti-tumor efficacy against glioblastoma xenografts in mice. These results suggested that rational design, asymmetric synthesis and biological evaluation of novel tetrahydronaphthalene fused spirooxindoles could generate promising MDM2-CDK4 dual inhibitors in glioblastoma therapy.

show abstract

Synthesis and evaluation of anti-inflammatory and analgesic activity of some substituted thiazolyl and thaizolidinonyl tetrahydronapthalene derivatives

Cited by 17 publications

References 27 publications

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles

Rational drug design, synthesis, and biological evaluation of novel chiral tetrahydronaphthalene-fused spirooxindole as MDM2-CDK4 dual inhibitor against glioblastoma

Contact Info

Product

Resources

About