Synthesis of β‐Hydroxypropanoic Acid Derivatives as Potential Anti‐inflammatory, Analgesic and Antimicrobial Agents

Abdel‐Rahman, Hamdy M.; Hussein, Mostafa A.

doi:10.1002/ardp.200600016

Cited by 33 publications

(14 citation statements)

References 23 publications

(19 reference statements)

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“…On the basis of such data, it is not unreasonable to conclude that the studied reactions are completely regioselective and accordingly 1,3,4-oxadiazole 5 is isolated as the sole product by reaction of hydrazide 3 with carbon disulfide, whereas the alternative site of cyclization to the corresponding thienopyrimidinone 4 results from the reaction of compound 3 with thiourea. This observation is in complete agreement with previous literature reports on the wellestablished formation of 1,3,4-oxadiazoles by heating hydrazides with carbon disulfide in the presence of bases [28][29][30].…”

Section: Chemistrysupporting

confidence: 93%

Regioselective synthesis and biological evaluation of some novel thiophene-containing heterocyclic scaffolds as potential chemotherapeutic agents

Gaber

Bagley

2011

Eur. J. Chem.

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KEYWORDSIn the reaction of 2-amino-3-carbethoxythiophene derivative 2b with hydrazine hydrate the respective aminocarbohydrazide 3 was isolated. Treatment of the latter product with carbon disulfide in alkaline medium caused a heterocyclization to give 1,3,4-oxadiazole-2-thione 5 rather than 3-amino-2-thioxothieno[2,3-d]pyrimidin-4-one 4, which could be obtained on treatment of carbohydrazide 3 with thiourea. The structure of products 4 and 5 was proved by spectroscopic methods and chemical transformations. Derivatization led to two novel series of condensed and uncondensed thiophenes, which were of significant interest for biological study. Since compound 4 contains two adjacent reactive functional groups, it reacted readily with different electrophilic reagents to provide a series of thieno[2,3-d]pyrimidin-4-one derivatives with annelated bridgehead nitrogen heterocycles 8-11, whereas a second series of 3-heteroaryl-substituted thiophenes 13-17 was obtained by thioamide functionalization in 1,3,4-oxadiazole derivative 5 using various chemical reagents. The new thiophene-based derivatives were evaluated for their preliminary antimicrobial activity against a representative panel of Gram-positive and Gram-negative bacteria as well as fungi strains. The compounds tested displayed different levels of inhibitory effects, with the assays carried out on two pathogenic bacteria and two pathogenic fungi. Of these compounds, the monocyclic aminothiophene derivative 15 showed the highest effect on pathogenic bacteria, while the tricyclic condensed thiophene derivative 8 was observed to have the same inhibitory effect against pathogenic mould (Aspergillus flavus) as the reference drug Amphotericin B. For those derivatives belonging to first series of condensed thiophenes with annelated bridgehead nitrogen heterocycles, it has been observed that the antibacterial effect was in general found to be significantly higher than the corresponding uncondensed analogues. Although most of the condensed and uncondensed thiophenes under investigation showed generally remarkable in vitro antibacterial activity, unfortunately, no significant antifungal activity was observed with any of the compounds tested except for 8. Surprisingly, compound 8 displayed an excellent effect on fungus (A. flavus) on the one hand, whereas the lowest effect on bacteria on the other. The attachment of a triazolothiadiazine moiety to a thiophene ring could be considered as a promising strategy for the development of new therapeutic antibacterial agents related to the aminothiophene system. Thienopyrimidinone Cyclocondensation Cyclodesulfurization Hydrazinolysis Alkylation Antimicrobial activity

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Section: Chemistrysupporting

confidence: 93%

Regioselective synthesis and biological evaluation of some novel thiophene-containing heterocyclic scaffolds as potential chemotherapeutic agents

Gaber

Bagley

2011

Eur. J. Chem.

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“…Exploration of the 1,3-thiazolidin-4-ones showed that the tibacterial activity not only depended on the 1,3-thiazolidin-4-one pharmacophore, but also on th ture and position of its substituents; for example, electron withdrawing group substitutions o omatic rings of biphenyl-4-thiazolidinone derivatives showed improved antibacterial activity [11 umerous new derivatives with the pharmacophoric 4-thiazolidinone ring were substituted wit e-membered heterocyclic rings, [12] such as thiadiazole, [13] thiazoles [14] or 1,2,4-triazoles [15 seen in Figure 2. Moreover, 1,2,4-triazoles are core structures in medicinal chemistry research wi verse biological activities [16][17][18]. The SAR of the antibacterial activity of the 1,3-thiazolidin-4-one scaffold has become the subject of intense research projects [10,11].…”

Section: Introductionmentioning

confidence: 99%

“…Numerous new derivatives with the pharmacophoric 4-thiazolidinone ring were substituted with five-membered heterocyclic rings, [12] such as thiadiazole, [13] thiazoles [14] or 1,2,4-triazoles [15], as seen in Figure 2. Moreover, 1,2,4-triazoles are core structures in medicinal chemistry research with diverse biological activities [16][17][18]. …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antimicrobial Evaluation and Molecular Modeling Study of 1,2,4-Triazole-Based 4-Thiazolidinones

et al. 2016

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A series of 3-(2H-1,2,4-triazol-5-yl)-1,3-thiazolidin-4-one derivatives (7c-l) was designed and synthesized. Their structures have been elucidated based on analytical and spectral data. They were evaluated for their antibacterial and antifungal activities. Compound 7h showed the highest activity against all tested strains, except P. vulgaris, with MIC 8 µg/mL and 4 µg/mL against S. aureus and C. albicans, respectively. Furthermore, Compounds 7c, 7h, and 7j demonstrated moderate anti-mycobacterium activity. The binding mode of the synthesized thiazolidinones to bacterial MurB enzyme was also studied. Good interactions between the docked compounds to the MurB active site were observed primarily with Asn83, Arg310, Arg188 and Ser82 amino acid residues.

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“…Moreover, chiral β-hydroxycarboxylic acids are important intermediates widely used as chiral precursors of anti-inflammatory products, [87] β-amino acids, [88] β-lactams, [89] β-lactones, [90] and pheromones [91].…”

Section: Brønsted-base-mediated Carboxylation Of C(sp 3 )-H Bonds Witmentioning

confidence: 99%

Direct Carboxylation of C(sp3)-H and C(sp2)-H Bonds with CO2 by Transition-Metal-Catalyzed and Base-Mediated Reactions

Tommasi

2017

Catalysts

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This review focuses on recent advances in the field of direct carboxylation reactions of C(sp 3 )-H and C(sp 2 )-H bonds using CO 2 encompassing both transition-metal-catalysis and base-mediated approach. The review is not intended to be comprehensive, but aims to analyze representative examples from the literature, including transition-metal catalyzed carboxylation of benzylic and allylic C(sp 3 )-H functionalities using CO 2 which is at a "nascent stage". Examples of light-driven carboxylation reactions of unactivated C(sp 3 )-H bonds are also considered. Concerning C(sp 3 )-H and C(sp 2 )-H deprotonation reactions mediated by bases with subsequent carboxylation of the carbon nucleophile, few examples of catalytic processes are reported in the literature. In spite of this, several examples of base-promoted reactions integrating "base recycling" or "base regeneration (through electrosynthesis)" steps have been reported. Representative examples of synthetically efficient, base-promoted processes are included in the review.

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Synthesis of β‐Hydroxypropanoic Acid Derivatives as Potential Anti‐inflammatory, Analgesic and Antimicrobial Agents

Cited by 33 publications

References 23 publications

Regioselective synthesis and biological evaluation of some novel thiophene-containing heterocyclic scaffolds as potential chemotherapeutic agents

Regioselective synthesis and biological evaluation of some novel thiophene-containing heterocyclic scaffolds as potential chemotherapeutic agents

Design, Synthesis, Antimicrobial Evaluation and Molecular Modeling Study of 1,2,4-Triazole-Based 4-Thiazolidinones

Direct Carboxylation of C(sp3)-H and C(sp2)-H Bonds with CO2 by Transition-Metal-Catalyzed and Base-Mediated Reactions

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