Synthesis of Oxazolidines, Thiazolidines, and 5,6,7,8-Tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole (or thiazole)-1,3-diones from β-Hydroxy- or β-Mercapto-α-amino Acid Esters

Badr, M. Z. A.; Aly, M. M.; Fahmy, Atiat Mohamed; Mansour, Mansour Esmael Younis

doi:10.1246/bcsj.54.1844

Cited by 21 publications

(3 citation statements)

References 2 publications

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“…2-Phenylthiazole-4-carboxylic Acid Methyl Ester (32). This compound was synthesized following a reported procedure …”

Section: Methodsmentioning

confidence: 99%

“…This compound was synthesized following a reported procedure. 14 N-Bromosuccinamide (2.48 g, 13.9 mmol) and benzoyl peroxide (0.05 g) were added to 31 (1.5 g, 6.7 mmol) dissolved in CCl4 (70 mL), and the solution was refluxed for 6 h. Solvent was removed in vacuo, and the crude product was purified by column chromatography to afford 32 (0.71 g, 48%). 1 2-Phenylthiazole-4-carboxylic Acid Octadecylamide (34).…”

Section: -Phenylthiazolidine-4-carboxylic Acid Methyl Ester (31)mentioning

confidence: 99%

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Discovery of 2-Arylthiazolidine-4-carboxylic Acid Amides as a New Class of Cytotoxic Agents for Prostate Cancer

et al. 2005

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To improve the selectivity and antiproliferative activity of previously reported serine amide phosphates (SAPs), we designed a new series of 4-thiazolidinone amides, in which the 4-thiazolidinone moiety was introduced as a phosphate mimic. However, these 4-thiazolidinone derivatives demonstrated less cytotoxicity in prostate cancer cells despite improved selectivity over RH7777 cells. To further optimize the thiazolidinone analogues in terms of cytotoxicity and selectivity, we made closely related structural modifications, which led us to the discovery of a new class of 2-arylthiazolidine-4-carboxylic acid amides. These compounds were potent cytotoxic agents with IC(50) values in the low micromolar concentration range and demonstrated enhanced selectivity in receptor-negative cells compared to SAPs and 4-thiazolidinone amides.

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“…2-Phenylthiazole-4-carboxylic Acid Methyl Ester (32). This compound was synthesized following a reported procedure …”

Section: Methodsmentioning

confidence: 99%

Section: -Phenylthiazolidine-4-carboxylic Acid Methyl Ester (31)mentioning

confidence: 99%

Discovery of 2-Arylthiazolidine-4-carboxylic Acid Amides as a New Class of Cytotoxic Agents for Prostate Cancer

et al. 2005

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“…5 N-Acylated oxazolidines have been synthesised using very drastic conditions. [6][7] Here we report the synthesis of some new β-lactams and N-acylated oxazolidines from ethanolimines and phenoxyacetic acid induced by benzenesulfonyl chloride under very mild reaction conditions.…”

mentioning

confidence: 99%

Synthesis of β-lactams and oxazolidines from phenoxyacetic acid and ethanolimines promoted by benzenesulfonyl chloride

Sharma

Bhaduri

2001

Journal of Chemical Research

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β−Lactams show diverse and interesting antibiotic activity. The N-(2-hydroxyethyl) β-lactams are very important precursors of N-unsubstituted β-lactams. Literature reports show that their syntheses have been carried out by the annelation of ethanolimines with acetic acids in the presence of phenyl dichlorophosphate 1,2 and Vilsmeier reagents. 3 These β-lactams have also been synthesised using the acid chloride-imine method. 4 Oxazolidines are useful synthetic intermediates. They are usually obtained by the condensation of secondary β-aminoalcohols with either aldehydes or their corresponding acetals. 5 N-Acylated oxazolidines have been synthesised using very drastic conditions. 6-7Here we report the synthesis of some new β-lactams and N-acylated oxazolidines from ethanolimines and phenoxyacetic acid induced by benzenesulfonyl chloride under very mild reaction conditions.Various imines (3a-e) have been synthesised by refluxing substituted primary β-aminoalcohols with aldehydes in methanol for 3-4 h in 93-94% yield. The 1 H NMR data (Table 1) clearly indicated them to exist as Schiff bases, azomethine protons appearing in the range δ 8-8.7 ppm. Further, these imines were protected by trimethylsilyl chloride in the presence of triethylamine by stirring the reactants at room temperature for 1h followed by successive addition of phenoxyacetic acid and benzenesulfonyl chloride at 0°C. The contents were then stirred at room temperature for 19-20 h followed by quenching with water to afford the N-2-hydroxyethyl β-lactams 4a-d in 60-70% yield (Scheme 1). The structures of the β-lactams were assigned on the basis of elemental analysis and spectroscopic (IR, 1 H NMR) data. The protons at C 3 and C 4 of all the βlactams were found to be in cis-orientation as evident from the coupling constants J 3,44 -5 Hz. The IR spectra showed the presence of the β-lactam carbonyl peak in the range of 1740-1755 cm -1 (Table 3) Similar results were obtained when phenoxyacetyl chloride was used instead of mixed anhydride for the β-lactam synthesis.However, the treatment of the unprotected imines with phenoxyacetic acid and benzenesulfonyl chloride in the presence of triethylamine in dichloromethane furnished N-acylated oxazolidines (5a-c) in 65-70% yield (Scheme 2). The IR spectra of these compounds showed amide carbonyl peak in the range of 1660-1670 cm -1 . NH, OH and β−lactam carbonyl stretching bands were found to be absent. 300 MHz 1 H NMR spectra indicated the presence of two singlets at δ 4.5-4.8 corresponding to the methylene protons adjacent to the phenoxy group and another at δ 6.4-6.7 from the C 2 proton of the oxazolidine which is flanked by N, O and aromatic group. In 5c, C 2 -H appeared as a doublet at δ 6.48. (Table 3) This cyclisation reaction under the influence of the acylating species led us to suggest that the reaction proceeds through the intermediacy of iminium ion 6, followed by nucleophilic attack by the hydroxyl group on the incipient carbonium ion to produce the oxazolidines. 8 However, when the hydroxyl group of th...

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ChemInform Abstract: SYNTHESIS OF OXAZOLIDINES, THIAZOLIDINES, AND 5,6,7,8‐TETRAHYDRO‐1H,3H‐PYRROLO(1,2‐C)OXAZOLE (OR THIAZOLE)‐1,3‐DIONES FROM β‐HYDROXY‐ OR β‐MERCAPTO‐α‐AMINO ACID ESTERS

Badr¹,

Aly²,

Fahmy³

et al. 1981

Chemischer Informationsdienst

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Synthesis of Oxazolidines, Thiazolidines, and 5,6,7,8-Tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole (or thiazole)-1,3-diones from β-Hydroxy- or β-Mercapto-α-amino Acid Esters

Cited by 21 publications

References 2 publications

Discovery of 2-Arylthiazolidine-4-carboxylic Acid Amides as a New Class of Cytotoxic Agents for Prostate Cancer

Discovery of 2-Arylthiazolidine-4-carboxylic Acid Amides as a New Class of Cytotoxic Agents for Prostate Cancer

Synthesis of β-lactams and oxazolidines from phenoxyacetic acid and ethanolimines promoted by benzenesulfonyl chloride

ChemInform Abstract: SYNTHESIS OF OXAZOLIDINES, THIAZOLIDINES, AND 5,6,7,8‐TETRAHYDRO‐1H,3H‐PYRROLO(1,2‐C)OXAZOLE (OR THIAZOLE)‐1,3‐DIONES FROM β‐HYDROXY‐ OR β‐MERCAPTO‐α‐AMINO ACID ESTERS

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