Synthesis of Potential Anticancer Agents. VI. N-(3-Hydroxypropyl)-benzaldimine and Related Compounds<sup>1,2</sup>

Vaughan, Wyman R.; Klonowski, Robert S.

doi:10.1021/jo01060a034

Cited by 6 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Applying GPB: from 12a (250 mg, 1.16 mmol): 12b (330 mg, 96%) [93] ; white solid; Rf = 0.49 (CHCl3/EtOAc, 2:3); m.p. = 79-81 °C; UV-Vis: 224 nm (3.91); IR: ν = 3358w, 3332w, 3265m, 1480w, 1448w, 1425w, 1377m, 1366s, 1322s, 1305m, 1238w, 1227w, 1178s, 1160s, 1148s, 1117w, 1098m, 1083s, 1033m, 1011s, 954m, 931s, 913m, 880w, 869w, 818m, 803m, 783s, 769s, 702m, 684s, 659m, 598m, 589m, 574s, 548vs, 529m, 509m, 487m, 471s, 448m, 431w, 411w cm −1 ; 1 Applying GPA: from 4-methylbenzenesulfonyl chloride (200 mg, 1.05 mmol) and 3amino-propanol (118 mg, 1.57 mmol): 13a (225 mg, 94%) [94][95][96][97][98][99] ; white solid; Rf = 0.12 (petrolether/EtOAc, 2:3); m.p. = 55-57 °C (lit.…”

Section: -[(4-methylphenyl)sulfonamido]ethyl Sulfamate (12b) [914083-...mentioning

confidence: 99%

“…= 55-57 °C (lit. : [98] 55-56 °C); UV-Vis: 227 nm (4.14); IR: ν = 3492br, 3274br, 2945w, 2879w, 1598m, 1495w, 1423m, 1318s, 1305s, 1296m, 1185w, 1153vs, 1091s, 1070s, 1019w, 1006w, 959m, 872w, 815s, 706w, 662s, 570w, 550s, 515w cm −1 ; 1 H NMR:δ =7. 69 Applying GPA: from 4-methylbenzenesulfonyl chloride (400 mg, 2.1 mmol) and 4amino-butanol (318 mg, 3.15 mmol): 14a (477 mg, 93%); white solid; Rf = 0.12 (petrolether/EtOAc, 2:3); m.p.…”

Section: -[(4-methylphenyl)sulfonamido]ethyl Sulfamate (12b) [914083-...mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Enzymatic Evaluation of a Small Library of Substituted Phenylsulfonamido-Alkyl Sulfamates towards Carbonic Anhydrase II

Denner,

Heise,

Al-Harrasi

et al. 2024

Molecules

View full text Add to dashboard Cite

A small library of 79 substituted phenylsulfonamidoalkyl sulfamates, 1b–79b, was synthesized starting from arylsulfonyl chlorides and amino alcohols with different numbers of methylene groups between the hydroxyl and amino moieties yielding intermediates 1a–79a, followed by the reaction of the latter with sulfamoyl chloride. All compounds were screened for their inhibitory activity on bovine carbonic anhydrase II. Compounds 1a–79a showed no inhibition of the enzyme, in contrast to sulfamates 1b–79b. Thus, the inhibitory potential of compounds 1b–79b towards this enzyme depends on the substituent and the substitution pattern of the phenyl group as well as the length of the spacer. Bulkier substituents in the para position proved to be better for inhibiting CAII than compounds with the same substituent in the meta or ortho position. For many substitution patterns, compounds with shorter spacer lengths were superior to those with long chain spacers. Compounds with shorter spacer lengths performed better than those with longer chain spacers for a variety of substitution patterns. The most active compound held inhibition constant as low as Ki = 0.67 μM (for 49b) and a tert-butyl substituent in para position and acted as a competitive inhibitor of the enzyme.

show abstract

Section: -[(4-methylphenyl)sulfonamido]ethyl Sulfamate (12b) [914083-...mentioning

confidence: 99%

Section: -[(4-methylphenyl)sulfonamido]ethyl Sulfamate (12b) [914083-...mentioning

confidence: 99%

Synthesis and Enzymatic Evaluation of a Small Library of Substituted Phenylsulfonamido-Alkyl Sulfamates towards Carbonic Anhydrase II

Denner,

Heise,

Al-Harrasi

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

“…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 the imine is protected as its trimethylsilyl ether, the iminium ion formation is followed by proton abstraction leading to the formation of zwitterionic intermediate followed by ring closure to furnish β-lactams 4a-d (Scheme 3).…”

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

View full text Add to dashboard Cite

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...

show abstract

Sulfonsäure‐[β‐chlor‐alkyl]‐ester und 1.2‐Alkylen‐glykol‐disulfonate aus Sulfochloriden und Alkylenoxiden

Klamann¹,

Ulm²,

Weyerstahl³

et al. 1967

Justus Liebigs Ann. Chem.

View full text Add to dashboard Cite

show abstract

Synthesis of Potential Anticancer Agents. VI. N-(3-Hydroxypropyl)-benzaldimine and Related Compounds^1,2

Cited by 6 publications

References 0 publications

Synthesis and Enzymatic Evaluation of a Small Library of Substituted Phenylsulfonamido-Alkyl Sulfamates towards Carbonic Anhydrase II

Synthesis and Enzymatic Evaluation of a Small Library of Substituted Phenylsulfonamido-Alkyl Sulfamates towards Carbonic Anhydrase II

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

Sulfonsäure‐[β‐chlor‐alkyl]‐ester und 1.2‐Alkylen‐glykol‐disulfonate aus Sulfochloriden und Alkylenoxiden

Contact Info

Product

Resources

About

Synthesis of Potential Anticancer Agents. VI. N-(3-Hydroxypropyl)-benzaldimine and Related Compounds1,2

Cited by 6 publications

References 0 publications

Synthesis and Enzymatic Evaluation of a Small Library of Substituted Phenylsulfonamido-Alkyl Sulfamates towards Carbonic Anhydrase II

Synthesis and Enzymatic Evaluation of a Small Library of Substituted Phenylsulfonamido-Alkyl Sulfamates towards Carbonic Anhydrase II

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

Sulfonsäure‐[β‐chlor‐alkyl]‐ester und 1.2‐Alkylen‐glykol‐disulfonate aus Sulfochloriden und Alkylenoxiden

Contact Info

Product

Resources

About

Synthesis of Potential Anticancer Agents. VI. N-(3-Hydroxypropyl)-benzaldimine and Related Compounds^1,2