Synthetic Anticonvulsants. The Preparation and Properties of Some Benzoxazoles<sup>1</sup>

Bywater, W. G.; Coleman, W. R.; Kamm, Oliver; Merritt, H. Houston

doi:10.1021/ja01222a008

Cited by 48 publications

(13 citation statements)

References 1 publication

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“…Reaction of 9 and ethyl bromoacetate in benzene in the presence of NaH and subsequent hydrolysis of ester 10 by 4 N HCl in dioxane gave the acid 11 in overall 40% yield. All the other acids were obtained commercially or prepared by the following methods: The N , N ‐phthaloyl‐amino acids were obtained according to previously described procedure (19,20). The N ‐saccharinyl acetic acid was prepared from sodium saccharin and chloroacetic acid (21).…”

Section: Methodsmentioning

confidence: 99%

Design, Biologic Evaluation, and SAR of Novel Pseudo‐peptide Incorporating Benzheterocycles as HIV‐1 Protease Inhibitors

Zhang

Yao

et al. 2010

Chem Biol Drug Des

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A series of novel HIV‐1 protease inhibitors based on the (hydroxyethylamino)‐sulfonamide isostere incorporating substituted phenyls and benzheterocycle derivatives bearing rich hydrogen bonding acceptors as P2 ligands were synthesized. Prolonged chain linking the benzhereocycle to the carbonyl group resulted in partial loss of binding affinities. Introduction of a small alkyl substituent with appropriate size to the ‐CH2‐ of P1‐P2 linkage as a side chain resulted in improved inhibitory potency, and in this study, isopropyl was the best side chain. Replacement of the isobutyl substituent at P1′group with phenyl substituent decreased the inhibitory potency. One of the most potent inhibitor, compound 23 showing high affinity to HIV‐1 protease with an IC50 value of 5 nm, also exhibited good anti‐SIV activity (EC50 = 0.8 μm) with low toxicity (TC50 > 100 μm). The flexible docking of inhibitor 23 to HIV‐1 protease active site rationalized the interactions with protease.

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Section: Methodsmentioning

confidence: 99%

Design, Biologic Evaluation, and SAR of Novel Pseudo‐peptide Incorporating Benzheterocycles as HIV‐1 Protease Inhibitors

Zhang

Yao

et al. 2010

Chem Biol Drug Des

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“…6-Acyl-3-alkyl-5-methyl-2(3H)-benzoxazolones were prepared according to the general synthetic pathway given in Scheme 1. The starting material, 5-methyl-2(3H)-benzoxazolone 1, was synthesized according to the literature method using 2-amino-4-methylphenol and urea [28]. This compound was then acylated with two different substituted benzoyl chlorides by using Friedel-Crafts acylation reaction with aluminium chloride-N,Ndimethylformamide (AlCl 3 -DMF), yielding 6-acyl-5-methyl-2benzoxazolones 2a, 2b.…”

Section: Synthesis Of 6-acyl-3-alkyl-5-methyl-2(3h)benzoxazolonesmentioning

confidence: 99%

Synthesis and Evaluation of Analgesic, Anti-Inflammatory and Antioxidant Activities of New 6-Acyl-3-alkyl-5-methyl-2(3H) -benzoxazolones

Koksal

Kelekçi

Mercanoğlu

et al. 2011

Arzneimittelforschung

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A new series of 6-acyl-3-alkyl-5-methyl-2(3H)-benzoxazolones have been obtained starting from 5-methyl-2(3H)-benzoxazolone. All the compounds have been characterized by IR, 1H-NMR and mass spectroscopy. The new compounds were screened for analgesic and anti-inflammatory activities and ulcerogenic effect. The in vitro antioxidant capacity of the synthesized compounds were tested by the nitric oxide radical scavenging assay. Most of the compounds showed antiinflammatory activity. Among them, 3-[4-(4-fluorophenyl)piperazinomethyl] -6-(3-chlorobenzoyl)-5-methyl-2(3H)-benzoxazolone (3j) was found more potent than the reference drug indometacin (CAS 53-86-1) with 41.66% decrease in edema. Compared with the control, some of the compounds exhibited analgesic effects. Similar to the anti-inflammatory activity results, compound 3j showed the highest analgesic profile with 48.56% inhibition. No active hemorragic focus was observed in the microscopic evaluation in the ulcerogenic effect studies of the tested compounds. 6-(3-Chlorobenzoyl)-5-methyl-2(3H)-benzoxazolone (2b) and 3-[4-(4-fluorophenyl-piperazino)methyl]-6-(3-chlorobenzoyl)-5-methyl-2(3H)-benzoxazolone (3j) showed nearly maximum antioxidant activity compared to ascorbic acid (CAS 50-81-7) with IC50 values of 27.6 and 30.1 microg/mL, respectively.

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“…Moreover, structure-activity relationships of benzoxazole derivatives have revealed that the substitution of the 2nd position is decisive for the biological activity and position 5 is important for the intensity of the activity [23][24][25].…”

Section: Formula IImentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Some 2-[p-Substituted-phenyl]benzoxazol-5-yl-arylcarboxyamides

Temiz-Arpacı

Aki-Sener

Yalçın

et al. 2002

Arch. Pharm. Pharm. Med. Chem.

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New 2‐[p‐substituted‐phenyl ]benzoxazol‐5‐yl‐arylcarboxyamides derivatives have been synthesized by reacting 5‐amino‐2‐[p‐substituted‐phenyl ]benzoxazoles with substituted‐arylcarboxylic acid chlorides. The structures of the synthesized compounds were confirmed by IR and 1H NMR spectral data. Antimicrobial activities of the compounds were investigated using the two‐fold serial dilution technique against different Gram‐positive and Gram‐negative bacteria and the yeast C. albicans in comparison with standard drugs. Microbiological results indicated that the synthesized compounds possess a broad spectrum of activity, having an MIC value of 25‐200 μg/mL at molar concentration values of 3.45 ? 10‐5 and 5.74 ? 10‐4 against the tested microorganisms.

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Synthetic Anticonvulsants. The Preparation and Properties of Some Benzoxazoles¹

Cited by 48 publications

References 1 publication

Design, Biologic Evaluation, and SAR of Novel Pseudo‐peptide Incorporating Benzheterocycles as HIV‐1 Protease Inhibitors

Design, Biologic Evaluation, and SAR of Novel Pseudo‐peptide Incorporating Benzheterocycles as HIV‐1 Protease Inhibitors

Synthesis and Evaluation of Analgesic, Anti-Inflammatory and Antioxidant Activities of New 6-Acyl-3-alkyl-5-methyl-2(3H) -benzoxazolones

Synthesis and Antimicrobial Activity of Some 2-[p-Substituted-phenyl]benzoxazol-5-yl-arylcarboxyamides

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Synthetic Anticonvulsants. The Preparation and Properties of Some Benzoxazoles1

Cited by 48 publications

References 1 publication

Design, Biologic Evaluation, and SAR of Novel Pseudo‐peptide Incorporating Benzheterocycles as HIV‐1 Protease Inhibitors

Design, Biologic Evaluation, and SAR of Novel Pseudo‐peptide Incorporating Benzheterocycles as HIV‐1 Protease Inhibitors

Synthesis and Evaluation of Analgesic, Anti-Inflammatory and Antioxidant Activities of New 6-Acyl-3-alkyl-5-methyl-2(3H) -benzoxazolones

Synthesis and Antimicrobial Activity of Some 2-[p-Substituted-phenyl]benzoxazol-5-yl-arylcarboxyamides

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Synthetic Anticonvulsants. The Preparation and Properties of Some Benzoxazoles¹