Studies in Chemotherapy. XV. Amides of Pantoyltaurine<sup>1</sup>

Winterbottom, Robert; Clapp, J. W.; Miller, Warren H.; English, J. P.; Roblin, Richard O.

doi:10.1021/ja01198a047

Cited by 60 publications

(41 citation statements)

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“…Title compounds 11-15 were synthesized starting from 2-phtalimidoethanesulfonyl chloride B which was prepared according to procedure described before (12,13). The chlorinated derivative B was reacted with sulfanilamide in pyridine to give the title compound 11 as a white solid ( Figure 2).…”

Section: Chemistrymentioning

confidence: 99%

“…The title compounds 1-10 were reported in our previous study whereas 11-15 were reported in different studies as intermediates of diverse compounds (12,13,23). None of the compounds have been tested for their antimicrobial activity before though taurine derivatives known to posses antimicrobial activity (12,24).…”

Section: Introductionmentioning

confidence: 99%

“…Taurinamide (II) is lipophilic derivative of taurine and known to posses antibacterial (12), histamine H 4 receptor inverse agonists (13) and anticonvulsant (14) activities which indicate its potential for generating pharmacologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

“…None of the compounds have been tested for their antimicrobial activity before though taurine derivatives known to posses antimicrobial activity (12,24). Literature survey indicates that there is a need for elucidating the structural requirements that mediates their phamacological activity (25).…”

Section: Introductionmentioning

confidence: 99%

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Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Akgül¹,

Öztürk²,

Aygül³

et al. 2017

Marmara Pharmaceutical Journal

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In this study, a series of taurinamide derivatives were synthesized and screened for their antimicrobial activity. The structures of the newly synthesized compounds 11-15 were evaluated by 1 H NMR, IR, MS-APCI and elemental analysis. Compounds (1-15) were tested against standard strains of Gram(+), Gram(−) bacteria and fungi by using disc diffusion and broth microdilution methods. Although disc diffusion method did not show any comparable results due to the solubility properties of the compounds; microdilution method results indicated that title compounds showed from poor to good activity against only Enterococcus faecalis. It can be concluded that phtalimido moiety, secondary aryl sulphonamide group and electrondonating group substitution on phenyl ring are essential for the antibacterial activity. Among the tested compounds, para substituted methyl and methoxy derivatives of N-phenyl-2-phthalimidotaurinamide (4, 7), displayed equipotent activity compared to standard drug gentamicin.

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Akgül¹,

Öztürk²,

Aygül³

et al. 2017

Marmara Pharmaceutical Journal

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“…The synthesis of the title compounds was performed in three steps according to the method reported by Winterbottom et al [19]. As illustrated in Scheme 1, in the first step, the reaction of 2-aminoethane sulfonic acid (taurine) with phthalic anhydride and potassium acetate in acetic acid solution furnished 2-phthalimidoethanesulfonic acid potassium salt.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Anticonvulsant Activity of Some N‐Phenyl‐2‐phtalimidoethanesulfonamide Derivatives

Akgül

Kılıç

Erol

et al. 2007

Archiv der Pharmazie

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In this study, inspired by the structures of the taltrimide, 2-phthalimidoethanesulphonamide, and the anilide pharmacophore known to be synthetically produced anticonvulsant compounds, fifteen N-phenyl-2-phtalimidoethanesulfonamide derivatives bearing substituents with diverse electronic and hydrophobic features on N-phenyl ring were synthesized. The structural confirmation of the title compounds was achieved by interpretation of spectral and analytical data. The anticonvulsant activity of the title compounds was determined against maximal electroshock seizure in mice at a dose level of 100 mg/kg. The preliminary screening results indicated that the exchange of the N-isopropyl moiety for an N-phenyl ring in the taltrimide molecule abolished the anticonvulsant activity. However, introducing certain substituents, such as nitro, methyl, and chloro, into the N-phenyl ring lead to more active compounds in comparison to the unsubstituted derivatives.

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Synthesis and anticonvulsant activity ofN,N-phthaloyl derivatives of central nervous system inhibitory amino acids

Usifoh¹,

Lambert²,

Wouters³

et al. 2001

Arch. Pharm. Pharm. Med. Chem.

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In order to study the influence of the length of the amino acid chain of N,N‐phthaloylamino acid amides as analogues of the former anticonvulsant taltrimide on the seizureantagonizing activity glycine, β‐alanine and γ‐aminobutyric acid (GABA) derivatives were synthesized. The corresponding taurine derivatives were also included. Generally, the glycine‐derived amides showed a higher activity than the β‐alanine and GABA derivatives in the maximal electroshock seizure (MES) test in mice upon intraperitoneal administration. The activity was comparable to the respective taurine derivatives. The N,N‐phthaloyl‐glycine amides were also active in the MES test upon oral administration to rats. No significant activity was noted in the seizure threshold test with subcutaneous pentylenetetrazole. The ED50 of N,N‐phthaloyl‐glycine ethyl amide (4b) in the MES test upon intraperitoneal administration to mice was 19.1 mg/kg. On a molar basis this activity is comparable to the activity of phenytoin with little toxicity in the rotorod test. In conclusion, N,N‐phthaloyl‐glycine amides might represent promising antiepileptic drugs.

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Studies in Chemotherapy. XV. Amides of Pantoyltaurine¹

Cited by 60 publications

References 0 publications

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Synthesis and Anticonvulsant Activity of Some N‐Phenyl‐2‐phtalimidoethanesulfonamide Derivatives

Synthesis and anticonvulsant activity ofN,N-phthaloyl derivatives of central nervous system inhibitory amino acids

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Studies in Chemotherapy. XV. Amides of Pantoyltaurine1

Cited by 60 publications

References 0 publications

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Synthesis and Anticonvulsant Activity of Some N‐Phenyl‐2‐phtalimidoethanesulfonamide Derivatives

Synthesis and anticonvulsant activity ofN,N-phthaloyl derivatives of central nervous system inhibitory amino acids

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Studies in Chemotherapy. XV. Amides of Pantoyltaurine¹