Synthesis of Alkyl Esters of 4-Amino-2-sulfamoylbenzoic Acid

Hamor, Glenn H.; Janfaza, Mehdi

doi:10.1002/jps.2600520126

Cited by 8 publications

(5 citation statements)

References 2 publications

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“….-Following is a variation of the previously reported method. [45] In an oven dried round bottom flask flushed with argon, nitrosaccharin (2) (1 g, 4.38 mmol, 1 equiv) was dissolved in 50 mL dry MeOH, cooled to 0 °C and 0.5 mL of dry TFA was added dropwise. The ice-bath was then removed, and the reaction mixture was allowed to warm to rt before refluxing it at 70 °C for 18 hours.…”

Section: Methyl 4-nitro-2-sulfamoylbenzoate (3)mentioning

confidence: 99%

Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy

Murray

Quadri

et al. 2019

Carbohydrate Research

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Carbonic anhydrase IX (CA IX) has been identified as a biomarker and drug target for several malignant tumors due to its role in cancer cell growth and proliferation. Simple cyclic sulfonamides, like saccharin (SAC), have shown up to a 60-fold selectivity towards CA IX over other ubiquitous CA isoforms, with greater selectivity obtained applying the "tail-approach" to derivatize SAC with a methylene triazole linker that connected to a "tail" beta glucoside. These modifications of SAC led to an increased selectivity of more than 1000-fold towards CA IX, whereas clinically available CA inhibitors show little to no isoform selectivity. As part of our interest in the development of new CA inhibitors, we found the existing synthetic protocol, which relies on a N-tert-butyl saccharin intermediate, to be problematic in the final deprotection steps. We therefore describe an alternative approach to the synthesis of these compounds featuring a gentle "one pot" deprotection/cyclization as the final synthetic step, and report new galactosyl and glucosyl conjugates with low to mid nM inhibition of CA IX.

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Section: Methyl 4-nitro-2-sulfamoylbenzoate (3)mentioning

confidence: 99%

Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy

Murray

Quadri

et al. 2019

Carbohydrate Research

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“…Sulfonamides currently represent a minor class of antiepileptic agents . Early structure−activity studies of sulfonamides examined phenyl and heteroaromatic primary sulfonamides, a number of which displayed anticonvulsant activity. Acetazolamide (2-(acetylamino)-1,3,4-thiadiazole-5-sulfonamide) has been used as an anticonvulsant for some time, and recently as an adjunct to carbamazepine in the treatment of partial seizures …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of N-(Phenylacetyl)trifluoromethanesulfonamides as Anticonvulsant Agents

et al. 1996

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A series of N-(phenylacetyl)trifluoromethanesulfonamides (3a-g) was prepared according to the Topliss scheme in order to determine if aryl substituents would influence anticonvulsant activity. In initial (phase I) screening and quantitative (phase II) evaluation, all seven compounds exhibited significant activity against MES- and scMet-induced seizures. N-(Phenylacetyl)trifluoromethanesulfonamide (3a) was then advanced through five additional testing phases (phases III-VII). Compound 3a displayed good oral bioavailability, low toxicity, and a larger protective index in mice than the prototype drugs, phenytoin, phenobarbital, valproate, and ethosuximide. Additionally, 3a exhibited a longer time to peak effect in all tests and a greater 24-h margin of safety (HD(50)/ED(50)) than the prototypes. Compound 3a blocked picrotoxin-induced seizures but was ineffective against seizures induced by bicuculline or strychnine. In vitro receptor binding studies revealed that 3a did not displace [(3)H]-labeled gamma-aminobutyric acid or [(3)H]-labeled flunitrazepam, and tolerance did not develop during a 5-day chronic administration.

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“…recently reported that the alkyl esters of ortho-sulfamoylbenzoic acid (I), 4-amino-2-sulfamoylbenzoic acid (II), and 6-chloro-2-sulfamoylbenzoic acid (111) were capable of preventing convulsions induced by strychnine or maximal electroshock in mice (1)(2)(3). Loev and Korrnendy also reported on the effectiveness of some 4-amino-2-sulfamoylbenzoates (4,5).…”

mentioning

confidence: 99%

Anticonvulsants IV: Vinylogs, Alkyl Esters of 2-Sulfamoylcinnamic Acid and Related Compounds

Rao¹,

Hamor

1969

Journal of Pharmaceutical Sciences

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Synthesis of Alkyl Esters of 4-Amino-2-sulfamoylbenzoic Acid

Cited by 8 publications

References 2 publications

Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy

Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy

Synthesis and Evaluation of N-(Phenylacetyl)trifluoromethanesulfonamides as Anticonvulsant Agents

Anticonvulsants IV: Vinylogs, Alkyl Esters of 2-Sulfamoylcinnamic Acid and Related Compounds

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