Dicarboxylic Acid Derivatives of Sulfonamides<sup>1</sup>

Moore, Maurice L.; Miller, Charles S.

doi:10.1021/ja01259a023

Cited by 24 publications

(13 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This route served to convert the poorly reactive aromatic p-amino group of sulfamethoxazole to a fully reactive aliphatic carboxyl group in 6 that when activated by a conventional route proved to be capable of acylating protein nucleophiles effectively. Compound 6 was prepared in 92% yield by treatment of SMX with succinic anhydride in the manner used for succinylsulfathiazole (21). To react 6 with protein nucleophiles the active ester approach was considered more promising than carbodiimide with its risk of protein crosslinking side reactions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of protein and polylysine conjugates of sulfamethoxazole and sulfanilic acid for investigation of sulfonamide drug allergy

Tatake

Knapp²,

Ressler³

1991

Bioconjugate Chem.

View full text Add to dashboard Cite

Conjugates of sulfamethoxazole (SMX) with human serum albumin (HSA), transferrin (TR), and poly(L-lysine) (PL, degrees of polymerization 16 and 430) have been prepared. As a model, succinylSMX-glycine methyl ester was synthesized by carbodiimide and active ester routes. The proteins and PL were acylated with succinylSMX succinimido ester, affording conjugates (succinylSMX)2-21-HSA, (succinylSMX)17,27-TR, (succinylSMX)11-Lys16, and (succinylSMX)71-Lys430 in which SMX was linked by a spacer chain of four carbons. This represents substitution of up to 35, 46, 65, and 17% of the amino groups of HSA, TR, PL16, and PL430, respectively. HSA was also acylated with the succinimido esters of succinylSMX-glycine and succinylSMX-epsilon-aminohexanoic acid, affording conjugates (succinylSMX-Gly)53-HSA and (succinylSMX-epsilon-NH2hex)51-HSA. In these conjugates SMX was linked by a spacer chain of 7 and 11 carbons, respectively, and almost all the amino groups of HSA were substituted. Factors apparently influencing the extent of conjugation to HSA were the stability of the active ester and the solubility of the conjugation reaction mixture. A sulfanilic acid (SA) conjugate, containing 12 mol of ligand/mol of HSA, was also prepared. The route of synthesis involved acylation of HSA with sulfanilyl fluoride. N-epsilon-Sulfanilyl-L-lysine dihydrochloride, required for quantitation of bound SA, was synthesized by a new route starting from alpha-Boc-L-lysine. Conjugates (sulfanilyl)12-HSA and (succinylSMX)13-HSA, differing in molecular weight from HSA by only 2.6 and 6.5%, were distinguishable from HSA by gel-filtration HPLC, as were the more highly substituted conjugates from their respective unsubstituted materials.(ABSTRACT TRUNCATED AT 250 WORDS)

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of protein and polylysine conjugates of sulfamethoxazole and sulfanilic acid for investigation of sulfonamide drug allergy

Tatake

Knapp²,

Ressler³

1991

Bioconjugate Chem.

View full text Add to dashboard Cite

show abstract

“…Sulfonamides 6 - 16 were synthesized earlier by other research groups [38-41]. While compounds 17 - 21 are novel sulfonamide derivatives.…”

Section: Resultsmentioning

confidence: 99%

“…In the current work, the desired N 4 -sulfonamido-succinamic, phthalamic, acrylic and benzoyl acetic acid derivatives 6 - 21 were prepared from the reaction of one of the benzenesulfonamide derivatives 1 - 5 with the required anhydride i - iv (succinic, maleic, phthalic and homophthalic, respectively) in dimethylformamide at 150 °C with overnight reflux, as illustrated in Scheme 1 . Sulfonamides 6 - 16 were synthesized earlier by other research groups [ 38 - 41 ]. While compounds 17 - 21 are novel sulfonamide derivatives.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of N4-Sulfonamido-Succinamic, Phthalamic, Acrylic and Benzoyl Acetic Acid Derivatives as Potential DPP IV Inhibitors

Khalaf¹,

Sheikha²,

Al-Sha’er³

et al. 2013

TOMCJ

View full text Add to dashboard Cite

As incidence rate of type II diabetes mellitus continues to rise, there is a growing need to identify novel therapeutic agents with improved efficacy and reduced side effects. Dipeptidyl peptidase IV (DPP IV) is a multifunctional protein involved in many physiological processes. It deactivates the natural hypoglycemic incretin hormone effect. Inhibition of this enzyme increases endogenous incretin level, incretin activity and should restore glucose homeostasis in type II diabetic patients making it an attractive target for the development of new antidiabetic drugs. One of the interesting reported anti- DPP IV hits is Gemifloxacin which is used as a lead compound for the development of new DPP IV inhibitors. In the current work, design and synthesis of a series of N4-sulfonamido-succinamic, phthalamic, acrylic and benzoyl acetic acid derivatives was carried out. The synthesized compounds were evaluated for their in vitro anti-DPP IV activity. Some of them have shown reasonable bioactivity, where the most active one 17 was found to have an IC50 of 33.5 μM.

show abstract

“…Synthesis: prepared by fusing N 4 -acetylsulfanilamide and dicyanodiamide [108]. Synthesis: prepared by refluxing sulfathiazole with a slight excess of succinic anhydride in alcohol [109]. Synthesis: prepared by refluxing sulfathiazole with a slight excess of succinic anhydride in alcohol [110].…”

Section: Sulfisoxazolementioning

confidence: 99%

Chemotherapeutics

Actor¹,

Chow²,

Dutko³

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

View full text Add to dashboard Cite

Dicarboxylic Acid Derivatives of Sulfonamides¹

Cited by 24 publications

References 0 publications

Synthesis and characterization of protein and polylysine conjugates of sulfamethoxazole and sulfanilic acid for investigation of sulfonamide drug allergy

Synthesis and characterization of protein and polylysine conjugates of sulfamethoxazole and sulfanilic acid for investigation of sulfonamide drug allergy

Design, Synthesis and Biological Evaluation of N4-Sulfonamido-Succinamic, Phthalamic, Acrylic and Benzoyl Acetic Acid Derivatives as Potential DPP IV Inhibitors

Chemotherapeutics

Contact Info

Product

Resources

About

Dicarboxylic Acid Derivatives of Sulfonamides1

Cited by 24 publications

References 0 publications

Synthesis and characterization of protein and polylysine conjugates of sulfamethoxazole and sulfanilic acid for investigation of sulfonamide drug allergy

Synthesis and characterization of protein and polylysine conjugates of sulfamethoxazole and sulfanilic acid for investigation of sulfonamide drug allergy

Design, Synthesis and Biological Evaluation of N4-Sulfonamido-Succinamic, Phthalamic, Acrylic and Benzoyl Acetic Acid Derivatives as Potential DPP IV Inhibitors

Chemotherapeutics

Contact Info

Product

Resources

About

Dicarboxylic Acid Derivatives of Sulfonamides¹