Sulfamide Research Articles

Sulfonamide disinfection byproducts exhibited severe toxicity to human commensal bacteria

Many antibiotic disinfection byproducts have been detected but their toxicity has not been evaluated adequately. In this report, the chlorination reaction kinetics of five common sulfamides (SAs), reaction intermediates and their toxicity were investigated. Chlorination of sulfapyridine (SPD), sulfamethazine (SMT), sulfathiazole (STZ), and sulfisoxazole (SIZ) followed the second-order kinetics, and were degraded completely within 10 min. A large number of reaction intermediates were deteced by LC-MS, among which a total of 16 intermediates were detected for the first time. Toxicity of the five SAs chlorination solutions was evaluated separately by examining their effects on the growth rate of S. salivarius K12, a commensal bacterium in the human digestive system. After 30 min chlorination, solutions of SMT, STZ and sulfadiazine (SDZ) each exhibited severe toxicity by inhibiting the bacteria growth completely, whereas the inhibition was only 50 % and 20 % by SIZ and SPD respectively. Based on the comparison between toxicity test results and mass spectra, three SA chlorination intermediates, m/z 187.2 (C10H10N4), m/z 287.2 (C9H7N3O4S2) and m/z 215 (C7H10N4O2S/C12H14N4) were proposed to be the primary toxicants in the chlorination products. Our study demonstrated the power of combined approach of chemical analysis and toxicity testing in identifying toxic disinfection byproducts, and highlighted the ne ed for more research on the toxicity evaluation and risk assessment of antibiotic disinfection byproducts.

Getting the SuFEx Right for Sulfamides

Getting the SuFEx Right for Sulfamides

Octadecylpropyl Sulfamide Reduces Neurodegeneration and Restores the Memory Deficits Induced by Hypoxia-Ischemia in Mice.

The PPAR-α agonist, oleoylethanolamide (OEA) has neuroprotective properties in stroke models. However, its rapid degradation represents a limitation for an effective therapeutic approach. In this study, we evaluated the effects of a stable OEA-modeled compound, octadecylpropyl sulfamide (SUL) on the cognitive, behavioral, cellular and molecular alterations associated with hypoxia-ischemia (HI) in mice. Mice subjected to HI were treated with the PPAR-α antagonist GW6471 (GW) (1 mg/kg) followed 15 min later by SUL (3 and 10 mg/kg). Behavioral, motor, and cognitive tests were carried out 24 h and 7 days after the HI. The levels of microglia, reactive astrocytes and neuronal nuclei were studied using immunofluorescence, and the expression of genes related to the N-acyl-ethanolamides/endocannabinoid signaling systems was determined by qRT-PCR at the end of the experimental sequence. HI induced brain damage in the ipsilateral hippocampus and cortex, which lead to severe memory impairments, and motor coordination deficits. Significant neuronal loss, increased microglia and reactive astrocytes, and compensatory changes in genes associated with the inflammation/immune and endocannabinoid systems were observed in these brain structures of lesioned mice. SUL reversed the memory and motor deficits, decreased the overexpression of microglia and astrocytes, and reduced neurodegeneration induced by HI. Cnr1 and Cnr2 gene expression was modulated by SUL in both sham and HI mice, while Pparα and Faah expression was regulated in HI mice. GW completely blocked the beneficial actions of SUL. These findings suggest that treatment with SUL reduces brain damage and the associated motor and memory deficits induced by HI probably by normalizing the changes in neuroinflammation/immune system mediators.

Chemical regulation of mycotoxin biosynthesis

Mycotoxins—metabolites of microscopic mold fungi widely spread in nature—are the most hazard� ous pollutants of agricultural raw materials and food� stuff. They are highly toxic and cause severe intoxica� tions in humans and animals; some of them are car� cinogens. The stability of mycotoxins determines the necessity of stringent control of their content in agri� cultural and food products (maximum allowable con� centrations of different mycotoxins are on the order of 0.1–20 mg/kg). The economic damage caused by mycotoxins reaches several billions of dollars every year. It is known that various natural and synthetic com� pounds (ginseng saponins, citrus essential oil, sulfa� mides, organic acids, mercaptoethanol, etc.) can decrease or increase mycotoxin production; however, the causes underlying their activity remain obscure [1]. It was shown that fungicidal activity of some nat� ural phenolic compounds may combine with the abil� ity to suppress toxigenesis [2]. The known method of detoxication of fodders and foodstuff by treatment with ammonia at elevated pressure and temperature has obvious limitations [3]. Thus, the possibility to selectively affect mycotoxin production remains a topical problem. One of its pos� →→ → → →→

α-Thioureidoalkylation of urea heteroanalogs

α-Thioureidoalkylation of urea heteroanalogs such as thiosemicarbazide, amino-guanidine, sulfamide, and sulfonamides with 4,5-dihydroxyimidazolidine-2-thiones has been studied. Previously unknown 4,5-bis[thiosemicarbazido(guanidinoamino)]imidazolidine-2-thiones, 5,7-dialkylperhydroimidazo[4,5- e][1,2,4]triazine-3,6-dithiones, 4,6-diethyl-5(3H)-thioxotetrahydro-1 H-imidazo[4,5- c][1,2,5]thiadiazole 2,2-dioxide, and 1,3-dialkyl-4-[guanidinoimino(arylsulfonylimino)]imidazolidine-2-thiones have been synthesized.

Glycolurils in α-ureido-and α-aminoalkylation reactions 1. α-Ureidoalkylation of sulfamides with N-(hydroxymethyl)glycolurils

α-Ureidoalkylation of sulfamides with 2-hydroxymethyl-, 2,6-and 2,8-bis(hydroxymethyl)-, and 2,4,6,8-tetrakis(hydroxymethyl)glycolurils gave novel bi-, tri-, and tetracyclic fused systems combining the glycoluril and sulfamide fragments.

Synthesis, Structure and Properties of Sulfamides (III) on the Basis of 1,3‐Dimethyl‐1‐H‐quinazoline‐2,4‐dione.

Synthesis, Structure and Properties of Sulfamides (III) on the Basis of 1,3‐Dimethyl‐1‐H‐quinazoline‐2,4‐dione.

Reaction of Cytisine with 4″-Substituted Dibenzo-18-crown-6 Sulfonylchlorides

Sulfamides were synthesized via the reaction of cytisine with 4′,4″(5″)-dibenzo-18-crown-6-disulfonyl-, 4′-sec-butyl-4′(5″)-dibenzo-18-crown-6-sulfonyl-, and 4′-acetyl-4′(5″)-dibenzo-18-crown-6-sulfonylchlorides. The structures of the prepared compounds were confirmed by PMR.

Proton pump inhibitors and acid-related diseases.

Proton pump inhibitors (PPIs) are targeted to the gastric acid pump, H+, K(+)-adenosine triphosphatase (ATPase). The drugs accumulate in the acid space of the parietal cell and convert to active sulfenamide by an acid-catalyzed reaction. Consequent covalent inhibition of H+, K(+)-ATPase blocks the final step of acid secretion, hence the PPIs omeprazole, lansoprazole, and pantoprazole are more effective than histamine2-receptor antagonists (H2RAs) in controlling acid secretion. Preclinical short- and long-term clinical surveillance data show these drugs to be well tolerated and safe. The PPIs heal the lesions of gastroesophageal reflux disease and lessen symptoms more effectively and more quickly than the H2RAs, and are effective and faster acting for peptic ulcer disease. Helicobacter pylori is causally implicated in the majority of peptic ulcers and in atrophic gastritis. Since PPIs, but not H2RAs, are synergistic with antibiotics in eradicating H. pylori, their use is appropriate in all acid-related diseases since all patients who are H. pylori positive require eradication as well as healing.

Sulfenamides as ligands in transition metal chemistry Pentacarbonyl(Sulfenamide)Chromium(0) Complexes

AbstractThe complexes Cr(CO)5(R′SNR2) [R′ = CH3; NR2 = N(CH3)2, N(C4H8)O. R′ = C6H5; NR2 = N(CH3)2, N(C4H4)O, N(CH2C6H5)2, N(C6H11)2] have been prepared by reaction of the sulfenamides with Cr(CO)5 · THF and characterized by analytical and spectroscopic methods. The IR, 1H‐NMR, UV‐VIS, and mass spectra of the complexes support the coordination of the sulfenamide via the sulfur atom. π‐acceptor abilities of sulfenamides in the prepared coordination compounds, determined from IR and UV‐VIS data, were compared with those of other divalent sulfur conpounds.

ChemInform Abstract: Alkyl‐ and Arylsulfenamides by Cycloelimination of Alkenes from Sulfimides. Part 3. Formation of Primary and Secondary Aliphatic Sulfenamides of Type RSNH2 or RSNHR.

ChemInform Abstract: Alkyl‐ and Arylsulfenamides by Cycloelimination of Alkenes from Sulfimides. Part 3. Formation of Primary and Secondary Aliphatic Sulfenamides of Type RSNH2 or RSNHR.

The chemistry of sulfenamides

The chemistry of sulfenamides

Curing reaction of elastomers with triazine thiols and sulfen amides

Curing reaction of elastomers with triazine thiols and sulfen amides in the presence of ZnO and stearic acid was investigated for curing parameters and curing mechanism. The curing parameters such as curing rate, induction period, and curing efficiency were influenced by the pKa of thiol groups in triazine thiols and amines corresponding in sulfen amides, by the steric hinderance of 6-substituted groups in triazine thiols and on amino groups in sulfen amides, by the molar ratio of sulfen amides to triazine thiols, and by the reacting positions and the properties of elastomers. Triazine thiols acted as curing agents. Sulfen amides played two important roles in curing elastomers with triazine thiols. They gave poly(triazinyl disulfide) which is a curing precursor. Curing activators are formed in the reaction of the precursors, sulfen amides, and ZnO. The activators react with elastomers to give crosslinks, pendants and triazine dithiols or triazinyl disulfide oligomers. The pendants react with sulfen amides to give the crosslinks. The triazine thiols or triazinyl disulfide oligomers react with sulfen amides to reproduce the curing precursors. The structure of crosslinks is estimated to be

Nucleophilicity of aromatic sulfenamides and the ".alpha. effect"

Nucleophilicity of aromatic sulfenamides and the ".alpha. effect"

Linear Deammonation Products of Sulfamide and Their Derivatives

Linear Deammonation Products of Sulfamide and Their Derivatives

Sulfamoyl Chloride, Sulfamides and Sulfimide

<b>Sulfamoyl Chloride, Sulfamides and Sulfimide</b>

Syntheses and Properties of Some N-Substituted Sulfamides

Syntheses and Properties of Some N-Substituted Sulfamides

Aliphatic Sulfenamides

Aliphatic Sulfenamides

Preparation and Properties of Certain Derivatives of Sulfamide

Preparation and Properties of Certain Derivatives of Sulfamide

Results obtained by the preventive use of the sulfamides during labor: Gueniot, P.: Rev. franç. de gynéc. et d'obst. 36: 27, 1941

Results obtained by the preventive use of the sulfamides during labor: Gueniot, P.: Rev. franç. de gynéc. et d'obst. 36: 27, 1941