Sulfamic Acid Derivatives Research Articles

Nano Pt/TiO2 photocatalyst for ultrafast production of sulfamic acid derivatives using 4-nitroacetanilides as nitrogen precursor in continuous flow reactors

The design of reactors based on high performance photocatalysts is an important research in catalytic hydrogenation. In this work, modification of titanium dioxide nanoparticles (TiO2 NPs) was achieved by preparation of Pt/TiO2 nanocomposites (NCs) through photo-deposition method. Both nanocatalysts were used for the photocatalytic removal of SOx from the flue gas at room temperature in the presence of hydrogen peroxide, water, and nitroacetanilide derivatives under visible light irradiation. In this approach, chemical deSOx was achieved along with protection of the nanocatalyst from sulfur poising through the interaction of the released SOx from SOx-Pt/TiO2 surface with p-nitroacetanilide derivatives to produce simultaneous aromatic sulfonic acids. Pt/TiO2 NCs have a bandgap of 2.64 eV in visible light range, which is lower than the bandgap of TiO2 NPs, whereas TiO2 NPs have a mean size of 4 nm and a high specific surface area of 226 m2/g. Pt/TiO2 NCs showed high photocatalytic sulfonation of some phenolic compounds using SO2 as a sulfonating agent along with the existence of p-nitroactanilide derivatives. The conversion of p-nitroacetanilide followed the combination processes of adsorption and catalytic oxidation–reduction reactions. Construction of an online continuous flow reactor–high-resolution time-of-flight mass spectrometry system had been investigated, realizing real-time and automatic monitoring of completion the reaction. 4-nitroacetanilide derivatives (1a-1e) was converted to its corresponding sulfamic acid derivatives (2a–2e) in 93–99% isolated yields of within 60 s. It is expected to offer a great opportunity for ultrafast detection of pharmacophores.

Study of triaryl-based sulfamic acid derivatives as HPTPβ inhibitors

A series of novel triaryl-based sulfamic acid analogs was designed, synthesized and evaluated as inhibitors of human protein tyrosine phosphatase beta (HPTPβ). A novel, easy and efficient synthetic method was developed for target compounds, and the activity determination results showed that most of compounds were good HPTPβ inhibitors. Interestingly, the compounds G4 and G25 with simple structure not only showed potent inhibitory activity on HPTPβ but also had good inhibitory selectivity over other PTPs (PTP1B, SHP2, LAR and TC-PTP). The molecular docking simulation of compounds with the protein HPTPβ helped us understand the structure–activity relationship and clarify some confusing assay results. This research provides references for further drug design of HPTPβ and other PTPs inhibitors.

Synthesis and biological evaluation of (3′-amino-[1,1′-biphenyl]-4-yl) sulfamic acid derivatives as novel HPTPβ inhibitors

A series of novel (3′-amino-[1,1′-biphenyl]-4-yl) sulfamic acid derivatives were designed as nonphosphonate-based phosphotyrosy (pTyr) mimetics, synthesized and screened for use as HPTPβ inhibitors. Compounds C22 and C2 showed favorable HPTPβ inhibitory activity and better selectivity for HPTPβ than for PTP1B and SHP2. Docking results suggested that compounds C2 and C22 could not only efficiently fit into the catalytic site of the HPTPβ enzyme but also interact with the Lys1807, Arg1809 and Lys1811 residues of the secondary binding site, which was next to the catalytic center of the enzyme. The mode of interaction of the synthesized compound with the protein was different from the one found in a complex crystal of small molecules with HPTPβ (2I4H), in which the inhibitory molecule formed hydrogen bonds with the Gln1948 and Asn1735 residues of the secondary binding site.

N-Alkylated Sulfamic Acid Derivatives as Organocatalyst in Multicomponent Synthesis of Fatty Dihydropyrimidinones

In this work, N-alkylated sulfamic acid derivatives are introduced as promising acidic organocatalysts with convenient acidity and easy synthesis. The new organocatalysts derived from different nitrogenated compounds (amines, chitosan, urea and thiourea) were applied in multicomponent reactions to synthesize several dihydropyrimidinones (DHPMs). All tested organocatalysts resulted in good DHPM yields, using classic 1,3-dicarbonyl compounds and long-chain 1,3-dicarbonyl derivatives, demonstrating catalytic efficiency. N-Alkylated sulfamic acid derived from benzylamine showed good results (ca. 80% yields). In addition, excellent results were obtained with organocatalysts based on sulfamic acid and thiourea (ca. 80-97% yields), demonstrating the catalytic efficiency of new derivatives of thiourea organosulfamic catalysts.

Water-soluble derivatives of 25-OCH3-PPD and their anti-proliferative activities

(20R)-25-Methoxyl-dammarane-3β,12β,20-triol (25-OCH3-PPD, AD-1) is a dammarane-type sapogenin showing anti-tumor potential. In the search for new anti-tumor agents with higher potency than our previously identified compound 25-OCH3-PPD, 11 novel sulfamic acid and diacid derivatives that could improve water solubility and contribute to good drug potency and pharmacokinetic profiles were designed and synthesized. Their in vitro anti-tumor activities in MCF-7, A-549, HCT-116, and BGC-823 cell lines and one normal cell line were tested by standard MTT assay. Results showed that compared with compound 25-OCH3-PPD, compounds 1, 4, and 5 exhibited higher cytotoxic activity on almost all cell lines, together with lower toxicity in the normal cell. In particular, compound 1 exhibited the best anti-tumor activity in the in vitro assays. The water solubility of 25-OCH3-PPD and its derivatives was tested and the results showed that the solubility of 25-OCH3-PPD sulfamic acid and diacid derivatives were better than that of 25-OCH3-PPD in water, which may provide valuable data for the research and development of new anti-tumor agents.

Sulfamic and succinic acid derivatives of 25-OH-PPD and their activities to MCF-7, A-549, HCT-116, and BGC-823 cell lines

In the search for new anti-tumor agents with higher potency than our previously identified compound 1 (25-OH-PPD, 25-hydroxyprotopanaxadiol), 12 novel sulfamic and succinic acid derivatives that could improve water solubility and contribute to good drug potency and pharmacokinetic profiles were designed and synthesized. Their in vitro anti-tumor activities in MCF-7, A-549, HCT-116, and BGC-823 cell lines and one normal cell line were tested by standard MTT assay. Results showed that compared with compound 1, compounds 2, 3, and 7 exhibited higher cytotoxic activity on A-549 and BGC-823 cell lines, together with lower toxicity in the normal cell. In particular, compound 2 exhibited the best anti-tumor activity in the in vitro assays, which may provide valuable data for the research and development of new anti-tumor agents.

Synthesis, spectral characteristics, and some properties of methylammonium sulfamate monohydrate. A new route to sulfamic acid derivatives

Redox transformations of the products of reactions of the CH3C(S)NH2-SO2-H2O system components yield methylammonium sulfamate monohydrate [CH3NH3]+[OSO2NH2]− · H2O and elemental sulfur. The synthesized compound was characterized by IR, 1H and 13C NMR, and mass spectroscopy and some of its properties were studied.

Isothiazoles. Part 13. Synthesis of Sulfamic Esters, [1,2]Thiazete S,S‐Dioxides, Benzo[e][1,2]thiazine S,S‐Dioxides or Triazoles by Reaction of Isothiazole Dioxides with Sodium Azide.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Isothiazoles. Part 13: Synthesis of sulfamic esters, [1,2]thiazete S, S-dioxides, benzo[ e][1,2]thiazine S, S-dioxides or triazoles by reaction of isothiazole dioxides with sodium azide

The reaction of NaN 3 with 5-substituted 3-diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxides is presented affording [2-cyano-1-diethylamino-2-(4-methoxyphenyl)-ethylidene]-sulfamic acid derivatives, 3-diethylamino-1,1-dioxo-4-(4-methoxyphenyl)-1,2-dihydro-[1,2]thiazete-4-carbonitrile, 3-diethylamino-7-methoxy-1,1-dioxo-1,4-dihydro-benzo[ e][1,2]thiazine-4-carbonitrile or triazole derivatives. The outcome of the reaction strongly depends on the C-5 substituent and the correct choice of the reaction conditions allows direction of the reaction towards the formation of the sulfamic esters or the [1,2]thiazete carbonitrile or the triazoles in satisfactory yield.

Carbonic Anhydrase Inhibitors: Inhibition of Isozymes I, II and IV by Sulfamide and Sulfamic Acid Derivatives

Sulfamide and sulfamic acid are the simplest compounds containing the SO2NH2 moiety, responsible for binding to the Zn(II) ion within carbonic anhydrase (CA, EC 4.2.1.1) active site, and thus acting as inhibitors of the many CA isozymes presently known. Here we describe two novel classes of CA inhibitors obtained by derivatizations of the lead molecules mentioned above. The new compounds, possessing the general formula RSO2NH-SO2X (X = OH, NH2), were obtained by reaction of sulfamide or sulfamic acid with alkyl/arylsulfonyl halides or arylsulfonyl isocyanates. A smaller series of derivatives has been obtained by reaction of aromatic aldehydes with sulfamide, leading to Schiff bases of the type ArCH = NSO2NH2. All the new compounds act as strong inhibitors of isozymes I, II and IV of carbonic anhydrase. Their mechanism of CA inhibition is also discussed based on electronic spectroscopic measurements on adducts with the Co(II)-substituted enzyme. These experiments led to the conclusion that the new inhibitors are directly coordinated (in a monodentate manner) to the metal ion within the enzyme active site, similarly to the classical inhibitors, the aromatic/heterocyclic sulfonamides.

Synthesis of β-nitramino derivatives ofgem-dinitroalkanes

A method for the synthesis of β-nitramino derivatives ofgem-dinitroalkanes by nitration of the products of condensation of sulfamic acid derivatives with the correspondinggem-dinitroalkanes was proposed.

Minalemines A-F: Sulfamic acid peptide guanidine derivatives isolated from the marine tunicate Didemnun rodriguesi

Six new guanidine compounds, named minalemines A-F 2, were isolated from the marine tunicate Didemnun rodriguesi by careful HPLC separation. Their structures were elucidated by MS, 1D- and 2D-NMR spectral analysis, and chemical degradation. These compounds incorporate one agmatine (Agma) and one homoagmatine (Hagma) terminal unit with their guanidine groups free and the primary amino groups linked through a peptidic bond to L-Leu and a very rare β- N-carboxymethyl amino acid (Ncma) bearing a saturated long chain. The saturated chains of minalemines A-C are homologs (C7, C8, and C9 respectively). Minalemines D-F are the sulfamic acid derivatives of minalemines A-C and constitute the first examples of such a functional group in a marine organism.

ChemInform Abstract: Reaction of Sulfamic Acid Derivatives with Epoxides. Part 5. Reactions of Sulfamates with Diglycidyl and Allylglycidyl Ethers and Synthesis of Corresponding Aminoethers.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Reaction of Sulfamic Acid Derivatives with Epoxides. Part 4. Hydrolysis of 3‐Chloro‐2‐hydroxypropylsulfamates.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Reaction of Sulfamic Acid Derivatives with Epoxides. Part 3. Condensation of 3‐Chloro‐2‐hydroxypropylsulfamates with Amines and Synthesis of 1,3‐Diaminopropanols‐2.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The reaction of sulfamic acid derivatives with epoxides

The reaction of sulfamic acid derivatives with epoxides

The reaction of sulfamic acid derivatives with epoxides. 4. Hydrolysis of 3-chloro-2-hydroxypropylsulfamates

Under basic hydrolysis conditions 3-chloro-2-hydroxypropylsulfamates transform into 2,3-dihydroxypropylsulfamates. Acidic hydrolysis of the latter leads to 3-alkylaminopropane-1,2-diols.

Sulfamic acid andN-alkylsulfamates in the synthesis of nitro derivatives of guanidine and aminofurazan

TheN-nitro derivatives of the products of the condensation of formaldehyde with sulfamic acid derivatives and guanidine, nitroguanidine, 3,4-diaminofurazan, and 3-amino-4-methylfurazan have been synthesized.

ChemInform Abstract: Reaction of Sulfamic Acid Derivatives with Epoxides. Part 2. Condensation of Sulfamic and N‐Alkylsulfamic Acid (I) with Glycidol ( II), Epichlorohydrin (IV) and Epoxy Ethers (VI).

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Reaction of Sulfamic Acid Derivatives with Epoxides.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.