121-02-8

Usage

Uses

Intermediate in the preparation of PDE7 inhibitors and kinase inhibitors.

InChI:InChI=1/C7H6ClNO4S/c1-5-2-3-6(9(10)11)4-7(5)14(8,12)13/h2-4H,1H3

Upstream product

• 99-55-8 2-methyl-5-nitroaniline 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 453-53-2 4-nitro-toluene-2-sulfonyl fluoride 
• 99-99-0 1-methyl-4-nitrobenzene 

Downstream Products

• 114500-27-5 4-nitro-toluene-2-sulfonic acid-[4]pyridylamide 
• 110146-30-0 2-methyl-5-nitro-benzenesulfonic acid-[(2-hydroxy-ethyl)-[1]naphthyl-amide] 
• 67320-39-2 N-(4-nitro-toluene-2-sulfonyl)-glycine 
• 860244-42-4 (2-methyl-5-nitro-phenyl)-phenyl sulfone 
• 463314-88-7 2-(2'-methyl-5'-nitrobenzenesulfonyl)-L-glutamic acid 
• 121-03-9 4-nitrotoluene-2-sulfonic acid 
• 123617-72-1 2-methyl-1-(2-methyl-5-nitro-phenylsulphonyl)-imidazole 
• 1232-21-9 1-(2-methyl-5-nitro-benzenesulfonyl)-1H-benzotriazole 
• 219814-20-7 1-(2-methyl-4-nitro-benezenesulphonyl)-2,4-dibromo-5-methyl-1H-imidazole 
• 1374832-89-9 C₁₄H₉Cl₂N₃O₃S₂ 
• 1374832-91-3 6-(N₃-(3,5-dichlorophenyl)thioureido)saccharin 
• 1374832-93-5 6-(N₃-(4-nitrophenyl)thioureido)saccharin 

Relevant academic research and scientific papers

Synthesis of some bisnitrosaccharins

Method for synthesis of previously unknown bisnitrosaccharins from 6-nitrosaccharin under the action of bishalide compounds in polar aprotic solvents in the presence of anhydrous potassium carbonate is suggested. Pleiades Publishing, Ltd., 2012.

Research on Controllable Degradation of Novel Sulfonylurea Herbicides in Acidic and Alkaline Soils

The degradation issue of sulfonylurea (SU) has become one of the biggest challenges that hamper the development and application of this class of herbicides, especially in the alkaline soils of northern China. On the basis of the previous discovery that some substituents on the fifth position of the benzene ring in Chlorsulfuron could hasten its degradation rate, apparently in acidic soil, this work on Metsulfuron-methyl showed more convincing results. Two novel compounds (I-1 and I-2) were designed and synthesized, and they still retained potent herbicidal activity in tests against both dicotyledons and monocotyledons. The half-lives of degradation (DT50) assay revealed that I-1 showed an accelerated degradation rate in acidic soil (pH 5.59). Moreover, we delighted to find that the degradation rate of I-1 was 9-10-fold faster than that of Metsulfuron-methyl and Chlorsulfuron when in alkaline soil (pH 8.46), which has more practical value. This research suggests that a modified structure that has potent herbicidal activity as well as accelerated degradation rate could be realized and this approach may provide a way to improve the residue problem of SUs in farmlands with alkaline soil.

BENZENESULFONAMIDE DERIVATIVES AS TRAP1 MODULATORS AND USES THEREOF

The present disclosure provides compounds of Formula (I): and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled compounds, and prodrugs thereof. The provided compounds may be tumor necrosis factor ("TNF") receptor associated protein 1 ("TRAP1") modulators (e.g., TRAP1 activators). The provided compounds may also rescue the activity in PTEN-induced kinase 1 ("PINK1") loss of function contexts. The provided compounds may also improve mitochondrial health, function, quality, quantity, and/or activity, and/or reduce the production of reactive oxygen species. The provided compounds may also refold or solubilize aggregated or misfolded proteins such as α-synuclein. The present disclosure also provides pharmaceutical compositions comprising the provided compounds; kits comprising the provided compounds or pharmaceutical compositions; and methods of using the provided compounds and pharmaceutical compositions (e.g., for treating a disease in a subject in need thereof).

Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur

We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.

Preparation method of 2-methyl-5-aminobenzenesulfonamide

The invention relates to a preparation method of 2-methyl-5-aminobenzenesulfonamide. The preparation method includes following steps: S1, allowing sulfonation: dissovling p-nitrotoluene and chlorosulfonic acid in an organic solvent I, stirring for reaction, and performing aftertreatment to obtain 2-methyl-5-nitrobenzene sulfonyl chloride; S2, allowing hydrogenation and addition: adding 2-methyl-5-nitrobenzene sulfonyl chloride obtained in the S1 into a hydrogenation kettle, sequentially adding a catalyst, ammonia water and an organic solvent II, allowing reaction at high temperature and high pressure, treating after reaction to obtain 2-methyl-5-aminobenzenesulfonamide which is light yellow solid. The preparation method has the advantages of short route, high product purify and easiness for industrial production.

2,4 SUBSTITUTED PYRIMIDINEDIAMINES FOR USE IN DISCOID LUPUS

no abstract published

Janus head type lone pair-π-lone pair and S?F?S interactions in retaining hexafluorobenzene

A series of eight tris-arylthiotriazines were synthesized to study the lone pair-π interaction between the triazine ring centroid of these molecules and halogenated solvents. All the eight compounds were characterized using 1H and 13C NMR spectroscopy and single crystal X-ray diffraction techniques. All these compounds show interesting structural properties in the solid state. Unprecedented Janus head type lp?π?lp and S?F?S interactions were observed between one of the tris-arylthiotriazines and hexafluorobenzene.

In vitro inhibition effect and structure-activity relationships of some saccharin derivatives on erythrocyte carbonic anhydrase i and II

In this study, in vitro inhibitory effects of some saccharin derivatives on purified carbonic anhydrase I and II were investigated using CO2 as a substrate. The results showed that all compounds inhibited the hCA I and hCA II enzyme activities. Among the compounds, 6-(p-tolylthiourenyl) saccharin (6m) was found to be the most active one for hCA I activity (IC50 = 13.67 μM) and 6-(m-methoxyphenylurenyl) saccharin (6b) was found to be the most active one for hCA II activity (IC50 = 6.54 μM). Structure-activity relationships (SARs) study showed that, generally, thiourea derivatives (6l - v) inhibited more hCA I and hCA II than urea derivatives (6a-k). All compounds (excluding 6c and 6r) have higher inhibitory activity on hCA II than on hCA I.

TREATMENT FOR VITILIGO

Compounds I and II, as well as prodrugs, hydrates, solvates, N-oxides, salts and pharmaceutical compositions containing them, are useful for treating vitiligo. In certain embodiments, the compounds are provided in topical compositions.

New saccharin derivatives as tyrosinase inhibitors

A newly series of 6-(phenylurenyl/thiourenyl) saccharin (6a-y) derivatives were synthesized and their inhibitory effects on the diphenolase activity of banana tyrosinase were evaluated. A 70-fold purification of the enzyme with 6.85% yield was achieved by using a Sepharose 4B-l-tyrosine-p-amino benzoic acid affinity column. The result showed that all the synthesized compounds inhibited the tyrosinase enzyme activity. Among the compounds synthesized, 6-(3-iodophenylthiourenyl) saccharin (6s) was found to be most active one (Ki = 3.95 μM) and the inhibition kinetics analyzed by Lineweaver-Burk double reciprocal plots revealed that compound 6s was a competitive inhibitor. Structure-activity relationships study showed that generally, most of the 6-(phenylthiourenyl) saccharin derivatives (6m-y) exhibited higher inhibitory activity than 6-(phenylurenyl) saccharin derivatives (6a-l). An electron-withdrawing group at 3-position of phenylurenyl-ring increased in activity and the halogen series at 3-position of phenylthiourenyl-ring showed a qualitative relationship for higher inhibitory activity with increasing size and polarizability. We also calculated HOMO-LUMO energy levels and dipole moments of some selected the synthesized compounds (6a, 6h, 6m and 6s) using Gaussian software.