Category: 489-17-8

Bajaj, Megha published the artcileDiscovery of Novel Pneumococcal Surface Antigen A (PsaA) Inhibitors Using a Fragment-based Drug Design Approach, Related Products of amides-buliding-blocks, the publication is ACS Chemical Biology (2015), 10(6), 1511-1520, database is CAplus and MEDLINE.

Streptococcus pneumoniae is a leading cause of life-threatening bacterial infections, especially in young children in developing countries. Pneumococcal infections can be treated with β-lactam antibiotics, but rapid emergence of multidrug-resistant strains of S. pneumoniae over the past two decades has emphasized the need to identify novel drug targets. Pneumococcal surface antigen A (PsaA) is one such target, found on the cell surface of S. pneumoniae. It functions as a high-affinity substrate-binding protein, facilitating acquisition of Mn²⁺, which has an important role in protecting S. pneumoniae from reactive oxygen species and, hence, oxidative stress. Consequently, PsaA is essential for bacterial survival and an important virulence factor, which makes it a promising target for antibiotic drug development. To design novel PsaA inhibitors, we used a combination of de novo fragment-based drug discovery and in silico virtual screening methods. We profiled a collection of low mol. weight compounds that were selected based on their structural diversity and ability to bind to apo-PsaA in a virtual docking experiment The screening resulted in two initial hits that were further optimized by structural variation to improve their potency while maintaining their ligand efficiency and favorable physicochem. properties. The optimized hits were validated using a cell-based assay and mol. dynamics simulations. We found that virtual screening substantially augmented fragment-based drug design approaches, leading to the identification of novel pneumococcal PsaA inhibitors.

ACS Chemical Biology published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C7H8FNO2S, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Pal, Manojit published the artcileSynthesis and Cyclooxygenase-2 Inhibiting Property of 1,5-Diarylpyrazoles with Substituted Benzenesulfonamide Moiety as Pharmacophore: Preparation of Sodium Salt for Injectable Formulation, Safety of 4-Fluoro-2-methylbenzenesulfonamide, the publication is Journal of Medicinal Chemistry (2003), 46(19), 3975-3984, database is CAplus and MEDLINE.

A series of 1,5-diarylpyrazoles having a substituted benzenesulfonamide moiety as pharmacophore, e.g. (I; Ar = 2 or 3-fluoro-4-sulfamoylphenyl, 3-methyl-4-sulfamoylphenyl; R = OMe, SMe) and (II; R¹ = 4-methoxyphenyl, 4-methylthiophenyl, 4-fluorophenyl; R²= propanoyl, butyryl) was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities. Through SAR and mol. modeling, it was found that fluorine substitution on the benzenesulfonamide moiety along with an electron-donating group at the 4-position of the 5-aryl ring yielded selectivity as well as potency for COX-2 inhibition in vitro. Among such compounds 3-fluoro-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl]-1-benzenesulfonamide 3 displayed interesting pharmacokinetic properties along with antiinflammatory activity in vivo. Among the sodium salts tested in vivo, 10, the propionyl analog of 3, showed excellent antiinflammatory activity and therefore represents a new lead structure for the development of injectable COX-2 specific inhibitors.

Journal of Medicinal Chemistry published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C7H8FNO2S, Safety of 4-Fluoro-2-methylbenzenesulfonamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Ma, Yao published the artcileIdentification of benzofused five-membered sultams, potent dual NOD1/NOD2 antagonists in vitro and in vivo, Related Products of amides-buliding-blocks, the publication is European Journal of Medicinal Chemistry (2020), 112575, database is CAplus and MEDLINE.

Nucleotide-binding oligomerization domain-containing proteins 1 and 2 play important roles in immune system activation. Recently, a shift has occurred due to the emerging knowledge that preventing nucleotide-binding oligomerization domains (NODs) signaling could facilitate the treatment of some cancers, which warrants the search for dual antagonists of NOD1 and NOD2. Herein, we undertook the synthesis and identification of a new class of derivatives of dual NOD1/NOD2 antagonists with novel benzofused five-membered sultams. Compound 14k(I) was finally demonstrated to be the most potent mol. that inhibits both NOD1-and NOD2-stimulated NF-κB and MAPK signaling in vitro and in vivo.

European Journal of Medicinal Chemistry published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C7H8FNO2S, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Hou, Hongcen published the artcileRhodium-catalyzed direct C-H bond alkynylation of aryl sulfonamides with bromoalkynes, Safety of 4-Fluoro-2-methylbenzenesulfonamide, the publication is Organic & Biomolecular Chemistry (2019), 17(11), 2948-2953, database is CAplus and MEDLINE.

An efficient protocol for the synthesis of ortho-(1-alkynyl)benzenesulfonamides I [R = H, 4-Me, 4-OCF₃, etc.] was developed via rhodium-catalyzed direct ortho-mono-alkynylation of aryl sulfonamides with triisopropylsilyl (TIPS)-substituted bromoalkyne. While triethylsilyl or trimethylsilyl (TES or TMS)-substituted bromoalkyne was also amenable to the alkynylation, affording six membered benzosultams II [R¹ = TMS, TES; R² = H, 6-Me, 6-Et, 6-OMe] via the alkynylation/intramol. cyclization cascade reaction. The present protocol displayed high functional group tolerance and broad substrate scope under an air atm. in good to high yields. Mechanistic studies indicated that the reaction proceeded by a turnover limiting C-H activation step and a plausible mechanism was proposed.

Organic & Biomolecular Chemistry published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C7H8FNO2S, Safety of 4-Fluoro-2-methylbenzenesulfonamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Hou, Hongcen published the artcileIridium-Catalyzed ortho-C-H Amidation of Benzenesulfonamides with Sulfonyl Azides, SDS of cas: 489-17-8, the publication is Advanced Synthesis & Catalysis (2019), 361(18), 4393-4398, database is CAplus.

An iridium-catalyzed direct C-H activation/C-N bond formation reaction of benzenesulfonamides RS(O)₂NHR¹ (R = Ph, 2-methyl-4-fluorophenyl, 3-chlorophenyl, etc.) with sulfonyl azides R²C₆H₄S(O)₂N₃ (R² = H, 4-Me, 2-Me, 4-OMe) was developed. The amidation reaction provides a protocol for the synthesis of 2-aminobenzenesulfonamides I (R³ = H, 2-Me-4-F, 3-Cl, 4-Ph, etc.) in good to excellent yields. This strategy features a wide substrate scope, tolerates a broad range of functional groups under external oxidant-free conditions and only releases mol. nitrogen as the sole byproduct. Moreover, the preliminary mechanism was investigated and the proposed reaction pathway was provided.

Advanced Synthesis & Catalysis published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C7H8FNO2S, SDS of cas: 489-17-8.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Teo, Yong-Chua published the artcileEfficient Manganese/Copper Bimetallic Catalyst for N-Arylation of Amides and Sulfonamides Under Mild Conditions in Water, Formula: C7H8FNO2S, the publication is European Journal of Organic Chemistry (2013), 2013(3), 515-524, database is CAplus.

An efficient and mild method using a bimetallic MnF₂/CuI catalyst at 60 °C in water was developed for the N-arylation of amides and sulfonamides with aryl halides. A variety of functionalized amides and sulfonamides were coupled with different substituted aryl halides to afford the corresponding N-arylated products in good to excellent yields (up to 97 %).

European Journal of Organic Chemistry published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C5H5N3S, Formula: C7H8FNO2S.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Teo, Yong-Chua published the artcileEfficient ligand-free, copper-catalyzed N-arylation of sulfonamides, HPLC of Formula: 489-17-8, the publication is Synlett (2011), 837-843, database is CAplus.

An efficient and convenient protocol has been developed for the N-arylation of sulfonamides with differently substituted aryl iodides using ligand-free copper iodide to afford the arylated products in good to excellent yields (up to 91%).

Synlett published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C25H47NO8, HPLC of Formula: 489-17-8.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Pal, Manojit published the artcileSynthesis and cyclooxygenase-2 (COX-2) inhibiting properties of 1,5-diarylpyrazoles possessing N-substitution on the sulfonamide (-SO₂NH₂) moiety, HPLC of Formula: 489-17-8, the publication is Letters in Drug Design & Discovery (2005), 2(4), 329-340, database is CAplus.

A number of novel 1,5-diarylpyrazoles possessing N-substitution on the sulfonamide (SO₂NH₂) moiety were synthesized and tested for COX-1/COX-2 inhibition in vitro. Many of these 1,1-dioxo-2,3-dihydrobenzo[d]isothiazolyl substituted 1,5-diarylpyrazoles, where the SO₂NH₂ group was a part of the fused ring, showed COX inhibitory activity. Few of them were identified as selective COX-2 inhibitors. A structure-activity relationship study within the series are discussed. Compounds prepared for this study included derivatives of 5-[3-(difluoromethyl)-5-[2-fluoro-4-(methylthio)phenyl]-1H-pyrazol-1-yl]-2,3-dihydro-1,2-benzisothiazole 1,1-dioxide and 5-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2,3-dihydro-1,2-benzisothiazole dioxide (i.e., cyclic benzenesulfonamide analogs).

Letters in Drug Design & Discovery published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C7H8FNO2S, HPLC of Formula: 489-17-8.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Pal, Manojit published the artcileSynthesis of fused sulfonamide (1,1-dioxoisothiazole)-substituted 1,5-diarylpyrazoles as cyclooxygenase inhibitors, Related Products of amides-buliding-blocks, the publication is Journal of the Indian Chemical Society (2003), 80(12), 1095-1101, database is CAplus.

First synthesis of novel 1,1-dioxo-2,3-dihydrobenzo[d]isothiazolyl substituted arylpyrazoles, e.g., I, has been accomplished via oxidative cyclization of 4-fluoro-2-Me benzenesulfonamide followed by the treatment with hydrazine and then with 1,3-dicarbonyl compounds A number of 1,5-diarylpyrazoles were synthesized in good yields and some of them were of potential biol. interest. In studies evaluating cyclooxygenase inhibiting activity, I was found to be more than 100 fold selective in COX-2 inhibition over COX-1.

Journal of the Indian Chemical Society published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C7H8FNO2S, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Xu, Liang published the artcileOxidative cyclization of N-alkyl-o-methyl-arenesulfonamides to biologically important saccharin derivatives, Application of 4-Fluoro-2-methylbenzenesulfonamide, the publication is Tetrahedron (2006), 62(33), 7902-7910, database is CAplus.

Various biol. important saccharin skeletons and their N-alkyl derivatives were efficiently prepared by Cr(VI) oxide-catalyzed H₅IO₆ oxidation of N-alkyl-o-methyl-arenesulfonamides in MeCN. N-tert-Bu saccharin skeletons were easily prepared by H₅IO₆-CrO₃ oxidation of N-tert-butyl-o-Me arenesulfonamides in the presence of acetic anhydride. The method that furnished the novel fluoro- and trifluoromethyl-substituted saccharin skeletons was characterized by two steps, a simple work-up procedure, a single purification and good overall yields from substituted toluene derivatives For example, 58 % 2-tert-butyl-6-trifluoromethyl-1,2-benzisothiazol-3-one 1,1-dioxide was obtained from 1-methyl-4-(trifluoromethyl)benzene.

Tetrahedron published new progress about 489-17-8. 489-17-8 belongs to amides-buliding-blocks, auxiliary class Fluoride,Sulfamide,Amine,Benzene, name is 4-Fluoro-2-methylbenzenesulfonamide, and the molecular formula is C17H20ClN3, Application of 4-Fluoro-2-methylbenzenesulfonamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics