Category: 1524-40-9

Hopkins, Megan D.; Ozmer, Garett L.; Witt, Ryan C.; Brandeburg, Zachary C.; Rogers, David A.; Keating, Claire E.; Petcoff, Presley L.; Sheaff, Robert J.; Lamar, Angus A. published the artcile< PhI(OAc)2 and iodine-mediated synthesis of N-alkyl sulfonamides derived from polycyclic aromatic hydrocarbon scaffolds and determination of their antibacterial and cytotoxic activities>, Computed Properties of 1524-40-9, the main research area is alkyl sulfonamide preparation antibacterial antitumor physicochem human.

The development of new approaches toward chemo- and regioselective functionalization of polycyclic aromatic hydrocarbon (PAH) scaffolds will provide opportunities for the synthesis of novel biol. active small mols. that exploit the high degree of lipophilicity imparted by the PAH unit. Herein, new synthetic method for C-X bond substitution that is speculated to operate via a N-centered radical (NCR) mechanism according to exptl. observations was reported. A series of PAH sulfonamides have been synthesized and their biol. activity has been evaluated against Gram-neg. and Gram-pos. bacterial strains (using a BacTiter-Glo assay) along with a series of mammalian cell lines (using CellTiter-Blue and CellTiter-Glo assays). The viability assays have resulted in the discovery of a number of bactericidal compounds that exhibit potency similar to other well-known antibacterials such as kanamycin and tetracycline, along with the discovery of a luciferase inhibitor. Addnl., the physicochem. and drug-likeness properties of the compounds were determined exptl. and using in silico approaches and the results are presented and discussed within.

Organic & Biomolecular Chemistry published new progress about Antibacterial agents. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Computed Properties of 1524-40-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Moukha-chafiq, Omar; Reynolds, Robert C. published the artcile< Parallel Solution-Phase Synthesis and General Biological Activity of a Uridine Antibiotic Analog Library>, Electric Literature of 1524-40-9, the main research area is uridine antibiotic analog preparation agonist antagonist activator enzyme receptor; nucleoside peptide preparation biol activity screening.

A small library of ninety four uridine antibiotic analogs was synthesized, under the Pilot Scale Library (PSL) Program of the NIH Roadmap initiative, from amine 2 and carboxylic acids 33 and 77 in solution-phase fashion. Diverse aldehyde, sulfonyl chloride, and carboxylic acid reactant sets were condensed to 2, leading after acid-mediated hydrolysis, to the targeted compounds 3-32 in good yields and high purity. Similarly, treatment of 33 with diverse amines and sulfonamides gave 34-75. The coupling of the amino terminus of D-phenylalanine Me ester to the free 5′-carboxylic acid moiety of 33 followed by sodium hydroxide treatment led to carboxylic acid analog 77. Hydrolysis of this material gave analog 78. The intermediate 77 served as the precursor for the preparation of novel dipeptidyl uridine analogs 79-99 through peptide coupling reactions to diverse amine reactants. None of the described compounds show significant anticancer or antimalarial activity. A number of samples exhibited a variety of promising inhibitory, agonist, antagonist, or activator properties with enzymes and receptors in primary screens supplied and reported through the NIH MLPCN program.

ACS Combinatorial Science published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Electric Literature of 1524-40-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Moukha-Chafiq, Omar; Reynolds, Robert C. published the artcile< Synthesis and General Biological Activity of a Small Adenosine-5'-(Carboxamide and Sulfanilamide) Library>, Safety of 3-Fluorobenzenesulfonamide, the main research area is preparation screening adenosine carboxamide sulfanilamide library; Adenosine peptide analogs; specific or general biological activities.

A small library of fifty-five adenosine peptide analogs was synthesized, under the Pilot Scale Library (PSL) Program of the NIH Roadmap initiative, from 2′,3′-O-isopropylideneadenosine-5′-carboxylic acid . The coupling of amine or sulfanilamide reactants to the free 5′-carboxylic acid moiety of , in automated solution-phase fashion, led after acid-mediated hydrolysis to target compounds in good yields and high purity. No marked anticancer or antimalarial activity was noted on preliminary cellular testing. Initial screening through the MLPCN program, however, indicates that these analogs may show diverse and interesting biol. activities.

Nucleosides, Nucleotides & Nucleic Acids published new progress about Antimalarials. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Safety of 3-Fluorobenzenesulfonamide.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Krishnamurthy, Vijay M.; Bohall, Brooks R.; Kim, Chu-Young; Moustakas, Demetri T.; Christianson, David W.; Whitesides, George M. published the artcile< Thermodynamic parameters for the association of fluorinated benzenesulfonamides with bovine carbonic anhydrase II>, COA of Formula: C6H6FNO2S, the main research area is thermodn crystal structure fluorinated benzenesulfonamide carbonic anhydrase.

This paper describes a calorimetric study of the association of a series of seven fluorinated benzenesulfonamide ligands (C6HnF5-nSO2NH2) with bovine carbonic anhydrase II (BCA). Quant. structure-activity relationships between the free energy, enthalpy, and entropy of binding and pKa and logP of the ligands allowed the evaluation of the thermodn. parameters in terms of the two independent effects of fluorination on the ligand: its electrostatic potential and its hydrophobicity. The parameters were partitioned to the three different structural interactions between the ligand and BCA: the ZnII cofactor-sulfon-amide bond (≈65% of the free energy of binding), the hydrogen bonds between the ligand and BCA (≈10%), and the contacts between the Ph ring of the ligand and BCA (≈25%). Calorimetry revealed that all of the ligands studied bind in a 1:1 stoichiometry with BCA; this result was confirmed by 19F NMR spectroscopy and X-ray crystallog. (for complexes with human carbonic anhydrase II).

Chemistry – An Asian Journal published new progress about Conformation. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, COA of Formula: C6H6FNO2S.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Basson, Ashley J.; McLaughlin, Mark G. published the artcile< Synthesis of Functionalized Isoindolinones via Calcium Catalyzed Generation and Trapping of N-Acyliminium Ions>, Computed Properties of 1524-40-9, the main research area is calcium catalyst acyliminium ion hydroxyisoindolinone nucleophilic addition; isoindolinone preparation.

Herein we report our full investigation into the calcium catalyzed generation and trapping of N-acyliminium ions from readily available 3-hydroxyisoindolinones. We have successfully employed a range of traditional nucleophiles including carbon, nitrogen, and sulfur containing reactive partners. The reaction is tolerant to a wide range of functionalities and provides high value scaffolds in good to excellent yields.

Journal of Organic Chemistry published new progress about Nucleophilic addition reaction. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Computed Properties of 1524-40-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Chen, Ming; Yang, Chao; Wang, Yanpei; Li, Dazhi; Xia, Wujiong published the artcile< UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides>, Formula: C6H6FNO2S, the main research area is phenanthrene preparation UV light induced tandem reaction arylarylsulfonyl propiolamide; photochem radical Smiles rearrangement carbon sulfur bonding Mallory reaction; gram scale reaction flow reactor phenanthrene preparation.

A novel photochem. approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.

Organic Letters published new progress about Alkynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Formula: C6H6FNO2S.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Scott, Andrew D.; Phillips, Chris; Alex, Alexander; Flocco, Maria; Bent, Andrew; Randall, Amy; O’Brien, Ronan; Damian, Luminita; Jones, Lyn H. published the artcile< Thermodynamic Optimisation in Drug Discovery: A Case Study using Carbonic Anhydrase Inhibitors>, Name: 3-Fluorobenzenesulfonamide, the main research area is benzene sulfonamide preparation carbonic anhydrase crystal structure thermodn binding.

The only method that directly measures the thermodn. of a binding event in solution is isothermal titration calorimetry (ITC). We chose human carbonic anhydrase (hCA II) as a favorable system for this investigation as there is already a wealth of both 3D structures and calorimetric data available, which has established this protein as the leading model system. The binding of BSA to hCA II is driven mainly through four H bonds from the sulfonamide, two H bonds to the Zn co-factor (which is itself coordinated by three histidine residues: His94, His96 and His119) and two H bonds to Thr199. ITC anal. was performed on seventeen benzenesulfonamide derivatives (1-17) and three benzylamide para-substituted benzene sulfonamides (18-20) by titration into hCA II. In the case described, ITC measurements, along with X-ray structural studies, indicated that one compound (2-F, 2) was binding to its target by specific (polar) interactions, as opposed to hydrophobicity (e.g. 3-F), and this ultimately led to a higher affinity lead-like compound that retained the enthalpic advantage of the smaller core compound It should be noted that in this case, the compounds chosen were small, fragment-like (< 250 Da) compounds with relatively high affinity for the target, limited flexibility, and a low number of possible interactions (i.e., typical compounds found in fragment libraries), and are therefore related to the concept of ""ligand efficient"" compounds These compounds are ideal for this type of anal. and the utilization of this approach for larger, lower affinity compounds, where the degree of complexity in the thermodn. is substantially greater, requires further investigation. ChemMedChem published new progress about Carbonic anhydrase inhibitors. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Name: 3-Fluorobenzenesulfonamide.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Song, Kwang-Seop; Kim, Min Ju; Seo, Hee Jeong; Lee, Sung-Han; Jung, Myung Eun; Kim, Soo-Un; Kim, Jeongmin; Lee, Jinhwa published the artcile< Synthesis and structure-activity relationship of novel diarylpyrazole imide analogues as CB1 cannabinoid receptor ligands>, Category: amides-buliding-blocks, the main research area is diarylpyrazole imide derivative preparation CB1 cannabinoid receptor antagonist.

A myriad of research groups have been engaged in searching for novel CB1 receptor antagonists, since SR141716A (rimonabant, I), a CB1 receptor antagonist, was discovered for an obesity treatment. In this research, extended series, based on the 1,5-diarylpyrazole template of rimonabant, was synthesized and tested for CB1 receptor binding affinity. In the present study, N-piperidinylcarboxamide group of rimonabant was replaced with the corresponding sulfonamide, imide, N-Me imide and methylenediamide, resp. The SAR studies to optimize the CB1 binding affinity led to the potent imide derivatives The in vivo efficacy test of a derivative II gave a promising result for this novel scaffold. In order to explore physicochem. properties (hydrophobic, steric and electronic) of the representative imide derivatives responsible for their CB1 receptor binding affinity, quant. structure activity relationship (QSAR) studies were performed. Hansch QSAR models, which were moderate in the explanation for SAR, were generated with hydrophobic, steric and electronic properties of substituents. Especially, the Taft Es-based parabolic model was obtained with the best correlation result (r 2 = 0.846).

Bioorganic & Medicinal Chemistry published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Category: amides-buliding-blocks.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Stanetty, Peter; Krumpak, Barbara; Emerschitz, Thomas; Mereiter, Kurt published the artcile< Synthesis of benzo[d]-1,2-thiazole-1,1-dioxide derivatives via directed lithiation of 2,2-dimethyl-N-(phenylsulfonyl)-propanamides>, COA of Formula: C6H6FNO2S, the main research area is benzothiazole dioxide preparation; dimethylphenylsulfonylpropanamide lithiation cyclization electrophilic addition.

A novel synthesis of 7-substituted benz[d]-1,2-thiazole-1,1-dioxides I (R = H, CHO, CONHCMe3, CO2H, Me, OH, X = H, F, Cl) is presented including directed lithiation of 2,2-dimethyl-N-(phenylsulfonyl)-propanamides 3-XC6H4SO2NHCOCMe3, aryne-mediated cyclization and subsequent quenching of aryllithium intermediates with various electrophiles. A proposed mechanism is rationalized by some control experiments

Tetrahedron published new progress about 1524-40-9. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, COA of Formula: C6H6FNO2S.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

D’Angelo, Noel D.; Kim, Tae-Seong; Andrews, Kristin; Booker, Shon K.; Caenepeel, Sean; Chen, Kui; Freeman, Dan; Jiang, Jian; McCarter, John D.; San Miguel, Tisha; Mullady, Erin L.; Schrag, Michael; Subramanian, Raju; Tang, Jin; Wahl, Robert C.; Wang, Ling; Whittington, Douglas A.; Wu, Tian; Xi, Ning; Xu, Yang; Yakowec, Peter; Zalameda, Leeanne P.; Zhang, Nancy; Hughes, Paul; Norman, Mark H. published the artcile< Discovery and Optimization of a Series of Benzothiazole Phosphoinositide 3-Kinase (PI3K)/Mammalian Target of Rapamycin (mTOR) Dual Inhibitors>, Electric Literature of 1524-40-9, the main research area is benzothiazole derivative preparation SAR mTOR PI3K inhibitor antitumor bioavailability.

Phosphoinositide 3-kinase α (PI3Kα) is a lipid kinase that plays a key regulatory role in several cellular processes. The mutation or amplification of this kinase in humans has been implicated in the growth of multiple tumor types. Consequently, PI3Kα has become a target of intense research for drug discovery. Our studies began with the identification of benzothiazole compound 1 from a high throughput screen. Extensive SAR studies led to the discovery of sulfonamide 45 as an early lead, based on its in vitro cellular potency. Subsequent modifications of the central pyrimidine ring dramatically improved enzyme and cellular potency and led to the identification of chloropyridine 70. Further arylsulfonamide SAR studies optimized in vitro clearance and led to the identification of 82 as a potent dual inhibitor of PI3K and mTOR. This mol. exhibited potent enzyme and cell activity, low clearance, and high oral bioavailability. In addition, compound 82 demonstrated tumor growth inhibition in U-87 MG, A549, and HCT116 tumor xenograft models.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Electric Literature of 1524-40-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics