- Photochemical C?H Amination of Ethers and Geminal Difunctionalization Reactions in One Pot
-
A mild, atom-economic, and metal-free α-C?H amination of ethers using relatively stable nonafluorobutanesulfonyl (nonaflyl, Nf) azide as the aminating reagent to give N-sulfonyl hemiaminals is reported. This enables unprecedented C(sp3) difunctionalization reactions, leading to diverse functionalized amino group containing compounds starting from simple ethers in one pot.
- Hernández-Guerra, Daniel,Hlava?ková, Anna,Pramthaisong, Chiranan,Vespoli, Ilaria,Pohl, Radek,Slanina, Tomá?,Jahn, Ullrich
-
-
Read Online
- Two New Diazonium Bis(perfluoroalkyl)arylsulfonyl Imide Zwitterionic Monomers from Perfluoro(3-oxa-4-pentene)sulfonyl Fluoride for Proton Exchange Membrane Fuel Cells
-
Two new bis(perfluoroalkyl)arylsulfonyl imide monomers, which contain the aryl diazonium moiety and intramolecular zwitterionic fragment, have been designed and prepared for the first time from perfluoro(3-oxa-4-pentene)sulfonyl fluoride. As promising monomer candidates for high-performance proton exchange membrane fuel cell electrolytes, these two monomers have furnished perfluorinated electrolytes that include the polymers from perfluorinated sulfonic acid or perfluorinated sulfonimide monomers. The synthesis strategies and NMR analysis are summarized and discussed in details.
- Mei, Hua,Ibrahim, Faisal
-
-
Read Online
- In situ formation of vilsmeier reagents mediated by oxalyl chloride: A tool for the selective synthesis of N-sulfonylformamidines
-
N-Sulfonylformamidines were produced from sulfonamides or N-acylated sulfonamides using Vilsmeier reagent obtained in situ from N,N-disubstituted formamides and oxalyl chloride. Optically active substrates did not racemize during the process. The efficient and mild cleavage of N-sulfonylformamidines can be achieved with hydrazine hydrate in ethanol. The entire procedure constitutes a simple method for protecting, and deprotecting, the sulfonamide moiety. A straightforward and efficient synthesis for N-sulfonylformamidines by employment of various Vilsmeier reagents generated in situ is described. The reactions proceed under mild reaction conditions and tolerate several sensitive functional groups. Copyright
- Gazvoda, Martin,Kocevar, Marijan,Polanc, Slovenko
-
-
Read Online
- Novel stereoselective 2,3-disubstituted quinazoline-4(3H)-one derivatives derived from glycine as a potent antimalarial lead
-
An optimization and modification of Grimmel's method leading to cyclization and incorporation of glycine linked sulphonamide at position-2 in 4-quinazolin-(3H)-ones was accomplished. Generation of a lipophilic site at position-3 of 4-quinazolinones was explored by synthesis of imines, unfortunately leading to an isomeric mixture of stereoisomers. These stereoisomeric mixtures were further converted to a single isomer utilizing the novel methodology developed by the use of an aprotic solvent system. Moreover, a mixture of (Z)/(E)-isomers and single configuration was identified and ascertained using NMR, HMQC, HMBC and NOESY spectroscopic techniques. The synthesized entities were further screened for their antimalarial efficacy pertaining two active scaffolds 8m and 8s. The active molecules were sent forth for enzyme inhibitory study against presumed receptors h-DHFR and Pf-DHFR computationally as well as in vitro, proving their potency as dihydrofolate reductase inhibitors. The oral bioavailability of these active molecules was also predicted by the study of ADME properties, indicating good bioavailability of the active entities.
- Patel, Tarosh S.,Vanparia, Satish F.,Gandhi, Sahaj A.,Patel, Urmila H.,Dixit, Ritu B.,Chudasama, Chaitanya J.,Dixit, Bharat C.
-
-
Read Online
- Condensation reactions of trifluoronitrosomethane CF3NO with sulfanilamide H2NC6H4SO2NH2 - Preparation of CF3NNC6H4SO2NH2, CF3NNC6H4SO2NNCF3, CH3C(O)N(H)C6H4SO2NNCF3
-
We report the condensations of trifluoronitrosomethane with sulfanilamide. The new compounds p-trifluoromethylazophenylsulfonamide CF3NNC6H4SO2NH2, p-trifluoromethylazosulfonyltrifluoromethylazobenzole CF3NNC6H4SO2NNCF3 and p-trifluoromethylazosulfonyl-acetanilide CH3C(O)N(H)C6H4SO2NNCF3 were characterized by elemental analysis, IR, Raman, mass, 1H, 19F and 13C NMR spectroscopy. In addition we present our approach to the preparation of p-trifluoromethylazosulfonylaniline H2NC6H4SO2NNCF3 by using protecting groups for the amino group.
- Minkwitz, Rolf,Jakob, Jens,Winter, Andreas
-
-
Read Online
- Switching on prodrugs using radiotherapy
-
Chemotherapy is a powerful tool in the armoury against cancer, but it is fraught with problems due to its global systemic toxicity. Here we report the proof of concept of a chemistry-based strategy, whereby gamma/X-ray irradiation mediates the activation of a cancer prodrug, thereby enabling simultaneous chemo-radiotherapy with radiotherapy locally activating a prodrug. In an initial demonstration, we show the activation of a fluorescent probe using this approach. Expanding on this, we show how sulfonyl azide- and phenyl azide-caged prodrugs of pazopanib and doxorubicin can be liberated using clinically relevant doses of ionizing radiation. This strategy is different to conventional chemo-radiotherapy radiation, where chemo-sensitization of the cancer takes place so that subsequent radiotherapy is more effective. This approach could enable site-directed chemotherapy, rather than systemic chemotherapy, with ‘real time’ drug decaging at the tumour site. As such, it opens up a new era in targeted and directed chemotherapy. [Figure not available: see fulltext.].
- Geng, Jin,Zhang, Yichuan,Gao, Quan,Neumann, Kevin,Dong, Hua,Porter, Hamish,Potter, Mark,Ren, Hua,Argyle, David,Bradley, Mark
-
-
Read Online
- Intensified Crystallization Processes for 1:1 Drug-Drug Cocrystals of Sulfathiazole-Theophylline, and Sulfathiazole-Sulfanilamide
-
The chemical synthesis and crystallization steps were integrated successfully for directly producing a 1:1 cocrystal of sulfathiazole-theophylline and a 1:1 cocrystal of sulfathiazole-sulfanilamide. The benefits of this process intensification were the reduction of number of steps, and the amount of energy consumption and solvent used. In addition, the overall cocrystal yields by Intensified Method I were much higher than the ones by the conventional method. Intensified Method I also gave high-purity cocrystals of ≥99%. Sulfathiazole not forming cocrystals with sulfanilamide by Intensified Method I was dissolved in the mother liquor by taking advantage of the pH-dependent solubility of sulfathiazole. Cocrystals of both sulfathiazole-theophylline and sulfathiazole-sulfanilamide systems remained stable under conditions of 40 °C and 75% relative humidity for a month.
- Yeh, Kuan Lin,Lee, Tu
-
-
Read Online
- Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets
-
Main observation and conclusion: We describe a practical and general protocol for immobilization of heterogeneous catalysts to mechanically robust porous ultra-high molecular weight polyethylene tablets using inter-facial Lifshitz-van der Waals Interactions. Diverse types of powderous catalysts, including Cu, Pd/C, Pd/Al2O3, Pt/C, and Rh/C have been immobilized successfully. The immobilized catalysts are mechanistically robust towards stirring in solutions, and they worked well in diverse synthetic reactions. The immobilized catalyst tablets are easy to handle and reused. Moreover, the metal leaching of immobilized catalysts was reduced significantly.
- Li, Tingting,Xu, Bo
-
supporting information
p. 2673 - 2678
(2021/08/03)
-
- Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture
-
The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.
- Kühl, Nikos,Leuthold, Mila M.,Behnam, Mira A. M.,Klein, Christian D.
-
p. 4567 - 4587
(2021/05/06)
-
- Inhibition of carbonic anhydrase II by sulfonamide derivatives
-
A series of sulfonamide derivatives were synthesized, and the enzyme inhibitory activity of the synthesized compounds on carbonic anhydrase II was evaluated. Through molecular docking studies, it was found that compounds 1b, 1e, 2a, 2b, 3a have a strong binding affinity to carbonic anhydrase II. The IC50 values of the four compounds 1e, 2b, 3a, and 3b were lower than that of the positive control drug acetazolamide. What’s more, the compounds had a high inhibitory activity for A549 lung cancer cell growth, among them, 1e and 3a could inhibit both carbonic anhydrase II and lung cancer cell proliferation.
- Xuan,Zhan,Zhang,Li,Zheng
-
p. 412 - 415
(2021/11/22)
-
- Inhibitory Evaluation and Molecular Docking Analysis of Benzenesulfonamides on Carbonic Anhydrase II
-
Abstract: Sulfonamides is an important class of compounds, which can be used as carbonic anhydrase inhibitors. Nine different benzenesulfonamide compounds were synthesized, and their inhibitory effects on carbonic anhydrase II were studied by esterase method and molecular docking. The results showed that compounds (IId)–(IIg) with nitro and acetamide groups on the benzene ring exhibited excellent carbonic anhydrase II inhibitory activities. Molecular docking showed that compared with the control inhibitor acetazolamide, the compounds (IId)–(IIg) docked at the carbonic anhydrase II active site and showed higher binding energy and stronger binding ability. The physical and chemical properties of all compounds were studied by Molinspiration, which showed outstanding drug-like properties and ADME properties. Cytotoxicity assay results showed that compounds (IIe) and (IIf) were almost non-toxic to HepG2 and RAW264.7 cells. In conclusion, the compounds (IIe) and (IIf) have a certain application prospect as new inhibitors of carbonic anhydrase II.
- Zhang,Wei,Liu,Wu,Xuan
-
p. 261 - 269
(2021/03/23)
-
- Green process synthesis method of sulfanilamide
-
The invention discloses a green process synthesis method of sulfanilamide, and belongs to the technical field of organic synthesis. The method comprises the following steps: carrying out amination reaction on an acetamidobenzene sulfonyl chloride dry product and ammonia gas in the presence of an anhydrous solvent; the method has the advantages that the solvent can be recycled by adjusting the reaction temperature and changing the process method, the yield is improved, the environment-friendly treatment cost is reduced, the reaction condition is mild, the operation is convenient, and the method is suitable for industrial production; p-acetamidobenzene sulfonyl chloride is prevented from being decomposed when encountering water, side reactions are reduced, and the yield is increased; during subsequent treatment and pH adjustment, a proper acid is used, so that generation of mixed high-salinity wastewater is avoided; ammonia gas is used for replacing ammonia water, so that raw materials are saved, the alkali consumption is reduced by 63%, and no various high-salinity wastewater is generated; operation is simple, automation degree is high, and waste water is little; the yield of the sulfanilamide can be increased, and the yield of the sulfanilamide is increased to 96.2%-98.3%.
- -
-
Paragraph 0019
(2021/09/04)
-
- An organocatalytic C-C bond cleavage approach: A metal-free and peroxide-free facile method for the synthesis of amide derivatives
-
A facile organocatalytic approach has been devised towards the synthesis of amide derivatives using 1,3-dicarbonyls as easily available acyl-sources under peroxide-free reaction conditions. This transformation was accomplished by the cleavage of the C-C bond in the presence of TEMPO as an organocatalyst and excludes the use of transition-metals and harsh reaction conditions. A broad range of substrates with diverse functional groups were well tolerated and delivered the products in high yields.
- Vodnala, Nagaraju,Gujjarappa, Raghuram,Polina, Saibabu,Satheesh, Vanaparthi,Kaldhi, Dhananjaya,Kabi, Arup K.,Malakar, Chandi C.
-
supporting information
p. 20940 - 20944
(2020/12/31)
-
- Design and synthesis of novel sulfonamide-derived triazoles and bioactivity exploration
-
Objective: Due to the incidence of resistance, a series of sulfonamide-derived 1,2,4-triazoles were synthesized and evaluated. Method: The novel sulfonamide-derived 1,2,4-triazoles were prepared starting from commercial acetaniline and chlorosulfonic acid by sulfonylation, aminolysis, N-alkylation and so on. The antimicrobial activity of the synthesized compounds were evaluated in vitro by two-fold serial dilution technique. Results: In vitro antimicrobial evaluation found that 2-chlorobenzyl sulfonamide 1,2,4-triazole 7c exhibited excellent antibacterial activities against MRSA, B. subtilis, B. typhi and E. coli with MIC values of 0.02?0.16 μmol/mL, which were comparable or even better than Chloromycin. The preliminary mechanism suggested that compound 7c could effectively bind with DNA, and also it could bind with human microsomal heme through hydrogen bonds in molecular docking. Computational chemical studies were performed on compound 7c to understand the structural features that are essential for activity. Additionally, compound 7c could generate a small amount of reactive oxygen species (ROS). Conclusion: Compound 7c could serve as a potential clinical antimicrobial candidate.
- He, Shi-Chao,Sun, Qing,Zhang, Hai-Juan,Zhang, Hui-Zhen,Zhou, Cheng-He
-
p. 104 - 118
(2020/02/04)
-
- Coolade. A Low-Foaming Surfactant for Organic Synthesis in Water
-
Several types of reduction reactions in organic synthesis are performed under aqueous micellar-catalysis conditions (in water at ambient temperature), which produce a significant volume of foam owing to the combination of the surfactant and the presence of gas evolution. The newly engineered surfactant “Coolade” minimizes this important technical issue owing to its low-foaming properties. Coolade is the latest in a series of designer surfactants specifically tailored to enable organic synthesis in water. This study reports the synthesis of this new surfactant along with its applications to gas-involving reactions.
- Lee, Nicholas R.,Cortes-Clerget, Margery,Wood, Alex B.,Lippincott, Daniel J.,Pang, Haobo,Moghadam, Farbod A.,Gallou, Fabrice,Lipshutz, Bruce H.
-
p. 3159 - 3165
(2019/04/26)
-
- Easy-handling and low-leaching heterogeneous palladium and platinum catalysts via coating with a silicone elastomer
-
We have developed a practical protocol for coating of commercial Pd/Al2O3 and Pt/Al2O3 catalysts in micro-powders with a silicone elastomer. Compared to original catalysts, the treated catalysts are easier to weight and transfer, and they are easier to recover by simple filtration. More importantly, the metal leaching of treated catalysts was significantly reduced. The treated catalysts worked very well in diverse hydrogenation reactions.
- Zhou, Mi,Li, Tingting,Xu, Bo
-
supporting information
p. 948 - 952
(2019/03/08)
-
- A Co2B Mediated NaBH4 Reduction Protocol Applicable to a Selection of Functional Groups in Organic Synthesis
-
A high-yielding and high-rate reduction method that operates with alkenes, alkynes, azides, nitriles, and nitroarenes was developed and optimized. The method makes use of sodium borohydride reduction of CoSO4 under release of hydrogen along with the formation of Co2B as a nanoparticle material. The produced Co2B activates the various functional groups for hydride reduction. The protocol was proven to operate with an assortment of functional groups to provide good to excellent yields. Furthermore, the reduction method was successfully adapted, implemented, and developed for a continuous flow approach using the multi-jet oscillating disk (MJOD) flow reactor platform at atmospheric pressure.
- Lundevall, Frida Johanne,Elumalai, Vijayaragavan,Drageset, Audun,Totland, Christian,Bj?rsvik, Hans-René
-
supporting information
p. 3416 - 3425
(2018/07/29)
-
- THIAZOLIDINONE COMPOUNDS AND USE THEREOF
-
A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.
- -
-
Paragraph 0054; 0446-0447; 0466-0467
(2017/09/21)
-
- Synthetic method of p-aminobenzenesulfonamide
-
The invention relates to a synthetic method of p-aminobenzenesulfonamide, which is characterized by successively includes the following steps: (a) adding chlorosulfonic acid into a reaction kettle, controlling the temperature to be 40-50 DEG C, adding acetanilide, increasing the temperature to 55-60 DEG C and performing a reaction for 1-2 h to obtain a first mixture; (b) adding dichloroethane, increasing the temperature to 65-75 DEG C, dropwisely adding a catalyst and SOCl2, and continuously performing the reaction for 1-3 h; (c) controlling the temperature in the reaction kettle to be 15-20 DEG C, dropwisely adding the mixed liquid obtained in the step (b) into ammonia water being 22-25% in mass concentration, stirring the liquid for 0.5-1 h, increasing the temperature to 40-42 DEG C and continuously performing the reaction with stirring for 1-2 h, and filtering the liquid to obtain a crude product of the p-aminobenzenesulfonamide; and (d) adding the crude product in a hydrolysis kettle, adding a NaOH solution being 20-30% in mass concentration, heating the mixture to 90-95 DEG C to perform reflux hydrolysis for 2-3 h, adding an acid solution to regulate the pH value to 6.5-6.7, performing centrifugation, and drying a filter residue to obtain the p-aminobenzenesulfonamide. In the method, the addition quantities of the reactants are accurately controlled so that the use amount of the chlorosulfonic acid is reduced. The method is reduced in cost and is increased in yield and purity of the product.
- -
-
-
- Synthesis and in vitro antimicrobial activity of some newer quinazolinone-sulfonamide linked hybrid heterocyclic entities derived from glycine
-
A novel series of 4-(amino or acetamido)-N-{[3-(substituted aryl)-4-oxo-3,4-dihydroquinazolin-2-yl]-methyl}benzenesulfonamide derivatives (1-19) were designed to assimilate 4-quinazolone and sulfonamide moieties in a single molecular framework. To derive entitled hybrid entities with structural diversity, an efficient multi-step synthetic approach initiated from glycine was developed, which involves milder conditions for emphasizing steps viz., reaction in aqueous-media, phosphazo-method of condensation, base mediated selective ester-cleavage, along with key-step, rapid and improved Grimmel's hetero-cyclization method. The structure of the synthesized compounds was confirmed by physico-chemical characteristics and spectroscopic investigations. All these compounds were screened for their in vitro antimicrobial activity. The minimum inhibitory concentrations of the synthesized compounds against various bacteria (S. aureus, B. cereus, E. coli, K. pneumonia, P. aeruginosa) and fungus (A. niger, C. albicans) was measured by broth microdilution assay. Further, results on the preliminary biological activity indicated that most of the screened compounds have displayed varied degree of inhibitory actions.
- Vanparia, Satish F.,Patel, Tarosh S.,Dixit, Ritu B.,Dixit, Bharat C.
-
p. 5184 - 5196
(2013/12/04)
-
- Synthesis of novel aliphatic N-sulfonylamidino thymine derivatives by Cu(I)-catalyzed three-component coupling reaction
-
A series of new aliphatic N-sulfonylamidino thymine derivatives containing nucleobase, N-sulfonyl and amidine pharmacophores in the structure were synthesized by Cu(I)-catalyzed three-component coupling of 1-propargyl thymine, benzenesulfonyl azides and a
- Krstulovic, Luka,Ismaili, Hamit,Bajic, Miroslav,Visnjevac, Aleksandar,Glavas-Obrovac, Ljubica,Zinic, Biserka
-
p. 525 - 534
(2013/06/05)
-
- A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-Narylacetamides catalyzed by SOCl2
-
Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides. Springer Science+Business Media B.V. 2011.
- Wang, Gong-Bao,Wang, Lin-Fa,Li, Chao-Zhang,Sun, Jing,Zhou, Guang-Ming,Yang, Da-Cheng
-
experimental part
p. 77 - 89
(2012/05/20)
-
- A practical and expeditious method for the preparation of the potential anticancer agent 5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b′: 7,8-b″:10,11-b?]tetraindole (CTet)
-
A new synthetic method to obtain the potential anticancer agent 5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b′:7, 8-b′′:10,11-b′′′]tetraindole (CTet), starting from 1H-indole-3-carboxaldehyde and sulfamide, is described. Although a mixture of CTet and cyclic indole trimer (CTr) is formed, higher CTet/CTr ratio (4:6) and CTet yield (15%) make our protocol more favorable than those reported in the literature. A discussion on the possible reaction mechanism is reported.
- Lucarini, Simone,Antonietti, Francesca,Tontini, Andrea,Mestichelli, Paola,Magnani, Mauro,Duranti, Andrea
-
experimental part
p. 2812 - 2814
(2011/06/19)
-
- Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities
-
A series of novel sulfanilamide-derived 1,2,3-triazole compounds were synthesized in excellent yields via 1,3-dipolar cycloaddition and confirmed by MS, IR and NMR spectra as well as elemental analyses. All the compounds were screened in vitro for their antibacterial and antifungal activities. Preliminary results indicated that some target compounds exhibited promising antibacterial potency. Especially, 4-amino-N-((1-dodecyl-1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide, N-((1-(2,4-dichlorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl)-4- aminobenzenesulfonamide and 4-amino-N-((1-(2,4-difluorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide were found to be the most potent compounds against all the tested strains except for Candida albicans (ATCC76615) and Candida mycoderma.
- Wang, Xian-Long,Wan, Kun,Zhou, Cheng-He
-
experimental part
p. 4631 - 4639
(2010/10/19)
-
- Generation of broad specificity antibodies for sulfonamide antibiotics and development of an enzyme-linked immunosorbent assay (ELISA) for the analysis of milk samples
-
Immunoreagents appropriately produced to detect a wide range of sulfonamide antibiotic congeners have been used to develop a highly sensitive enzyme4inked immunosorbent assay (ELISA). The selectivity has been achieved by combining antibodies raised against 5-[6-(4-aminobenzenesulfo-nylamino)pyridin-3-yl]-2- methylpentanoic acid (SA1), covalently coupled to horseshoe crab hemocyanin (HCH), and 5-[4-(amino)phenylsulfonamide]-5-oxopentanoic acid (SA2), coupled to ovalbumin (OVA), on an indirect ELISA format. The immunizing hapten has been designed to address selectivity against the common aminobenzenesulfonylamino moieties, using theoretical calculations and molecular modeling tools. Hapten SA1 has been synthesized in four steps from methyl 5-(4-amino-3-pyridinyl)-2- methyl-4-pentenoate through a Heck reaction, under Jeffery conditions, to avoid introduction of additional epitopes in the linker. The microplate immunoassay developed is able to reach the necessary detectability for the determination of the sulfonamide antibiotics most frequently used in the veterinary field, in compliance with the EC Regulation 2377/90. As an example, the IC50 and LOD values accomplished for sulfapyridine are 2.86 ± 0.24 and 0.13 ± 0.03 μg L-1, respectively. Studies performed with different types of milk samples demonstrate that direct and accurate measurements can be performed in this type of matrix without any previous sample cleanup method.
- Adrian, Javier,Font, Hector,Diserens,Sanchez-Baeza, Francisco,Marco, M.-Pilar
-
experimental part
p. 385 - 394
(2010/05/19)
-
- THIOPHENE AND THIAZOLE SUBSTITUTED TRIFLUOROETHANONE DERIVATIVES AS HISTONE DEACETYLASE (HDAC) INHIBITORS
-
The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt or stereoisomer thereof. The compounds of the present invention are inhibitors of histone deacetylase (HDAC) and are useful for treating cellular proliferative diseases, including cancer. Further, the compounds of the present invention are useful for treating neurodegenerative diseases, schizophrenia and stroke among other diseases.
- -
-
Page/Page column 73
(2008/06/13)
-
- Novel tricycloimidazoline derivatives method for production and use thereof as medicaments
-
The invention relates to compounds of general formula (1) in which R1=H, F or OCH3 and may occupy the 2, 3, 4 or 5 position on the aromatic carbocycle, R2=H or CH3, R3=H, CH3, OH or OCH3, R4=H and R3 and R4 together can be a carbonyl group (C=0), the addition salts and optionally the hydrates of additional salts with pharmaceutically-acceptable mineral or organic acids and the isomers and tautomers thereof.
- -
-
Page/Page column 4-5
(2010/02/11)
-
- Novel N-dealkylation of N-alkyl sulfonamides and N,N-dialkyl sulfonamides with periodic acid catalyzed by chromium(III) acetate hydroxide
-
Chromium(III) acetate hydroxide has been found to be an efficient catalyst for N-dealkylation of N-alkyl sulfonamides and N,N-dialkyl sulfonamides to furnish sulfonamides in good to excellent yields with periodic acid in acetonitrile at room temperature.
- Xu, Liang,Zhang, Suhong,Trudell, Mark L.
-
p. 1901 - 1904
(2007/10/03)
-
- Carbonic Anhydrase Inhibitors. Inhibition of Mitochondrial Isozyme V with Aromatic and Heterocyclic Sulfonamides
-
The first inhibition study of the mitochondrial isozyme carbonic anhydrase (CA) V (of murine origin) with a series of aromatic and heterocyclic sulfonamides is reported. Inhibition data of the cytosolic isozymes CA I and CA II and the membrane-bound isozyme CA IV with these inhibitors are also provided for comparison. Several low nanomolar CA V inhibitors were detected (K I values in the range of 4-15 nM), most of them belonging to the acylated sulfanilamide, ureido-benzenesulfonamide, 1,3,4-thiadiazole-2-sulfonamide, and aminobenzolamide type of compounds. The clinically used inhibitors acetazolamide, methazolamide, ethoxzolamide, dorzolamide, brinzolamide, and topiramate on the other hand were less effective CA V inhibitors, showing inhibition constants in the range of 47-63 nM. Some of the investigated sulfonamides, such as the ureido-benzenesulfonamides and the acylated sulfanilamides showed higher affinity for CA V than for the other isozymes, CA II included, which is a remarkable result, since most compounds investigated up to now inhibited the cytosolic isozyme CA II better. These results prompt us to hypothesize that the selective inhibition of CA V, or the dual inhibition of CA II and CA V, may lead to the development of novel pharmacological applications for such sulfonamides, for example in the treatment or prevention of obesity, by inhibiting CA-mediated lipogenetic processes.
- Vullo, Daniela,Franchi, Marco,Gallori, Enzo,Antel, Jochen,Scozzafava, Andrea,Supuran, Claudiu T.
-
p. 1272 - 1279
(2007/10/03)
-
- Chemoselective conversion of azides to t-butyl carbamates and amines
-
Azides were converted to the corresponding carbamates using a system of 20 mol% of decaborane (B10H14) and 20 weight% of 10% Pd/C in methanol in the presence of di-tert-butyl dicarbonate at rt in high yields and to the corresponding amines using a system of 10 mol% of decaborane and 20 weight% of 10% Pd/C in methanol in the absence of di-tert-butyl dicarbonate at rt in high yields.
- Jung, Yeon Joo,Chang, Yu Mi,Lee, Ji Hee,Yoon, Cheol Min
-
p. 8735 - 8739
(2007/10/03)
-
- Process for preparing 3-hydroxymethyl-4-(aryl or heterocyclic)-cyclopentanones
-
Processes are disclosed for preparing 3-hydroxymethylcyclopentanone compounds, which are useful as intermediates in the preparation of HIV chemokine CCR-5 receptor antagonists. A process is described in which the compounds are prepared by opening the cyclopropyl ring of a (1-alkoxycarbonyl-2-oxo)-trans-bicyclo[3.1.0]hexane compound by addition of a nucleophile to the cyclopropyl ring, and then decarboxylating the resulting 2-alkoxycarbonyl-3-(Nu-methyl)-cyclopentanone (Nu=the added nucleophilic group) via base solvolysis. Also described is a process for preparing the bicyclo[3.1.0]hexane precursors by the catalyzed cyclopropanation of a suitable alpha-diazo-beta-ketoester. The preparation of the alpha-diazo-beta-ketoesters and precursors thereto are also disclosed.
- -
-
-
- N-cyclopentyl modulators of chemokine receptor activity
-
The present invention is directed to compounds of the formula I: (wherein R1, R3, R4, R5, R6, R7, R8, X, n, x and y are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.
- -
-
-
- 4-Sulfonamidoanilide tertiary carbinols: A novel series of potassium channel openers
-
Sulfonamides are viable replacements for the phenylsulfonyl and benzoyl moieties initially described for the anilide tertiary carbinol series of K(ATP) potassium channel openers. The SAR of this new series and the synthetic chemistry employed to generate its members are described.
- Empfield,Mayhugh,Ohnmacht,Frank,Grant,Li
-
p. 775 - 778
(2007/10/03)
-
- Effects of medium and substituents on dissociation of 4,4′-disubstituted bis(benzenesulfon)imides
-
Ten 4,4′-disubstituted bis(arenesulfon)imides of the general formula XC6H4SO2NHSO2C6H 4X have been synthesized and their structures confirmed by their 1H NMR spectra. Elemental analyses are presented for the compounds not yet described. The dissociation constants of these model substances have been measured potentiometrically in pyridine, dimethylformamide, methanol, ethanol, propylene carbonate, acetone, acetonitrile, 1,2-dichloroethane and tetramethylene sulfone. The pKHA values obtained have been correlated with three sets of the Hammett substituent constants and the results have been used to discuss the solvent and substituent effects on the dissociation of the compounds studied. Sulfonimides with electron-acceptor substituents behave as rather strong acids in some solvents (pyridine, dimethylformamide, methanol and ethanol), whereas normal substituent dependences are found in other solvents. The experimental data have also been interpreted with the help of the statistical methods based on latent variables. From the calculations it follows that only the first principal component, which correlates well with the substituent constant sets adopted, is statistically significant in describing the substituent effect on the acid-base process studied.
- Ludwig, Miroslav,Stverka, Pavel
-
p. 1205 - 1214
(2007/10/03)
-
- Intramolecular Cycloadditions of Mesionic Carbonyl Ylides with Alkynes. Synthesis of 5,6-Dihydro-4H-cyclopenta- and 4,5,6,7-Tetrahydrobenzofuran Derivatives
-
Intramolecular cycloaddition reactions of acetylenic isomuenchnones, formed in situ by rhodium acetate catalyzed decomposition of N-(diazoacetyl)-N-methylalkynamide derivatives 16a-c, 18c, and 18d have been studied.The intermediate cycloadducts fragmentate spontaneously under the reaction conditions (110 deg C) to afford the annulated furans 19a-c, 20c, and 20d. - Keywords: Carbonyl ylides; Furans; Intramolecular cycloadditions; Isomuenchnones
- Maier, Martin E.,Schoeffling, Baerbel
-
p. 1081 - 1088
(2007/10/02)
-
- Footprint Catalysis. II. Molecular Recognition of Footprint Catalytic Sites
-
In order to investigate the molecular recognition capability of "footprint" catalytic sites, the affinities of nine "footprint" catalysts for eleven competitive inhibitors, closely related to template molecules, were estimated through the competitive inhibition constants, Ki .An examination of the affinity revealed that the recognition by "footprint" catalytic sites was so highly specific that it could recognize not only the whole, but also the partial, stuctures of the bound molecules.
- Morihara, Kensaku,Nishihata, Emiko,Kojima, Mari,Miyake, Sayoko
-
p. 3999 - 4004
(2007/10/02)
-
- Spectrophotometric and Titrimetric Determination of Carboxylic Acid Anhydrides
-
Two redox methods are described for the determination of carboxylic acid anhydrides involving reaction with either an excess of 4-aminophenol or a measured but excessive amount of sulfanilamide and photometric titration of N-acyl-4-aminophenol with 2-iodylbenzoate by measuring the absorbance of orange-red product at 444 nm or the residual amount of sulfanilamide is determined by titration with chloramine-T in the presence of acidified potassium bromide using methyl red as visual indicator.Mixtures of certain anhydrides have also been analyzed by the 2-iodylbenzoate method.The methods are rapid, precise, and accurate.No correlation is needed if carboxylic and mineral acids are also present.Carboxylic acid chlorides also react quantitatively.
- Verma, Krishna K.,Tyagi, Pramila
-
p. 2157 - 2160
(2007/10/02)
-
- The metabolism of four sulphonamides in cows
-
The metabolism of sulphanilamide, sulphadimidine (4,6 dimethyl 2 sulphanilamido pyrimidine), sulphamethoxazole (5 methyl 3 sulphanilamidoisoxazole) and sulphadoxine (5,6 dimethoxy 4 sulphanilamidopyrimidine) given by intravenous injection has been examined in cows. The sulphonamides were present mainly as unchanged drugs in blood samples collected 2 hr after administration. The sulphonamides were excreted in the milk partly as unchanged drugs and partly as conjugated metabolites whereas only small amounts were excreted as the N4 acetyl derivatives. The unchanged drug and the N4 acetyl derivative were the major constituents in urine samples after administration of sulphanilamide, sulphamethoxazole and sulphadoxine. Besides the unchanged drug, the N4 acetyl derivative and the conjugated metabolites, three further metabolites of sulphadimidine were isolated from urine samples and identified. They were 5 hydroxy 4,6 dimethyl 2 sulphanilamidopyrimidine, 4 hydroxymethyl 6 methyl 2 sulphanilamido pyrimidine and sulphaguanidine.
- Nielsen
-
p. 1039 - 1045
(2007/10/04)
-
