cas 3144-09-0, Methanesulfonamide | Articles data

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Boyer,Ellzey
p. 127
(1958)
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The coordination chemistry of sulfonyl-substituted thioureas towards the d8 metal centres platinum(II), palladium(II), nickel(II) and gold(III)
Reactions of the complexes cis-[PtCl2(PPh3)2], [PtCl2(dppp)] (dppp = Ph2P(CH2)3PPh2), [MCl2(dppe)] (dppe = Ph2P(CH2)2PPh2, M = Ni, Pd), [PdCl2(bipy)] (bipy = 2,2′-bipyridine) and [AuCl2(bp)] (bp = cyclometallated 2-benzylpyridine) with p-TolSO2NHC(S)NHPh and Et3N in refluxing methanol gave a series of new thiourea complexes containing the ligand bound as a dianion through the S and the NPh groups. The related thioureas RSO2NHC(S)NHPh (R = Me, Et) and p-TolSO2NHC(S)NHCH2CH=CH2 were also reacted with cis-[PtCl2(PPh3)2] to form the corresponding complexes [Pt{RSO2NC(S)NPh}(PPh3)2] and [Pt{TolSO2NC(S)NCH2CH=CH2}(PPh3)2] respectively. X-ray structure determinations were carried out on the thiourea MeSO2NHC(S)NHPh and its platinum complex [Pt{MeSO2NC(S)NPh}(PPh3)2], as well as [Pt{TolSO2NC(S)NPh}(PPh3)2]. Both complexes form the distal isomer with a remote NSO2R group, and no evidence was observed for isomerisation of these platinum complexes in solution. The palladium complexes [Pd{TolSO2NC(S)NPh}L2] [L2 = Ph2PCH2CH2PPh2 (dppe), or 2,2′-bipyridine (bipy)] undergo decomposition in solution to form the sulfide-bridged aggregates [Pd3S2(L2)3]2+, identified by ESI MS and 31P NMR.
Henderson, William,Risi, Matthew C.,Saunders, Graham C.
(2021/07/13)

Development of succinimide-based inhibitors for the mitochondrial rhomboid protease PARL
While the biochemistry of rhomboid proteases has been extensively studied since their discovery two decades ago, efforts to define the physiological roles of these enzymes are ongoing and would benefit from chemical probes that can be used to manipulate the functions of these proteins in their native settings. Here, we describe the use of activity-based protein profiling (ABPP) technology to conduct a targeted screen for small-molecule inhibitors of the mitochondrial rhomboid protease PARL, which plays a critical role in regulating mitophagy and cell death. We synthesized a series of succinimide-containing sulfonyl esters and sulfonamides and discovered that these compounds serve as inhibitors of PARL with the most potent sulfonamides having submicromolar affinity for the enzyme. A counterscreen against the bacterial rhomboid protease GlpG demonstrates that several of these compounds display selectivity for PARL over GlpG by as much as two orders of magnitude. Both the sulfonyl ester and sulfonamide scaffolds exhibit reversible binding and are able to engage PARL in mammalian cells. Collectively, our findings provide encouraging precedent for the development of PARL-selective inhibitors and establish N-[(arylsulfonyl)oxy]succinimides and N-arylsulfonylsuccinimides as new molecular scaffolds for inhibiting members of the rhomboid protease family.
Andrews, Charlotte L.,Cardozo, Joaquin M.,Chow, Alyssa S.,Crainic, Jennifer A.,Parsons, William H.,Rutland, Nicholas T.,Sheehan, Brendan K.
supporting information

(2021/08/04)

Method for preparing methanesulfonamide by water method
The invention discloses a method for preparing methanesulfonamide by a water method, comprising the following steps of: by using triethylamine as a catalyst, letting methanesulfonyl chloride react with ammonia water to generate a mixed solution of ammonium chloride and methanesulfonamide; and carrying out triethylamine separation, deamination and desalination on the mixed solution to obtain the methanesulfonamide. The method adopts a water method for preparation, and no organic solvent is involved in the whole preparation process; the defects of high toxicity, high price, high risk and high cost of an organic solvent are overcome; the catalyst triethylamine is added, so that the defect of low reaction selectivity of ammonia water is overcome, and the yield of the process method is greatlyimproved; in conclusion, the method has the characteristics of safe process, environment-friendly process, high raw material selectivity, high yield and the like.
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Paragraph 0022-0033

(2020/12/10)

An optimised series of substituted N-phenylpyrrolamides as DNA gyrase B inhibitors
ATP competitive inhibitors of DNA gyrase and topoisomerase IV have great therapeutic potential, but none of the described synthetic compounds has so far reached the market. To optimise the activities and physicochemical properties of our previously reported N-phenylpyrrolamide inhibitors, we have synthesized an improved, chemically variegated selection of compounds and evaluated them against DNA gyrase and topoisomerase IV enzymes, and against selected Gram-positive and Gram-negative bacteria. The most potent compound displayed IC50 values of 6.9 nM against Escherichia coli DNA gyrase and 960 nM against Staphylococcus aureus topoisomerase IV. Several compounds displayed minimum inhibitory concentrations (MICs) against Gram-positive strains in the 1–50 μM range, one of which inhibited the growth of Enterococcus faecalis, Enterococcus faecium, S. aureus and Streptococcus pyogenes with MIC values of 1.56 μM, 1.56 μM, 0.78 μM and 0.72 μM, respectively. This compound has been investigated further on methicillin-resistant S. aureus (MRSA) and on ciprofloxacin non-susceptible and extremely drug resistant strain of S. aureus (MRSA VISA). It exhibited the MIC value of 2.5 μM on both strains, and MIC value of 32 μM against MRSA in the presence of inactivated human blood serum. Further studies are needed to confirm its mode of action.
Tiz, Davide Benedetto,Skok, ?iga,Durcik, Martina,Toma?i?, Tihomir,Ma?i?, Lucija Peterlin,Ila?, Janez,Zega, Anamarija,Draskovits, Gábor,Révész, Tamás,Nyerges, ákos,Pál, Csaba,Cruz, Cristina D.,Tammela, P?ivi,?igon, Du?an,Kikelj, Danijel,Zidar, Nace
p. 269 - 290
(2019/02/20)

Stoichiometric Nitroxyl Photorelease Using the (6-Hydroxy-2-naphthalenyl)methyl Phototrigger
The design and synthesis of a photoactivatable HNO donor incorporating the (6-hydroxynaphthalen-2-yl)methyl (6,2-HNM) photocage coupled to the trifluoromethanesulfonamidoxy analogue of the well-established HNO generator Piloty's acid is described. The photoactive HNO donor stoichiometrically generates HNO (～98%) at neutral pH conditions, and evidence for concerted C-O and N-S bond cleavage was obtained. The methanesulfonamidoxy analogue primarily undergoes undesired N-O bond cleavage.
Zhou, Yang,Cink, Ruth B.,Seed, Alexander J.,Simpson, M. Cather,Sampson, Paul,Brasch, Nicola E.
supporting information
p. 1054 - 1057
(2019/05/16)

Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs
Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.
Shao, Zhuzhou,Liu, Wei,Tao, Huimin,Liu, Fang,Zeng, Ruxin,Champagne, Pier Alexandre,Cao, Yang,Houk,Liang, Yong
supporting information
p. 14089 - 14092
(2019/01/03)

Design, synthesis and pharmacological evaluation of new acyl sulfonamides as potent and selective Bcl-2 inhibitors
The antiapoptotic protein Bcl-2, overexpressed in many tumor cells, is an attractive target for potential small molecule anticancer drug discovery. Herein, we report a different structural modification approach on ABT-263 by merging the piperazinyl-phenyl fragment into a bicyclic framework leading to a series of novel analogues, among which tetrahydroisoquinoline 13 was nearly equally potent against Bcl-2 as ABT-263. Further SAR in the P4-interaction pocket affored the difluoroazetidine substituted analogue 55, which retained good Bcl-2 activity with improved Bcl-2/Bcl-xL selectivity.
Liu, Xiaohua,Zhang, Yu,Huang, Wenjing,Tan, Wenfu,Zhang, Ao
p. 443 - 454
(2018/01/05)

Development of Photoactivatable Nitroxyl (HNO) Donors Incorporating the (3-Hydroxy-2-naphthalenyl)methyl Phototrigger
A new family of photoactivatable HNO donors of general structure RSO2NHO-PT [where PT represents the (3-hydroxy-2-naphthalenyl)methyl (3,2-HMN) phototrigger] has been developed, which rapidly releases HNO. Photogeneration of HNO was demonstrated using the vitamin B12 derivative aquacobalamin as a trapping agent. The amount of sulfonate RSO2– produced was essentially the same as the amount of HNO released upon photolysis, providing a convenient method to indirectly quantify HNO release. Two competing pathways were also observed; a pathway involving O–N bond cleavage leading to release of a sulfonamide, and a pathway resulting in release of the parent Nhydroxysulfonamide RSO2NHOH (for HNO donors with Me- and Ph-containing leaving groups only). Up to approximately 70 % of the HNO-generating pathway was observed with the CF3-containing leaving group, with HNO generation favored for small percentages of aqueous buffer in the acetonitrile/pH 7.00 phosphate buffer solvent mixture. Characterization of the photoproducts obtained from steady-state irradiation by NMR spectroscopy showed that the desired HNO-generating pathway was less favored for HNO donors with Me- and Ph-containing leaving groups compared to the CF3-containing leaving group, suggesting that the excellent CF3-containing leaving group promotes HNO generation.
Zhou, Yang,Cink, Ruth B.,Fejedelem, Zachary A.,Cather Simpson,Seed, Alexander J.,Sampson, Paul,Brasch, Nicola E.
p. 1745 - 1755
(2018/04/17)

Highly chemoselective reduction of azides to amines by Fe(0) nanoparticles in water at room temperature
A highly chemoselective reduction of aryl, heteroaryl, acyl and sulfonyl azides to the corresponding amines has been achieved by Fe(0) nanoparticles in water at room temperature in the absence of external hydride source. Several readily reducible functionalities including alkene, alkyne, S-S linkage, OTBDMS remain unaffected during reduction.
Panja, Subir,kundu, Debasish,Ahammed, Sabir,Ranu, Brindaban C.
supporting information
p. 3457 - 3460
(2017/08/10)

Silver(I)-Catalyzed Deprenylation of Allylsulfonamide Derivatives
The silver(I)-catalyzed deprenylation of sulfonamide bearing prenyl functional groups on the nitrogen atom has been developed. In this reaction, the prenyl moiety was selectively eliminated without allyl or benzyl cleavage on the nitrogen atom. In addition, geranyl was also applicable for this elimination reaction. Furthermore, sulfonamide possessing two prenyl groups underwent a double deprenylation to form the corresponding deprenylated sulfonamide. Thus, a novel reactivity between the silver cation and double bond was observed.
Inagaki, Fuyuhiko,Hira, Shisen,Mukai, Chisato
p. 2143 - 2146
(2017/09/26)

Preparing method for methyl sulfamide
The invention discloses a preparing method for methyl sulfamide. Methylsufonyl chloride is used as a raw material, and the preparing method includes the following steps that 1, raw materials are mixed; 2, reaction is carried out; 3, heating and filtering are carried out; 4, the steps 2 and 3 are repeated, and reaction is stopped when introducing amount of ammonia gas is equal to discharging amount in the step 2; 5, concentrating and drying are carried out. The preparing method for methyl sulfamide is simple and easy to implement, ammonia gas and methylsufonyl chloride are subjected to an ammoniation reaction, on one hand, raw material cost is reduced, and the price of the finished methyl sulfamide product is substantially reduced; on the other hand, the reaction process is stable, safe and high in operability; the obtained product is high in purity and large in yield, and enterprise benefits can be substantially increased.
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Paragraph 0013

(2016/12/22)

Carbazole-containing sulfonamides and sulfamides: Discovery of cryptochrome modulators as antidiabetic agents
A series of novel carbazole-containing sulfonamides and sulfamides were synthesized. A structure-activity relationship study of these compounds led to the identification of potent cryptochrome modulators. Based on the results of efficacy studies in diet-induced obese (DIO) mice, and the desired pharmacokinetic parameters, compound 41 was selected for further profiling.
Humphries, Paul S.,Bersot, Ross,Kincaid, John,Mabery, Eric,McCluskie, Kerryn,Park, Timothy,Renner, Travis,Riegler, Erin,Steinfeld, Tod,Turtle, Eric D.,Wei, Zhi-Liang,Willis, Erik
p. 757 - 760
(2016/05/24)

Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature
A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is
Yang, Kai,Ke, Miaolin,Lin, Yuanguang,Song, Qiuling
supporting information
p. 1395 - 1399
(2015/03/18)

The development of a new class of inhibitors for betaine-homocysteine S-methyltransferase
Betaine-homocysteine S-methyltransferase (BHMT) is an important zinc-dependent methyltransferase that uses betaine as the methyl donor for the remethylation of homocysteine to form methionine. In the liver, BHMT performs to half of the homocysteine remethylation. In this study, we systematically investigated the tolerance of the enzyme for modifications at the "homocysteine" part of the previously reported potent inhibitor (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid (1). In the new compounds, which are S-alkylated homocysteine derivatives, we replaced the carboxylic group in the "homocysteine" part of inhibitor 1 with different isosteric moieties (tetrazole and oxadiazolone); we suppressed the carboxylic negative charge by amidations; we enhanced acidity by replacing the carboxylate with phosphonic or phosphinic acids; and we introduced pyrrolidine steric constraints. Some of these compounds display high affinity toward human BHMT and may be useful for further pharmacological studies of this enzyme. Although none of the new compounds were more potent inhibitors than the reference inhibitor 1, this study helped to completely defi ne the structural requirements of the active site of BHMT and revealed the remarkable selectivity of the enzyme for homocysteine.
Pi?ha, Jan,Vaňek, Václav,Budě??sińsky, Milo?,Mlad?ková, Jana,Garrow, Timothy A.,Ji??acek, Ji??i
p. 256 - 275
(2013/10/01)

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
p. 5381 - 5386
(2013/09/02)

Hydrogenation of azides over copper nanoparticle surface using ammonium formate in water
Aryl azides undergo clean reduction by copper nanoparticles and ammonium formate in water. The surface hydrogen on copper nanoparticles is considered to be the active reducing species. A variety of functionalized aryl azides and aryl sulfonyl azides are reduced by this procedure to the corresponding amines with excellent chemoselectivity in high yields.
Ahammed, Sabir,Saha, Amit,Ranu, Brindaban C.
experimental part
p. 7235 - 7239
(2011/10/18)

HETEROCYCLIC ANTIVIRAL COMPOUNDS
Compounds having the formula I wherein wherein R1, R2 and R3 are as defined herein are Hepatitis C virus NS5b polymerase inhibitors with improved bioavailability. Also disclosed are compositions and methods for treating an HCV infection and inhibiting HCV replication.
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(2011/06/19)

ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters
Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity.
Tamaddon, Fatemeh,Sabeti, Mohammad Reza,Jafari, Abbas Ali,Tirgir, Farhang,Keshavarz, Elham
experimental part
p. 41 - 45
(2012/01/12)

Heterocyclic antiviral compounds
Compounds having the formula I wherein R1, R2, R3, R4a, R4b, R4c, R5, R6, R9 and n are as defined herein are Hepatitis C virus NS5b polymerase inhibitors. Also disclosed are compositions and methods for treating an HCV infection and inhibiting HCV replication.
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(2010/02/17)

Multiple decomposition pathways for the oxenium ion precursor O-(4-(4′-methylphenyl)phenyl)-N-methanesulfonylhydroxylamine
(Chemical Equation Presented) Although O-arylhydroxylamine derivatives have been claimed to be sources of oxeniumions in a large number of studies, it is not clear that the products of these reactions are due to oxenium ions. Previously, we had shown thro
Wang, Yue-Ting,Novak, Michael
body text
p. 7697 - 7706
(2010/03/01)

Photochemistry of N-acetyl-, N-trifluoroacetyl-, N- mesyl-, and N-tosyldibenzothiophene sulfilimines
(Chemical Equation Presented) Time-resolved infrared (TRIR) spectroscopy, product studies, and computational methods were applied to the photolysis of sulfilimines derived from dibenzothiophene that were expected to release acetylnitrene, trifluoroacetylnitrene, mesylnitrene, and tosylnitrene. All three methods provided results for acetylnitrene consistent with literature precedent and analogous experiments with the benzoylnitrene precursor, i.e., that the ground-state multiplicity is singlet. In contrast, product studies clearly indicate triplet reactivity for trifluoroacetylnitrene, though TRIR experiments were more ambiguous. Product studies suggest that these sulfilimines are superior sources for sulfonylnitrenes, which have triplet grounds states, to the corresponding azides, and computational studies shed light on the electronic structure of the nitrenes.
Desikan, Vasumathi,Liu, Yonglin,Toscano, John P.,Jenks, William S.
p. 4398 - 4414
(2008/09/21)

Simple and efficient reduction of azides to amines using recyclable polymer-supported formate and zinc
Polymer supported formate in conjunction with commercial zinc dust provides a mild and efficient procedure for the reduction of organic azides to corresponding amines. A variety of alkyl and aryl azides were selectively reduced in high yield and purity at room temperature.
Prakasha, Kothathi C.,Sindhumol, Methatta,Ramesha Baba,Channe Gowda
p. 284 - 286
(2008/02/08)

PIPERIDINYL-AND PIPERAZINYL-SULFONYLMETHYL HYDROXAMIC ACIDS AND THEIR USE AS PROTEASE INHIBITORS
This invention is directed generally to proteinase (also known as "protease”) inhibitors, and, more particularly, to piperidinyl-and piperazinyl-sulfonylmethyl hydroxamic acids that, inter alia, inhibit matrix metalloproteinase (also known as "matrix metalloprotease” or "MMP”) activity and/or aggrecanase activity. Such hydroxamic acids generally correspond in structure to the following formula: (wherein A1, A2, Y, E1, E2, E 3, and Rx are as defined in this specification), and further include salts of such compounds. This invention also is directed to compositions of such hydroxamic acids, intermediates for the syntheses of such hydroxamic acids, methods for making such hydroxamic acids, and methods for treating conditions (particularly pathological conditions) associated with MMP activity and/or aggrecanase activity. "
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(2008/06/13)

Versatile Reagent for Reduction of Azides to Amines
Triphenylphosphine (TPP) in refluxing methanol effectively reduces a variety of azides 1a-k to amines 2a-k in very good yields.
Pal, Bikash,Jaisankar, Parasuraman,Giri, Venkatachalam S.
p. 1317 - 1323
(2007/10/03)

Aromatic sulfone hydroxamic acid metalloprotease inhibitor
A treatment process is disclosed that comprises administering an effective amount of an aromatic sulfone hydroxamic acid that exhibits excellent inhibitory activity of one or more matrix metalloprotease (MMP) enzymes, such as MMP-2, MMP-9 and MMP-13, while exhibiting substantially less inhibition at least of MMP-1 to a host having a condition associated with pathological matrix metalloprotease activity. Also disclosed are metalloprotease inhibitor compounds having those selective activities, processes for manufacture of such compounds and pharmaceutical compositions using an inhibitor. A contemplated compound corresponds in structure to formula B, below,
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(2008/06/13)

Inhibitors of the ICE/ced-3 family of cysteine proteases
This invention is directed to novel oxamyl dipeptide ICE/ced-3 family inhibitor compounds having the following structure: wherein A, B, R, R1, R1′ p and q are as defined herein. The invention is also directed to pharmaceutical compositions containing one or more of these compounds, as well as to the use of such compositions in the treatment of patients suffering inflammatory, autoimmnune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.
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(2008/06/13)

Preparation and use of ortho-sulfonamido aryl hydroxamic acids as matrix metalloproteinase inhibitors
Ortho-sulfonamido aryl hydroxamic acids are provided which are useful, inter alia, for the inhibition of matrix metalloproteinases and the treatment of conditions associated with overexpression of MMPs.
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(2008/06/13)

Sulfamato hydroxamic acid metalloprotease inhibitor
A sulfamato hydroxamic acid compound that, inter alia, inhibits matrix metalloprotease (mmp) activity is disclosed as are a process for preparing the same, intermediate compounds useful in those syntheses, and a treatment process that comprises administering a contemplated sulfamato hydroxamic acid compound in a MMP enzyme-inhibiting effective amount to a host having a condition associated with pathological matrix metalloprotease activity.
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(2008/06/13)

ACETYLENIC ORTHO-SULFONAMIDO AND PHOSPHINIC ACID AMIDO BICYCLIC HETEROARYL HYDROXAMIC ACIDS AS TACE INHIBITORS
Compounds of the formula are provided wherein P and Q are provided that when P is Q is and vice versa; which are useful in disease conditions mediated by TNF- alpha , such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.
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(2008/06/13)

Acetylenic sulfonamide thiol tace inhibitors
The compounds of formula B: which are useful in disease conditions mediated by TNF-α, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss
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(2008/06/13)

Heteroaryl acetylenic sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors
Compounds of the formula: are useful in treating disease conditions mediated by TNF-α such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.
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(2008/06/13)

HETEROSUBSTITUTED PYRIDINE DERIVATIVES AS PDE 4 INHIBITORS
The invention encompasses the novel compound of Formula I useful in the treatment of diseases, including asthma, by raising the level of cyclic adenosine-3',5'-monophosphate (cAMP) through the inhibition of phosphodiesterase IV (PDE 4)
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(2008/06/13)

Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors
Hydroxamic acids having the formula are useful in treating disease conditions mediated by TNF-α, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.
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(2008/06/13)

Acetylenic α-amino acid-based sulfonamide hydroxamic acid tace inhibitors
Compounds of the formula: are useful in treating disease conditions mediated by TNF-α, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.
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(2008/06/13)

THE PREPARATION AND USE OF ORTHO-SULFONAMIDO ARYL HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE AND TACE INHIBITORS
The present invention relates to the discovery of novel, low molecular weight, non-peptide inhibitors of matrix metalloproteinases (e.g. gelatinases, stromelysins and collagenases) and TNF- alpha converting enzyme (TACE, tumor necrosis factor- alpha converting enzyme) which are useful for the treatment of diseases in which these enzymes are implicated such as arthritis, tumor growth and metastasis, angiogenesis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, proteinuria, aneurysmal aortic disease, degenerative cartilage loss following traumatic joint injury, demyelinating diseases of the nervous system, graft rejection, cachexia, anorexia, inflammation, fever, insulin resistance, septic shock, congestive heart failure, inflammatory disease of the central nervous system, inflammatory bowel disease, HIV infection, age related macular degeneration, diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, ocular inflammation, keratoconus, Sjogren's syndrome, myopia, ocular tumors, ocular angiogenesis/neovascularization. The TACE and MMP inhibiting ortho-sulfonamido aryl hydroxamic acids of the present invention are represented by formula (I) where the hydroxamic acid moiety and the sulfonamido moiety are bonded to adjacent carbons on group A where: A is phenyl or naphthyl, optionally substituted by R, R, R and R; Z is aryl, heteroaryl, or heteroaryl fused to a phenyl, where aryl is phenyl or naphthyl optionally substituted by R, R, R and R; heteroaryl is a 5-6 membered heteroaromatic ring having from 1 to 3 heteroatoms independently selected from N, O and S, and optionally substituted by R, R, R and R; and when heteroaryl is fused to phenyl, either or both of the rings can be optionally substituted by R, R, R and R; and R, R, R, R, R, R, R, R and R are described in the specification, and the pharmaceutically acceptable salts thereof and the optical isomers and diastereomers thereof.
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(2008/06/13)

Oxidatively sonochemical dealkylation of various N-alkylsulfonamides to free sulfonamides and aldehydes
Various N-alkylsulfonamides were easily dealkylated to give the corresponding free sulfonamides in moderate to good yields in the presence of (diacetoxyiodo)benzene and iodine under ultrasonic irradiation. Application of this methodology to various N-prot
Katohgi, Masashi,Togo, Hideo
p. 7481 - 7486
(2007/10/03)

Prodrugs of benzenesulfonamide-containing COX-2 inhibitors
Prodrugs of COX-2 inhibitors are described as being useful in treating inflammation and inflammation-related disorders.
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(2008/06/13)

SPIRO-SUBSTITUTED AZACYCLES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
The present invention is directed to spiro-substituted azacycles of the Formula 1: STR1 (wherein R 1, l, m, Q, W, X, Y, and Z 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-1, CCR-2, CCR-2A, CCR-2B, CCR-3, CCR-4, CCR-5, CXCR-3, and/or CXCR-4.
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(2008/06/13)

EXCITATORY AMINOACID RECEPTOR MODULATORS
Compounds of the formula STR1 in which R 1 and R 2 are as defined in the specification, and non-toxic metabolically labile ester and amides thereof are useful as modulators of metabotropic glutamate receptor function.
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(2008/06/13)

PREPARATION AND USE OF ORTHO-SULFONAMIDO ARYL HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE AND TACE INHIBITORS
The present invention relates to the discovery of novel, low molecular weight, non-peptide inhibitors of matrix metalloproteinases (e. g. gelatinases, stromelysins and collagenases) and TNF-α converting enzyme (TACE, tumor necrosis factor-α converting enzyme) which are useful for the treatment of diseases in which these enzymes are implicated such as arthritis, tumor growth and metastasis, angiogenesis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, proteinuria, aneurysmal aortic disease, degenerative cartilage loss following traumatic joint injury, demyelinating diseases of the nervous system, graft rejection, cachexia, anorexia, inflammation, fever, insulin resistance, septic shock, congestive heart failure, inflammatory disease of the central nervous system, inflammatory bowel disease, HIV infection, age related macular degeneration, diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, ocular inflammation, keratoconus, Sjogren's syndrome, myopia, ocular tumors, ocular angiogenesis/neovascularization. The TACE and MMP inhibiting ortho-sulfonamido aryl hydroxamic acids of the present invention are represented by the formula STR1 where the hydroxamic acid moiety and the sulfonamido moiety are bonded to adjacent carbons on group A.
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(2008/06/13)

The rhodium(II)-catalyzed aziridination of olefins with {[(4- nitrophenyl)sulfonyl]imino}phenyl-λ3-iodane
The aziridination of olefins with {(4- nitrophenylsulfonyl)imino}phenyl-λ3-iodane, NsN=IPh (1c), in the presence of [Rh2(OAc)4] proceeds in yields of up to 85% when the olefin is used in large excess. Under optimized conditions, styrene (4a) is aziridinated with 1 equiv. of NsN=IPh (1c) in 64% yield with 2 mol% of catalyst. The aziridines derived from electron-rich olefins undergo ring-opening under the conditions of the aziridination and afford rearrangement products or pyrrolidines. The aziridination is sterospecific with 1,2-dialkyl- and 1,2-arylalkyl- disubstituted olefins, but nonstereospecific with stilbene. The ρ-value for aziridination of substituted styrenes iS -0.61. No ring-opened products are observed upon aziridination of vinylcyclopropanes. In the presence of chiral Rh(II) catalysts, the aziridination is enantioselective, affording an ee of 73% with cis-β-methylstyrene (4k) and Pirrungs [Rh2{(R)-(-)-bnp}4] catalyst. The experimental results are consistent with a one-step mechanism for transfer of the nitrenoid moiety from the catalyst to the olefin.
Müller, Paul,Baud, Corine,Jacquier, Yvan
p. 738 - 750
(2007/10/03)

Preparation of sulfonamides from sodium sulfonates: Ph3P·Br2 and Ph3P·Cl2 as a mild halogenating reagent for sulfonyl bromides and sulfonyl chlorides
Arene- and alkanesulfonamides were prepared by treatment of the corresponding sodium sulfonates with triphenylphosphine dibromide or dichloride followed by amines in the presence of triethylamine via sulfonyl halides. Reactions of sodium aminosulfonates gave cyclized products. Amidation of p-toluenesulfonic acid with triphenylphosphine dichloride was also examined to give N-benzyl-p-toluenesulfonamide. Methyl p- toluenesulfonate was obtained by esterification of sodium p-toluenesulfonate via p-toluenesulfonyl chloride.
Kataoka, Tadashi,Iwama, Tetsuo,Setta, Tomofumi,Takagi, Atsuko
p. 423 - 426
(2007/10/03)

SULFONYLUREIDOPYRAZOLE DERIVATIVES
A sulfonylureidopyrazole derivative of formula (1) or (2) is disclosed. The derivative has an inhibitory activity on endothelin converting enzyme, and is useful for treating or preventing various cardiac failures, tracheal constrictions, nervous disorders, parasecretion, vascular disorders, various ulcers and the like.
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(2008/06/13)

An efficient and convenient synthesis of formamidines
A set of new reagents, aryl sulfonyl chlorides, were used as coupling agents in the syntheses of formamidines from primary amines and N,N-dimethyl formamide in excellent yields.
Han, Ying,Cai, Lisheng
p. 5423 - 5426
(2007/10/03)

Lyophilized thioxanthenone antitumor agents
Disclosed are reconstituted lyophilized formulations for the treatment of mammalian tumors comprising a thioxanthenone antitumor agent in combination with mannitol or sucrose as a stabilizer in a lactate buffer.
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(2008/06/13)

Die elektrochemische fluorierung von alkansulfonamiden und alkandisulfonamiden
Alkane sulphonylamides and disulphonylamides are stable in anhydrous (HF)x and undergo quantitative fission of S-N bonds during electrochemical fluorination. Besides NF3, the corresponding perfluoroalkane sulphonyl fluorides and disulphonyl fluorides are formed.
Satori,Juenger
p. 71 - 75
(2007/10/03)

Reaction of Azides with Tetrathiomolybdate: Reduction and Imine Formation
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Ramesha, A. R.,Bhat, Shridhar,Chandrasekaran, Srinivasan
p. 7682 - 7683
(2007/10/03)

Process to prepare alkansulphonamides
A process to prepare alkansulphonamides of formula RSO2 NR1 R2 --wherein R is an alkyl group containing from 1 to 15 carbon atoms, or an alkyl group containing from 1 to 15 carbon atoms substituted by one or more chlorine or bromine atoms, and R1 and R2 are equal or different and may be hydrogen or an alkyl group containing from 1 to 15 carbon atoms--provides to treat an alkansulphonylhalide of formula RSO2 X--wherein X is chlorine, bromine or iodine--with a suitable quantity of a compound of formula NHR1 R2, using as solvent for said treatment an aliphatic nitrile.
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(2008/06/13)

Spirocycles
Compounds of the general formula: STR1 or a pharmaceutically acceptable salt, hydrate or crystal form enantiomer, diastereomer or mixtures thereof are Class III antiarrhythmic agents.
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(2008/06/13)

A Novel One-Pot Conversion of Methyl Sulfones to Sulfonamides
A one-pot synthesis of sulfonamides from methyl sulfones has been developed.Treatment of methyl sulfones with base and trialkylboranes gave the corresponding rearranged sulfinic acid salts which were converted to sulfonamides during oxidative-amination workup.
Huang, Horng-Chih,Reinhard, Emily J.,Reitz, David B.
p. 7201 - 7204
(2007/10/02)