10099-08-8

Upstream product

• 34239-78-6 bromomethanesulfonic acid,sodium salt 
• 74-95-3 1,1-dibromomethane 
• 18143-34-5 methanesulfonyl trimethylsilyl chloride 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 51270-38-3 N-cyclohexyl bromomethanesulfonamide 
• 22457-12-1 4-((bromomethyl)sulfonyl)morpholine 
• 698350-87-7 N-benzylbromomethanesulfonamide 
• 54114-59-9 N-phenyl-1-bromomethanesulfonamide 
• 1092495-05-0 1,3,2'-tri-N-(tert-butoxycarbonyl)-6'-N-bromomethanesulfonylneamine 
• 53412-78-5 bromomethanesulfonamide 
• 919769-36-1 N-(2-methylphenyl)-1-bromomethanesulfonamide 
• 54114-52-2 Bromo-methanesulfonic acid 2-chloro-ethyl ester 
• 51270-39-4 1-bromo-N,N-dimethylmethanesulfonamide 

Relevant academic research and scientific papers

INHIBITORS OF PURINE NUCLEOSIDE PHOSPHORYLASE - SYNTHESIS AND USE THEREOF FOR TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA AND LYMPHOMA

The present invention relates to new compounds of general formula I, their synthesis, their pharmaceutically acceptable salts, and their use in treatment of T-cell acute lymphoblastic leukemia and lymphoma.

Nickel-Catalyzed Enantioconvergent Reductive Hydroalkylation of Olefins with α-Heteroatom Phosphorus or Sulfur Alkyl Electrophiles

Substantial advances in enantioconvergent C(sp3)-C(sp3) bond formation reactions have been made in recent years through the use of transition-metal-catalyzed cross-coupling reactions of racemic secondary alkyl electrophiles with organometallic reagents. Herein, we report a general process for the asymmetric construction of alkyl-alkyl bonds adjacent to heteroatoms, namely, a nickel-catalyzed enantioconvergent reductive hydroalkylation of olefins with α-heteroatom phosphorus or sulfur alkyl electrophiles. Including the use of readily available olefins, this reaction has considerable advantages, such as mild reaction conditions, a broad substrate scope, and good functional group compatibility, making it a desirable alternative to traditional electrophile-nucleophile cross-coupling reactions.

Protocol for Stereoselective Construction of Highly Functionalized Dienyl Sulfonyl Fluoride Warheads

A pyrrolidine-mediated Knoevenagel-type reaction for highly stereoselective construction of novel α-halo-1,3-dienylsulfonyl fluorides was achieved in up to 100% Z-selectivity and high yields at room temperature from condensation of the readily available aldehydes and halomethanesulfonyl fluorides. This protocol provided a class of unique α-halo-1,3-dienylsulfonyl fluorides with wide scope and excellent functional group compatibility. The α-halo-1,3-dienylsulfonyl fluorides were used as versatile building blocks in sulfur fluoride exchange click chemistry, Suzuki reaction, and Sonogashira reaction for the assembly of highly functionalized dienyl sulfonyl fluoride derivatives to be applied as covalent warheads for the discovery of new drugs.

Next-Generation Hypoxic Cell Radiosensitizers: Nitroimidazole Alkylsulfonamides

Innovations in the field of radiotherapy such as stereotactic body radiotherapy, along with the advent of radio-immuno-oncology, herald new opportunities for classical oxygen-mimetic radiosensitizers. The role of hypoxic tumor cells in resistance to radiotherapy and in suppression of immune response continues to endorse tumor hypoxia as a bona fide, yet largely untapped, drug target. Only nimorazole is used clinically as a radiosensitizer, and there is a dearth of new radiosensitizers in development. Here we present a survey of novel nitroimidazole alkylsulfonamides and document their cytotoxicity and ability to radiosensitize anoxic tumor cells in vitro. We use a phosphate prodrug approach to increase aqueous solubility and to improve tumor drug delivery. A 2-nitroimidazole and a 5-nitroimidazole analogue demonstrated marked tumor radiosensitization in either ex vivo assays of surviving clonogens or tumor regrowth delay.

Synthesis and use of sulfonamide-, sulfoxide-, or sulfone-containing aminoglycoside-CoA bisubstrates as mechanistic probes for aminoglycoside N-6′-acetyltransferase

Aminoglycoside-coenzyme A conjugates are challenging synthetic targets because of the wealth of functional groups and high polarity of the starting materials. We previously reported a one-pot synthesis of amide-linked aminoglycoside-CoA bisubstrates. These molecules are nanomolar inhibitors of aminoglycoside N-6′-acetyltransferase Ii (AAC(6′)-Ii), an important enzyme involved in bacterial resistance to aminoglycoside antibiotics. We report here the synthesis and biological activity of five new aminoglycoside-CoA bisubstrates containing sulfonamide, sulfoxide, or sulfone groups. Interestingly, the sulfonamide-linked bisubstrate, which was expected to best mimic the tetrahedral intermediate, does not show improved inhibition when compared with amide-linked bisubstrates. On the other hand, most of the sulfone- and sulfoxide-containing bisubstrates prepared are nanomolar inhibitors of AAC(6′)-Ii.

Aminoxyl radicals from N-phenyl-1-(2-oxo-1-azacycloalkyl)- methanesulfonamides

The synthesis and reaction with two oxidation agents is described for N-phenyl-1-(2-oxo-1-azacycloalkyl)methanesulfonamides. Their oxidation was carried out using RO2? radicals and 3-chloroperbenzoic acid. In both cases, the EPR spectra of corr

Generic synthesis of β-sultams via domino alkylation of bromomethanesulfonamides

Reaction of N-substituted bromomethanesulfonamides with 2 equiv of potassium carbonate and an α-halo ketone, ester, or nitrile leads directly to 3-substituted β-sultams. The first step is intermolecular and is followed by an intramolecular alkylation. The

New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides

Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinemia dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.

A NEW SULFENE SYNTHESIS

Treatment of trimethylsilylmethanesulfonyl chloride with cesium fluoride in acetonitrile at room temperature has been found to produce sulfene which can be trapped in good yield.