57850-02-9

Basic information

• Product Name: methyl 1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate
• Synonyms: methyl 1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate
• CAS NO: 57850-02-9
• Molecular Weight: 265.29
• Mol File: 57850-02-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate(57850-02-9)
• EPA Substance Registry System: methyl 1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate(57850-02-9)

Safety Data

• Hazardous Substances Data: 57850-02-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 86688-94-0 1-(Phenylsulfonyl)-2-(chlorocarbonyl)pyrrole 
• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 98-09-9 benzenesulfonyl chloride 
• 16851-82-4 N-phenylsulfonylpyrrole 

Downstream Products

• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 6156-25-8 tetrathioorthocarbonic acid tetramethyl ester 
• 171897-81-7 1-(1-Benzenesulfonyl-1H-pyrrol-2-yl)-2,2,2-tris-methylsulfanyl-ethanone 

Relevant articles and documents

Discovery and Optimization of Thiazolidinyl and Pyrrolidinyl Derivatives as Inhaled PDE4 Inhibitors for Respiratory Diseases

Phosphodiesterase 4 (PDE4) is a key cAMP-metabolizing enzyme involved in the pathogenesis of inflammatory disease, and its pharmacological inhibition has been shown to exert therapeutic efficacy in chronic obstructive pulmonary disease (COPD). Herein, we describe a drug discovery program aiming at the identification of novel classes of potent PDE4 inhibitors suitable for pulmonary administration. Starting from a previous series of benzoic acid esters, we explored the chemical space in the solvent-exposed region of the enzyme catalytic binding pocket. Extensive structural modifications led to the discovery of a number of heterocycloalkyl esters as potent in vitro PDE4 inhibitors. (S?,S??)-18e and (S?,S??)-22e, in particular, exhibited optimal in vitro ADME and pharmacokinetics properties and dose-dependently counteracted acute lung eosinophilia in an experimental animal model. The optimal biological profile as well as the excellent solid-state properties suggest that both compounds have the potential to be effective topical agents for treating respiratory inflammatory diseases.

DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS

The invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to compounds that are derivatives of 1 -phenyl-2-pyridinyl alkyl alcohols, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

Regioselective Synthesis of Acylpyrroles

The regioselective synthesis of several pyrrole derivatives is described.AlCl3-catalyzed acylation reactions of 1-(phenylsulfonyl)pyrrole (1) give 3-acyl derivatives, whereas the corresponding BF3*OEt2-catalyzed reactions give 2-acyl derivatives predominantly.Mild alkaline hydrolysis gives the corresponding acyl-1H-pyrroles in excellent yields.AlCl3-catalyzed reactions of 1 with 1,1-dichloromethyl methyl ether and oxalyl chloride give 1-(phenylsulfonyl)-2-formylpyrrole (6) and 1-(phenylsulfonyl)-2-(chlorocarbonyl)pyrrole (7), respectively. 3-Pyrrolylacetic acid (10) was prepared by thallium(III) nitrate promoted rearrangement of 1-(phenylsulfonyl)-3-acetylpyrrole (2a).Trifluoroacetic anhydride catalyzed cyclization of 4-butyric acid (14) gives 1-(phenylsulfonyl)-7-oxo-4,5,6,7-tetrahydroindole (17).Attempts to cyclize 14 at the 4-position have been unsuccessful.