941585-96-2

Basic information

• Product Name: methyl 6-N-((2′S)-1′-N-(2′′-nitrophenylsulfonyl)-5′-n-propyl-2′,3′,6′,7′-tetrahydro-1H-azepine-2′-carbonyl)-α-thiolincosaminide
• Synonyms: methyl 6-N-((2′S)-1′-N-(2′′-nitrophenylsulfonyl)-5′-n-propyl-2′,3′,6′,7′-tetrahydro-1H-azepine-2′-carbonyl)-α-thiolincosaminide
• CAS NO: 941585-96-2
• Molecular Weight: 603.715
• Mol File: 941585-96-2.mol

Chemical Properties

• CAS DataBase Reference: methyl 6-N-((2′S)-1′-N-(2′′-nitrophenylsulfonyl)-5′-n-propyl-2′,3′,6′,7′-tetrahydro-1H-azepine-2′-carbonyl)-α-thiolincosaminide(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-N-((2′S)-1′-N-(2′′-nitrophenylsulfonyl)-5′-n-propyl-2′,3′,6′,7′-tetrahydro-1H-azepine-2′-carbonyl)-α-thiolincosaminide(941585-96-2)
• EPA Substance Registry System: methyl 6-N-((2′S)-1′-N-(2′′-nitrophenylsulfonyl)-5′-n-propyl-2′,3′,6′,7′-tetrahydro-1H-azepine-2′-carbonyl)-α-thiolincosaminide(941585-96-2)

Safety Data

• Hazardous Substances Data: 941585-96-2(Hazardous Substances Data)

Upstream product

• 794514-83-3 methyl (S)-2-(N-(3-methylenehexyl)-N-(2-nitro-phenylsulfonyl)-amino)-pent-4-enoate 
• 794514-81-1 (S)-methyl 2-(2-nitrophenylsulfonamido)pent-4-enoate 
• 1803-71-0 3-propyl-3-buten-1-ol 
• 14810-93-6 Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside 
• 1089133-09-4 (2S)-1-(2-nitrophenylsulfonyl)-5-n-propyl-2,3,6,7-tetrahydro-1H-azepine-2-carboxylic acid 
• 794514-84-4 methyl (S,Z)-1-(2-nitrophenylsulfonyl)-5-propyl-2,3,6,7-tetrahydro-1H-azepine-2-carboxylate 

Relevant articles and documents

Synthesis and SARs of novel lincomycin derivatives Part 5: Optimization of lincomycin analogs exhibiting potent antibacterial activities by chemical modification at the 6- and 7-positions

In order to modify lincomycin at the C-6 and C-7 positions, we prepared target molecules, which have substituted pipecolinic acid at the 6-amino group and a para-substituted phenylthio group at the C-7 position, in application of palladium-catalyzed cross-coupling as a key reaction. As the result of structure-activity relationship (SAR) studies at the 6-position, analogs possessing 4′-cis-(cyclopropylmethyl)piperidine showed significantly strong antibacterial activities against Streptococcus pneumoniae and Streptococcus pyogenes with an erm gene. On the basis of SAR, we further synthesized novel analogs possessing 4′-cis-(cyclopropylmethyl)piperidine by transformation of a C-7 substituent. Consequently, novel derivatives possessing a para-heteroaromatic-phenylthio group at the C-7 position exhibited significantly strong activities against S. pneumoniae and S. pyogenes with an erm gene even when compared with those of telithromycin. Finally, in vivo efficacy of selected two derivatives was evaluated in a rat pulmonary infection model with resistant S. pneumoniae with erm + mef genes. One of them exhibited strong and constant in vivo efficacy in this model, and both compounds showed strong in vivo efficacy against resistant S. pneumoniae with a mef gene.

LINCOMYCIN DERIVATIVES AND ANTIBACTERIAL AGENTS CONTAINING THE SAME AS THE ACTIVE INGREDIENT

An objective of the present invention is to provide compounds of formula (1) or their pharmacologically acceptable salts or solvates wherein A represents aryl; R1 represents N-optionally substituted C1-6 alkyl-N-optionally substituted C1-6 alkylamino-C1-6 alkyl; R2 represents a hydrogen atom or optionally substituted C1-6 alkyl; R3 represents optionally substituted C1-6alkyl or C3-6 cycloalkyl-C1-4 alkyl; m is 1 to 3; n is 0; and p is 0 to 2. The compounds are novel lincomycin derivatives that have a potent activity against resistant Streptococcus pneumoniae, which have recently posed problems, in the treatment of infectious diseases. Further, the compounds are usable as antimicrobial agents and are useful for preventing or treating bacterial infectious diseases.

LINCOSAMIDE DERIVATIVE, AND ANTIBACTERIAL AGENT COMPRISING THE SAME AS ACTIVE INGREDIENT

An objective of the present invention is to provide compounds of formula (I) or their pharmacologically acceptable salts or solvates wherein A represents aryl while R1 represents a five- or six-membered monocyclic heterocyclic group, or A represents a four- to six-membered monocyclic heterocyclic group while R1 represents aryl or a five- or six-membered monocyclic heterocyclic group; R2 represents a hydrogen atom or C1-6 alkyl; R3 represents C1-6 alkyl or C3-6 cycloalkyl-C1-4 alkyl; R4, R5, and R6 represent a hydrogen atom; R7 represents C1-6 alkyl; and m is 1 to 3. The compounds are novel lincosamide derivatives that have a potent activity against resistant Streptococcus pneumoniae. Further, the compounds are usable as antimicrobial agents and are useful for preventing or treating bacterial infectious diseases.

LINCOMYCIN DERIVATIVE AND ANTIBACTERIAL AGENT CONTAINING THE SAME AS ACTIVE INGREDIENT

This invention provides compounds of formula (I) or its pharmacologically acceptable salt or solvate, wherein A represents aryl or a monocyclic or bicyclic heterocyclic group, R1 represents a halide, nitro, substituted C1-6 alkyl, optionally substituted amino, C1-6 alkyloxycarbonyl, optionally substituted aryl, a heterocyclic group, or heterocyclic carbonyl, R2 represents a hydrogen atom or C1-6 alkyl, R3 represents C1-6 alkyl, all of R4, R5, and R6 represent a hydrogen atom, R7 represents C1-6 alkyl, m is 1 or 2, and n is 1. The compounds are novel lincomycin derivatives having a potent activity against resistant pneumococci. The compounds can be used as an antimicrobial agent and are useful for preventing or treating bacterial infectious diseases.