1088411-06-6

Basic information

• Product Name: methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(npropyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(pyrimidin-5-yl)phenylthio)-α-thiolincosaminide
• Synonyms: methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(npropyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(pyrimidin-5-yl)phenylthio)-α-thiolincosaminide
• CAS NO: 1088411-06-6
• Molecular Weight: 676.899
• Mol File: 1088411-06-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(npropyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(pyrimidin-5-yl)phenylthio)-α-thiolincosaminide(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(npropyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(pyrimidin-5-yl)phenylthio)-α-thiolincosaminide(1088411-06-6)
• EPA Substance Registry System: methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(npropyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(pyrimidin-5-yl)phenylthio)-α-thiolincosaminide(1088411-06-6)

Safety Data

• Hazardous Substances Data: 1088411-06-6(Hazardous Substances Data)

Upstream product

• 14810-93-6 Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside 
• 941585-70-2 methyl (7S)-7-acetylthio-6-N-((2′S,4′R)-1′-N-(tertbutoxycarbonyl)-4′-(n-propyl)piperidine-2′-carbonyl)-7-deoxy-2,3,4-tris-O-(trimethylsilyl)-α-thiolincosaminide 
• 941585-64-4 methyl 6-N-[(2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(n-propyl)piperidine-2′-carbonyl]-2,3,4-tris-O-(trimethylsilyl)-α-thiolincosaminide 
• 941585-72-4 methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(n-propyl)piperidine-2′-carbonyl)-7-deoxy-7-mercapto-α-thiolincosaminide 
• 160377-42-4 5-(4-bromophenyl)pyrimidine 
• 941585-71-3 methyl 7-acetylthio-6-N-((2S,4R)-1-(N-tert-butoxycarbonyl)-4-propylpiperidine-2-carbonyl)-7-deoxy-7-epi-1-thio-α-lincosamide 
• 941585-69-9 methyl 6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(n-propyl)piperidine-2′-carbonyl)-7-O-methanesulfonyl-2,3,4-tris-O-(trimethylsilyl)-α-thiolincosaminide 

Downstream Products

• 1088409-22-6 methyl (7S)-6-N-((2′S,4′R)-4′-(n-propyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(pyrimidin-5-yl)phenylthio)-α-thiolincosaminide 

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.