1089127-79-6

Basic information

• Product Name: 7(S)-7-deoxy-7-(4-(3-(dimethylamino)propyl)phenylthio)lincomycin
• Synonyms: 7(S)-7-deoxy-7-(4-(3-(dimethylamino)propyl)phenylthio)lincomycin
• CAS NO: 1089127-79-6
• Molecular Weight: 583.857
• Mol File: 1089127-79-6.mol

Chemical Properties

• CAS DataBase Reference: 7(S)-7-deoxy-7-(4-(3-(dimethylamino)propyl)phenylthio)lincomycin(CAS DataBase Reference)
• NIST Chemistry Reference: 7(S)-7-deoxy-7-(4-(3-(dimethylamino)propyl)phenylthio)lincomycin(1089127-79-6)
• EPA Substance Registry System: 7(S)-7-deoxy-7-(4-(3-(dimethylamino)propyl)phenylthio)lincomycin(1089127-79-6)

Safety Data

• Hazardous Substances Data: 1089127-79-6(Hazardous Substances Data)

Upstream product

• 23474-34-2 7(S)-7-deoxy-7-mercaptolincomycin 
• 1089131-39-4 3-(4-bromophenyl)-N,N-dimethylprop-2-yn-1-amine 
• 1089127-75-2 7(S)-7-deoxy-7-(4-(3-(dimethylamino)prop-1-yn-1-yl)phenylthio)lincomycin 

Relevant articles and documents

Synthesis and structure-activity relationships of novel lincomycin derivatives part 3: Discovery of the 4-(pyrimidin-5-yl)phenyl group in synthesis of 7(S)-thiolincomycin analogs

Novel lincomycin derivatives possessing an aryl phenyl group or a heteroaryl phenyl group at the C-7 position via sulfur atom were synthesized by Pd-catalyzed cross-coupling reactions of 7(S)-7-deoxy-7-thiolincomycin (5) with various aryl halides. This reaction is the most useful method to synthesize a variety of 7(S)-7-deoxy-7-thiolincomycin derivatives. On the basis of analysis of structure-activity relationships of these novel lincomycin derivatives, we found that (a) the location of basicity in the C-7 side chain was an important factor to enhance antibacterial activities, and (b) compounds 22, 36, 42, 43 and 44 had potent antibacterial activities against a variety of Streptococcus pneumoniae with erm gene, which cause severe respiratory infections, even compared with our C-7-modified lincomycin analogs (1-4) reported previously. Furthermore, 7(S)-configuration was found to be necessary for enhancing antibacterial activities from comparison of configurations at the 7-position of 36 (S-configuration) and 41 (R-configuration).

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.