1365478-25-6

Basic information

• Product Name: (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methylcyclohexanecarboxylic acid
• Synonyms: (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methylcyclohexanecarboxylic acid
• CAS NO: 1365478-25-6
• Molecular Weight: 740.799
• Mol File: 1365478-25-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methylcyclohexanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methylcyclohexanecarboxylic acid(1365478-25-6)
• EPA Substance Registry System: (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methylcyclohexanecarboxylic acid(1365478-25-6)

Safety Data

• Hazardous Substances Data: 1365478-25-6(Hazardous Substances Data)

Upstream product

• 1026074-51-0 C₅₁H₆₂O₁₈ 
• 1026073-56-2 {(1R,3R,4R,5S)-4-[(α-L-fucopyranosyl)oxy]-1-methoxycarbonyl-5-methylcyclohex-3-yl} 2-O-benzoyl-3-O-[(1S)-1-carboxy-2-cyclohexylethyl]-β-D-galactopyranoside 

Downstream Products

• 1365478-26-7 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-[3-(trimethylsilyl)prop-2-yn-1-yl]cyclohexanecarboxamide 
• 1365478-91-6 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-(3-{1-[3-(5-nitro-1H-indol-1-yl)propyl]piperazin-1-yl}propyl)cyclohexanecarboxamide 
• 1365478-65-4 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-({1-[(6-nitro-1H-indol-3-yl)methyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide 
• 1365478-66-5 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide 
• 1365478-30-3 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-(prop-2-yn-1-yl)cyclohexanecarboxamide 
• 1365478-27-8 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-[4-(trimethylsilyl)but-3-yn-1-yl]cyclohexanecarboxamide 
• 1365478-28-9 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-[5-(trimethylsilyl)pent-4-yn-1-yl]cyclohexanecarboxamide 
• 1365478-29-0 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-[6-(trimethylsilyl)hex-5-yn-1-yl]cyclohexanecarboxamide 
• 1365478-79-0 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-({1-[2-(6-nitro-1H-indol-3-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide 
• 1365478-81-4 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-(2-{1-[2-(6-nitro-1H-indol-3-yl)ethyl]-1H-1,2,3-triazol-4-yl}ethyl)cyclohexanecarboxamide 
• 1365478-83-6 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-(3-{1-[2-(6-nitro-1H-indol-3-yl)ethyl]-1H-1,2,3-triazol-4-yl}propyl)cyclohexanecarboxamide 
• 1365478-80-3 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-({1-[3-(6-nitro-1H-indol-3-yl)propyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide 
• 1365478-82-5 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-(2-{1-[3-(6-nitro-1H-indol-3-yl)propyl]-1H-1,2,3-triazol-4-yl}ethyl)cyclohexanecarboxamide 
• 1365478-84-7 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-(3-{1-[3-(6-nitro-1H-indol-3-yl)propyl]-1H-1,2,3-triazol-4-yl}propyl)cyclohexanecarboxamide 

Relevant articles and documents

Nanomolar e-selectin antagonists with prolonged half-lives by a fragment-based approach

Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewisx (sLex), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLex mimic were identified. A library of antagonists obtained by connecting the sLex mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with KD values ranging from 30 to 89 nM. In contrast to carbohydrate-lectin complexes with typical half-lives (t1/2) in the range of one second or even less, these fragment-based selectin antagonists show t1/2 of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.