Syntheses and immunomodulatory activity of 3-O-[2'-hydroxy-3'-N,N-disubstituted aminopropan-1'-yl]-alpha-D-glucofuranoses.
A number of 3-O-[2'-hydroxy-3'-N,N-aminopropan-1'-yl]-alpha-D-glucofuranoses were synthesised by regioselective oxirane ring opening in compound 2 with different secondary amines followed by selective deacetalisation. All the compounds were tested for their immunomodulatory potential in vitro; seven of them expressed significant immunostimulant activity.
Khan
A R
AR
Division of Medicinal Chemistry, Central Drug Research Institute, Lucknow 226001, India.
Tripathi
R P
RP
Bhaduri
A P
AP
Sahai
R
R
Puri
A
A
Tripathi
L M
LM
Srivastava
V M
VM
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D002855:Chromatography, Thin Layer; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology*; D015195:Drug Design; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D008213:Lymphocyte Activation / Q000187:drug effects; D008214:Lymphocytes / Q000166:cytology / Q000187:drug effects* / Q000276:immunology; D051379:Mice; D019265:Spectroscopy, Near-Infrared; D013154:Spleen; D013329:Structure-Activity Relationship
D000276:Adjuvants, Immunologic; D004187:Disaccharides; D005947:Glucose