Butyryl-tyrosinyl spermine, analogs thereof and methods of preparing and using same

• Main Authors: HUANG; DANWEN, NAKANISHI; KOJI, KALIVRETENOS; ARISTOTLE, GOODNOW; ROBERT, CHOI; SEOK-KI
• Format: Patent
• Language: English
• Published: 14.12.1999
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY

The present invention provides a compound having the structure: wherein R1 is a saturated or unsaturated linear or branched chain alkyl group, or a cholestanyl group; wherein R2 is a 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 4-hydroxyphenyl, 4-(arylalkyloxy)phenyl, 3,4-dihalophenyl, 4-hydroxy-3,5-dihalophenyl, 4-azidophenyl or 4-halophenyl group; wherein R3 is H, a linear or branched chain alkyl or alkenyl group, or a phenyl, 2-azidophenyl, 3-azidophenyl, 4-azidophenyl group, or an a alkenylacyl, 3-amino-3-butylpropyl, N-[N-(N-{4-azidobenzoyl}aminopropyl) aminopropyl], cis- or trans-cinnamyl, 2-amino-2-[(4'-azidophenyl)acetyl, (trifluoromethyl)aminoacetyl or D- or L-arginyl group bonded through the alpha -carbonyl moiety thereof; R4 is H, or a linear or branched chain alkyl group; wherein R5, R6 and R7 are independently the same or different and are H, a linear or branched chain alkyl group, an aryl group or an arylalkyl group; wherein n, j and t are each 0 or 1; wherein m, o, p, q, r and s are independently the same or different and are 0, 1 or 2; wherein r+s and m+o are each equal to 2; wherein, if j is 0, p+q is 2; wherein, if j is 1, then p is 1, q is 0 and R6 is H; and wherein * denotes a D or L configuration. The invention also provides a method of synthesizing the compound. Another aspect of the invention concerns a method of treating a subject afflicted by a disorder associated with binding of an etiological agent to a glutamate receptor.