- Novel acyl-dipeptide-like compounds bearing an accessory functional side chain spacer, a method for preparing the same and pharmaceutical compositions containing such products
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The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants, In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targetting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.
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- Acyl pseudodipeptides which carry a functionalised auxialiary arm
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The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants, In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targetting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.
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- Role of the hydrophobic moiety of tumor promoters. Synthesis and activity of 2-alkylated benzolactams
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The size and position of a hydrophobic moiety on a benzolactam skeleton, which reproduces the active conformation and biological activity of teleocidins, play an important role in the appearance of the activity. Compounds with alkyl groups of various sizes and shapes at the 2-position of benzolactam were synthesized. Structure-activity results indicate that a hydrophobic substituent at the C-2 position plays a critical role in the appearance of biological activities, as in the case of substitution at C-9.
- Endo, Yasuyuki,Yokoyama, Akihiro
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- α-Amino Acids as Chiral Educts for Asymmetric Products. Chirospecific Syntheses of the 5-Butyl-2-heptylpyrrolidines from Glutamic Acid
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Both enantiomers of trans-5-butyl-2-heptylpyrrolidine, an active and major component in the repellent venom of the ant Solenopsis fugax, have been synthesized with very high diastereomeric and optical purity from glutamic acid.Both enantiomers of the cis isomer also have been synthesized in an extension of our methodology to encompass the preparation of both cis and trans, optically pure, 2,5-disubstituted pyrrolidines and because of their potential entomological interest.Initially, a sulfide contraction process efficiently introduces the first side chain onto a pyroglutamate intermediate.Various strategies to elaborate the second side chain have been developed along with methods to control and establish the relative steroechemistry at C-2 and C-5 of the pyrrolidine ring with high selectivity. 2,5-Dialkyl-1-pyrrolidines, which also have been identified in the ant venom, can be prepared by these processes as well with specific absolute stereochemistry.
- Shiosaki, Kazumi,Rapoport, Henry
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p. 1229 - 1239
(2007/10/02)
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