NDLI: Solid-phase synthesis of model libraries of 3 α17β-dihydroxy-16α-(aminoethyl-N-substituted)-5α-androstanes for the development of steroidal therapeutic agents

Content Provider	Springer Nature Link
Author	Maltais, René Mercier, Caroline Labrie, Fernand Poirier, Donald
Copyright Year	2005
Abstract	The solid-phase synthesis of 16α-derivatives of 5α-androstane-3α,17β-diol with one, two or three levels of molecular diversity was accomplished using the diethylsilyloxy linker. Libraries with one level of diversity (10 members) and two levels of diversity (40 members) were synthesized in a parallel fashion in good yields and acceptable HPLC purities for the majority of library members. Compounds with three levels of diversity (15 pools) were realized in a split and pool fashion to allow further deconvolution by the positional scanning method. The screening of the generated model libraries revealed interesting preliminary structure–activity relationships related to their antiproliferative activities on androgen-sensitive Shionogi cells. In the case of the two-level library, the presence of a hydrophobic amino acid at R$_{1}$ (isoleucine (Ile) or phenylalanine (Phe)) and a six-membered ring (aromatic or not) at R$_{2}$ seems an important requirement for activity. In the three-level library, the amino acid residues isoleucine and phenylalanine clearly provided a better antiproliferative activity than glycine (Gly) and proline (Pro). These model libraries will serve as basis for the generation of larger libraries of peptidosteroids toward the development of therapeutic agents.
Starting Page	67
Ending Page	79
Page Count	13
File Format	PDF
ISSN	13811991
Journal	Molecular Diversity
Volume Number	9
Issue Number	1-3
e-ISSN	1573501X
Language	English
Publisher	Kluwer Academic Publishers
Publisher Date	2005-01-01
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	androstane chemical synthesis peptide solid-phase synthesis steroid Analytical Chemistry Organic Chemistry Polymer Sciences Pharmacy
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Medicine Drug Discovery Molecular Biology Physical and Theoretical Chemistry Information Systems Catalysis Inorganic Chemistry

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