Sesquiterpenoid- and steroid-amino acid conjugates demonstrate a broad array of interesting biological properties, as the different segments of the conjugate function collectively to regulate conformation, recognition, transport and solubility. The current project involved developing a facile methodology to synthesize metabolically stable facially amphiphilic conjugates by appending either amino acids (chapter 2) or cationic metal ligand-amino acid complexes (chapter 3) as hydrophilic segments on steroid progesterone and sesquiterpene amorpha-4,11-diene scaffolds. Aminosteroids and C-11 substituted steroids have attracted long lasting interest due to their diverse pharmacological properties. As the stereoselective C- 11β functionalization of a steroid imposes severe steric hindrance due to the C-18 and C-19 angular methyl groups, access to 11β-aminoprogesterone is a challenge. Chapter 2 describes stereoselective syntheses of a new family of aminosteroids: 11β-aminoprogesterone (11 -NH2-Pro) (76) and its derivatives, including its glycine 77 and L-/D- alanine- 78/79 based conjugates, by nucleophilic substitution or reductive amination.
Dr. Keyur Pandya is a seasoned technocrat with more than 15 years of hands-on experience developing sustainable innovation chemicals/processes from a dawn to commercialization. He received his PhD in Chemistry from University of Alberta, Canada and published several scientific papers. In 2017 he earned the Best & Brightest Young Professional Award.
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LAP LAMBERT Academic Publishing
Novel Amino Steroids, Amorphadiene-Amino Acids, metal complexes, surfactants, Amphiphilic Conjugates, Stereo-Selective Synthesis, 11β-steroids, Aminoprogesterone, Amorpha-4, 11-Diene, 11β-Hydroxysteroid Dehydrogenase Type 2, 11β-HSD2, antagonist, Mineralocorticoid Receptor (MR), 11β-Hydroxyprogesterone, Sesquiterpenoid, Ligand amino acid complexes, Modulators of Corticosteroid, Treating Electrolyte Disturbances, Inflammatory Disorders, Tethered Cationic Cobalt(III) based Biometallosurfactant Complexes
SCIENCE / Chemistry / General