92772-95-7

Upstream product

• 188918-50-5 (1S,3R)-3-[(tert-butoxycarbonyl)amino]-2,2-dimethylcyclobutane-1-carboxylic acid 
• 308287-84-5 Methyl (1S,3R)-(+)-3-acetamido-2,2-dimethylcyclobutanecarboxylate 
• 136780-45-5 methyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylate 
• 22571-78-4 (+)-cis-pinononoic acid 
• 188918-44-7 tert-butyl [(1R,3S)-3-acetyl-2,2-dimethylcyclobutyl]carbamate 
• 865799-11-7 (1R,3S)-3-acetamido-2,2-dimethylcyclobutane-carboxylic acid 
• 1017279-76-3 (1R,3S)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutan-1-carboxylic acid 
• 865799-14-0 (1S,3S)-methyl (3-acetamido-2,2-dimethylcyclobutyl)acetate 
• 865799-07-1 (-)-(1'S,3'S)-2-(3'-acetamido-2',2'-dimethylcyclobutyl)acetic acid 
• 64396-97-0 (+)-cis-pinonic acid 
• 865799-08-2 (1S,3S)-N-[3-(2,2-diphenyl-2-hydroxyethyl)-2,2-dimethylcyclobutyl]acetamide 
• 865799-10-6 (1S,3S)-N-[3-(2,2-diphenylethenyl)-2,2-dimethylcyclobutyl]acetamide 

Relevant academic research and scientific papers

Replacement of Thr32 and Gln34 in the C -terminal neuropeptide y fragment 25-36 by cis -cyclobutane and cis -cyclopentane β-amino acids shifts selectivity toward the Y4 receptor

Neuropeptide Y (NPY) and pancreatic polypeptide (PP) control central and peripheral processes by activating the G protein coupled receptors Y xR (x = 1, 2, 4, 5). We present analogs of the C-terminal fragments 25-36 and 32-36 of NPY and PP containing (1R,2S)-cyclobutane (βCbu) or (1R,2S)-cyclopentane (βCpe) β-amino acids, which display exclusively Y4R affinity. In particular, [βCpe34]-NPY-(25-36) is a Y4R selective partial agonist (EC50 41 ± 6 nM, Emax 71%) that binds Y4R with a Ki of 10 ± 2 nM and a selectivity >100-fold relative to Y1R and Y2R and >50-fold relative to Y5R. Comparably, [Y 32, βCpe34]-NPY(PP)-(32-36) selectively binds and activates Y4R (EC50 94 ± 21 nM, Emax 73%). The NMR structure of [βCpe34]-NPY-(25-36) in dodecylphosphatidylcholine micelles shows a short helix at residues 27-32, while the C-terminal segment R33βCpe34R35Y 36 is extended. The biological properties of the βCbu- or βCpe-containing NPY and PP C-terminal fragments encourage the future application of these β-amino acids in the synthesis of selective Y 4R ligands.

NOVEL BETULINIC ACID DERIVATIVES AS HIV INHIBITORS

(I)The invention relates to novel novel betulinic acid derivatives and related compounds, and pharmaceutical compositions useful for therapeutic treatment of viral diseases and particularly HIV mediated diseases.

Synthesis of enantiopure cyclobutane amino acids and amino alcohols

(-)-(1R,3S)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid and (+)-(1R,3S)-3-amino-2,2-dimethylcyclobutylmethanol, which can be used to prepare enantiopure oligopeptides and cyclobutane-based carbocyclic nucleosides, were synthesized from (+)-(1R)-α-pinen

Stereoselective synthesis of chiral precursors to cyclobutane carbocyclic nucleosides and oligopeptides

Versatile and highly efficient synthetic routes leading to optically active cyclobutanones, γ-amino acids and δ-amino alcohols are described. These compounds are relevant synthetic precursors to enantiopure cyclobutane carbocyclic nucleosides and oligopeptides. (-)-(S)-Verbenone is the chiral starting material used and the key synthetic steps involve concerted rearrangements in acidic medium.

Chiral 1,3-cyclobutane amino acids: Syntheses and extended conformations

Optically active samples of the N-protected 1,3-cyclobutane amino acids 1 and 2 were prepared from α-pinene. The synthesis of 1 is enantiodivergent insofar as both optical antipodes of the product can be prepared from the same α-pinene enantiomer. Single crystal X-ray diffraction studies of derivatives of 1 reveal these compounds can have extended conformations.