256384-34-6

Upstream product

• 18942-49-9 Boc-D-Phe-OH 
• 129095-62-1 (R)-tert-butyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate 
• 70-23-5 ethyl Bromopyruvate 
• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 

Downstream Products

• 1315334-25-8 (R)-tert-butyl 1-(4-carbamoylthiazol-2-yl)-2-phenylethylcarbamate 
• 1315334-26-9 (R)-tert-butyl 1-(4-cyanothiazol-2-yl)-2-phenylethylcarbamate 
• 1315334-27-0 (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid 
• 1453167-98-0 EtO-Thiazole-D-Phe-NH₂ 
• 1414375-91-9 EtO-Thiazole-D-Phe-Val-NHBoc 
• 1414375-75-9 San B 8 
• 1453167-97-9 C₄₈H₅₅N₉O₈S₂ 
• 1453168-03-0 C₄₀H₄₉N₉O₆S₂ 
• 1453168-04-1 C₆₁H₈₄N₁₂O₁₃S₃ 
• 1453168-00-7 C₃₃H₄₂N₄O₇S 
• 1453168-01-8 C₂₈H₃₄N₄O₅S 

Relevant academic research and scientific papers

RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles

The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI50 values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI50 of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.

Synthesis of macrocycles that inhibit protein synthesis: Stereochemistry and structural based studies on sanguinamide B derivatives

We report the synthesis of seven new sanguinamide B (SanB) analogues. Substitution of amino acids along the backbone of SanB and testing in HCT-116 colon cancer cell lines identified new biologically active SanB derivatives. These compounds establish a st

Mechanistic studies of sanguinamide B derivatives: A unique inhibitor of eukaryotic ribosomes

Described are mechanistic studies of two Sanguinamide B (San B) derivatives. These compounds were identified as eukaryotic ribosomal inhibitors. Two biotinylated San B derivatives were synthesized and used to capture protein targets in a pull-down assay.

Synthesis, structurea-activity analysis, and biological evaluation of sanguinamide B analogues

We report the first synthesis of sanguinamide B analogues. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and l-or d-phenylalanine (Phe) into the backbone of sanguinamide B showed that only l-and d-Phe residues controlled the macrocycle conf

Synthesis of the thiazole-thiazoline fragment of largazole analogues

The thiazole - thiazoline fragment of the marine natural product largazole, a potent histone deacetylase 1 inhibitor, has been synthesized in five steps. The methodology provides rapid access to thiazole-4-carbonitrile, thiazole-4-carbimidate, thiazole -