99281-95-5

Upstream product

• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 191405-19-3 [(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester 
• 1343489-69-9 (S)-tert-butyl 1-(4-cyanothiazol-2-yl)-2-phenylethylcarbamate 
• 1343489-91-7 (R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid 
• 131148-64-6 (S)-ethyl 2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazole-4-carboxylate 
• 218288-94-9 EtO-Thiazole-Phe-NH₂ 
• 1414375-90-8 EtO-Thiazole-Phe-Val-NHBoc 
• 1414375-74-8 San B 7 
• 1026007-03-3 C₁₉H₂₆N₂O₅S 

Relevant academic research and scientific papers

Comprehensive Synthesis of Amino Acid-Derived Thiazole Peptidomimetic Analogues to Understand the Enigmatic Drug/Substrate-Binding Site of P-Glycoprotein

A novel set of 64 analogues based on our lead compound 1 was designed and synthesized with an initial objective of understanding the structural requirements of ligands binding to a highly perplexing substrate-binding site of P-glycoprotein (P-gp) and their effect on modulating the ATPase function of the efflux pump. Compound 1, a stimulator of P-gp ATPase activity, was transformed to ATPase inhibitory compounds 39, 53, and 109. The ATPase inhibition by these compounds was predominantly contributed by the presence of a cyclohexyl group in lieu of the 2-aminobenzophenone moiety of 1. The 4,4-difluorocyclohexyl analogues, 53 and 109, inhibited the photolabeling by [125I]-IAAP, with IC50 values of 0.1 and 0.76 μM, respectively. Selected compounds were shown to reverse paclitaxel resistance in HEK293 cells overexpressing P-gp and were selective toward P-gp over CYP3A4. Induced-fit docking highlighted a plausible binding pattern of inhibitory compounds in the putative-binding pocket of P-gp. The current study underscores the stringent requirement by P-gp to bind to chemically similar molecules.

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.

Metastin derivatives and use thereof

The invention provides stable metastin derivatives having excellent biological activities (a cancer metastasis suppressing activity, a cancer growth suppressing activity, etc.). By modifying the constituent amino acids of metastin with specific modifying groups, metastin derivatives having more improved blood stability, etc. than native metastin and showing excellent cancer metastasis suppressing activity or cancer growth suppressing activity have been found. Furthermore, it has been found that these metastin derivatives exhibit effects of suppressing gonadotropic hormone secretion, suppressing sex hormone secretion, etc., which are wholly different from the effects heretofore known.

CYTOTOXIC PEPTIDES AND ANTIBODY DRUG CONJUGATES THEREOF

The present invention is directed to cytotoxic pentapeptides, to antibody drug conjugates thereof, and to methods for using the same to treat cancer.

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 -

In Situ Reagent for Thionation of Amides, Peptides and Lactams

An in situ reagent 1A for thionation of amides, peptides and lactams is prepared from phosphorus decasulfide/sodium carbonate (1:1 ratio) in THF at 25 deg C.

Carboxyl-Modified Amino Acids and Peptides as Protease Inhibitors

Several types of carbonyl-modified amino acids and peptides were prepared in forms having N-terminal modifications (carrier fragments) suitable for one of several representative protease enzymes, and their inhibitory action toward those enzymes were evalu