61535-47-5

Upstream product

• 2717-76-2 (S)-N-benzyloxycarbonyl-L-tryptophan methyl ester 
• 501-53-1 benzyl chloroformate 
• 154-09-6 L-tryptophanol 
• 154-09-6 (2R)-2-amino-3-(1H-indol-3-yl)propan-1-ol 
• 2279-15-4 N-(benzyloxycarbonyl)-D-tryptophan 
• 73-22-3 L-Tryptophan 
• 50305-28-7 Cbz-L-Tryptophan-OSu 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 

Downstream Products

• 154-09-6 L-tryptophanol 
• 1039025-31-4 (2S)-2-[(benzyloxycarbonyl)amino]-3-(1H-indol-3-yl)propyl methanesulfonate 
• 1379661-52-5 C₂₄H₂₉N₃O₂ 
• 1379661-53-6 (S)-1-(1-(1H-indol-3-yl)-3-(piperidin-1-yl)propan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea 
• 61535-48-6 C₂₆H₂₆N₂O₅S 
• 61587-85-7 (S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propyl 4-methylbenzenesulfonate 
• 161708-61-8 N-benzyloxycarbonyl-(L)-phenylalanyl-(L)-tryptophanol 
• 131442-94-9 (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 
• 110815-30-0 Acetic acid (R)-2-benzyloxycarbonylamino-3-(6-nitro-1H-indol-3-yl)-3-oxo-propyl ester 
• 110815-29-7 Acetic acid (R)-2-benzyloxycarbonylamino-3-(4-nitro-1H-indol-3-yl)-3-oxo-propyl ester 
• 110815-31-1 Acetic acid (R)-3-(4-amino-1H-indol-3-yl)-2-benzyloxycarbonylamino-3-oxo-propyl ester 
• 110815-28-6 (R)-(1-((acetoxy)methyl)-2-(1H-indol-3-yl)-2-oxoethyl)carbamic acid phenylmethyl ester 
• 110815-32-2 (S)-(2-(4-amino-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 
• 84590-48-7 indolactam V 

Relevant academic research and scientific papers

COMPOUNDS AND METHOD OF USE

This present disclosure relates to compounds with ferroptosis inducing activity, a method of treating a subject with cancer with the compounds, and combination treatments with a second therapeutic agent.

ESTROGEN RECEPTOR MODULATORS

Compounds of Formula (I) are estrogen receptor alpha modulators, where the variables in Formula (I) are described in the disclosure. Such compounds, as well as pharmaceutically acceptable salts and compositions thereof, are useful for treating diseases or conditions that are estrogen receptor alpha dependent and/or estrogen receptor alpha mediated, including conditions characterized by excessive cellular proliferation, such as breast cancer.

Efficient access to enantiopure γ4-amino acids with proteinogenic side-chains and structural investigation of γ4- asn and γ4-ser in hybrid peptide helices

Hybrid peptides composed of α- and β-amino acids have recently emerged as new class of peptide foldamers. Comparatively, γ- and hybrid γ-peptides composed of γ4-amino acids are less studied than their β-counterparts. However, recent investigations reveal that γ4-amino acids have a higher propensity to fold into ordered helical structures. As amino acid side-chain functional groups play a crucial role in the biological context, the objective of this study was to investigate efficient synthesis of γ4-residues with functional proteinogenic side-chains and their structural analysis in hybrid-peptide sequences. Here, the efficient and enantiopure synthesis of various N- and C-terminal free-γ4-residues, starting from the benzyl esters (COOBzl) of N-Cbz-protected (E)-α,β-unsaturated γ-amino acids through multiple hydrogenolysis and double-bond reduction in a single-pot catalytic hydrogenation is reported. The crystal conformations of eight unprotected γ4-amino acids (γ4-Val, γ4-Leu, γ4-Ile, γ4-Thr(OtBu), γ4-Tyr, γ4-Asp(OtBu), γ4- Glu(OtBu), and γ-Aib) reveals that these amino acids adopted a helix favoring gauche conformations along the central Cγi￡ Cβ bond. To study the behavior of γ4- residues with functional side chains in peptide sequences, two short hybrid γ-peptides P1 (Ac-Aib-γ4-Asn-Aib-γ4-Leu- Aib-γ4-Leu-CONH2) and P2 (Ac-Aib- γ4-Ser-Aib-γ4-Val-Aib-γ4-Val- CONH2) were designed, synthesized on solid phase, and their 12-helical conformation in single crystals were studied. Remarkably, the γ4-Asn residue in P1 facilitates the tetrameric helical aggregations through interhelical H bonding between the side-chain amide groups. Furthermore, the hydroxyl side-chain of γ4-Ser in P2 is involved in the interhelical H bonding with the backbone amide group. In addition, the analysis of 87 γ4-residues in peptide single-crystals reveal that the γ4-residues in 12-helices are more ordered as compared with the 10/12- and 12/14-helices. Copyright

Enantioselective Friedel-Crafts reactions between phenols and N-tosylaldimines catalyzed by a leucine-derived bifunctional catalyst

Enantioselective Friedel-Crafts reactions between phenols and N-tosylaldimines were developed using a bifunctional catalyst readily prepared from l-leucine. The chiral benzylic amine products were obtained in high yields (up to 96% yield) and good to high enantiomeric excesses (up to 95% ee).

Spirotetrahydro β-carbolines (spiroindolones): A new class of potent and orally efficacious compounds for the treatment of malaria

The antiplasmodial activity of a series of spirotetrahydro β-carbolines is described. Racemic spiroazepineindole (1) was identified from a phenotypic screen on wild type Plasmodium falciparum with an in vitro IC50 of 90 nM. Structure-activity relationships for the optimization of 1 to compound 20a (IC50 = 0.2 nM) including the identification of the active 1R,3S enantiomer and elimination of metabolic liabilities is presented. Improvement of the pharmacokinetic profile of the series translated to exceptional oral efficacy in the P. berghei infected malaria mouse model where full cure was achieved in four of five mice with three daily doses of 30 mg/kg.

ORGANIC COMPOUNDS

The invention relates to organic compounds which have interesting pharmaceutical properties. In particular, the compounds are useful in the treatment and/or prevention of infections such as those caused by Plasmodium falciparum, Plasmodium vivax, Plasmodium malariae, Plasmodium ovale, Trypanosoma cruzi and parasites of the Leishmania genus such as, for example, Leishmania donovani. The invention also relates to pharmaceutical compositions containing the compounds, as well as processes for their preparation.

Synthesis of a β-tetrapeptide analog as a mother compound for the development of matrix metalloproteinase-2-imaging agents

Matrix metalloproteinase-2 (MMP-2) is an attractive target for the diagnosis of cancer and atherosclerosis in nuclear imaging. A cyclic decapeptide, cCTTHWGFTLC (cCTT), has been used as the mother compound for the development of MMP-2-imaging agents with high potency and selectivity. Most of radiolabeled derivatives of cCTT currently developed for in vivo studies of MMP-2, however, suffer from low accumulation in the target tissues, such as tumors. For enhanced in vivo stability and tissue penetration, we designed a linear β-tetrapeptide analog, H-β3-Phe-β-Ala- β3-Trp-β3-His-OH (1), to mimic cCTT. The component β-amino acids were prepared by reduction of N-protected α-amino acid methyl esters to the alcohols, followed by conversion into the cyanides, and subsequent hydrolysis. Compound 1 was obtained from these β-amino acids by the conventional solution method. In MMP-2 inhibition assay, compound 1 displayed desirably significant inhibition, which was comparable to cCTT. These findings suggest that compound 1 may serve as a mother compound in the design and development of in vivo MMP-2-imaging agents.

Pinacol Homocoupling of (S)-2- Aldehydes by 2. Synthesis of C2-Symmetric (1S,2R,3R,4S)-1,4-Diamino 2,3-Diols

Six (S)-2- aldehydes 3a-f were homocoupled by 2 (1) to give C2-symmetric (1S,2R,3R,4S)-1,4-bis 2,3-diols 4a-f in good yield.High-yield conversions of the diols to biso

A Regio- and stereocontrolled total synthesis of (-)-indolactam-V

(-)-Indolactam-V (IL-V) (1)-was prepared in 10 steps from L-tryptophan methyl ester in 17.1% overall yield. The key steps involve regiospecific thallation of the acylindole intermediate (4), followed by azide displacement and reduction to introduce the 13-amino group. Control of the C-11 stereocenter was achieved by SN2 displacement of the chiral inflate (10), derived from D-valine. The thallium mediated closure of dipeptide (17) did not provide an alternative route to IL-V.