227288-15-5

Upstream product

• 615-43-0 2-iodophenylamine 
• 92136-39-5 N-tert-Butoxycarbonyl-1-amino-3-propyne 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 227288-21-3 2-[2-(3-tert-butoxycarbonylamino-prop-1-ynyl)-phenylamino]-4-methyl-pentanoic acid methyl ester 
• 103549-24-2 tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate 
• 114622-04-7 ascididemin 
• 227288-28-0 (R)-2-[2-(3-{(R)-2-[2-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-phenylamino]-propionylamino}-prop-1-ynyl)-phenylamino]-4-methyl-pentanoic acid 
• 227288-25-7 (R)-2-[2-(3-{(R)-2-[2-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-phenylamino]-propionylamino}-prop-1-ynyl)-phenylamino]-4-methyl-pentanoic acid methyl ester 
• 744185-23-7 (R)-2-[2-(3-{(R)-2-[2-(3-Amino-prop-1-ynyl)-phenylamino]-propionylamino}-prop-1-ynyl)-phenylamino]-4-methyl-pentanoic acid 
• 227288-23-5 2-[2-(3-tert-butoxycarbonylamino-prop-1-ynyl)-phenylamino]-propionic acid 
• 227288-19-9 2-[2-(3-tert-butoxycarbonylamino-prop-1-ynyl)-phenylamino]-propionic acid methyl ester 

Relevant academic research and scientific papers

Total synthesis of ascididemin-type alkaloids using alkyne building blocks

A common approach to ascididemin-type alkaloids, including ascididemin, bromoleptoclinidinone, neocalliactine acetate, and 11-hydroxyascididemin, based on a Bronsted acid-promoted tandem annulation has been developed. Alkyne building blocks were first des

G-quadruplex and duplex DNA binding studies of novel Ruthenium(II) complexes containing ascididemin ligands

In this paper, three new Ruthenium(II) polypyridyl complexes containing ascididemin (ASC) as main ligand have been synthesized and characterized. Their interactions with different G-quadruplex (Htelo, c-myc and c-kit) (Htelo: human telomeric DNA, c-myc: cellular-myelocytomatosis viral oncogene, c-kit: oncogene c-kit promoter sequences) and duplex (ds26) DNA sequences were comparatively studied with the free ligand ASC by a series of spectroscopic techniques including UV–vis (ultraviolet-visible) spectroscopy, FID (fluorescent intercalator displacement) assay, and FRET (fluorescence resonance energy transfer) melting assay. Molecular docking studies were also performed to support the binding mode of the compounds with G-quadruplex DNA. Results indicated that [Ru(bpy)2ASC]·(PF6)2 (1), [Ru(phen)2ASC]·(PF6)2 (2), [Ru(tatp)2ASC]·(PF6)2 (3) (bpy = 2,2′?bipyridine, phen = 1,10?phenanthroline, tatp = 1,4,8,9?tetra?aza?triphenylene) and ASC can effectively bind G-quadruplex and duplex DNA and stabilization ability lies in the order 3 > 2 > 1 > ASC. Complex 3 was determined to be the most promising candidate for further in vitro studies and potential anticancer drug.

Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles

A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 %) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises RhI(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 % for the desired 3-substituted indoles.

Synthesis and structure of a small macrocyclic hexapeptide model for antiparallel β-sheet containing two restrained 2-(3'-aminopropynyl)-aniline reverse-turn mimetics

A new reverse-turn mimetic containing a 2-(3'-aminopropynyl)-phenyl moiety in place of the natural i + 1 and i + 2 turn residues is described in which the key C-C bond was formed from an N-protected propargylamine and 2- iodoaniline using Heck chemistry. Nucleophilic displacement of triflate from activated (2S)-2-hydroxyalkanoate esters by the anilino N-atom, with inversion at C-2, gave homochiral tripeptide mimetics. Two variants of these were coupled and the product was deprotected and then cyclised to give a stable cyclo-hexapeptide analogue that possessed an anti-parallel β-sheet structure as determined by NMR spectroscopy.