13209-32-0

Upstream product

• 856803-28-6 5-bromo-1,3-dimethoxy-phthalan 
• 859782-02-8 4-bromo-1,2-bis-diacetoxymethyl-benzene 
• 4235-46-5 4,α,α,α',α'-pentabromo-o-xylene 
• 861928-15-6 1,4-dibromo-2-(dimethoxymethyl)benzene 
• 68-12-2 N,N-dimethyl-formamide 
• 74553-29-0 2,5-dibromobenzaldehyde 
• 583-71-1 4-bromo-o-xylene 
• 171011-37-3 4-bromo-2-(hydroxymethyl)benzyl alcohol 
• 6968-28-1 4-bromophthalic acid 
• 86-90-8 4-bromophthalic anhydride 

Downstream Products

• 220513-49-5 5-bromo-1,3-dihydroisobenzofuran 
• 660830-63-7 7-bromoisoquinoline-3-carboxylic acid 
• 660830-62-6 ethyl 7-bromoisoquinoline-3-carboxylate 
• 19064-74-5 6-bromophthalazine 
• 942229-74-5 C₂₄H₁₇O₂Br 

Relevant academic research and scientific papers

FlICk (fluorescent isoindole crosslinking) for peptide stapling

The rigidification of peptide secondary structure via stapling is an important and enduring goal in the development of functional peptides for biochemical and pharmaceutical applications. In addition, the incorporation of fluorophores and chromophores has

CYCLIC PEPTIDE ANALOGS OF MELANOCORTIN AND AMANITIN AND METHODS OF MAKING SUCH

The invention described herein is based in part on the discovery of a protein/peptide crosslink, which introduces fluorescent properties, and which has been applied to synthesize analogues of melanocortin and amanitin as choice peptides to be explored in the context of isoindole peptides. Without limitation, it is expected that those trained in the art of peptide synthesis and stapling would appreciate the consequences of this invention such that other peptides of varied length can be similarly constrained by isoindole staples as featured herein.

Site-Selective Functionalization of (sp3)C?H Bonds Catalyzed by Artificial Metalloenzymes Containing an Iridium-Porphyrin Cofactor

The selective functionalization of one C?H bond over others in nearly identical steric and electronic environments can facilitate the construction of complex molecules. We report site-selective functionalizations of C?H bonds, differentiated solely by rem

Fluorescent Isoindole Crosslink (FlICk) Chemistry: A Rapid, User-friendly Stapling Reaction

The stabilization of peptide secondary structure via stapling is a ubiquitous goal for creating new probes, imaging agents, and drugs. Inspired by indole-derived crosslinks found in natural peptide toxins, we employed ortho-phthalaldehydes to create isoindole staples, thus transforming inactive linear and monocyclic precursors into bioactive monocyclic and bicyclic products. Mild, metal-free conditions give an array of macrocyclic α-melanocyte-stimulating hormone (α-MSH) derivatives, of which several isoindole-stapled α-MSH analogues (Ki≈1 nm) are found to be as potent as α-MSH. Analogously, late-stage intra-annular isoindole stapling furnished a bicyclic peptide mimic of α-amanitin that is cytotoxic to CHO cells (IC50=70 μm). Given its user-friendliness, we have termed this approach FlICk (fluorescent isoindole crosslink) chemistry.

Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine

One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.

ISOQUINOLINE DERIVATIVES AS PERK INHIBITORS

The invention is directed to substituted isoquinoline derivatives and uses thereof. Specifically, the invention is directed to compounds according to Formula I and the use of compounds of Formula (I) in treating disease states: (I) wherein R1,

Selective lithiation of 4- and 5-halophthalans

The reaction of 4- and 5-halophthalans 5 with lithium and a catalytic amount of DTBB at -78 °C leads to the formation of the corresponding functionalized organolithium intermediates 6 and 11, which by reaction with carbonyl compounds give, after hydrolysis, the expected substituted phthalans 8 and 13, respectively. When after reaction with the carbonyl compound the system is allowed to react at 0 °C, a second lithiation occur: A reductive opening of the heterocycle takes place with some regioselectivity leading to new organolithium intermediates 9 and 14/15 that by reaction with electrophiles lead, after hydrolysis, to polyfunctionalized molecules 10 and 16/17, respectively.

USE OF TRIFLUOROMETHYL SUBSTITUTED BENZAMIDES IN THE TREATMENT OF NEUROLOGICAL DISORDERS

The invention relates to methods of using the compounds of the invention, including trifluoromethyl substituted benzamide compounds and salts thereof, as well as pharmaceutical compositions comprising the same, in the treatment of Eph receptor-related (e.g., neurological) injuries and disorders. The invention also relates to modulating the activity of an Eph receptor in a cell, stimulating neural regeneration, and reversing neuronal degeneration, by administering a compound of the invention to a cell or subject in an effective amount.

Trifluoromethyl substituted benzamides as kinase inhibitors

The invention relates to trifluoromethyl substituted benzamide compounds of the formula I, pharmaceuticals comprising these compounds, their use as or for the manufacture of pharmaceuticals, particularly as inhibitors of protein kinases, especially of ephrin receptor kinases, and/or the treatment of a condition, disorder or disease state mediated by a protein kinase activity and/or a proliferative disease, methods of treatment comprising administering the compounds, especially of therapeutic and prophylactic treatment, methods for the manufacture of the compounds and novel intermediates and partial steps for their synthesis.

Halogen-lithium exchange between substituted dihalobenzenes and butyllithium: Application to the regioselective synthesis of functionalized bromobenzaldehydes

Halogen-lithium interconversion reactions between unsymmetrically substituted mono- and bifunctional dihalobenzenes C6H 3XHal2 and C6H2XYHal2 (Hal=Br, I; X, Y=F, OR, CF3, CH(OMe)2) and butyllithium were investigated. The resultant organolithium intermediates were converted into the corresponding benzaldehydes in moderate to good yields. As a rule, bromine atoms in the position ortho to the functional group were replaced preferentially with lithium. Intramolecular competition experiments with bifunctional systems revealed that fluorine is capable of activating the neighboring bromine atom more strongly than methoxy and dimethoxymethyl groups. On the replacement of the non-activated bromine with iodine a complete reversal of this reactivity pattern can be accomplished due to the preferred iodine-lithium exchange.