162356-90-3

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C12H16BrNO2/c1-12(2,3)16-11(15)14-8-9-6-4-5-7-10(9)13/h4-7H,8H2,1-3H3,(H,14,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 5465-63-4 2-bromobenzylamine hydrochloride 
• 126799-87-9 o-bromobenzyl azide 
• 3959-05-5 2-bromobenzylamine 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 168059-24-3 2'-[(t-butoxycarbonylamino)methyl]-4-[(t-butyldiphenylsiloxy)methyl]-1,1'-biphenyl 
• 433969-27-8 2-((tert-butoxycarbonylamino)methyl)phenylboronic acid 
• 449758-18-3 [2-(1H-pyrazol-3-yl)benzyl]carbamic acid tert-butyl ester 
• 180913-12-6 3-[2-(tert-butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester 
• 444583-14-6 ethyl 2-(isoindolin-1-yl)acetate 
• 444892-24-4 (R)-3-(4-Chloro-phenyl)-2-[2-((S)-1-methyl-2,3-dihydro-1H-isoindol-1-yl)-acetylamino]-propionic acid methyl ester 
• 444892-18-6 (R)-3-(4-Chloro-phenyl)-2-[2-((R)-1-methyl-2,3-dihydro-1H-isoindol-1-yl)-acetylamino]-propionic acid methyl ester 
• 444892-17-5 1-{[2-(4-chloro-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-methyl}-1-methyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 
• 444892-19-7 (R)-1-{[(R)-2-(4-Chloro-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-methyl}-1-methyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 
• 444892-20-0 (S)-1-{[(R)-2-(4-Chloro-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-methyl}-1-methyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 
• 603127-40-8 3-{[5-(2-aminomethyl-phenyl)-thiophene-2-carbonyl]-amino}-2-benzenesulfonylamino-propionic acid tert-butyl ester 
• 312760-12-6 C₃₆H₄₇N₅O₉S₂ 
• 171662-92-3 3-[2-(tert-butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester 

Relevant academic research and scientific papers

Characterization of a novel multifunctional resveratrol derivative for the treatment of atrial fibrillation

Background and Purpose Atrial fibrillation (AF) is the most common cardiac arrhythmia and is associated with an increased risk for stroke, heart failure and cardiovascular-related mortality. Candidate targets for anti-AF drugs include a potassium channel Kv1.5, and the ionic currents I KACh and late INa, along with increased oxidative stress and activation of NFAT-mediated gene transcription. As pharmacological management of AF is currently suboptimal, we have designed and characterized a multifunctional small molecule, compound 1 (C1), to target these ion channels and pathways. Experimental Approach We made whole-cell patch-clamp recordings of recombinant ion channels, human atrial IKur, rat atrial I KACh, cellular recordings of contractility and calcium transient measurements in tsA201 cells, human atrial samples and rat myocytes. We also used a model of inducible AF in dogs. Key Results C1 inhibited human peak and late Kv1.5 currents, frequency-dependently, with IC50 of 0.36 and 0.11 μmol·L-1 respectively. C1 inhibited I KACh (IC50 of 1.9 μmol·L-1) and the Nav1.5 sodium channel current (IC50s of 3 and 1 μmol·L-1 for peak and late components respectively). C1 (1 μmol·L-1) significantly delayed contractile and calcium dysfunction in rat ventricular myocytes treated with 3 nmol·L -1 sea anemone toxin (ATX-II). C1 weakly inhibited the hERG channel and maintained antioxidant and NFAT-inhibitory properties comparable to the parent molecule, resveratrol. In a model of inducible AF in conscious dogs, C1 (1 mg·kg-1) reduced the average and total AF duration. Conclusion and Implications C1 behaved as a promising multifunctional small molecule targeting a number of key pathways involved in AF.

A Rh(II)- or Ag(I)-Catalyzed Formal C-O Bond Insertion of Cyclic Hemiaminal with Aryl Diazoacetate

A mild and facile synthetic method via convergent assembly of two reactive intermediates generated in situ has been developed. This method provides an efficient way to construct six- and sevenmembered N-heterocycles containing a biaryl linkage. This react

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.

First Contact: 7-Phenyl-2-Aminoquinolines, Potent and Selective Neuronal Nitric Oxide Synthase Inhibitors That Target an Isoform-Specific Aspartate

Inhibition of neuronal nitric oxide synthase (nNOS), an enzyme implicated in neurodegenerative disorders, is an attractive strategy for treating or preventing these diseases. We previously developed several classes of 2-aminoquinoline-based nNOS inhibitor

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

Asymmetric Hydrogenation of Dibenzo[ c,e]azepine Derivatives with Chiral Cationic Ruthenium Diamine Catalysts

An efficient Ru-catalyzed asymmetric hydrogenation of dibenzo[c,e]azepines is reported. A series of seven-membered cyclic amines were obtained with moderate to excellent enantioselectivity. The catalyst counteranion played an important role in achieving high-level chiral induction. Moreover, a one-pot synthesis of chiral 6,7-dihydro-5H-dibenz[c,e]azepines via two-step reductive amination was also developed.

Palladium-Catalyzed α-Arylation of Silylenol Ethers in the Synthesis of Isoquinolines and Phenanthridines

A diverse array of isoquinolines and phenanthridines have been accessed by developing a two-step, one-pot method constituting regioselective palladium-catalyzed Kuwajima-Urabe α-arylation of silylenol ethers and acid-mediated deprotection, annulation, and aromatization. Structural diversity in the silylenol ethers leads to three different classes of isoquinolines and phenanthridines from which related natural products can be derived. The synthetic utility of this method by the quick assembly of the natural product trispheridine is also demonstrated.

Aminolithiation–arylation consecutive cyclization of N-(2-fluorophenyl)methylaminoalkylstyryls giving aryl-substituted pyrido[1,2-b]isoquinolines

Aminolithiation–arylation tandem cyclization of N-(2-fluorophenyl)methylaminoalkylstyryls proceeded smoothly to give hexahydro-2H-pyrido[1,2-b]isoquinoline using a stoichiometric amount of n-BuLi with high trans selectivity. The arylation reaction was highly accelerated by the addition of HMPA. Both pyrido- and pyrrolo-[1,2-b]isoquinoline were successfully constructed by this tandem reaction.

2-METHYL-QUINAZOLINES

The present invention describes 2-methyl-quinazoline compounds of general formula (I), methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions. The 2-methyl substituted quinazoline compounds of general formula(I) effectively and selectively inhibit the Ras-Sos interaction without significantly targeting the EGFR receptor. They are therefore useful for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, such as cancer as a sole agent or in combination with other active ingredients.

REMOTE HETEROARYL ALKENYLATION WITH CATALYTIC BIFUNCTIONAL TEMPLATE

We report the design of a catalytic, bifunctional template that binds heterocyclic substrate via reversible coordination instead of covalent linkage, allowing remote site- selective C-H olefination of heterocycles. The two metal centers coordinated to this template play different roles; anchoring substrates to the proximity of catalyst and cleaving the remote C-H bonds respectively. Using this strategy, we demonstrate remote site-selective C-H olefination of heterocyclic substrates which do not have functional group handles for covalently attaching templates. For instance the olefination can be an alkenylation of a 3- phenylpyridine with an acrylate alkyl ester selective for the meta position of the phenyl group with respect to the pyridine, or can be an alkenylation of a quinoline with an acrylate alkyl ester selective for the 5-position of the quinoline.