94838-55-8

Usage

Uses

Used in Organic Synthesis:
4-(N-BOC-AMINOMETHYL)ANILINE is used as a key intermediate in the preparation of various organic synthase inhibitors and other bio-active compounds. Its protected amine structure allows for selective reactions and the synthesis of complex organic molecules with potential applications in pharmaceuticals and other industries.
Used in Hapten Synthesis:
In the field of immunology, 4-(N-BOC-AMINOMETHYL)ANILINE may be used in the synthesis of haptens. Haptens are small molecules that can elicit an immune response when coupled to a larger carrier protein. The protected amine group in 4-(N-BOC-AMINOMETHYL)ANILINE facilitates the formation of stable conjugates with carrier proteins, enhancing their immunogenic properties.
Used in the Preparation of Benzene Diazonium Salts:
4-(N-BOC-AMINOMETHYL)ANILINE can also be used in the synthesis of 4-(N-boc-aminomethyl)benzene diazonium tetrafluoroborate salt. Diazonium salts are versatile reagents in organic chemistry, used for the modification of various substrates through diazotization reactions. The presence of the protected amine group in 4-(N-BOC-AMINOMETHYL)ANILINE allows for the controlled formation of diazonium salts, which can be further utilized in the synthesis of a wide range of organic compounds.

InChI:InChI=1/C12H18N2O2/c1-12(2,3)16-11(15)14-8-9-4-6-10(13)7-5-9/h4-7H,8,13H2,1-3H3,(H,14,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4403-71-8 (4-aminomethyl)aniline 
• 285119-75-7 1,1-dimethylethyl [4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]carbamate 
• 619-73-8 4-nitrobenzyl chloride 
• 62133-07-7 2-(4-nitrobenzyl)-1H-isoindole-1,3(2H)-dione 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 619-72-7 4-nitrobenzonitrile 
• 39628-94-9 4-nitrobenzyl methanesulfonate 
• 7409-30-5 p-nitrobenzylamine 
• 18600-42-5 4-nitrobenzylamine hydrochloride 
• 94838-58-1 tert-butyl 4-nitrobenzylcarbamate 

Downstream Products

• 195717-92-1 {4-[3-(tert-Butyl-dimethyl-silanyloxy)-propylamino]-benzyl}-carbamic acid tert-butyl ester 
• 238427-63-9 tert-butyl N-[[4-(methanesulfonamido)phenyl]methyl]carbamate 
• 182315-21-5 3-{2-[4-(tert-butoxycarbonylamino-methyl)-phenylcarbamoyl]-vinyl}-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester 
• 263551-61-7 (4-{4-[4-(tert-butoxycarbonylamino-methyl)-phenylamino]-6-chloro-[1,3,5]triazin-2-ylamino}-benzyl)-carbamic acid tert-butyl ester 
• 265664-80-0 {4-[(4-nitro-1H-pyrrole-2-carbonyl)-amino]-benzyl}-carbamic acid tert-butyl ester 
• 265664-81-1 {4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-benzyl}-carbamic acid tert-butyl ester 
• 265664-82-2 {4-[(1-benzyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-benzyl}-carbamic acid tert-butyl ester 
• 269054-83-3 1,3,5-benzene tris(N-(tert-butyloxycarbonyl)-4'-aminomethylphenyl carboxamide) 
• 358680-96-3 7,8-dimethoxy-3-(4-(tert-butoxycarbonylaminomethyl)anilinocarbonyl)-1H-pyrrolo[3,2-c]quinoline 
• 374929-32-5 4-(methylamino-t-butylcarbonyl)-aniline isocyanate 
• 390406-71-0 (4-{3-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-3-isopropyl-ureido}-benzyl)-carbamic acid tert-butyl ester 
• 395062-80-3 [Fmoc-Tyr(O-Pic)]-4-(Boc-aminomethyl)anilide 
• 299189-19-8 {4-[(thiophene-2-carboximidoyl)-amino]-benzyl}-carbamic acid tert-butyl ester 
• 502481-67-6 methyl (3S)-3-{2-[(4-{[(tert-butoxycarbonyl)amino]methyl}phenyl)amino]-2-oxoethyl}-7-chloro-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate 

Relevant academic research and scientific papers

Cannabinoid receptor light-operated ligand and preparation method and application thereof

The invention relates to the technical field of biology, in particular to a novel cannabinoid receptor light-operated ligand and a preparation method and application thereof. Disclosed is the cannabinoid receptor light-operated ligand or the isomer prodrug, the solvate and the pharmaceutically acceptable salt of the cannabinoid receptor light-operated ligand, wherein the structural formula of thecannabinoid receptor light-operated ligand is A-linker-B; A is a transmembrane domain ligand structure, and B is a light-operated element; Linker is a subunit which is linear and has no activity on acannabinoid receptor light-operated ligand. According to the invention, the cannabinoid receptor ligand is integrated with azobenzene through a proper connector, so that the ligand configuration is changed under an illumination condition, and the activation or inhibition state of the cannabinoid receptor is regulated and controlled.

Identification of First-in-Class Inhibitors of Kallikrein-Related Peptidase 6 That Promote Oligodendrocyte Differentiation

Multiple sclerosis (MS) is an autoimmune demyelinating disease of the central nervous system (CNS) that causes severe motor, sensory, and cognitive impairments. Kallikrein-related peptidase (KLK)6 is the most abundant serine protease secreted in the CNS, mainly by oligodendrocytes, the myelin-producing cells of the CNS, and KLK6 is assumed to be a robust biomarker of MS, since it is highly increased in the cerebrospinal fluid (CSF) of MS patients. Here, we report the design and biological evaluation of KLK6's low-molecular-weight inhibitors, para-aminobenzyl derivatives. Interestingly, selected hit compounds were selective of the KLK6 proteolytic network encompassing KLK1 and plasmin that also participate in the development of MS physiopathology. Moreover, hits were found noncytotoxic on primary cultures of murine neurons and oligodendrocyte precursor cells (OPCs). Among them, two compounds (32 and 42) were shown to promote the differentiation of OPCs into mature oligodendrocytes in vitro constituting thus emerging leads for the development of regenerative therapies.

"Photo-Rimonabant": Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar " Cis-On" CB1R Antagonist

Human cannabinoid receptor type 1 (hCB1R) plays important roles in the regulation of appetite and development of addictive behaviors. Herein, we describe the design, synthesis, photocharacterization, molecular docking, and in vitro characterization of "photo-rimonabant", i.e., azo-derivatives of the selective hCB1R antagonist SR1411716A (rimonabant). By applying azo-extension strategies, we yielded compound 16a, which shows marked affinity for CB1R (Ki (cis form) = 29 nM), whose potency increases by illumination with ultraviolet light (CB1R Kitrans/cis ratio = 15.3). Through radioligand binding, calcium mobilization, and cell luminescence assays, we established that 16a is highly selective for hCB1R over hCB2R. These selective antagonists can be valuable molecular tools for optical modulation of CBRs and better understanding of disorders associated with the endocannabinoid system.

Rational Remodeling of Atypical Scaffolds for the Design of Photoswitchable Cannabinoid Receptor Tools

Azobenzene-embedded photoswitchable ligands are the widely used chemical tools in photopharmacological studies. Current approaches to azobenzene introduction rely mainly on the isosteric replacement of typical azologable groups. However, atypical scaffolds may offer more opportunities for photoswitch remodeling, which are chemically in an overwhelming majority. Herein, we investigate the rational remodeling of atypical scaffolds for azobenzene introduction, as exemplified in the development of photoswitchable ligands for the cannabinoid receptor 2 (CB2). Based on the analysis of residue-type clusters surrounding the binding pocket, we conclude that among the three representative atypical arms of the CB2 antagonist, AM10257, the adamantyl arm is the most appropriate for azobenzene remodeling. The optimizing spacer length and attachment position revealed AzoLig 9 with excellent thermal bistability, decent photopharmacological switchability between its two configurations, and high subtype selectivity. This structure-guided approach gave new impetus in the extension of new chemical spaces for tool customization for increasingly diversified photo-pharmacological studies and beyond.

Oxidative Approach Enables Efficient Access to Cyclic Azobenzenes

Azobenzenes are versatile photoswitches that have found widespread use in a variety of fields, ranging from photopharmacology to the material sciences. In addition to regular azobenzenes, the cyclic diazocines have recently emerged. Although diazocines have fascinating conformational and photophysical properties, their use has been limited by their synthetic accessibility. Herein, we present a general, high-yielding protocol that relies on the oxidative cyclization of dianilines. In combination with a modular substrate synthesis, it allows for rapid access to diversely functionalized diazocines on gram scales. Our work systematically explores substituent effects on the photoisomerization and thermal relaxation of diazocines. It will enable their incorporation into a wide variety of functional molecules, unlocking the full potential of these emerging photoswitches. The method can be applied to the synthesis of a new cyclic azobenzene with a nine-membered central ring and distinct properties.

A Straightforward Approach to Multifunctional Graphene

Graphene has been covalently functionalized through a one-pot reductive pathway using graphite intercalation compounds (GICs), in particular KC8, with three different orthogonally protected derivatives of 4-aminobenzylamine. This novel multifunctional platform exhibits excellent bulk functionalization homogeneity (Hbulk) and degree of addition while preserving the chemical functionalities of the organic addends through different protecting groups, namely: tert-butyloxycarbonyl (Boc), benzyloxycarbonyl (Cbz) and phthalimide (Pht). We have employed (temperature-dependent) statistical Raman spectroscopy (SRS), X-ray photoelectron spectroscopy (XPS), magic angle spinning solid state 13C NMR (MAS-NMR), and a characterization tool consisting of thermogravimetric analysis coupled with gas chromatography and mass spectrometry (TG-GC-MS) to unambiguously demonstrate the covalent binding and the chemical nature of the different molecular linkers. This work paves the way for the development of smart graphene-based materials of great interest in biomedicine or electronics, to name a few, and will serve as a guide in the design of new 2D multifunctional materials.

ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE 1 (ENPP-1) INHIBITORS AND USES THEREOF

Disclosed herein are methods and compounds of augmenting and enhancing the production of type I IFNs in vivo. In some embodiments, the compounds disclosed herein are ENPP-1 inhibitors, pharmaceutical compositions, and methods for the treatment of cancer or a viral infection.

Design, synthesis, and structure-activity relationship of 7-propanamide benzoxaboroles as potent anticancer agents

Benzoxaboroles, as a novel class of bioactive molecules with unique physicochemical properties, have been shown to possess excellent antimicrobial activities with tavaborole approved in 2014 as an antifungal drug. Although urgently needed, the investigation of benzoxaboroles as anticancer agents has been lacking so far. In this study, we report the design, synthesis, and anticancer structure-activity relationship of a series of 7-propanamide benzoxaboroles. Compounds 103 and 115 showed potent activity against ovarian cancer cells with IC50 values of 33 and 21 nM, respectively. Apoptosis was induced by these compounds and colony formation was effectively inhibited. Furthermore, they also showed excellent efficacy in ovarian tumor xenograft mouse model.

Synthesis and structure-activity relationships of small-molecular di-basic esters, amides and carbamates as flaviviral protease inhibitors

Inhibitors of the flaviviral serine proteases, which are crucial for the replication of dengue and West-Nile virus, have attracted much attention over the last years. A dibasic 4-guanidinobenzoate was previously reported as inhibitor of the dengue protease with potency in the low-micromolar range. In the present study, this lead structure was modified with the intent to explore structure-activity relationships and obtain compounds with increased drug-likeness. Substitutions of the guanidine moieties, the aromatic rings, and the ester with other functionalities were evaluated. All changes were accompanied by a loss of inhibition, indicating that the 4-guanidinobenzoate scaffold is an essential element of this compound class. Further experiments indicate that the target recognition of the compounds involves the reversible formation of a covalent adduct.

ADENINE DERIVATIVES AS PROTEIN KINASE INHIBITORS

The present invention relates to a compound suitable for use as a kinase inhibitor according to general formula (I) [compound (C), herein after], or the N- oxide, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or stereoisomer thereof, formula (I) wherein A, R1, R2, R3, R3', R4, R4', X, Y, Z, T are as defined in the claims. The invention further relates to an in vitro method of inhibiting protein kinase activity which comprises contacting a protein kinase with a compound of formula (I), or the N-oxide, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or stereoisomer thereof. The invention further relates to the compounds of formula (I) per se, as well as to their use as a medicament, and for use or in a method of treatment of a disease mediated by a protein kinase selected from cancer, inflammatory disorders, cardiovascular diseases, viral induced diseases, circulatory diseases, fibro-proliferative diseases and pain sensitization disorders.