65795-95-1

Usage

Structure

Nitro derivative of indole with a nitro group at the 5th position and a phenylmethyl group at the 1st position of the indole ring

Usage

Commonly used in organic synthesis and pharmaceutical research

Biological activities

Exhibits antimicrobial, antifungal, and anticancer properties

Value

Unique structure and diverse biological activities make it a valuable compound in the development of new drugs and bioactive molecules.

Upstream product

• 3459-92-5 DBC 
• 6146-52-7 5-nitroindole 
• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 
• 501658-21-5 C₁₂H₁₈N₂O₄ 
• 100-39-0 benzyl bromide 
• 1429616-72-7 N-benzyl-N-(2,2-diethoxyethyl)-4-nitroaniline 
• 100-44-7 benzyl chloride 

Downstream Products

• 26807-73-8 5-amino-1-benzyl-(1H)-indole 
• 512787-46-1 N-(1-benzyl-1H-indole-5-yl)-methanesulfonamide 
• 120627-50-1 (1-Benzyl-5-nitro-1H-indol-4-yl)-acetonitrile 
• 120627-51-2 1-Benzyl-5-nitro-4-(toluene-4-sulfonylmethyl)-1H-indole 

Relevant academic research and scientific papers

Targeting Her2-insYVMA with Covalent Inhibitors - A Focused Compound Screening and Structure-Based Design Approach

Mutated or amplified Her2 serves as a driver of non-small cell lung cancer or mediates resistance toward the inhibition of its family member epidermal growth factor receptor with small-molecule inhibitors. To date, small-molecule inhibitors targeting Her2 which can be used in clinical routine are lacking, and therefore, the development of novel inhibitors was undertaken. In this study, the well-established pyrrolopyrimidine scaffold was modified with structural motifs identified from a screening campaign with more than 1600 compounds, which were applied against wild-type Her2 and its mutant variant Her2-A775_G776insYVMA. The resulting inhibitors were designed to covalently target a reactive cysteine in the binding site of Her2 and were further optimized by means of structure-based drug design utilizing a set of obtained complex crystal structures. In addition, the analysis of binding kinetics and absorption, distribution, metabolism, and excretion parameters as well as mass spectrometry experiments and western blot analysis substantiated our approach.

The palladium-catalyzed direct C3-cyanation of indoles using acetonitrile as the cyanide source

The ligand-free palladium-catalyzed C3-cyanation of indoles via direct C-H functionalization was achieved. This protocol, utilizing CH3CN as a green and readily available cyanide source, produced the desired products in moderate to good yields through transition-metal-catalyzed C-CN bond cleavage. This journal is

Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage

In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.

Indole derivatives or salts thereof as well as preparation method and application of indole derivatives or salts thereof

The invention belongs to the technical field of chemical medicine, and relates to an Hh (Hedgehog) signal pathway Smoothed (SMO) receptor small molecule inhibitor, in particular to indole derivativesor salts thereof with Smoothed inhibitory activity, which are shown in chemical general formula (I) in the description, as well as a preparation method and pharmaceutical composition of the indole derivatives or salts thereof. Tests on inhibitory activity of Hh signal pathways show that most compounds have better inhibitory activity on the Hh signal pathways. The invention further discloses the application of the compounds to preparation of medicines for treating diseases associated with Hh, wherein the diseases are BCC (basal cell carcinoma), MB (medullblastoma), SCLC (small cell lung cancer), medulloblastoma, rhabdomyosarcoma, or a combination of the diseases.

Catalytic Electrophilic C?H Borylation Using NHC?Boranes and Iodine Forms C2-, not C3-, Borylated Indoles

Activation of N-heterocyclic carbene boranes (NHC?BH3) by I2 enables the metal-free catalytic C?H borylation of heteroarenes with formation of H2 as the by-product in a process that uses only bench stable precursors. The borylation of indoles using NHC?BH3/I2 produces C2-borylated indoles exclusively in contrast to other catalytic electrophilic C?H borylation methods. Mechanistic studies indicate that this is due to C3 to C2 boron migration facilitated by the absence of exogenous Br?nsted bases. Thus this C?H borylation methodology proceeds under sufficiently Br?nsted acidic conditions to enable the thermodynamic C2-borylated indole isomer to be formed instead of the C3 borylated-isomer. This demonstrates that electrophilic C?H borylation can be used to access a wider range of borylated regioisomers than reported to date.

NOVEL AMINE DERIVATIVE OR SALT THEREOF

A novel amine derivative expressed by general formula (1) (in the formula: G1, G2, and G3 are the same or different and represent CH or a nitrogen atom; R1 represents a chlorine atom, an optionally-substituted C3-8 cycloalkyl group, or the like; R2 represents -COOR5 (in the formula, R5 represents a hydrogen atom or a carboxyl protective group), or the like; R3 represents a hydrogen atom, or the like; and R4 represents an optionally-substituted condensed bicyclic hydrocarbon group, an optionally-substituted bicyclic heterocyclic group, or the like), or a salt thereof is useful in procedures such as the treatment or prevention of conditions related to excessive keratinocyte proliferation.

General and efficient synthesis of 2,3-unsubstituted indoles catalyzed by acidic mesoporous molecular sieves

A general and efficient method for the synthesis of 2,3-unsubstituted indoles has been established by the intramolecular cyclization of N-benzyl 2-anilinoacetals. Acidic mesoporous molecular sieve (MCM-41-SO3H) has shown excellent catalytic activity on this transformation, and the 2,3-unsubstituted indoles bearing 7-substituent or strong electron-withdrawing substituents also could be achieved by this protocol. Moreover, the heterogeneous catalyst, MCM-41-SO3H, could be conveniently recovered and reused without obvious loss of the catalytic activity. This work will provide an economic and environmental-benign method for the construction of various indole derivatives.

Synthesis and evaluation of aniline headgroups for alkynyl thienopyrimidine dual EGFR/ErbB-2 kinase inhibitors

Aniline 'headgroups' were synthesized and incorporated into an alkynyl thienopyrimidine series of EGFR and ErbB-2 inhibitors. Potent inhibition of enzyme activity and cellular proliferation was observed. In certain instances, protein binding was reduced a

N-1H-Benzimidazol-5-ylbenzenesulfonamide derivatives as potent hPXR agonists

The Human Pregnane X Receptor (hPXR) is a nuclear receptor that regulates the expression of phase I and phase II drug-metabolizing enzymes, as well as that of drug transporters. Because this receptor plays a critical role in protecting tissues from potentially toxic endo- and xenobiotics, highly active agonists could represent novel therapeutic tools in treating several human diseases. Using an in vitro screening reporter system that allow to characterize hPXR activators and a first step of chemical modifications of an original agonist ligand (C2BA-4, 1-(2-chlorophenyl)-N-[1-(1-phenylethyl)-1H-benzimidazol-5-yl]methanesulf onamide), we identified compounds with a N-1H-benzimidazol-5-ylbenzenesulfonamide scaffold as a potent family of hPXR agonists. Further chemical modifications allowed us to identify enhanced activators, notably N-(1-benzyl-1H-benzimidazol-5-yl)-2,3,4,5,6-pentamethylbenzenesulfonamid e (6n) with an EC50 value in the subnanomolar range. Accordingly to their potent EC50, these compounds induced an efficient protection of hPXR against proteolytic digestion by trypsin even at very low ligand concentrations and were able to induce the expression of the main target genes of hPXR, CYP3A4 and CYP2B6, in primary cultures of human hepatocytes.

3-Substituted 7-phenyl-pyrroloquinolinones show potent cytotoxic activity in human cancer cell lines

A novel series of 3-alkyl-substituted 7-phenyl-3H-pyrrolo[3,2-f]quinolin-9- ones (7-PPyQs) was synthesized with the aim to optimize the cytotoxic activity of recently identified PPyQs, promising inhibitors of tubulin polymerization. All compounds inhibited the growth of 11 human tumor cell lines at submicromolar concentrations as well as two human resistant cancer sublines, A549-T12 and A549-T24. FACS analysis indicated that all compounds caused significant arrest of the A549 cell cycle in G2/M phase at 0.1 and 1 μM and a good correlation between the cytotoxicity IC50 and their ability to block the cell cycle was observed.