81524-74-5

Usage

InChI:InChI=1/C8H6N4/c9-12-11-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H

Upstream product

• 5192-03-0 5-amino-1H-indole 
• 6146-52-7 5-nitroindole 
• 10075-50-0 5-bromo-1H-indole 
• 16066-91-4 5-iodo-1H-indole 
• 144104-59-6 1H-indole-5-boronic acid 

Downstream Products

• 1266605-81-5 C₂₅H₂₇F₂N₉O 
• 1397395-29-7 1-(indol-5-yl)-4-cyclohexyl-1H-1,2,3-triazole 
• 1421345-22-3 C₂₁H₁₇N₅O₃ 
• 1421345-23-4 C₂₁H₁₇N₅O₃ 
• 1608463-99-5 (S)-1-(1-(1H-indol-5-yl)-1H-1,2,3-triazol-4-yl)-3-(2-((S)-3-(biphenyl-4-yl)-2-hydroxypropoxy)ethoxy)propan-2-ol 

Relevant academic research and scientific papers

ISOINDOLINE COMPOUND, AND PREPARATION METHOD, PHARMACEUTICAL COMPOSITION, AND APPLICATION OF ISOINDOLINE COMPOUND

The present invention relates to an isoindoline compound as represented by general formula (I) and used as a CRBN regulator, and a preparation method, a pharmaceutical composition, and an application of the isoindoline compound. Specifically, a class of polysubstituted isoindoline compound provided in the present invention, as a class of CRL4CRBN E3 ubiquitin ligase regulator having a novel structure, has good anti-tumor activity and immunoregulatory activity, and can be used for preparing drugs for treating diseases associated with a CRL4CRBN E3 ubiquitin ligase.

Chan-Lam-type Azidation and One-Pot CuAAC under CuI-Zeolite Catalysis

The copper(I)-exchanged zeolite CuI-USY proved to efficiently catalyze the direct azidation of arylboronic acids with sodium azide under simple and practical conditions, namely at room temperature under air with methanol as solvent and without any additive. This easy-to-prepare and cheap catalytic material has been demonstrated to be recyclable and the mild azidation conditions further showed good functional-group tolerance, leading to a variety of substituted (hetero)aryl azides (18 examples). Interestingly, the azidation reaction has been successfully coupled to a CuAAC reaction, thus allowing access to triazoles from arylboronic acids via a one-pot CuI-catalyzed process.

Synthesis and antimicrobial activity of 4-substituted 1,2,3-triazole-coumarin derivatives

A new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3) or N-propargylated coumarin (6) with alkyl or aryl azides. Based on their minimal inhibitory concentrations (MICs) against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis (MIC = 12.5–50 μg/mL). Moreover, the synthesized triazoles show relatively low toxicity against human erythrocytes.

QUINOLIN-2-ONE DERIVATIVES

Compounds of the formula (I) in which X1, X2, X3, X4, R1, R2, R3, Q and Y have the meanings indicated in Claim 1, are inhibitors of c-Kit kinase, and can be employed for the treatment of cancer.

Palladium-catalyzed cross-coupling reaction of azides with isocyanides

An efficient palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides with excellent yields. This method shows a broad substrate scope, including not only aryl azides, but also unactivated benzyl and alkyl azides. Furthermore, from readily available substrates, Pd-catalyzed coupling with a tandem amine insertion cascade to obtain unsymmetric trisubstituted guanidines has been achieved in a one-pot fashion.

Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands

The dopamine D3 receptor (D3R) is a target of pharmacotherapeutic interest in a variety of neurological disorders including schizophrenia, Parkinson's disease, restless leg syndrome, and drug addiction. A common molecular template used in the development of D3R-selective antagonists and partial agonists incorporates a butylamide linker between two pharmacophores, a phenylpiperazine moiety and an extended aryl ring system. The series of compounds described herein incorporates a change to that chemical template, replacing the amide functional group in the linker chain with a 1,2,3-triazole group. Although the amide linker in the 4-phenylpiperazine class of D3R ligands has been previously deemed critical for high D3R affinity and selectivity, the 1,2,3-triazole moiety serves as a suitable bioisosteric replacement and maintains desired D3R-binding functionality of the compounds. Additionally, using mouse liver microsomes to evaluate CYP450-mediated phase I metabolism, we determined that novel 1,2,3-triazole-containing compounds modestly improves metabolic stability compared to amide-containing analogues. The 1,2,3-triazole moiety allows for the modular attachment of chemical subunit libraries using copper-catalyzed azide-alkyne cycloaddition click chemistry, increasing the range of chemical entities that can be designed, synthesized, and developed toward D3R-selective therapeutic agents.

Biological evaluation of new mimetics of annonaceous acetogenins: Alteration of right scaffold by click linkage with aromatic functionalities

A small library of analogues of annonaceous acetogenins through click linkage with aromatic moieties is established using a convergent modular fragment-assembly approach. These analogues exhibited low micromolar inhibitory activities against the proliferation of several human cancer cell lines. Structure-activity relationship (SAR) of these analogues indicates that replacement of the methoxy groups of ubiquinone ring with methyl groups is proved to be a useful strategy for improving the anticancer activity of quinone-acetogenin hybrids.

Copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate)-catalyzed coupling of sodium azide with aryl iodides/boronic acids to aryl azides or aryl amines

This work reports an efficient protocol for the coupling reaction of aryl iodides/boronic acids with sodium azide to aryl azides/amines in the presence of copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate) Cu(TMHD)2 catalyst. The Cu(TMHD)2 catalyst is a structurally well-defined, O-containing, air- and moisture-stable, transition-metal complex and works at mild reaction conditions. It was observed that aryl azides can be reduced further to corresponding aniline derivatives using the same catalyst under basic reaction conditions for a prolonged period. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Synthesis and biological evaluation of triazole-containing N-acyl homoserine lactones as quorum sensing modulators

Many bacterial species are capable of assessing their local population densities through a cell-cell signaling mechanism termed quorum sensing (QS). This intercellular communication process is mediated by small molecule or peptide ligands and their cognate protein receptors. Numerous pathogens use QS to initiate virulence once they achieve a threshold cell number on a host. Consequently, approaches to intercept QS have attracted considerable attention as potential anti-infective therapies. Our interest in the development of small molecule tools to modulate QS pathways motivated us to evaluate triazole-containing analogs of natural N-acyl l-homoserine lactone (AHL) signals as non-native QS agonists and antagonists in Gram-negative bacteria. We synthesized 72 triazole derivatives of five broad structure types in high yields and purities using efficient Cu(i)-catalyzed azide-alkyne couplings. These compounds were evaluated for their ability to activate or inhibit two QS receptors from two prevalent pathogens-LasR from Pseudomonas aeruginosa and AbaR from Acinetobacter baumannii-using bacterial reporter strains. Several triazole derivatives were identified that were capable of strongly modulating the activity of LasR and AbaR. These compounds represent a new and synthetically accessible class of AHL analogs, and could find utility as chemical tools to study QS and its role in bacterial virulence.

Recyclable clay supported Cu (II) catalyzed tandem one-pot synthesis of 1-aryl-1,2,3-triazoles

Montmorillonite KSF clay supported CuO nanoparticles efficiently catalyzes one-pot aromatic azidonation of aryl boronic acids followed by regioselective azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction producing corresponding 1-aryl-1,2,3-triazole derivatives at room temperature in excellent yields without use of any additives. Investigations on mechanism of CuAAC revealed that sodium azide, which is used as azidonating reagent in one-pot protocol reduces Cu(II) to click-active Cu(I). The catalytic efficiency of another Cu(II) source CuSO4 in combination with NaN3 for this one-pot CuAAC protocol, further supported our mechanism. This is the first report for use of Cu(II)/NaN3 catalytic system for CuAAC protocol. The clay-Cu(II) catalyst being ligand-free, leaching-free, easy to synthesize from inexpensive commercially available precursors, recyclable, and environmentally friendly will be highly useful for economical synthesis of 1,4-disubstituted 1,2,3-triazoles.