124940-34-7

Usage

Chemical class

Triazole derivative and aldehyde

Usage

Building block in the synthesis of various organic compounds

Application

Medicinal chemistry, particularly in the development of pharmaceutical drugs

Suitability

Synthesis of heterocyclic compounds and as a versatile intermediate in the production of pharmaceuticals, agrochemicals, and other fine chemicals

Structural feature

Benzyl group, allowing for easy modification and functionalization

Role

Valuable starting material in organic synthesis

Upstream product

• 624-67-9 Propargylic aldehyde 
• 622-79-7 benzyl azide 
• 28798-81-4 (1-benzyl-[1,2,3]triazol-4-yl)methanol 
• 129027-62-9 [1-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-meth-(E)-ylidene]-phenyl-amine 
• 133902-60-0 [1-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-meth-(E)-ylidene]-phenyl-amine 
• 133902-48-4 Benzyl-[1-(1-phenyl-1H-[1,2,3]triazol-4-yl)-meth-(E)-ylidene]-amine 
• 133735-81-6 1-benzyl-4-(diethoxymethyl)-1H-1,2,3-triazole 
• 100-39-0 benzyl bromide 
• 107-19-7 propargyl alcohol 
• 107-02-8 acrolein 
• 100-44-7 benzyl chloride 
• 10160-87-9 Propiolaldehyde diethyl acetal 
• 113934-26-2 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxaldehyde 
• 100-46-9 benzylamine 

Downstream Products

• 124940-35-8 1-benzyl-4-(1-methoxycarbonyl-2-oxiranyl)-1,2,3-triazole 
• 915362-45-7 C₂₆H₁₈Cl₂FN₇ 
• 79318-05-1 1-benzyl-4-ethynyl-1H-1,2,3-triazole 
• 1252653-67-0 C₂₆H₂₄N₈ 
• 1034194-08-5 N,N-bis[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]prop-2-yn-1-amine 
• 28798-81-4 (1-benzyl-[1,2,3]triazol-4-yl)methanol 

Relevant academic research and scientific papers

Synthesis of fluorinated triazole and isoxazole derivatives by electrochemical fluorination

Partially fluorinated triazole derivatives were synthesized through anodic fluorination of alkynes having arylthio group and following Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) with benzyl azide. The other route toward the fluorinated triazoles,

Triazolyl RuII, RhIII OsII, and IrIII Complexes as Potential Anticancer Agents: Synthesis, Structure Elucidation, Cytotoxicity, and DNA Model Interaction Studies

Novel conjugated ruthenium(II), rhodium(III), and iridium(III) organometallic complexes of triazoles 1 and 2 synthesized and evaluated for anticancer activity against cervical (HeLa), kidney (HEK293), nonsmall lung cancer (A549), and leukemia (MT4) cancer cell lines are reported herein. The complexes are κ2-N,C coordinated and have the formula [ML(Ar)Cl] (where L is 1-benzyl-4-phenyl-1H-1,2,3-triazole for 1 and 1-benzyl-4-hydroxymethyl-1H-1,2,3-triazole for 2, Ar is p-cymene for RuII and OsII and Cp? for RhIII and IrIII, and M is metal). NMR studies, including HMBC and NOESY, were employed to unambiguously elucidate their structures and provide their conformational information in solution. Single-crystal X-ray diffraction data have been used to establish the solid-state structures of selected complexes, which further confirm the structural elucidation by NMR. Dynamic NMR studies, such as differential transferred NOE, have been employed to distinguish between isomers 1a_I and 1a_II of ruthenium(II) complexes of triazole 1. The rhodium(III) (1b) and iridium(III) (1c) complexes exhibited good cytotoxic activities (CC50 = 4-6 μM) comparable to that of the drug auranofin against lung cancer A549 cell lines (CC50 = 4.69 μM). While triazole 1 based ruthenium(II) (1a) and osmium(II) (1d) complexes displayed modest anticancer activities against HeLa and HEK293 cell lines, the analogous rhodium(III) and iridium(III) complexes exhibited good potential (CC50 = 9-54 μM versus auranofin (3-9 μM)) against these cancer cell lines. Insightful NMR studies on the interaction between the DNA model guanosine 5′-GMP and the complexes 1b,c reveal a possible mode of action of the aquated complexes involving carbenylation with DNA bases or purines through the triazolyl proton H-5. From the findings, these complexes could possibly confer their cytotoxic activities through intercalation with the DNA of pathological cells. Therefore, carbenylation of the triazolylrhodium(III) and iridium(III) complexes by DNA guanosine 5′-GMP is proposed as a novel mode of DNA intercalation of these complexes in cancer cells.

Synthesis, antiproliferative and antitrypanosomal activities, and DNA binding of novel 6-amidino-2-arylbenzothiazoles

A series of 6-amidinobenzothiazoles, linked via phenoxymethylene or directly to the 1,2,3-triazole ring with a p-substituted phenyl or benzyl moiety, were synthesised and evaluated in?vitro against four human tumour cell lines and the protozoan parasite T

Tuning the optical properties of BODIPY dyes by N-rich heterocycle conjugation using a combined synthesis and computational approach

The increased number of N-atoms induced a blueshift in absorption and a gain in fluorescence quantum yield, from 750 nm and ～0% for pyrrole to 635 nm and ～40% for triazole, respectively. DFT calculations indicated a decrease in HOMO energy levels with the

Selective aerobic oxidation of benzylic and allylic alcohols catalyzed by Cu(OAc)2/TEMPO/Et2NH

Selective oxidation of benzylic and allylic alcohols to their corresponding aldehyde/ketone derivative without affecting saturated alcohols is still a challenging endeavor in organic synthesis. Various metal complexes, especially the copper complexes in the presence of TEMPO are being used very often for such transformations under aerobic conditions, but they are not selective to allylic and benzylic alcohols. The use of copper salt for oxidation of alcohols in the absence of a ligand are very scarcely studied except for the one catalyzed by CuCl/TEMPO where chloride inhibition and lack of selective oxidation have been noted upon use of CuCl2. Herein we report a Cu(OAc)2 catalyzed and TEMPO mediated selective aerobic oxidation of benzylic and allylic alcohols to aldehyde/ketone in the presence of Et2NH. The method avoids pre-synthesis of the catalyst as in the case of Cu(II)/(I) complexes/TEMPO catalyzed oxidation reactions, requires low catalyst loading, employs cheaper copper salt, and gives excellent selectivity for oxidation of benzylic and allylic alcohols.

Triazole-based, optically-pure metallosupramolecules; highly potent and selective anticancer compounds

Functionalised triazole aldehydes are used in the highly selective self-assembly of water-compatible, optically pure, low symmetry Fe(ii)- and Zn(ii)-based metallohelices. Sub-micromolar antiproliferative activity is observed against various cancerous cel

Triazolecarbaldehyde Reagents for One-Step N-Terminal Protein Modification

Site-specific modification of peptides and proteins is a key aspect of protein engineering. We developed a method for modification of the N terminus of proteins using 1H-1,2,3-triazole-4-carbaldehyde (TA4C) derivatives, which can be prepared in one step. The N-terminal specific labeling of bioactive peptides and proteins with the TA4C derivatives proceeds under mild reaction conditions in excellent conversion (angiotensin I: 92 %, ribonuclease A: 90 %). This method enables site-specific conjugation of various functional molecules such as fluorophores, biotin, and polyethylene glycol attached to the triazole ring to the N terminus. Furthermore, a functional molecule modified with a primary amine moiety can be directly converted into a TA4C derivative through a Dimroth rearrangement reaction with 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbaldehyde. This method can be used to obtain N-terminal-modified proteins via only two steps: 1) convenient preparation of a TA4C derivative with a functional group and 2) modification of the N terminus of the protein with the TA4C derivative.

A molybdenum based metallomicellar catalyst for controlled and chemoselective oxidation of activated alcohols in aqueous medium

A surfactant based oxodiperoxo molybdenum complex, which could activate molecular oxygen, has been employed as a catalyst for controlled oxidation of benzylic alcohols to corresponding carbonyls. The oxidation reactions were carried out under aqueous environment, however, in the absence of any extraneous base or co-catalyst. Sensitive/oxidizable functional groups like cyano, sulfide, hydroxyl, aryl-hydroxyl, alkene (internal/terminal), alkyne (internal/terminal), and acetal were tolerated during the transformations. Such selectivity is attributed to the mild nature of the catalyst. The methodology could also be scaled-up for multi-gram synthesis and the protocol is likely to find practical use since it requires an inexpensive recyclable-catalyst and easily available oxidant (under green conditions). A plausible mechanism is proposed with the help of preliminary computational study.

Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles

A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.

Synthesis, spectroscopic characterization, and DFT studies of 1,2,3-triazole-based organosilicon compounds

A series of triorgnosilicon compounds containing 1,2,3-triazole cores, tris(trimethylsilyl)ethyl) 1,2,3-triazoles (TTMSTs), tris(dimethyl(phenyl)silyl)ethyl) 1,2,3-triazoles (TDMPSTs), and bis(trimethylsilyl)vinyl) 1,2,3-triazoles (BTMSVTs) was synthesized and characterized by elemental analysis, FT-IR, 1H, 13C NMR spectroscopy, and density functional theory (DFT). The structure of the synthesized compounds was optimized using the B3LYP method of DFT at 6–311++G(d) basis set. Conjugate interactions or charge transfer in molecular systems was investigated using natural bond orbital (NBO) analysis. In addition, the FMOs (frontier molecular orbitals) and the associated band gaps were calculated and depicted. The mapped molecular electrostatic potential (MEP) surfaces of the title compounds were also calculated with the same level of theory.