62103-13-3

Upstream product

• 112-30-1 1-Decanol 
• 112-29-8 1-bromo dodecane 
• 98750-95-9 (decylselenonyl)benzene 
• 53059-89-5 1-(tert-butyldimethylsilyl)oxydecane 
• 99-24-1 methyl galloate 
• 106-96-7 propargyl bromide 
• 51250-91-0 bis(p-nitrophenyl) azidophosphonate 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 41233-29-8 methanesulfonic acid decyl ester 
• 872-05-9 1-Decene 
• 2050-77-3 Iododecane 

Downstream Products

• 1009089-51-3 1-decyl-4-phenyl-1H-[1,2,3]triazole 
• 1174917-37-3 3,5-bis-(5-hexylcarbamoyl-pentyloxy)-benzoic acid 9-(3-decyl-3H-[1,2,3]triazol-4-yl)-nonyl ester 
• 1253801-12-5 4-amino-N-((1-decyl-1H-1,2,3-triazol-4-yl)methyl)benzenesulfonamide 
• 1314535-18-6 3-((1-decyl-1H-1,2,3-triazol-4-yl)methyl)-2-ethyl-7-phenyl-5-(trifluoromethyl)pyrido[2,3-d]pyrimidin-4(3H)-one 
• 1314535-14-2 3-((1-decyl-1H-1,2,3-triazol-4-yl)methyl)-2-methyl-7-phenyl-5-(trifluoromethyl)pyrido[2,3-d]pyrimidin-4(3H)-one 
• 1314535-11-9 3-((1-decyl-1H-1,2,3-triazol-4-yl)methyl)-7-phenyl-5-(trifluoromethyl)pyrido[2,3-d]pyrimidine-4(3H)-one 
• 1300743-71-8 1-decyl-4-p-tolyl-1H-1,2,3-triazole 
• 1300743-85-4 1-decyl-4-(4-(1-decyl-1H-1,2,3-triazol-4-yl)-2,5-bis(octyloxy)phenyl)-1H-1,2,3-triazole 
• 1300743-73-0 1-decyl-4-p-methoxyphenyl-1H-1,2,3-triazol 
• 1300743-86-5 4-(3,5-bis(1-decyl-1H-1,2,3-triazol-4-yl)phenyl)-1-decyl-1H-1,2,3-triazole 
• 1300743-84-3 1-decyl-4-(4-ethynylphenyl)-1H-1,2,3-triazole 
• 1258941-47-7 1-decyl-4-(3-(1-decyl-1H-1,2,3-triazol-4-yl)phenyl)-1H-1,2,3-triazole 
• 1300743-74-1 1-decyl-4-o-methoxyphenyl-1H-1,2,3-triazol 
• 1300743-72-9 1-decyl-4-o-tolyl-1H-1,2,3-triazol 

Relevant academic research and scientific papers

Effect of 1,2,3-triazole salts, non-classical bioisosteres of miltefosine, on Leishmania amazonensis

Here, we report the effect of new non-classical bioisosteres of miltefosine on Leishmania amazonensis. Fifteen compounds were synthesized and the compound dhmtAc, containing an acetate anion, a side chain of 10 carbon atoms linked to N-1 and a methyl group linked to N-3, showed high and selective biological activity against L. amazonensis. On the intracellular amastigotes, stages of the parasite related to human disease, the IC50 values were near or similar to the 1.0?μM (0.9, 0.8 and 1.0?μM on L. amazonensis-WT, and two transgenic L. amazonensis expressing GFP and RFP, respectively), being more active than miltefosine. Furthermore, dhmtAc did not show toxic effects on human erythrocytes and macrophages (CC50?=?115.9?μM) being more destructive to the intracellular parasites (selectivity index?>?115). Promastigotes and intramacrophage amastigotes treated with dhmtAc showed low capacity for reversion of the effect of the compound. A study of the mechanism of action of this compound showed some features of metazoan apoptosis, including cell volume decreases, loss of mitochondrial membrane potential, ROS production, an increase in the intracellular lipid bodies, in situ labeling of DNA fragments by TUNEL labeling and phosphatidylserine exposure to the outerleaflet of the plasma membrane. In addition, the plasma membrane disruption, revealed by PI labeling, suggests cell death by necrosis. No increase in autophagic vacuoles formation in treated promastigotes was observed. Taken together, the data indicate that the bioisostere of miltefosine, dhmtAc, has promising antileishmanial activity that is mediated via apoptosis and necrosis.

Thermochemistry of organic azides revisited Dedicated to Prof. Ch. Rüchardt on the Occasion of His 85th Birthday

Highly pure samples of 4-nitro-phenyl azide, 1-octyl azide and 1 decyl-azide were prepared for thermochemical studies. Vapour pressures over the solid and the liquid sample of 4-nitro-phenyl azide have been determined by the transpiration method. The molar enthalpies of vaporization/sublimation for this compound were derived from the temperature dependencies of vapour pressures. The molar enthalpy of fusion of 4-nitro-phenyl azide was measured by DSC. The measured data set for 4-nitro-phenyl azide was successfully checked for internal consistency. Molar enthalpies of vaporization of 1-octyl azide and 1 decyl-azide were measured by transpiration. The molar enthalpies of formation of the liquid 1-octyl azide and 1 decyl-azides were derived from the combustion calorimetry. New experimental results for these organic azides have been used to derive their molar enthalpies of formation in the gas state and for comparison with results from quantum-chemical method G4.

Antitubercular activity of 1,2,3-triazolyl fatty acid derivatives

A collection of 1,2,3-triazoles unsaturated fatty acid mimics were efficiently synthesized by click chemistry. The 1,4-disubstituted analogs prepared covered different alkyl chain lengths and triazole positions. The compounds were subsequently tested against Mycobacterium tuberculosis, being most of them active with some of the analogs displaying activity at micromolar concentration. The most potent member of the series has the triazole moiety on the C-2 position with a carbon chain of eight or ten carbon atoms. The 1,5-isomers of the most active analog were significantly less active than the original isomer. The activity of the selected hit was assayed on several clinical MTB multi-drug resistant strains providing the same MIC.

Adding diversity to ruthenium(II)-arene anticancer (RAPTA) compounds via click chemistry: The influence of hydrophobic chains

The application of click chemistry to develop libraries of organometallic ruthenium-arene complexes with potential anticancer properties has been investigated. A series of ruthenium-imidazole-triazole complexes, with hydrophobic tails, were prepared from a common precursor via click chemistry. The tail could be attached to the ligand prior to coordination to the ruthenium complex or following coordination, the former giving the product in superior yield. The complexes were screened for cytotoxicity in tumourigenic and non-tumourigenic cell lines, and while the compounds were only moderately cytotoxic, good selectivity for tumourigenic cells was observed.

Synthesis of new chrysin derivatives with substantial antibiofilm activity

Abstract: Multidrug resistance mechanism of microorganisms towards conventional antimicrobials nowadays faces a common health problem. So, searching and development of new antibacterials are in the frontier areas of biochemistry. Functionalizations of various natural products or synthesis of compounds through molecular modeling followed by virtual screening are the ways to obtain potential leads. Chrysin is one of the plant secondary metabolites and is ubiquitously present in majority of plants. It has multi-dimensional potentiality however, with a very low bioavailability causing a very low efficacy. Very few chrysin derivatives possessing antimicrobial activity with a low anti-biofilm efficacy have been found in the literature. Thus, it has been attempted to synthesize a series of new chrysin derivatives (CDs). In this study, twenty-two new derivatives have been synthesized via its 7-OH modulation and antibiofilm activity was evaluated against a model bacterium viz. Escherichia coli MTCC 40 (Gram negative). Eleven CDs coded as 2a, 2b, 2c, 2e, 2f, 2g, 2h, 2i, 3j, 3k and 3l have been found more potent compared to chrysin (precursor of CDs) against planktonic form of E. coli. Biofilm inhibition studies indicated a noteworthy results for 2a (93.57%), 2b (92.14%), 2f (92.14%) and 3l (93.57%) compared to chrysin (33.57%). E. coli motility was also highly restricted by 2a, 2b, 2f and 3l than chrysin at their sub-inhibitory concentrations. Solubility studies indicated an extended-release of 2a, 2b, 2f and 3l in physiological systems. Relatively higher bioavailability of 2a, 2b, 2f and 3l than chrysin was revealed from the dissolution experiments and was further validated through in silico ADME-based SAR analysis. Hence, this study is more interesting in regard to antibacterial potentiality of chrysin derivatives against Escherichia coli MTCC 40 (Gram negative). Thus, this article might be useful for further design and development of new leads in the context of biofilm-associated bacterial infections. Graphic abstract: [Figure not available: see fulltext.].

Synthesis, surface properties and bioactivity of novel 4-Substituted 1,2,3-Triazole quaternary ammonium surfactants

Series of novel 1,2,3-triazole based quaternary ammonium surfactants with different hydrophobic chain length and head group substituents were synthetized and characterized. Their surface properties and aggregation behavior were discussed on the basis of tensiometry and conductimetry measurements by using several parameters, including critical micelle concentration (CMC), surface tension at the cmc (γcmc), adsorption efficiency (pC20), effectiveness of surface tension reduction (Πcmc), minimum surface area occupied by a molecule (Amin) at the air ? water interface and standard Gibbs free energy of micellization ΔGMic0. These heterocyclic surfactants exhibit much lower CMC values as compared with those reported for conventional alkyltriethyl ammoniums and alkylbenzyldiethyl ammonium salts. Their micelles formation and surface adsorption in aqueous media can be tuned out through a suitable choice of the substituent attached to the polar head. Triethyl ammonium (CnTzTEA] and diethylbenzyl ammonium surfactants (CnTzBz) showed improved micellization behavior than tetradecyl diethyl ammonium (CnTzC14) homologous. The in vitro antimicrobial activity of the surfactants against B. subtilis, P. aerugenosa and A.niger strains was also investigated. CnTzBz series possessing benzyl chain showed better activity against all the tested microorganisms with minimum inhibitory concentration ranging from 6 to 57 μmol/L.

Room temperature perylene based columnar liquid crystals as solid-state fluorescent emitters in solution-processable organic light-emitting diodes

The finding of pure organic emitter materials is the need of the hour for the mass production of cost-effective and metal-free fluorescent organic light-emitting diodes (FOLEDs). In this paper, we report a new series of perylene tetraesters (PTEs) that exhibit the room temperature columnar (Col) mesophase and can act as efficient fluorescent emitter materials in OLEDs. The molecular design involves the attachment of triazole moieties with the PTE discotic coreviaclick chemistry. Triazole groups were chosen as they can improve the electron transport as well as tune the luminescence behavior of discogens. All the PTE derivatives3a-dexhibited ordered columnar rectangular (Colro) mesophases at ambient temperatures suitable for various device applications. The electron mobility of perylene tetraester derivative3awas measured in the mesophase by time of flight (TOF) technique and found to be 0.014 cm2V?1s?1. However, the balanced hole and electron charge transport behaviour was observed in fabricated hole-only and electron-only devices. Taking advantage of both charge transport and the luminescence nature of the PTE derivative in OLEDs, a series of devices were fabricated by utilizing3aas a sole emitter and in the dispersed form at 1, 5 and 8 wt% with the CBP host and at 5 wt% in the SimCP2 host. A significantly high value of the external quantum efficiency (EQE) of 6.5% is obtained in doped devices with the CBP host at 5 wt% dopant (3a) concentration with CIE coordinates of (0.37, 0.53) corresponding to green color. The obtained high EQE value will certainly offer an important step forward to expand the application of smart DLC materials in OLEDs.

Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,2,3-Triazole-5-carboxamides Using Dimethyl Carbonate as Sustainable Solvent

A simple and direct palladium-catalyzed aminocarbonylation of 5-iodo-1,2,3-triazoles backbone for the incorporation of an amide functional group is presented. The approach is based on the palladium catalyzed carbonylative coupling reaction of iodo-triazole with different amines employing formic acid and sulfuric acid as CO source (Morgan's reaction) to provide the 1,2,3-triazole-5-carboxamides in good to excellent yields. The important features of this methodology include short reaction time, high yields, the use of dimethyl carbonate as a sustainable solvent, and the use of efficient alternative source of carbon monoxide, avoiding pressurized cylinder. The methodology described herein for the synthesis of 1,4,5-trisubstituted 1,2,3-triazole-5-carboxamides, can offers an alternative path for functionalization of other heterocycles.

Thiophenol-formaldehyde triazole causes apoptosis induction in ovary cancer cells and prevents tumor growth formation in mice model

In the present study a library of thiophenol-formaldehyde-triazole (TFT) derivatives was synthesized and screened against CAOV3, CAOV4 and ES-2 ovary cancer cell lines. Initial screening revealed that five-compounds 5a, 5b, 5j, 5h and 5i inhibited the viability of tested cell lines. Analysis of apoptosis revealed that increase in compound 5a (most active) concentration from 0.25 to 2.0 μM enhanced apoptotic cell proportion. Transwell assay showed reduction in invasive potential of CAOV3 cells on treatment with compound 5a. In wound healing assay increasing the concentration of compound 5a from 0.5 to 2.0 μM caused a significant (P 0.05) decrease in the migration potential. Western blotting showed that compound 5a treatment markedly decreased the level of matrix metalloproteinase (MMP)-2 and ?9 in CAOV3 cells. Treatment of CAOV3 cells with compound 5a caused a marked decrease in Focal Adhesion Kinase (FAK) activation. Tumor growth was inhibited in the compound 5a treated mice markedly than those of untreated group. The tumor metastasis to liver, intestine, spleen and peritoneal cavity was markedly decreased in mice treated with 10 mg/kg dose of compound 5a. Examination of Von Willebrand factor (vWF) expression in liver, intestinal and pulmonary lesions showed a marked decrease in the compound 5a-treated mice. The infiltration of macrophages in the metastatic lesions showed a significant decrease in compound 5a-treated mice. In conclusion, the compound 5a inhibited ovary cancer cell viability and induced apoptosis through decrease in expression of vWF and metalloproteinase, suppression of FAK activation and decrease in infiltration of macrophages. The compound 5a therefore can be investigated further for the treatment of ovary cancer.

NCN-Coordinating Ligands based on Pyrene Structure with Potential Application in Organic Electronics

Five novel derivatives of pyrene, substituted at positions 1,3,6,8 with 4-(2,2-dimethylpropyloxy)pyridine (P1), 4-decyloxypyridine (P2), 4-pentylpyridine (P3), 1-decyl-1,2,3-triazole (P4), and 1-benzyl-1,2,3-triazole (P5), are obtained through a Suzuki–Miyaura cross-coupling reaction or CuI-catalyzed 1,3-dipolar cycloaddition reaction, respectively, and characterized thoroughly. TGA measurements reveal the high thermal stability of the compounds. Pyrene derivatives P1–P5 all show photoluminescence (PL) quantum yields (Φ) of approximately 75 % in solution. Solid-state photo- and electroluminescence characteristics of selected compounds as organic light-emitting diodes are tested. In the guest–host configuration, two matrixes, that is, poly(N-vinylcarbazole) (PVK) and a binary matrix consisting of PVK and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt %), are applied. The diodes show red, green, or blue electroluminescence, depending on both the compound chemical structure and the actual device architecture. In addition, theoretical studies (DFT and TD-DFT) provide a deeper understanding of the experimental results.