Category: Triazoles

Zhang, Qian published the artcileDiscovery of Triazolo-pyridazine/-pyrimidine Derivatives Bearing Aromatic (Heterocycle)-Coupled Azole Units as Class II c-Met Inhibitors, SDS of cas: 24415-66-5, the main research area is triazolopyridazine triazolopyrimidine preparation cMet kinase inhibition SAR anticancer human.

Two series of novel triazolo-pyridazine/-pyrimidine derivatives were designed, synthesized, and evaluated for their inhibitory activity against c-Met kinase, as well as three c-Met overexpressed cancer cell lines (A549, MCF-7, and HeLa) and one normal human hepatocytes cell line LO2 in vitro. The most promising compound I exhibited significant cytotoxicity against A549, MCF-7, and HeLa cell lines with IC50 values of 1.06 +/- 0.16, 1.23 +/- 0.18, and 2.73 +/- 0.33μM, resp. Moreover, the inhibitory activity of compound I against c-Met kinase (IC50 = 0.090μM) was equal to that of Foretinib (IC50 = 0.019μM). The result of the acridine orange single staining test demonstrated that compound I could remarkably induce apoptosis of A549 cells. The results of apoptosis and cycle distribution of cells showed that compound I could induce late apoptosis of A549 cells and stimulate A549 cells arresting in the G0/G1 phase. Structure-activity relationships (SARs), pharmacol. results, and docking studies indicated that the introduction of 5-methylthiazole fragment to the five-atom moiety was beneficial for the activity. So far, the existing data indicated that I may become a potential class II c-Met inhibitor.

ACS Omega published new progress about Antitumor agents. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, SDS of cas: 24415-66-5.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Maekawa, Kazuyuki published the artcileControl of seedling growth by pseudopurine and pyrimidine derivatives, Synthetic Route of 24415-66-5, the main research area is pseudopurine pyrimidine seedling growth.

The effects of ∼60 pseudopurine and guanidinopyrimidine derivatives on rice, radish, barnyard grass, and Atriplex gmelinii seedling growth were reported. Thus, I [35186-71-1] and II [37140-02-6] strongly inhibited rice seedling root growth. Some thiadiazolo[3,2-a]pyrimidine derivatives repressed leaves and stalks. III [56347-19-4] and IV [51646-15-2] and alkanesulfinyl derivatives of thiadiazolo[3,2-a]pyrimidine markedly inhibited barnyard grass but not rice. On the other hand V [275-02-5] and VI [16018-49-8] inhibited only radish germination.

Journal of the Faculty of Agriculture, Kyushu University published new progress about Atriplex gmelini. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Synthetic Route of 24415-66-5.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Liu, Luxiao published the artcileDeep eutectic solvent promoted one-pot synthesis of nitriles from alcohols, Category: triazoles, the main research area is aryl nitrile green preparation; alc tandem aerobic oxidation condensation deep eutectic solvent.

Various aryl nitriles RCN [R = Ph, 4-BrC6H4, 2-thienyl, etc.] were readily synthesized from aerobic oxidation of substituted benzyl alcs. in deep eutectic solvent composed of choline chloride and p-toluenesulfonic acid in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl, followed by condensation with hydroxylamine hydrochloride. High yields of corresponding nitriles had obtained under mild reactions conditions. This strategy belonged to a novel and environmentally benign transition-metal-free one-pot cascade process for the synthesis of nitriles.

Journal of Chemical Sciences (Berlin, Germany) published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 143426-50-0 belongs to class triazoles, name is 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, and the molecular formula is C9H9N3O, Category: triazoles.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Yuan, Shuo published the artcileBronsted acid-promoted ‘on-water’ C(sp3)-H functionalization for the synthesis of isoindolinone/[1,2,4]triazolo[1,5-a]pyrimidine derivatives targeting the SKP2-CKS1 interaction, Name: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, the main research area is trimethoxyphenyl triazolopyrimidinyl methyl isoindolinone preparation SKP2 CKS1 inhibition SAR.

An efficient Bronsted acid-promoted C(sp3)-H functionalization approach that enabled the rapid construction of biol. important isoindolinone/[1,2,4]triazolo[1,5-a]pyrimidine hybrids from 5-methyl-7-(2,4,6-trimethoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 2-formylbenzoic acid and various anilines was reported. The title compounds were generated in high to excellent yields (up to 96%) regardless of the electronic nature and steric effects of the substituents. In this reaction, an isoindolinone scaffold, one C-C single bond and two C-N bonds were formed simultaneously with high atom economy. It was concluded that the Me group linked to the electron-deficient N-heterocycles was used as a new synthetic handle for late-state diversification and may have broad applications in the field of organic and medicinal chem. Besides, the title compounds exhibited promising activity against the SKP2-CKS1 interaction.

Chinese Chemical Letters published new progress about Anilines Role: RCT (Reactant), RACT (Reactant or Reagent). 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Name: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Matsuda, Yoshiro published the artcileReaction of 4-amino-1,2,4-triazolium salts with polarized olefins, Name: 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, the main research area is aminotriazolium salt cyclization polarized olefin; triazolium salt amino cyclization polarized olefin; betaine mesomeric preparation; triazolopyrazole preparation.

The reaction of 4-amino-1,2,4-triazolium salts I (R = Me, CH2Ph, X = iodo, Br) with polarized olefins EtOCH:CR1CO2Et (R1 = CO2Et, NO2) and (MeS)2C:CXY (X = CO2Me, Y = cyano) in the presence of K2CO3 in EtOH or DMSO directly yielded the back-donated 1,6-cyclization products, mesomeric betaines II (R1 = CO2Et, NO2, R2 = H; R1 = cyano, R2 = SMe) via N-vinylimino ylides, while the reaction of the salts I with polarized olefins (MeS)2C:CXY (X = H, Y = NO2; X = SO2Ph, Y = cyano) gave the 1,5-dipolar cyclization products, pyrazoles III and [1,2,4]-triazolo[4,3-b]pyrazole IV.

Heterocycles published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 39602-93-2 belongs to class triazoles, name is 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, and the molecular formula is C3H7IN4, Name: 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Himaja, M. published the artcileSynthesis, antibacterial and insecticidal activities of a new series of 4-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-ylamino)-N-(aryl)benzamides, COA of Formula: C6H5ClN4, the main research area is chlorotriazolopyrimidine aminobenzoic acid amination; triazolopyrimidinylaminobenzoic acid preparation amidation HATU coupling reagent; aryl triazolopyrimidinylaminobenzamide preparation antibacterial insecticidal.

A new series of 4-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-ylamino)-N-(aryl)benzamides were synthesized by coupling 4-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-ylamino)benzoic acid with different substituted amines using O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) as coupling reagent. The key intermediate 4-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-ylamino)benzoic acid was synthesized by the reaction of 7-chloro-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine with p-aminobenzoic acid in ethanol. The structure of the newly synthesized compounds were confirmed by FT-IR, 1H NMR, 13C NMR and Mass spectral anal. and were evaluated for their antimicrobial and insecticidal activities. Some of the synthesized compounds exhibited potent insecticidal activity and significant antibacterial activity with respect to the standard drugs.

Indian Journal of Heterocyclic Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, COA of Formula: C6H5ClN4.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Silveira, Flavia F. published the artcileComparative study between the anti-P. falciparum activity of triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives and the identification of new PfDHODH inhibitors, Recommanded Product: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, the main research area is triazolopyrimidine derivative preparation antimalarial PfDHODH inhibitor; pyrazolopyrimidine derivative preparation antimalarial PfDHODH inhibitor; quinoline derivative preparation antimalarial PfDHODH inhibitor; Malaria; P. falciparum; PfDHODH; Pyrazolopyrimidine; Quinoline; Triazolopyrimidine.

Three series of triazolopyrimidine I [R = H, Me, CF3; R1 = Ph, 4-MeC6H4, 4-ClC6H4, etc.], pyrazolopyrimidine II [R2 = Ph, 4-MeOC6H4, 4-FC6H4, etc.] and quinoline derivatives III [R3 = Ph, 2-naphthyl, 4-ClC6H4, etc.] as P. falciparum inhibitors (3D7 strain) was reported. Some of the compounds of I, II and III exhibited anti-P. falciparum activity, with IC50 values ranging from 0.030 to 9.1μM. Compounds I were more potent than the compounds II and III. Compounds I [R = CF3; R1 = 2-naphthyl, 4-MeC6H4, 4-FC6H4, 4-F3CC6H4] were the most potent inhibitors, with IC50 values in the range of 0.030-0.086μM and were equipotent to chloroquine. In addition, the compounds were selective, showed no cytotoxic activity against the human hepatoma cell line HepG2. All compounds I inhibited PfDHODH activity in the low micromolar to low nanomolar range (IC50 values of 0.08-1.3μM) and did not show significant inhibition against the HsDHODH homolog (0-30% at 50μM). Mol. docking studies indicated the binding mode of compounds I to PfDHODH and the highest interaction affinities for the PfDHODH enzyme were in agreement with the in vitro exptl. evaluation. Thus, the most active compounds against P. falciparum parasites I [R = CF3; R1 = 4-MeC6H4, 4-FC6H4, 4-F3CC6H4, 2-naphthyl] (IC50 = 0.086μM, 0.032μM, 0.030μM, 0.050μM, resp.) and the most active inhibitor against PfDHODH I [R = CF3; R1 = 4-ClC6H4] (IC50 = 0.08μM – PfDHODH) stood out as new lead compounds for antimalarial drug discovery. Their potent in vitro activity against P. falciparum and the selective inhibition of the PfDHODH enzyme strongly suggested that this was the mechanism of action underlying this series of compounds I.

European Journal of Medicinal Chemistry published new progress about Acids Role: RCT (Reactant), RACT (Reactant or Reagent). 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Recommanded Product: 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Huang, Yangen published the artcileHighly dense nitranilates-containing nitrogen-rich cations, Formula: C3H7IN4, the main research area is high density nitrogen heterocycle cation nitranilate explosive; detonation formation enthalpy nitranilate salt explosive.

High d. energetic salts containing nitrogen-rich cations and the nitranilic anion were readily synthesized in high yield by metathesis reactions of sodium nitranilate and an appropriate halide. All of the new compounds were fully characterized by elemental, spectral (IR, 1H, 13C NMR), and thermal (DSC) analyses. The structure of hydrazinium nitranilate was also determined by single-crystal X-ray anal. The high symmetry and oxygen content of the anion give these salts extensive hydrogen bonding capability which further results in the high densities, low water solubilities, and high thermal stabilities (Td >200°) of these compounds Theor. performance calculations were carried out by using Gaussian 03 and Cheetah 5.0. The calculated detonation pressures (P) for these new salts fall between 17.5 GPa and 31.7 GPa, and the detonation velocities (νD) range between 7022 m/s and 8638 m/s.

Chemistry – A European Journal published new progress about Crystal structure (of hydrazinium nitranilate). 39602-93-2 belongs to class triazoles, name is 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, and the molecular formula is C3H7IN4, Formula: C3H7IN4.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Stanovnik, Branko published the artcileAn unequivocal synthesis of some substituted 1,2,4-triazolo[1,5-a]pyrimidines, Synthetic Route of 24415-66-5, the main research area is aminopyrimidine condensation formamide acetal; intramol cyclocondensation chlorohydroxyiminomethyleneaminomethylpyrimidine; pyrimidine hydroxyiminomethyleneamino cyclization; triazolopyrimidine chloro methyl.

Condensation of 2-amino-4-chloro-6-methylpyrimidine (I, R = NH2) with Me2NCH(OMe)2 gave imino derivative I (R = N:CHNMe2) (II) in 22% yield. Condensation of II with HONH2.HCl gave 93% I (R = NHCH:NOH), which underwent cyclization with polyphosphoric acid to give triazolopyrimidine III (R1 = Me, R2 = Cl) in 11% yield. Reductive dechlorination gave 90% III (R1 = Me, R2 = H). Cyclocondensation of 3-amino-1,2,4-triazole with EtO2CCH2Ac, chlorination, and reductive dechlorination gave isomeric triazolopyrimidine III (R1 = H, R2 = Me).

Monatshefte fuer Chemie published new progress about Cyclocondensation reaction, regioselective. 24415-66-5 belongs to class triazoles, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and the molecular formula is C6H5ClN4, Synthetic Route of 24415-66-5.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Shackelford, Scott A. published the artcilePairing heterocyclic cations with closo-icosahedral borane and carborane anions. I. benchtop aqueous synthesis of binary triazolium and imidazolium salts with limited water solubility. [Erratum to document cited in CA151:033689], Product Details of C3H7IN4, the main research area is erratum pairing triazolium imidazolium cation icosahedral borane carborane anion; crystal mol structure salt erratum.

On page 2623, the corresponding author e-mail address, “”[email protected]””, was incorrectly given, and should read: “”scottshack@roadrunner””. On page 2626, in Table 3, in row 11, in column 1, the designation X = H for the 1-ethyl-3-methylimidazolium carborane salt 11, was incorrectly given, and should read: “”X = CH3″”.

Organic Letters published new progress about Anions (borane and carborane anions). 39602-93-2 belongs to class triazoles, name is 4-Amino-1-methyl-4H-1,2,4-triazol-1-ium iodide, and the molecular formula is C3H7IN4, Product Details of C3H7IN4.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics