1H-1,2,3-triazole - CAS 288-36-8
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
1H-1,2,3-triazole
Catalog Number:
288-36-8
Synonyms:
LABOTEST-BB LT02056574; 1H-1,2,3-TRIAZOLE; 1,2,3-TRIAZOLE; 1,2,3-1H-TRIAZOLE; TRIAZOLE(1,2,3-); 1,2,3-Triazol; 1H-1,2,3-Triazol; Osotriazole
CAS Number:
288-36-8
Description:
A potent IDO inhibitor
Molecular Weight:
69.07
Molecular Formula:
C2H3N3
Quantity:
Grams-Kilos
Quality Standard:
In-house
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1=NNN=C1
InChI:
1S/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5)
InChIKey:
QWENRTYMTSOGBR-UHFFFAOYSA-N
Targets:
IDO
Chemical Structure
CAS 288-36-8 1H-1,2,3-triazole

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Reference Reading


1.Crystal structure of 3-O-benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-yl)-1,2-O-iso-propyl-idene-α-d-erythro-furan-ose.
Semjonovs N1, Rjabovs V1, Stepanovs D2, Turks M1. Acta Crystallogr E Crystallogr Commun. 2015 Nov 28;71(Pt 12):1542-4. doi: 10.1107/S2056989015022434. eCollection 2015.
The title compound, C23H25N3O4, {systematic name: 1-benzyl-4-[(3aR,5R,6R,6aR)-6-benz-yloxy-2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxol-5-yl]-1H-1,2,3-triazole}, consists of a substituted 2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxole. The furan-ose ring adopts an envelope conformation close to C 3-exo, where the C atom substituted by the benz-yloxy group is the flap. The fused dioxolane ring also adopts an envelope conformation, with the methyl-ene C atom as the flap. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming zigzag chains along [010].
2.Crystal structure of 1-(1-methyl-1H-imidazol-2-yl)-4-phenyl-1H-1,2,3-triazole dihydrate.
Haslinger S1, Laus G1, Wurst K1, Schottenberger H1. Acta Crystallogr E Crystallogr Commun. 2015 Nov 14;71(Pt 12):o945-6. doi: 10.1107/S2056989015020721. eCollection 2015.
The title compound, C12H11N5·2H2O, which crystallizes as a dihydrate, was obtained by Cu(I)-catalysed azide-alkyne cyclo-addition from 2-azido-1-methyl-imidazole and phenyl-ethyne. The dihedral angles between the central triazole ring (r.m.s. deviation = 0.004 Å) and the pendant imidazole (r.m.s. deviation = 0.006 Å) and phenyl rings are 12.3 (2) and 2.54 (19)°, respectively. In the crystal, the water mol-ecules are connected into [010] chains by O-H⋯O hydrogen bonds, while O-H⋯N hydrogen bonds connect the water mol-ecules to the organic mol-ecules, generating corrugated (100) sheets.
3.A novel triazole derivative of betulinic acid induces extrinsic and intrinsic apoptosis in human leukemia HL-60 cells.
Khan I1, Guru SK2, Rath SK3, Chinthakindi PK1, Singh B1, Koul S1, Bhushan S4, Sangwan PL5. Eur J Med Chem. 2016 Jan 27;108:104-16. doi: 10.1016/j.ejmech.2015.11.018. Epub 2015 Nov 19.
In an attempt to arrive at more potent cytotoxic agent than the bioactive natural product betulinic acid, influence of small structural modifications of its 1, 2, 3 triazole derivatives tethered at C-28 and both C3, C-28 using click chemistry approach has been studied. The chemically characterized triazoles have been screened for in vitro cytotoxicity against four human cancer cell lines HL-60, MiaPaCa-2, PC-3 and A549 which has allowed to identify triazole derivative 28{1N (4-fluoro phenyl)-1H-1, 2, 3-triazol-4-yl} methyloxy betulinic ester having better potency profile than the parent compound with IC50 values in the range of 5-7 μM. It caused disruption of mitochondrial membrane potential, rendered Bcl-2 cleavage, Bax translocation and decrease Bcl-2/Bax ratio. These events are accompanied by activation of caspases -9, -3, which cleave the PARP-1. It also induces caspase-8, which is involved in extrinsic apoptotic pathway. Therefore, it induces apoptosis through both intrinsic and extrinsic pathways in human leukemia HL-60 cells.
4.Study of thermal decomposition mechanisms and absorption cross section of nitro-rich phenyl- and bis-series 1,2,3-triazoles.
Chaudhary AK, Rao KS, Sudheer Kumar A. Appl Opt. 2016 Feb 1;55(4):817-24. doi: 10.1364/AO.55.000817.
This paper reports the investigation of thermal decomposition mechanisms and evaluation of thermally released NO<sub>2</sub> from two newly synthesized high-energy materials named 1-(4-nitrophenyl)-1H-1,2,3-triazole (S<sub>8</sub>) and 2,6-bis ((4-(nitromethyl)-1H-1,2,3-triazol-1-yl)methyl) pyridine (S<sub>9</sub>) using time-resolved pulsed photoacoustic (PA) pyrolysis technique. The PA spectra were recorded between the 30°C and 350°C range and by varying the pressure of compounds vapor using 532 nm wavelength of pulse duration 7 ns at 10 Hz repetition rate obtained from Q-switched Nd:YAG laser pulses. The PA results were cross verified with thermogravimetric-differential thermal analysis data. The quality factor "&=&Q"&=& of the PA cavity was measured to test the thermal stability of the compound. In addition, we have ascertained the molecular density, absorption cross sections of high-energy materials vapor in terms of NO<sub>2</sub>.