3325-11-9

Usage

Uses

5-Amino-1H-benzotriazole is used as azole building block.

InChI:InChI=1/C6H6N4/c7-4-1-2-5-6(3-4)9-10-8-5/h1-3H,7H2,(H,8,9,10)

Upstream product

• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 2338-12-7 5-nitrobenzotriazole 

Downstream Products

• 233-62-5 3-methyl-3H-triazolo<4,5-f>quinoline 
• 133041-91-5 N-(quinolin-4-yl)benzene-1,4-diamine 
• 474453-54-8 N-(1-benzyl-1H-benzotriazol-5-yl)-2,2,2-trifluoro-acetamide 
• 474453-55-9 1-[(4-methoxy-phenyl)-diphenyl-methyl]-1H-benzotriazol-5-ylamine 
• 474453-53-7 2,2,2-trifluoro-N-{1-[(4-methoxy-phenyl)-diphenyl-methyl]-1H-benzotriazol-5-yl}-acetamide 
• 474453-57-1 5-dimethylamino-naphthalene-1-sulfonic acid {1-[(4-methoxy-phenyl)-diphenyl-methyl]-1H-benzotriazol-5-yl}-amide 
• 1219937-84-4 C₁₈H₂₁N₇O 

Relevant academic research and scientific papers

Discovery of benzotriazole-azo-phenol/aniline derivatives as antifungal agents

A series of benzotriazole-azo-phenol/aniline derivatives were prepared and evaluated for their antifungal activities against six phytopathogenic fungi such as Fusarium graminearum, Fusarium solani, Alternaria alternate, Valsa mali, Botrytis cinerea, and Curvularia lunata. Among them, compounds IIf, IIn, and IIr showed a broad-spectrum of potent antifungal activities. Especially some compounds displayed 3.5–10.8 folds more potent activities than carbendazim against A. alternata and C. lunata. Notably, compounds IIc, IIm, and IIr exhibited good protective and therapeutic effects against B. cinerea at 200 μg/mL. Their structure-activity relationships were also discussed.

Relative role of halogen bonds and hydrophobic interactions in inhibition of human protein kinase CK2α by tetrabromobenzotriazole and some C(5)-substituted analogues

To examine the relative role of halogen bonding and hydrophobic interactions in the inhibition of human CK2α by 4,5,6,7- tetrabromobenzotriazole (TBBt), we have synthesized a series of 5-substituted benzotriazoles (Bt) and the corresponding 5-substituted 4,6,7- tribromobenzotriazoles (Br3Bt) and examined their inhibition of human CK2α relative to that of TBBt. The various C(5) substituents differ in size (H and CH3), electronegativity (NH2 and NO 2), and hydrophobicity (COOH and Cl). Some substituents were halogen bond donors (Cl, Br), while others were fluorine bond donors (F and CF 3). Most of the 5-substituted analogues of Br3Bt (with the exception of COOH and NH2) exhibited inhibitory activity comparable to that of TBBt, whereas the 5-substituted analogues of the parent Bt were only weakly active (Br, Cl, NO2, CF3) or inactive. The observed effect of the volume of a ligand molecule pointed to its predominant role in inhibitory activity, indicating that presumed halogen bonding, identified in crystal structures and by molecular modeling, is dominated by hydrophobic interactions. Extended QSAR analysis additionally pointed to the monoanion and a preference for the N(1)-H protomer of the neutral ligand as parameters crucial for prediction of inhibitory activity. This suggests that the monoanions of TBBt and its congeners are the active forms that efficiently bind to CK2α, and the binding affinity is coupled with protomeric equilibrium of the neutral ligand.

Pyrazole compounds

Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

Addition reactions of 5-aminobenzotriazoles with dimethyl acetylenedicarboxylate (DMAD). Formation of (Z/E) Michael adducts, (benzotriazol-5-yl)-2-pyridones, a triazolo-9,10-dihydrobenzoazepine and a triazolo-2-oxindole

5-Aminobenzotriazoles (1a-d) reacted with DMAD to give the regioselective Michael adducts (Z)-(2a-d), accompanied with (benzotriazol-5-yl)-2-pyridones (3b-d), and in one case (2c) with the triazolo-9,10-dihydrobenzoazepine (4).Cyclisation of the adducts (Z)-(2b-d) in Dowtherm gave the triazoloquinolinones (6b-d), which were converted into chloro derivatives (9b-d), in turn hydrolysed and decarboxylated to 9-chloro-1(2)-methyltriazoloquinolines (11c-d).Compound (1c) in refluxing acetonitrile with DMAD undergoes unusual cyclisation into triazolo-2-oxindole (5), then converted into 2-methyltriazolocarbostyril-9-carboxylate (17).

4-N-BENZAZOLYLAMINO DERIVATIVES OF 3-Y-3-BUTEN-2-ONE

Ethoxymethylene derivatives of 2,4-pentanedione (Ia), 3-oxobutanenitrile (Ib), methyl (Ic) or ethyl (Id) 3-oxobutanoate give with 4- or 5-aminobenzimidazole or benzotriazole, respectively, under mild conditions products of nucleophilic substitution II-V.Structure of these compounds was discussed on the basis of their spectral measurements -IR, UV, 1H, 13C NMR and mass spectra.