Boc-4-amino-1-methylpyrrole-2-carboxylic acid 1,2,3-benzotriazol-1-yl-ester
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Boc-4-amino-1-methylpyrrole-2-carboxylic acid 1,2,3-benzotriazol-1-yl-ester

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Category
BOC-Amino Acids
Catalog number
BAT-007032
CAS number
77716-16-6
Molecular Formula
C17H19N5O4
Molecular Weight
357.36
Boc-4-amino-1-methylpyrrole-2-carboxylic acid 1,2,3-benzotriazol-1-yl-ester
IUPAC Name
benzotriazol-1-yl 1-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrole-2-carboxylate
Synonyms
Boc-Py-OBt; Boc Py OBt
Appearance
Light tan solid
Purity
≥ 98% (HPLC)
Melting Point
133-136 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C17H19N5O4/c1-17(2,3)25-16(24)18-11-9-14(21(4)10-11)15(23)26-22-13-8-6-5-7-12(13)19-20-22/h5-10H,1-4H3,(H,18,24)
InChI Key
UMOAGHPTFVVSHR-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC1=CN(C(=C1)C(=O)ON2C3=CC=CC=C3N=N2)C
1. N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines with Enamines Promoted by the Lewis Acid ZnCl2
Zixi Zhu, Dale L Boger J Org Chem. 2022 May 6;87(9):6288-6301. doi: 10.1021/acs.joc.2c00543. Epub 2022 Apr 13.
The second example of selective N1/N4 1,4-cycloaddition (vs C3/C6 1,4-cycloaddition) of 1,2,4,5-tetrazines with preformed or in situ generated enamines now promoted by the Lewis acid ZnCl2 and with an expanded scope is described. The reaction constitutes a formal [4 + 2] cycloaddition across two nitrogen atoms (N1/N4 vs C3/C6) of a 1,2,4,5-tetrazine followed by retro [4 + 2] cycloaddition loss of a nitrile and aromatization to provide 1,2,4-triazines. Optimization of reaction parameters, simplification of its implementation through in situ enamine generation from ketones, definition of the enamine reaction scope for 3,6-bis(thiomethyl)-1,2,4,5-tetrazine, exploration of the 1,2,4,5-tetrazine scope, and representative applications of the product 1,2,4-triazines are detailed. The work establishes and further extends a powerful method for efficient one-step regioselective synthesis of 1,2,4-triazines under mild reaction conditions directly now from easily accessible ketones. It extends the substrate scope of a solvent (hexafluoroisopropanol) hydrogen bonding-promoted reaction that we recently reported with aryl-conjugated enamines, permitting the use of simple ketone-derived enamines and expanding the generality of the remarkable reaction. The reaction is regioselective with respect to the site of reaction with unsymmetrical ketones and provides exclusively a single 1,2,4-triazine regioisomer consistent with our previously established stepwise mechanism of formal N1/N4 1,4-cycloaddition, overcoming the challenges observed in conventional approaches to 1,2,4-triazines.
2. Cross-Coupling Reactions of 5-Bromo-1,2,3-triazine
Lukas V Hoff, Joana M Hauser, Karl Gademann J Org Chem. 2022 Nov 18;87(22):15684-15692. doi: 10.1021/acs.joc.2c02082. Epub 2022 Oct 28.
An efficient Pd catalyzed cross-coupling method for 5-bromo-1,2,3-triazine is described. Optimization of the reaction conditions allowed for the preparation of a representative scope of (hetero)aryl-1,2,3-triazines (20 examples, up to 97% yield). The reaction scope was evaluated using a data science enabled boronic acid chemical space to assess the generality of the method. Additionally, diversification of the resulting products enabled the preparation of pyrimidines and pyridines in yields of up to 80% and in only two steps.
3. New potent steroid sulphatase inhibitors based on 6-(1-phenyl-1 H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives
Olga Ciupak, Mateusz Daśko, Karol Biernacki, Janusz Rachon, Maciej Masłyk, Konrad Kubiński, Aleksandra Martyna, Sebastian Demkowicz J Enzyme Inhib Med Chem. 2021 Dec;36(1):238-247. doi: 10.1080/14756366.2020.1858820.
In the present work, we report a new class of potent steroid sulphatase (STS) inhibitors based on 6-(1-phenyl-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives. Within the set of new STS inhibitors, 6-(1-(1,2,3-trifluorophenyl)-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate 3L demonstrated the highest activity in the enzymatic assay inhibiting the STS activity to 7.98% at 0.5 µM concentration. Furthermore, to verify whether the obtained STS inhibitors are able to pass through the cellular membrane effectively, cell line experiments have been carried out. We found that the lowest STS activities were measured in the presence of compound 3L (remaining STS activity of 5.22%, 27.48% and 99.0% at 100, 10 and 1 nM concentrations, respectively). The measured STS activities for Irosustat (used as a reference) were 5.72%, 12.93% and 16.83% in the same concentration range. Moreover, a determined IC50 value of 15.97 nM for 3L showed that this compound is a very promising candidate for further preclinical investigations.
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