1,2,3,4-Tetrahydroisoquinoline-2-sulfonamide

Bouasla, Radia; Berredjem, Malika; Aouf, Nour‐Eddine; Barbey, Carole

doi:10.1107/s1600536807068158

Cited by 17 publications

(4 citation statements)

References 9 publications

(9 reference statements)

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“…14; for compound 8, the reduced cell corresponds to the P2 1 /c setting, while for compounds 6 and 7, the reduced cells correspond to the P2 1 /n setting. Bond lengths and angles (cf supporting information) are in concurrence with the requisite structures (Bouasla et al, 2008;Larsen et al, 2016).…”

Section: Crystal Structuressupporting

confidence: 63%

Synthesis, crystal structure and docking studies of tetracyclic 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine 12,12-dioxide and its precursors

et al. 2020

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The title compound, 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine 12,12-dioxide, C15H11IN2O2S (8), was synthesized via the metal-free intramolecular N-iodosuccinimide (NIS)-mediated radical oxidative sp 3-C—H aminative cyclization of 2-(2′-aminobenzenesulfonyl)-1,3,4-trihydroisoquinoline, C15H16N2O2S (7). The amino adduct 7 was prepared via a two-step reaction, starting from the condensation of 2-nitrobenzenesulfonyl chloride (4) with 1,2,3,4-tetrahydroisoquinoline (5), to afford 2-(2′-nitrobenzenesulfonyl)-1,3,4-trihydroisoquinoline, C15H14N2O4S (6), in 82% yield. The catalytic hydrogenation of 6 with hydrogen gas, in the presence of 10% palladium-on-charcoal catalyst, furnished 7. Products 6–8 were characterized by their melting points, IR and NMR (1H and 13C) spectroscopy, and single-crystal X-ray diffraction. The three compounds crystallized in the monoclinic space group, with 7 exhibiting classical intramolecular hydrogen bonds of 2.16 and 2.26 Å. All three crystal structures exhibit centrosymmetric pairs of intermolecular C—H...π(ring) and/or π–π stacking interactions. The docking studies of molecules 6, 7 and 8 with deoxyribonucleic acid (PDB id: 1ZEW) revealed minor-groove binding behaviours without intercalation, with 7 presenting the most favourable global energy of the three molecules. Nonetheless, molecule 8 interacted strongly with the DNA macromolecule, with an attractive van der Waals energy of −15.53 kcal mol−1.

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Section: Crystal Structuressupporting

confidence: 63%

Synthesis, crystal structure and docking studies of tetracyclic 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine 12,12-dioxide and its precursors

et al. 2020

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“…The vast majority of sulfonamides are synthesized by the reaction of a sulfonyl/sulfuryl chloride with primary or secondary amines, usually, in the presence of a base in an aprotic solvent, or via related transformations. [9][10][11] The synthesis of sulfonamides can also be performed by reacting an amine with N-chlorosulfonyl carbamate (CSC) at 0 C. [12][13][14] In addition, there are a limited number of reports on the use of various catalysts to perform sulfonylation. These include CsF-Celite, 15 metal oxide (ZnO, MgO, CuO, Ag 2 O), [16][17][18] and Zn-Al-hydrotalcite under ultrasound irradiation.…”

Section: Introductionmentioning

confidence: 99%

A simple and eco-sustainable method for the sulfonylation of amines under microwave-assisted solvent-free conditions

et al. 2014

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“…The synthesis was carried out in two steps [44] . First, carbamoylation under anhydrous conditions of commercial chlorosulfonyl isocyanate with the corresponding oxazolidinones (1-4)A , easily prepared in a two-step quantitatively afforded the corresponding N-chlorosulfonyl carbamate intermediate (1-4)B .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, in silico study (DFT, ADMET) and crystal structure of novel sulfamoyloxy-oxazolidinones: Interaction with SARS-CoV-2

Bouzina

Berredjem

Bouacida

et al. 2022

Journal of Molecular Structure

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A new series of sulfamoyloxyoxazolidinone (SOO) derivatives have been synthesized and characterized by single-crystal X-ray diffraction, NMR, IR, MS and EA. Chemical reactivity and geometrical characteristics of the target compounds were investigated using DFT method. The possible binding mode between SOO and Main protease (Mpro) of SARS-CoV-2 and their reactivity were studied using molecular docking simulation. Single crystal X-ray diffraction showed that SOO crystallizes in a monoclinic system with P 2 1 space group. The binding energy of the SARS-CoV-2/Mpro-SOO complex and the calculated inhibition constant using docking simulation showed that the active SOO molecule has the ability to inhibit SARS-CoV2. We studied the prediction of absorption, distribution, properties of metabolism, excretion and toxicity (ADMET) of the synthesized molecules.

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1,2,3,4-Tetrahydroisoquinoline-2-sulfonamide

Cited by 17 publications

References 9 publications

Synthesis, crystal structure and docking studies of tetracyclic 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine 12,12-dioxide and its precursors

Synthesis, crystal structure and docking studies of tetracyclic 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine 12,12-dioxide and its precursors

A simple and eco-sustainable method for the sulfonylation of amines under microwave-assisted solvent-free conditions

Synthesis, in silico study (DFT, ADMET) and crystal structure of novel sulfamoyloxy-oxazolidinones: Interaction with SARS-CoV-2

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