Synthesis, crystal and molecular structure of two biologically active aromatic sulfonamides and their hydrochloride salts

Remko, Milan; Kožı́šek, Jozef; Semanová, Jana; Gregáň, Fridrich

doi:10.1016/j.molstruc.2010.03.013

Cited by 10 publications

(7 citation statements)

References 24 publications

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“…Our strategy to improve solubility was to introduce polarity on the "tail" part of molecule by polar morpholine substituent. In comparison with the parent brinzolamide and dorzolamide three basic compounds (I-1, I-2, I-3) exhibit improved solubility (Table 1) and can be easily prepared in the form of corresponding salts 16 . All three new compounds were each assayed for hCA I, hCA II, hCA IV and hCA XII isozymes binding by stopped flow technique and results of which are presented in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…16 and depicted in Scheme 1 and 2. N-(4-diethylaminoethoxybenzyl)benzene-1,4-bis(sulfonamide) (I-3) was prepared as depicted in Scheme 3.…”

Section: Research Articlementioning

confidence: 99%

“…In this work, we report the synthesis of a novel drug-like aromatic sulfonamides 4-sulfamoyl-N-(3-morpholinopropyl) benzamide (I-1), N-(3-morpholinopropyl)benzene-1,4-disulfonamide (I-2) and N-(4-diethylaminoethoxybenzyl)benzene-1, 4-bis(sulfonamide (I-3), with favorable structural, physicochemical and some pharmacokinetic properties comparable to those obtained for clinically useful acetazolamide, dorzolamide and brinzolamide [13][14][15][16] . The new compounds reported here were in vitro tested on the enzymatic hCA I, hCA II, hCA IV and hCA XII activities.…”

Section: Introductionmentioning

confidence: 97%

See 2 more Smart Citations

Three new aromatic sulfonamide inhibitors of carbonic anhydrases I, II, IV and XII

Supuran

Maresca

Gregáň

et al. 2012

Journal of Enzyme Inhibition and Medicinal Chemistry

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Section: Resultsmentioning

confidence: 99%

“…16 and depicted in Scheme 1 and 2. N-(4-diethylaminoethoxybenzyl)benzene-1,4-bis(sulfonamide) (I-3) was prepared as depicted in Scheme 3.…”

Section: Research Articlementioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

See 1 more Smart Citation

Three new aromatic sulfonamide inhibitors of carbonic anhydrases I, II, IV and XII

Supuran

Maresca

Gregáň

et al. 2012

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The sulfonamide group occurs in many biologically active compounds, including antimicrobial, antithyroid, antitumor and antimalarial drugs (Ozdemir et al, 2009;Seo et al, 2010;Dominguez et al, 2005;Connor, 1998;Hanson et al, 1999). In addition, several substituted aromatic and heterocyclic sulfonamides have been synthesized and evaluated for their potential therapeutic use as antiglaucoma agents (Remko et al, 2010).…”

Section: Commentmentioning

confidence: 99%

The discrete role of chlorine substitutions in the conformation and supramolecular architecture of arylsulfonamides

et al. 2011

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Two arylsulfonamide derivatives, N-(4-acetylphenyl)benzenesulfonamide, C(14)H(13)NO(3)S, and N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide, C(14)H(11)Cl(2)NO(3)S, differing by the absence or presence of two chloro substituents on one of the phenyl rings, were synthesized and characterized in order to establish structural relationships and the role of chloro substitution on the molecular conformation and crystal assembly. Both arylsulfonamides form inversion-related dimers through C-H···π and π-π interactions. These dimers pack in a similar way in the two structures. The substitution of two H atoms at the 2- and 5-positions of one phenyl ring by Cl atoms did not substantially alter the molecular conformation or the intermolecular architecture displayed by the unsubstituted sulfonamide. The structural information controlling the assembly of such compounds in their crystal phases is in the (phenyl)benzenesulfonamide molecular framework.

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“…Compounds bearing the -SO 2 -NH-group (the sulfonamide group) have long been known to be potent inhibitors of carbonic anhydrase (CA) (Remko et al, 2010;Supuran et al, 2003), and are widely used as antibacterial agents. Synthesis of sulfonamides involves the nucleophilic attack of ammonia or amine on a sulfonyl halide (Chan et al, 2002;Shaabani et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

2-Phenitidine derivatives as suitable inhibitors of butyrylcholinesterase

Abbasi

Aziz-Ur-Rehman

Qureshi

et al. 2013

Braz. J. Pharm. Sci.

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This manuscript reports the synthesis of a series of N-substituted derivatives of 2-phenitidine. First, the reaction of 2-phenitidine (1) with benzene sulfonyl chloride (2) yielded N-(2-ethoxyphenyl) benzenesulfonamide (3), which further on treatment with sodium hydride and alkyl halides (4a-g) furnished into new sulfonamides (5a-g). Second, the phenitidine reacted with benzoyl chloride (6) and acetyl chloride (8) to yield the reported N-benzoyl phenitidine (7) and N-acetyl phenitidine (9), respectively. These derivatives were characterized by infrared spectroscopy, ¹H-NMR, and EI-MS, and then screened against acetylcholinesterase, butylcholinesterase, and lipoxygenase enzyme, and were found to be potent inhibitors of butyrylcholinesterase alone.

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Synthesis, crystal and molecular structure of two biologically active aromatic sulfonamides and their hydrochloride salts

Cited by 10 publications

References 24 publications

Three new aromatic sulfonamide inhibitors of carbonic anhydrases I, II, IV and XII

Three new aromatic sulfonamide inhibitors of carbonic anhydrases I, II, IV and XII

The discrete role of chlorine substitutions in the conformation and supramolecular architecture of arylsulfonamides

2-Phenitidine derivatives as suitable inhibitors of butyrylcholinesterase

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