4-(3-Chloro-2,2-dimethylpropanamido)benzenesulfonamide

Yalçın, Şerife Pınar; Akkurt, Mehmet; Durgun, Mustafa; Türkkan, Baki; Türkmen, Hasan

doi:10.1107/s1600536812046806

Cited by 3 publications

(2 citation statements)

References 11 publications

(17 reference statements)

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“…1, the N2-C7-C8-C9, Cl1-C11-C10-C9 and O3 -C7-C8-C9 torsion angles are 165.7 (2), 63.2 (3) and -16.5 (3) °, respectively. The bond lengths and bond angles are within the normal range and are comparable to those reported previously for the isomer 4-(3-chloro-2,2-dimethylpropanoylamino)-benzenesulfonamide (Yalçın et al, 2012) and other related compounds (Akkurt et al, 2010a,b).…”

Section: -(5-chloropentanamido)benzenesulfonamidesupporting

confidence: 80%

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4-(5-Chloropentanamido)benzenesulfonamide

et al. 2012

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The molecular conformation of the title compound, C11H15ClN2O3S, is stabilized by a C—H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by two pairs of inversion-related N—H⋯O hydrogen bonds, generating R 2 2(8) and R 2 2(20) ring motifs, resulting in chains running along [0-11]. These chains are connected by N—H⋯O hydrogen bonds along [100], forming layers parallel to (011). There are also C—H⋯π interactions between the layers, which consolidate the three-dimensional structure.

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Section: -(5-chloropentanamido)benzenesulfonamidesupporting

confidence: 80%

“…For their antiviral properties, such as HIV protease inhibitors, see : De Clercq (2001) and as inhibitors of cysteine protease enzyme, see: Danial & Korsmeyer (2004). For related structures, see: Yalçın et al (2012); Akkurt et al (2010a,b). For hydrogen-bond motifs, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 98%

4-(5-Chloropentanamido)benzenesulfonamide

et al. 2012

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Effective Anticancer Potential of a New Sulfonamide as a Carbonic Anhydrase IX Inhibitor Against Aggressive Tumors

Koyuncu,

Temiz,

Güler

et al. 2024

ChemMedChem

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This study examines efficiency of a newly synthesized sulfonamide derivative 2‐bromo‐N‐(4‐sulfamoylphenyl)propanamide (MMH‐1) on the inhibition of Carbonic Anhydrase IX, which is overexpressed in many solid tumors including breast cancer. The inhibitory potential of MMH‐1 compound against hCA I, II, IX, and XII, was evaluated. To this context, the cytotoxic effect of MMH‐1 on cancer and normal cells was tested and found to selectively affect MDA‐MB‐231 cells. MMH‐1 reduced cell proliferation by holding cells in the G0/G1 phase (72%) and slowed the cells' wound healing capacity. MMH‐1 inhibited CA IX under both hypoxic and normoxic conditions and altered the morphology of triple negative breast cancer cells. In MDA‐MB‐231 cells, inhibition of CA IX was accompanied by a decrease in extracellular pH acidity (7.2), disruption of mitochondrial membrane integrity (80%), an increase in reactive oxygen levels (25%), and the triggering of apoptosis (40%). In addition, the caspase cascade was activated in MDA‐MB‐231 cells, triggering both the extrinsic and intrinsic apoptotic pathways. TThese results propose that the MMH‐1 compound could triggers apoptosis in MDA‐MB‐231 cells via the pH/MMP/ROS pathway through the inhibition of CA IX. This compound is thought to have high potential and promising anticancer properties in the treatment of aggressive tumors.

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