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Journal articles on the topic 'Benzenesulfonamide'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Sheikh, Tahir Ali, Islam Ullah Khan, William T. A. Harrison, and Ejaz. "N-[3-(Benzenesulfonamido)propyl]benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 67, no. 7 (June 18, 2011): o1737. http://dx.doi.org/10.1107/s1600536811020150.

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2

Ashfaq, Muhammad, M. Nawaz Tahir, Islam Ullah Khan, Muhammad Nadeem Arshad, and Syed Saeed-ul-Hassan. "N-Acetyl-4-(benzenesulfonamido)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 5 (April 30, 2009): o1180. http://dx.doi.org/10.1107/s1600536809015876.

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3

Szafrański, Krzysztof, Jarosław Sławiński, Łukasz Tomorowicz, and Anna Kawiak. "Synthesis, Anticancer Evaluation and Structure-Activity Analysis of Novel (E)- 5-(2-Arylvinyl)-1,3,4-oxadiazol-2-yl)benzenesulfonamides." International Journal of Molecular Sciences 21, no. 6 (March 23, 2020): 2235. http://dx.doi.org/10.3390/ijms21062235.

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To learn more about the structure–activity relationships of (E)-3-(5-styryl-1,3,4-oxadiazol-2-yl)benzenesulfonamide derivatives, which in our previous research displayed promising in vitro anticancer activity, we have synthesized a group of novel (E)-5-[(5-(2-arylvinyl)-1,3,4-oxadiazol-2-yl)]-4-chloro-2-R1-benzenesulfonamides 7–36 as well as (E)-4-[5-styryl1,3,4-oxadiazol-2-yl]benzenesulfonamides 47–50 and (E)-2-(2,4-dichlorophenyl)-5-(2-arylvinyl)-1,3,4-oxadiazols 51–55. All target derivatives were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7 human tumor cell lines. The obtained results were analyzed in order to explain the influence of a structure of the 2-aryl-vinyl substituent and benzenesulfonamide scaffold on the anti-tumor activity. Compound 31, bearing 5-nitrothiophene moiety, exhibited the most potent anticancer activity against the HCT-116, MCF-7, and HeLa cell lines, with IC50 values of 0.5, 4, and 4.5 µM, respectively. Analysis of structure-activity relationship showed significant differences in activity depending on the substituent in position 3 of the benzenesulfonamide ring and indicated as the optimal meta position of the sulfonamide moiety relative to the oxadizole ring. In the next stage, chemometric analysis was performed basing on a set of computed molecular descriptors. Hierarchical cluster analysis was used to examine the internal structure of the obtained data and the quantitative structure–activity relationship (QSAR) analysis with multiple linear regression (MLR) method allowed for finding statistically significant models for predicting activity towards all three cancer cell lines.

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4

Bouz, Ghada, Martin Juhás, Lluis Pausas Otero, Cristina Paredes de la Red, Ondřej Janďourek, Klára Konečná, Pavla Paterová, et al. "Substituted N-(Pyrazin-2-yl)benzenesulfonamides; Synthesis, Anti-Infective Evaluation, Cytotoxicity, and In Silico Studies." Molecules 25, no. 1 (December 29, 2019): 138. http://dx.doi.org/10.3390/molecules25010138.

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We prepared a series of substituted N-(pyrazin-2-yl)benzenesulfonamides as an attempt to investigate the effect of different linkers connecting pyrazine to benzene cores on antimicrobial activity when compared to our previous compounds of amide or retro-amide linker type. Only two compounds, 4-amino-N-(pyrazin-2-yl)benzenesulfonamide (MIC = 6.25 μg/mL, 25 μM) and 4-amino-N-(6-chloropyrazin-2-yl)benzenesulfonamide (MIC = 6.25 μg/mL, 22 μM) exerted good antitubercular activity against M. tuberculosis H37Rv. However, they were excluded from the comparison as they—unlike the other compounds—possessed the pharmacophore for the inhibition of folate pathway, which was proven by docking studies. We performed target fishing, where we identified matrix metalloproteinase-8 as a promising target for our title compounds that is worth future exploration.

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5

Gowda, B. Thimme, Roopa Nayak, Jozef Kožíšek, Miroslav Tokarčík, and Hartmut Fuess. "Benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 63, no. 6 (May 26, 2007): o2967. http://dx.doi.org/10.1107/s1600536807024221.

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6

Gelbrich, Thomas, Terence L. Threlfall, and Michael B. Hursthouse. "Eight isostructural 4,4′-disubstitutedN-phenylbenzenesulfonamides." Acta Crystallographica Section C Crystal Structure Communications 68, no. 10 (September 21, 2012): o421—o426. http://dx.doi.org/10.1107/s0108270112039297.

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The isostructural crystals of 4-cyano-N-(4-methoxyphenyl)benzenesulfonamide, C14H12N2O3S, (I),N-(4-methoxyphenyl)-4-(trifluoromethyl)benzenesulfonamide, C14H12F3NO3S, (II), 4-iodo-N-(4-methoxyphenyl)benzenesulfonamide, C13H12INO3S, (III), 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide, C13H12BrNO3S, (IV), 4-chloro-N-(4-methoxyphenyl)benzenesulfonamide, C13H12ClNO3S, (V), 4-fluoro-N-(4-methoxyphenyl)benzenesulfonamide, C13H12FNO3S, (VI),N-(4-chlorophenyl)-4-methoxybenzenesulfonamide, C13H12ClNO3S, (VII), and 4-cyano-N-phenylbenzenesulfonamide, C13H10N2O2S, (VIII), contain infinite chains composed of N—H...O(sulfonyl) hydrogen-bonded molecules. The crystal structures of (I)–(VIII) have been compared using theXPac software and quantitative descriptors of isostructurality were generated [Gelbrich, Threlfall & Hursthouse (2012).CrystEngComm,14, 5454–5464]. Certain isostructural relationships in this series involve molecules with substantially different spatial demands,e.g.(VI) and (VIII) are related by the simultaneous interchange of F→CN on the benzenesulfonamide ring and OMe→H on theN-phenyl ring, which indicates that the geometry of the three-dimensional crystal-packing mode of (I)–(VIII) is unusually adaptable to different molecular shapes.

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7

Loughrey, Bradley T., Michael L. Williams, and Peter C. Healy. "4-(Benzylideneamino)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 9 (August 8, 2009): o2087. http://dx.doi.org/10.1107/s1600536809030256.

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8

Wang, Shu-Yan, Wan-Cheng Guo, and Ning Ma. "2-(Hydrazinocarbonyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 63, no. 7 (June 15, 2007): o3192. http://dx.doi.org/10.1107/s1600536807027584.

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9

Chang, Jun, Tie-Jun Zhang, Chang-Xiao Liu, and Xue-Ming Zhao. "N-(2,4-Dimethylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 63, no. 9 (August 3, 2007): o3670. http://dx.doi.org/10.1107/s160053680703677x.

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10

Ibrahim, Saba, M. Nawaz Tahir, Nadeem Iqbal, Durre Shahwar, and Muhammad Asam Raza. "N-(4-Methoxyphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 67, no. 2 (January 8, 2011): o298. http://dx.doi.org/10.1107/s1600536811000365.

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11

Türkmen, Hasan, Şerife Pınar Yalçın, Mehmet Akkurt, and Mustafa Durgun. "4-(5-Chloropentanamido)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 68, no. 12 (November 28, 2012): o3475—o3476. http://dx.doi.org/10.1107/s1600536812048118.

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12

Sreenivasa, S., M. S. Nanjundaswamy, S. Madankumar, N. K. Lokanath, E. Suresha, and P. A. Suchetan. "N-(4-Methoxybenzoyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (January 22, 2014): o192. http://dx.doi.org/10.1107/s1600536814001330.

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In the title compound, C14H13NO4S, the dihedral angle between the aromatic rings is 69.81 (1)°; the dihedral angle between the planes defined by the S—N—C=O segment of the central chain and the sulfonyl benzene ring is 74.91 (1)°. In the crystal, the molecules are linked by weak N—H...O hydrogen bonds intoC(4) chains running along [100]. The molecules in adjacent chains are linked by weak C—H...O interactions, generatingR22(16) dimeric pairs. Weak C—H...π interactions connect the double chains into (001) sheets.

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13

Thenmozhi, S., S. Ranjith, A. SubbiahPandi, V. Dhayalan, and A. K. MohanaKrishnan. "N-(2-Formylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 9 (August 22, 2009): o2210. http://dx.doi.org/10.1107/s1600536809032681.

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14

Saravanan, R. R., V. Dhayalan, A. K. Mohanakrishnan, G. Chakkaravarthi, and V. Manivannan. "N-(2-Acetylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 9 (August 26, 2009): o2241. http://dx.doi.org/10.1107/s1600536809033273.

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15

Aziz-ur-Rehman, Muhammad Arif Sajjad, Mehmet Akkurt, Shahzad Sharif, Muhammad Athar Abbasi, and Islam Ullah Khan. "N-(2-Methoxyphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 7 (June 26, 2010): o1769. http://dx.doi.org/10.1107/s1600536810023871.

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16

Suchetan, P. A., B. Thimme Gowda, Sabine Foro, and Hartmut Fuess. "N-(4-Methylbenzoyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 7 (June 26, 2010): o1772. http://dx.doi.org/10.1107/s1600536810023974.

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17

John, Peter, Shahzad Sharif, Islam Ullah Khan, Saima Khizar, and Edward R. T. Tiekink. "N-(3,4-Dimethylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 8 (July 10, 2010): o1983. http://dx.doi.org/10.1107/s1600536810026656.

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18

Gowda, B. Thimme, Sabine Foro, K. S. Babitha, and Hartmut Fuess. "N-(2-Methylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 64, no. 9 (August 6, 2008): o1692. http://dx.doi.org/10.1107/s1600536808024562.

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19

Gowda, B. Thimme, Sabine Foro, K. S. Babitha, and Hartmut Fuess. "N-(2,6-Dimethylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 64, no. 9 (August 6, 2008): o1691. http://dx.doi.org/10.1107/s1600536808024653.

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20

Gowda, B. Thimme, Sabine Foro, K. S. Babitha, and Hartmut Fuess. "N-(3-Chlorophenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 64, no. 9 (August 23, 2008): o1825. http://dx.doi.org/10.1107/s1600536808026895.

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21

Nirmala, P. G., Sabine Foro, B. Thimme Gowda, and Hartmut Fuess. "N-(2,6-Dichlorophenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 12 (November 6, 2010): o3061. http://dx.doi.org/10.1107/s160053681004420x.

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22

Gowda, B. Thimme, Sabine Foro, K. S. Babitha, and Hartmut Fuess. "N-(3,5-Dichlorophenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 64, no. 11 (October 25, 2008): o2190. http://dx.doi.org/10.1107/s1600536808034351.

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23

Gowda, B. Thimme, Sabine Foro, K. S. Babitha, and Hartmut Fuess. "N-(2,3-Dimethylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 2 (January 23, 2009): o366. http://dx.doi.org/10.1107/s1600536809002098.

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24

Zhang, Sifang, Yuewen Zhang, Chuntao Wang, and Ruitao Zhu. "N-(1-Naphthyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 67, no. 11 (October 5, 2011): o2831. http://dx.doi.org/10.1107/s1600536811039201.

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25

Suchetan, P. A., B. Thimme Gowda, Sabine Foro, and Hartmut Fuess. "N-(4-Chlorobenzoyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 12 (November 21, 2009): o3156. http://dx.doi.org/10.1107/s1600536809048399.

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26

Nirmala, P. G., B. Thimme Gowda, Sabine Foro, and Hartmut Fuess. "N-(3,5-Dimethylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 12 (November 28, 2009): o3225. http://dx.doi.org/10.1107/s1600536809050089.

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27

Gowda, B. Thimme, Sabine Foro, P. A. Suchetan, and Hartmut Fuess. "N-(3-Chlorobenzoyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 11 (October 17, 2009): o2750. http://dx.doi.org/10.1107/s1600536809041051.

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28

Gowda, B. Thimme, Sabine Foro, P. G. Nirmala, and Hartmut Fuess. "N-(2,5-Dimethylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 65, no. 11 (October 17, 2009): o2763. http://dx.doi.org/10.1107/s1600536809041841.

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29

Gowda, B. Thimme, Sabine Foro, P. G. Nirmala, and Hartmut Fuess. "N-(2,4-Dichlorophenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 1 (December 24, 2009): o229. http://dx.doi.org/10.1107/s160053680905452x.

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30

Gowda, B. Thimme, Sabine Foro, P. A. Suchetan, and Hartmut Fuess. "N-(2-Chlorobenzoyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 2 (January 9, 2010): o326. http://dx.doi.org/10.1107/s1600536809055482.

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31

Gowda, B. Thimme, Sabine Foro, P. G. Nirmala, and Hartmut Fuess. "N-(4-Methylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 2 (January 23, 2010): o435. http://dx.doi.org/10.1107/s1600536810002278.

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32

Gowda, B. Thimme, Sabine Foro, P. G. Nirmala, and Hartmut Fuess. "N-(3-Methylphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 2 (January 23, 2010): o434. http://dx.doi.org/10.1107/s1600536810002291.

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33

Gowda, B. Thimme, Sabine Foro, P. G. Nirmala, and Hartmut Fuess. "N-(2,5-Dichlorophenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 3 (February 13, 2010): o594. http://dx.doi.org/10.1107/s1600536810004769.

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34

Perlovich, German L., Valery V. Tkachev, Klaus-Jürgen Schaper, and Oleg A. Raevsky. "N-(4-Chlorophenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 62, no. 1 (December 23, 2005): o376—o378. http://dx.doi.org/10.1107/s1600536805041929.

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35

Perlovich, German L., Valery V. Tkachev, Klaus-Jürgen Schaper, and Oleg A. Raevsky. "N-(2-Chlorophenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 62, no. 2 (January 25, 2006): o780—o782. http://dx.doi.org/10.1107/s1600536806002303.

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36

Khan, Islam Ullah, Irfana Mariam, Muhammad Zia-ur-Rehman, Muhammad Arif Sajjad, and Shahzad Sharif. "N-(4-Hydroxyphenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 66, no. 5 (April 14, 2010): o1088. http://dx.doi.org/10.1107/s160053681001322x.

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37

Suchetan, P. A., Sabine Foro, and B. Thimme Gowda. "N-(3-Methylbenzoyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 68, no. 5 (April 6, 2012): o1327. http://dx.doi.org/10.1107/s1600536812013931.

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38

Suchetan, P. A., Sabine Foro, and B. Thimme Gowda. "N-(3-Nitrobenzoyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 68, no. 5 (April 21, 2012): o1507. http://dx.doi.org/10.1107/s1600536812016765.

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39

Siddiqui, Waseeq Ahmad, Adnan Ashraf, Hamid Latif Siddiqui, Muhammad Akram, and Masood Parvez. "2-(N-Cyclohexylcarbamoyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 68, no. 2 (January 14, 2012): o370. http://dx.doi.org/10.1107/s1600536812000633.

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40

Tkachev, Valery V., Klaus-Jürgen Schaper, Nadezda N. Strakhova, and Vladimir P. Kazachenko. "N-(2,3-Dichlorophenyl)benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 62, no. 6 (May 31, 2006): o2514—o2515. http://dx.doi.org/10.1107/s160053680601943x.

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41

Gordetsov, A. S., S. V. Zimina, E. M. Moseeva, S. E. Skobeleva, N. V. Kulagina, and V. V. Pereshein. "N-(?5-Cyclopentadienylvanadium)benzenesulfonamide." Russian Chemical Bulletin 42, no. 12 (December 1993): 2021–23. http://dx.doi.org/10.1007/bf00698888.

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42

Singh, Sunil K., S. Shivaramakrishna, V. Saibaba, K. Srinivas Rao, K. Ravi Ganesh, R. Vasudev, P. Praveen Kumar, et al. "Pharmacophoric 2-hydroxyalkyl benzenesulfonamide: A single-step synthesis from benzenesulfonamide via hemiaminal." European Journal of Medicinal Chemistry 42, no. 4 (April 2007): 456–62. http://dx.doi.org/10.1016/j.ejmech.2006.09.021.

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43

Ghorab, Mostafa, Fatma Ragab, Helmy Heiba, Marwa El-Gazzar, and Mostafa El-Gazzar. "Synthesis, in vitro anticancer screening and radiosensitizing evaluation of some new 4-[3-(substituted)thioureido]-N-(quinoxalin-2-yl)-benzenesulfonamide derivatives." Acta Pharmaceutica 61, no. 4 (December 1, 2011): 415–25. http://dx.doi.org/10.2478/v10007-011-0040-4.

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Synthesis, in vitro anticancer screening and radiosensitizing evaluation of some new 4-[3-(substituted)thioureido]-N-(quinoxalin-2-yl)-benzenesulfonamide derivatives Sulfonamides and quinoxaline derivatives possess many types of biological activities and have been recently reported to show substantial antitumor activity. This paper reports the synthesis of novel thioureido sulfaquinoxaline derivatives. All the newly synthesized compounds were evaluated for their in vitro anticancer activity against a human liver cell line (HEPG2) and showed higher activity than the reference drug doxorubicin. 4-(3-(4-Ethylbenzoate) thioureido)-N-(quinoxalin-2-yl)benzenesulfonamide (9) (IC50 = 15.6 μmol L-1), N-(pyridin-2-yl)-4-(3-(4-(N-quinoxalin-2-yl-sulfamoyl)phenyl)thioureido)benzenesulfonamide (10) (IC50 = 26.8 μmol L-1) and N-(quinoxalin-2-yl)-4-(3-(4-(N-thiazol-2-ylsulfamoyl)phenyl)thioureido)benzenesulfonamide (11) (IC50 = 24.4 μmol L-1) were the most potent compared to doxorubicin (IC50 = 71.8 μmol L-1). The most potent compounds 9, 10 and 11 were evaluated as radiosensitizing agents by subjecting the compounds to γ-irradiation (8 kGy).

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44

Gupta, Apoorva, and Anand K. Halve. "Synthesis & Antifungal Screening of Novel Azetidin-2-ones." Open Chemistry Journal 2, no. 1 (February 27, 2015): 1–6. http://dx.doi.org/10.2174/1874842201502010001.

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A new series of 4-[3-chloro-2-(4-hydroxy-3-methoxybenzyllidene)-4-oxoazetidin-1-yl]amino-N-(substituted)benzenesulfonamide, 4-{3-chloro-2-[5-methoxy-2-nitro-4-(prop-2-en-1-yloxy)benz yllidene]-4-oxoazetidin-1-yl}]amino}-N-(substituted)benzenesulfonamide and 4-{3-chloro-2-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-4-oxoazetidin-1-yl}amino}-N-(substituted) benzenesulfonamide were synthesized using appropriate synthetic route. The chemical structures of all the synthesized compounds were deduced on the basis of elemental analysis and spectroscopic data. The antifungal activity of the synthesized compounds was screened against several fungus. The synthesized compounds show potent antifungal activity against Aspergillus niger & Aspergillus flavus and significant structure-activity relationship (SAR) trends.

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45

Purandara, H., Sabine Foro, and B. Thimme Gowda. "Crystal structures of three N-acylhydrazone isomers." Acta Crystallographica Section E Crystallographic Communications 77, no. 8 (July 9, 2021): 780–84. http://dx.doi.org/10.1107/s2056989021006885.

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The crystal structures of three isomers of (E)-4-chloro-N-{2-[2-(chlorobenzylidene)hydrazinyl]-2-oxoethyl}benzenesulfonamide, namely, (E)-4-chloro-N-{2-[2-(2-chlorobenzylidene)hydrazinyl]-2-oxoethyl}benzenesulfonamide (I), (E)-4-chloro-N-{2-[2-(3-chlorobenzylidene)hydrazinyl]-2-oxoethyl}benzenesulfonamide (II) and (E)-4-chloro-N-{2-[2-(4-chlorobenzylidene)hydrazinyl]-2-oxoethyl}benzenesulfonamide (III), with the general formula C15H13Cl2N3O3S are described, with the chloro group in ortho, meta and para positions in the benzylidene benzene ring. All the three isomeric compounds crystallize in the centrosymmetric triclinic P\overline{1} space group with one molecule each in the asymmetric unit and two molecules in the unit cell. The dihedral angles between the two phenyl rings are 11.09 (14), 53.79 (18) and 72.37 (11)° in (I), (II) and (III), respectively. The central part of the molecule (–C—N—N=C–) is almost linear with C—N—N—C torsion angles of 179.1 (2), −169.5 (3) and 178.5 (2)° for (I), (II) and (III), respectively. In all the three crystals, the molecules form inversion dimers with R 2 2(8) ring motifs, which are further augmented by C—H...O interactions.

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46

Idemudia, Omoruyi G., Alexander P. Sadimenko, Anthony J. Afolayan, and Eric C. Hosten. "4-[(4-Methoxybenzylidene)amino]benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 2, 2012): o1599. http://dx.doi.org/10.1107/s1600536812018818.

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The title Schiff base compound, C14H14N2O3S, is non-planar, with a dihedral angle of 24.16 (7)° between the benzene rings. In the crystal, N—H...O and N—H...N hydrogen bonds link the molecules into a layer parallel to (011). Intra- and interlayer C—H...O interactions and π–π interactions [centroid–centroid distances = 3.8900 (9) and 3.9355 (8) Å] are also present.

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47

Shakuntala, K., S. Naveen, N. K. Lokanath, and P. A. Suchetan. "Crystal structures of isomeric 3,5-dichloro-N-(2,3-dimethylphenyl)benzenesulfonamide, 3,5-dichloro-N-(2,6-dimethylphenyl)benzenesulfonamide and 3,5-dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide." Acta Crystallographica Section E Crystallographic Communications 73, no. 5 (April 11, 2017): 673–77. http://dx.doi.org/10.1107/s2056989017005230.

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Abstract:

The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-dichloro-N-(2,3-dimethylphenyl)-benzenesulfonamide (I), 3,5-dichloro-N-(2,6-dimethylphenyl)benzenesulfonamide (II) and 3,5-dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide (III) are described. The molecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The molecular conformation of (II) is stabilized by intramolecular C—H...O hydrogen bonds and C—H...π interactions. The crystal structure of (I) features N—H...O hydrogen-bondedR22(8) loops interconnectedvia C(7) chains of C—H...O interactions, forming a three-dimensional architecture. The structure also features π–π interactions [Cg...Cg= 3.6970 (14) Å]. In (II), N—H...O hydrogen-bondedR22(8) loops are interconnectedviaπ–π interactions [intercentroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to theaaxis. In (III), adjacentC(4) chains of N—H...O hydrogen-bonded molecules running parallel to [010] are connectedviaC—H...π interactions, forming sheets parallel to theabplane. Neighbouring sheets are linkedviaoffset π–π interactions [intercentroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.

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YONEYAMA, Koichi, Nobumasa ICHIZEN, Makoto KONNAI, Tetsuo TAKEMATSU, Kazuyuki USHINOHAMA, and Tetsuo JIKIHARA. "Phytotoxic activity of benzenesulfonamide derivatives. Part IV. Herbicidal activity of N-(2,3-epoxypropyl)benzenesulfonamide derivatives." Agricultural and Biological Chemistry 49, no. 11 (1985): 3265–69. http://dx.doi.org/10.1271/bbb1961.49.3265.

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Nemr, Mohamed T. M., Asmaa M. AboulMagd, Hossam M. Hassan, Ahmed A. Hamed, Mohamed I. A. Hamed, and Mohamed T. Elsaadi. "Design, synthesis and mechanistic study of new benzenesulfonamide derivatives as anticancer and antimicrobial agents via carbonic anhydrase IX inhibition." RSC Advances 11, no. 42 (2021): 26241–57. http://dx.doi.org/10.1039/d1ra05277b.

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Glöckner, Steffen, Khang Ngo, Björn Wagner, Andreas Heine, and Gerhard Klebe. "The Influence of Varying Fluorination Patterns on the Thermodynamics and Kinetics of Benzenesulfonamide Binding to Human Carbonic Anhydrase II." Biomolecules 10, no. 4 (March 27, 2020): 509. http://dx.doi.org/10.3390/biom10040509.

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The fluorination of lead-like compounds is a common tool in medicinal chemistry to alter molecular properties in various ways and with different goals. We herein present a detailed study of the binding of fluorinated benzenesulfonamides to human Carbonic Anhydrase II by complementing macromolecular X-ray crystallographic observations with thermodynamic and kinetic data collected with the novel method of kinITC. Our findings comprise so far unknown alternative binding modes in the crystalline state for some of the investigated compounds as well as complex thermodynamic and kinetic structure-activity relationships. They suggest that fluorination of the benzenesulfonamide core is especially advantageous in one position with respect to the kinetic signatures of binding and that a higher degree of fluorination does not necessarily provide for a higher affinity or more favorable kinetic binding profiles. Lastly, we propose a relationship between the kinetics of binding and ligand acidity based on a small set of compounds with similar substitution patterns.

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