N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin

被引:1
作者
Maganhi, Stella H. [1 ]
Tavares, Mauricio T. [2 ]
Damiao, Mariana C. F. C. B. [2 ]
Parise Filho, Roberto [2 ]
机构
[1] Univ Fed Sao Carlos, Dept Phys, BR-13565905 Sao Carlos, SP, Brazil
[2] Univ Sao Paulo, Dept Pharm, BR-05508000 Sao Paulo, SP, Brazil
来源
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS | 2013年 / 69卷
基金
巴西圣保罗研究基金会;
关键词
D O I
10.1107/S1600536813028481
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
The title compound, C14H13NO4S, an analogue of capsaicin, differs from the latter by having a 1,3-benzodioxole ring rather than a 2-methoxyphenol moiety, and having a benzenesulfonamide group instead of an aliphatic amide chain. The five-membered ring is in an envelope conformation with the methylene C atom lying 0.221 (6) A degrees out of the plane formed by the other four atoms. The dihedral angle between the phenyl ring and the mean plane of the 1,3-benzodioxole fusedring system is 84.65 (4)degrees. In the crystal, molecules aggregate into supramolecular layers in the ac plane through C-H center dot center dot center dot center dot O, N-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions.
引用
收藏
页码:O1700 / +
页数:7
相关论文
共 12 条
[1]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[2]  
[Anonymous], 2010, MARV
[3]   GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].
CREMER, D ;
POPLE, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358
[4]   RPF101, a new capsaicin-like analogue, disrupts the microtubule network accompanied by arrest in the G2/M phase, inducing apoptosis and mitotic catastrophe in the MCF-7 breast cancer cells [J].
de-Sa-Junior, Paulo Luiz ;
Mesquita Pasqualoto, Kerly Fernanda ;
Ferreira, Adilson Kleber ;
Tavares, Mauricio Temotheo ;
Costa Bernstorff Damiao, Mariana Celestina Frojuello ;
de Azevedo, Ricardo Alexandre ;
Dias Camara, Diana Aparecida ;
Pereira, Alexandre ;
de Souza, Dener Madeiro ;
Parise Filho, Roberto .
TOXICOLOGY AND APPLIED PHARMACOLOGY, 2013, 266 (03) :385-398
[5]   WinGX and ORTEP for Windows: an update [J].
Farrugia, Louis J. .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2012, 45 :849-854
[6]   Effects of Capsaicin on Lipid Catabolism in 3T3-L1 Adipocytes [J].
Lee, Mak-Soon ;
Kim, Chong-Tai ;
Kim, In-Hwan ;
Kim, Yangha .
PHYTOTHERAPY RESEARCH, 2011, 25 (06) :935-939
[7]   The vanilloid capsaicin induces IL-6 secretion in prostate PC-3 cancer cells [J].
Malagarie-Cazenave, Sophie ;
Olea-Herrero, Nuria ;
Vara, Diana ;
Morell, Cecilia ;
Diaz-Laviada, Ines .
CYTOKINE, 2011, 54 (03) :330-337
[8]  
Nonius, 1999, COLLECT
[9]   Processing of X-ray diffraction data collected in oscillation mode [J].
Otwinowski, Z ;
Minor, W .
MACROMOLECULAR CRYSTALLOGRAPHY, PT A, 1997, 276 :307-326
[10]  
Sheldrick G.M., 1996, SADABS VERSION 2008