Crystal structure of 4,5-bis(3,4,5-trimethoxyphenyl)-2H-1,2,3-triazole methanol monosolvate

被引:2
作者
Madadi, Nikhil Reddy [1 ]
Penthala, Narsimha Reddy [1 ]
Bommagani, Shobanbabu [1 ]
Parkin, Sean [2 ]
Crooks, Peter A. [1 ]
机构
[1] Univ Arkansas Med Sci, Coll Pharm, Dept Pharmaceut Sci, Little Rock, AR 72205 USA
[2] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA
关键词
crystal structure; hydrogen bonds; 1,2,3-triazole;
D O I
10.1107/S1600536814020911
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
The title compound, C20H23N3O6 center dot CH3OH was synthesized by [3 + 2] cycloaddition of (Z)-2,3-bis(3,4,5-trimethoxyphenyl)-acrylonitrile with sodium azide and ammonium chloride in DMF/water. The central nitrogen of the triazole ring is protonated. The dihedral angles between the triazole ring and the 3,4,5-trimethoxyphenyl ring planes are 34.31 (4) and 45.03 (5)degrees, while that between the 3,4,5-trimethoxyphenyl rings is 51.87 (5)degrees. In the crystal, the molecules, along with two methanol solvent molecules are linked into an R-4(4)(10) centrosymmetric dimer by N-H center dot center dot center dot O and O-H center dot center dot center dot N hydrogen bonds.
引用
收藏
页码:O1128 / +
页数:10
相关论文
共 12 条
[1]  
[Anonymous], 1998, COLLECT
[2]   Synthesis and biological evaluation of 3-(trimethoxyphenyl)-2(3H)-thiazole thiones as combretastatin analogs [J].
Banimustafa, Mandana ;
Kheirollahi, Asma ;
Safavi, Maliheh ;
Ardestani, Sussan Kabudanian ;
Aryapour, Hassan ;
Foroumadi, Alireza ;
Emami, Saeed .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 70 :692-702
[3]   Lead identification of conformationally restricted β-lactam type combretastatin analogues: Synthesis, antiproliferative activity and tubulin targeting effects [J].
Carr, Miriam ;
Greene, Lisa M. ;
Knox, Andrew J. S. ;
Lloyd, David G. ;
Zisterer, Daniela M. ;
Meegan, Mary J. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) :5752-5766
[4]   Synthesis and antiproliferative activity of conformationally restricted 1,2,3-triazole analogues of combretastatins in the sea urchin embryo model and against human cancer cell lines [J].
Demchuk, Dmitry V. ;
Samet, Alexander V. ;
Chernysheva, Natalia B. ;
Ushkarov, Vladimir I. ;
Stashina, Galina A. ;
Konyushkin, Leonid D. ;
Raihstat, Mikhail M. ;
Firgang, Sergei I. ;
Philchenkov, Alex A. ;
Zavelevich, Michael P. ;
Kuiava, Ludmila M. ;
Chekhun, Vasyl F. ;
Blokhin, Dmitry Yu. ;
Kiselyov, Alex S. ;
Semenova, Marina N. ;
Semenov, Victor V. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (02) :738-755
[5]   Pharmaceutical design of antimitotic agents based on combretastatins [J].
Hsieh, HP ;
Liou, JP ;
Mahindroo, N .
CURRENT PHARMACEUTICAL DESIGN, 2005, 11 (13) :1655-1677
[6]   Preparation of 4,5 disubstituted-2H-1,2,3-triazoles from (Z)-2,3-diaryl substituted acrylonitriles [J].
Madadi, Nikhil Reddy ;
Penthala, Narsimha Reddy ;
Song, Lin ;
Hendrickson, Howard P. ;
Crooks, Peter A. .
TETRAHEDRON LETTERS, 2014, 55 (30) :4207-4211
[7]  
Otwinowski Z., 2006, INT TABLES CRYSTALLO, P226
[8]   L-Proline catalyzed one-step synthesis of 4,5-diaryl-2H-1,2,3-triazoles from heteroaryl cyanostilbenes via [3+2]cycloaddition of azide [J].
Penthala, Narsimha Reddy ;
Madadi, Nikhil Reddy ;
Janganati, Venumadhav ;
Crooks, Peter A. .
TETRAHEDRON LETTERS, 2014, 55 (40) :5562-5565
[9]   ANTINEOPLASTIC AGENTS .291. ISOLATION AND SYNTHESIS OF COMBRETASTATINS A-4, A-5, AND A-6 [J].
PETTIT, GR ;
SINGH, SB ;
BOYD, MR ;
HAMEL, E ;
PETTIT, RK ;
SCHMIDT, JM ;
HOGAN, F .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (10) :1666-1672
[10]  
Sheldrick G.M., 2008, SADABS