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1.
Molecules ; 21(2): 156, 2016 Jan 27.
Article in English | MEDLINE | ID: mdl-26828467

ABSTRACT

A series of 5,8-quinolinedione derivatives containing one or two alkoxy groups was synthesized and characterized by ¹H- and (13)C-NMR, IR and MS spectra. X-ray diffraction was used to investigate the crystal structures of 6-chloro-7-(2-cyjanoethoxy)-5,8-quinolinedione and 6,7-di(2,2,2-trifloroethoxy)-5,8-quinolinedione. All studied compounds were tested in vitro for their antiproliferative activity against three human cancer cell lines and human normal fibroblasts. Most of the compounds showed higher cytotoxicity than the starting compound, 6,7-dichloro-5,8-quinolinedione, and cisplatin, which was used as a reference agent.


Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Quinolines/chemical synthesis , Quinolines/pharmacology , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Fibroblasts/cytology , Fibroblasts/drug effects , Humans , Molecular Structure , Quinolines/chemistry , Structure-Activity Relationship
2.
J Pharm Sci ; 101(12): 4458-71, 2012 Dec.
Article in English | MEDLINE | ID: mdl-22987400

ABSTRACT

X-ray diffraction and infrared spectroscopy measurements for the N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) solvatomorphs of betulonic acid (BA) were investigated. BA [3-oxolup-20(29)-en-28-oic acid, C(30)H(46)O(3)] exhibits a wide spectrum of biological activities and is considered to be a promising natural agent for the treatment of various cancer diseases. BA as a noncrystalline substance was obtained by oxidation of betulin. Crystal structures and the spectral data allowed analysis of hydrogen bonding (H-bonding), molecular conformation, and crystal packing differences in the solvatomorphs. Crystals of BA solvates were grown from the DMF-acetone (1:10, v/v) and DMSO-water (9:1, v/v) solutions. BA-DMF (1:1) solvate crystallizes in the monoclinic P2(1) space group, Z = 2. The unit cell parameters are as follows: cell lengths a = 13.2458(5) Å, b = 6.6501(2) Å, c = 17.9766(7) Å, and ß = 110.513(4)°. BA-DMSO (1:1) solvate crystallizes in the orthorhombic P2(1)2(1)2(1) (Z = 4) space group with the following unit cell parameters: a = 6.6484(4) Å, b = 13.3279(8) Å, and c = 32.6821(19) Å. Conformational analysis of the six-membered rings, cyclopentane ring, and isopropenyl group showed differences in comparison with other betulin derivatives examined earlier. For both solvates, the intermolecular packing arrangement was governed mainly by H-bonds. The shortest H-bonds with D···A distances of 2.604 and 2.657 Å, and almost linear DH···A connection occurred between OH of carboxylic group of BA and oxygen atoms from O=C and O=S groups of DMF and DMSO, respectively.


Subject(s)
Antineoplastic Agents/chemistry , Dimethyl Sulfoxide/chemistry , Dimethylformamide/chemistry , Oleanolic Acid/analogs & derivatives , Crystallography, X-Ray , Models, Molecular , Oleanolic Acid/chemistry , Spectrophotometry, Infrared
3.
Nucleosides Nucleotides Nucleic Acids ; 27(12): 1250-6, 2008 Dec.
Article in English | MEDLINE | ID: mdl-19003570

ABSTRACT

Synthesis of N(3),2',3'-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5'-O-(2-deoxy-alpha-d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman's catalyst without competing side reactions.


Subject(s)
Benzyl Compounds/chemistry , Hydrogen/chemistry , Uridine/chemistry , Catalysis , Hydrogenation , Molecular Structure
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