ABSTRACT
New potentially biologically active amidoethanesulfonamides of betulonic acid were synthesized by the acid chloride method via conjugation of betulonic acid with 2-aminoethanesulfonamides as the free bases.
ABSTRACT
Under the action of PCl(5), the Beckman rearrangement of a 3 : 1 mixture of Z- and E-ketoximes of 18beta-hydroxydihydroquinopimaric acid resulted in 5'-caprolactam and isomeric caprolactams containing fragments of cyclic ether. Z- and E-ketoximes were separated as acetates. Using a carrageenan inflammation model, we demonstrated that the anti-inflammatory activity of quinopimaric acid derivatives was comparable with that of diclofenac.
Subject(s)
Abietanes/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Abietanes/chemistry , Abietanes/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Antiviral Agents/chemical synthesis , Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Carrageenan , Edema/chemically induced , Edema/drug therapy , Influenza A virus/drug effects , Mice , Stereoisomerism , Structure-Activity Relationship , Toxicity Tests, AcuteABSTRACT
The interaction of betulin diacetate with formaldehyde by the Prins reaction in various media was studied. As a result, 3beta,28-di-O-acetyl-30-hydroxymethyl-(20)29-lupene, 3beta-acetyl-28-hydroxy-(20)29-lupene, and 3beta,28-di-O-acetoxy-19-(5',6'-dihydro-2'H-pyran-4'-yl)-20,29,30-trinorlupane were obtained.
Subject(s)
Acetates/chemistry , Formaldehyde/chemistry , Triterpenes/chemistry , Esters , Magnetic Resonance Spectroscopy , Spectrophotometry, InfraredABSTRACT
A reductive transformation of the peroxide products of ozonolysis of derivatives of 3beta-O-acetyl-22(17-->28)-abeo-lupa-17(28),20(29)-diene and the subsequent intramolecular ketalization led to a compound with a trioxane fragment. This is a new approach to a skeletal modification of triterpenoid cycle E. An activity of the synthesized compounds was found toward the viruses of type A influenza and herpes simplex.
Subject(s)
Alphainfluenzavirus/drug effects , Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Simplexvirus/drug effects , Triterpenes/chemistry , Triterpenes/pharmacology , Antiviral Agents/chemical synthesis , Catalysis , Humans , Ruthenium Compounds/chemistry , Saponins/chemistry , Triterpenes/chemical synthesisABSTRACT
Uraline, a new norditerpenoid alkaloid, was isolated from aerial parts of Delphinium uralense. The structure of 1alpha,7,8-trihydroxy-6beta,14alpha,16beta-trimethoxy-18-N-(2-methyl)succinylanthranoyloxyaconane was ascribed to the new compound on the basis of 1H and 13C NMR, IR, and mass spectra. The known alkaloids methyllycaconitine and delcorine were also isolated from the plant.
Subject(s)
Alkaloids/isolation & purification , Delphinium/chemistry , Diterpenes/isolation & purification , Chromatography, Liquid , Magnetic Resonance Spectroscopy , Mass Spectrometry , Plant Components, Aerial/chemistry , Plant Extracts/chemistryABSTRACT
The effect of pyridine on the electronic structure and conformational state of cell phosphatidylcholine was studied by the methods of quantum chemistry and 13C NMR spectroscopy. It was shown that the interaction of the pi-system of pyridine electrons with the choline group of phosphatidylcholine leads to the formation of a complex. Changes in the conformational states due to the formation of this complex were revealed.
Subject(s)
Phosphatidylcholines/chemistry , Pyridines/chemistry , Magnetic Resonance Spectroscopy , Molecular Conformation , Molecular Structure , Quantum TheoryABSTRACT
The assignment of NMR resonances of lupane triterpenoids was refined by the example of 3,28-dinicotinoylbetulin, obtained by acylation of betulin. Hepatoprotective, untiulcer, antiinflammatory, reparative, and anti-HIV activities were found for the compound. In addition, it was demonstrated to have immunomodulatory activity, for the first time detected among lupane triterpenoids. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2002, vol. 28, no. 6; see also http://www.maik.ru.
Subject(s)
Adjuvants, Immunologic/chemical synthesis , Anti-HIV Agents/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Triterpenes/chemical synthesis , Adjuvants, Immunologic/therapeutic use , Adjuvants, Immunologic/toxicity , Animals , Anti-HIV Agents/therapeutic use , Anti-HIV Agents/toxicity , Anti-Inflammatory Agents, Non-Steroidal/therapeutic use , Anti-Inflammatory Agents, Non-Steroidal/toxicity , Antibody Formation/drug effects , Arthritis/drug therapy , Betula/chemistry , Burns/drug therapy , Cell Line , Cell Survival/drug effects , Disease Models, Animal , Dose-Response Relationship, Drug , HIV Core Protein p24/analysis , HIV-1/drug effects , Humans , Lethal Dose 50 , Mice , Plant Bark/chemistry , Rats , Stomach Ulcer/drug therapy , Triterpenes/chemistry , Triterpenes/isolation & purification , Triterpenes/therapeutic use , Triterpenes/toxicityABSTRACT
Hemisuccinates, hemiphthalates, acetylsalicylates, cinnamates, and p-methoxycinnamates of lupeol, betulin, and 3-O-acetylbetulin were synthesized via interaction with corresponding acid anhydrides or acid chlorides. A number of betulin esters in position 3 and 28 were shown to exhibit a pronounced hepatoprotective effect similar to that of betulin and silibor. These experimental data were in a good agreement with the computer prediction of their biological activity. Betulin 3,28-bis-hemiphthalate was more effective than carsil in models of experimental hepatitis caused by carbon tetrachloride, tetracycline, and ethanol.
