C15 FUNCTIONALIZED DERIVATIVES OF ent-KAUR-16-EN-19-OIC ACID: ISOLATION FROM THE SUNFLOWER HELIANTHUS ANNUUS L. AND SYNTHESIS

The known diterpenic ester – 15α-angeloyl-ent-kaur-16-en-19-oic (angeloylgrandifl oric) acid has been isolated from the dry wastes of Helianthus annuus L. The synthesis of 15α-hydroxy- and 15-oxo-ent-kaur-16-en-19- oic acids starting from ent-kaur-16-en-19-oic acid has been performed

Synthesis of New Homodrimane Sesquiterpenoids Containing Diazine, 1,2,4-triazole and Carbazole Rings

The study describes the synthesis of 11-homodrim-6,8-dien-12-oic acid N-substituted amides containing diazine, 1,2,4-triazole and carbazole rings based on commercially available sclareolide. The mentioned compounds were prepared for the first time by interaction of the generated in situ acyl chloride with some heterocyclic amines: 2- and 4-aminopyrimidine, 2-aminopyrazine, 3-amino-1,2,4-triazole and N-aminocarbazole. Their structures were fully elucidated by elemental and spectral analyses (IR, 1H and 13C NMR)

SYNTHESIS AND CHARACTERIZATION OF [(5-MERCAPTO-1,3,4-OXADIAZOL-2-YL)ARYL]-3,5-DIARYL-4,5-DIHYDRO-1H-PYRAZOLE-1-CARBOTHIOAMIDES

The synthesis and characterization of [(5-mercapto-1,3,4-oxadiazol-2-yl)aryl]-3,5-diaryl-4,5-dihydro-1Hpyrazole-1-carbothioamides - derivatives of pyrazolines and 5-[4(3)-isothiocyanatophenyl]-2-thio-1,3,4-oxadiazoles were realized. The synthesized compounds, are crystalline substances, stable in storage and when exposed to air and light

NEW ROOM TEMPERATURE LIQUIDS: SYNTHESIS AND CHARACTERIZATION

Room temperature ionic liquids (ILs) have been recognized as a new generation of solvents for “green chemistry” and represent remarkably promising classes of technologically useful and fundamentally interesting materials [1-6]. Most of them are quaternary imidazolium cations with inorganic counterions. Cation in these salts is appended to the organic group (usually saturated hydrocarbon fragments). However, some problems regarding the functionalization [2,7], coordination properties [4] of ILs still remain to be solved. It seems to us that functionalization of imidazoles by ethylcarbonitrile, allyl, 2,3-epoxypropyl fragments will lead to new properties of synthesized ILs. There are no literature data on use of 2-(1H-1-imidazolyl)ethylcarbonitrile 4 for synthesis of imidazolium salts with ILs properties

Synthesis, structural elucidation and biological evaluations of new guanidine-containing terpenoids as anticancer agents

Using sclareol and sclareolide as starting materials, the guanidine derivatives of 12-amino-11-dihomodrimane-8α-ol and 13-amino-14,15-bis-dinorlabd-8(9)-ene were synthesized by the reaction of the corresponding amines with sodium hydrogencyanamide in ethanol - water solution. Monoacyl- and diacylguanidines were prepared from activated with N,N-carbonyldiimidazole Δ8,9-bicyclohomofarnesenoic acid by the reaction with guanidine. Their structures were confirmed by the 1H and 13C NMR, IR spectral and elemental analysis data. The compounds 12, 13 and 15 were screened for their antiproliferative and cytotoxicity activities against Colo 205, Colo 320 and MRC 5 human lung fibroblasts with respect to standard drug, Cisplatin. The compounds 12 and 15 exhibits excellent results than positive control. Hence these two compounds may be act as drug lead molecules in cancer chemotherapy

SYNTHESIS AND ANTIVIRAL ACTIVITY OF NEW THIAZOLE, 1,2,4-TRIAZOL AND OXINDOLE DERIVATIVES

The synthesis and antiviral activity evaluation of new derivatives of 2-aminothiazole, 1,2,4-triazole, as well as oxindoles has been realized. The synthesized compounds exhibited different cytotoxicity, in particular, oxindols 4 , 5 , 7 , 8 , 9, 10, 11, 12, 13, 58 as well as thiazole/triazole 73 and 75 turned out to be the most cytotoxic for MT-4 cell lines. The compounds 11, 12, 73, and 75 are more toxic than reference compound Efavirenz. As far as the antiviral activity is concerned, none of the title compounds turned out active against Reo-1, Sb-1, VSV, RSV, YFV and VV viruses. The results obtained against Bovine Viral Diarrhoea Virus (BVDV) showed that nine compounds (six from oxindol’s seria 6, 12, 13, 52, 56, 58 and three 73, 75, 77 of triazole homologues) resulted moderate active. Among all of them, the most potent compound was 52, with EC50 of 6.6 μM. Studies of effect of synthesized compounds against Coxsakie Virus (CVB-2) revealed that only two compounds, 13 and 73 exhibit moderate activity (EC50 >40 and >18 μM, respectively). It should be noticed that eleven compounds, 4, 5, 7, 8, 9, 10, 11, 12, 13, 58, and 75 showed moderate activity against HIV-1 (EC50 >16 – m >59μM)

MOLECULAR REARRANGEMENTS OF HIGHLY FUNCTIONALIZED TERPENES. AN UNIQUE REACTIVITY OF BICYCLIC FRAMEWORK AND POLIENIC CHAIN INHIBITION UNDER SUPERACIDIC TREATMENT

Synthesis of polyfunctional triterpene derivative [8(27),13E,17E,21E]-15-phenylsulfonyl-16-oxobicyclofarnesylfarnesol benzyl ether (8) from commercially available monoterpene geraniol and diterpene manool has been accomplished in 73% yield and its chemical transformation in superacid medium has been investigated. An unexpected rearrangement of 8 occurred, which involved methyl migration in the bicyclic fragment and total inhibition of the lateral polienic chain. A new bicyclic triterpene product [5(10),13E,17E,21E]-15-phenylsulfonyl- 16-oxo-30(10→9)-abeo-bicyclofarnesylfarnesol benzyl ether (9), with rearranged new carbon skeleton has been obtained. Its bicyclic moiety is analogous to this of a natural triterpene neopolypodatetraene

ISOLATION OF ENT-KAUR-16-EN-19-OIC AND ENT-TRACHILOBAN-19-OIC ACIDS FROM THE SUNFLOWER HELIANTHUS ANNUUS L.DRY WASTE

A relatively simple method for isolation of the mixture of ent-kaur-16-en-19-oic (1) and ent-trachiloban-19-oic (2) acids from dry waste of sunflower processing has been elaborated, and it has been shown that the waste can serve as an accessible source of ent-kauranic and ent-trachilobanic diterpenoids

Synthesis, structural elucidation and biological evaluations of new guanidine-containing terpenoids as anticancer agents

Using sclareol and sclareolide as starting materials, the guanidine derivatives of 12-amino-11-dihomodrimane-8α-ol and 13-amino-14,15-bis-dinorlabd-8(9)-ene were synthesized by the reaction of the corresponding amines with sodium hydrogencyanamide in ethanol - water solution. Monoacyl- and diacylguanidines were prepared from activated with N,N-carbonyldiimidazole Δ8,9-bicyclohomofarnesenoic acid by the reaction with guanidine. Their structures were confirmed by the 1H and 13C NMR, IR spectral and elemental analysis data. The compounds 12, 13 and 15 were screened for their antiproliferative and cytotoxicity activities against Colo 205, Colo 320 and MRC 5 human lung fibroblasts with respect to standard drug, Cisplatin. The compounds 12 and 15 exhibits excellent results than positive control. Hence these two compounds may be act as drug lead molecules in cancer chemotherapy

Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation

Based on some homodrimane carboxylic acids and their acyl chlorides, a series of fourteen 2-homodrimenyl-1,3-benzothiazoles, N-homodrimenoyl-2-amino-1,3-benzothiazoles, 4′-methyl-homodrimenoyl anilides and 4′-methyl-homodrimenthioyl anilides were synthesized and their biological activities were evaluated on five species of fungi (Aspergillus niger, Fusarium solani, Penicillium chrysogenum, P. frequentans, and Alternaria alternata) and two strains of bacteria (Bacillus sp. and Pseudomonas aeruginosa). The synthesis involved the decarboxylative cyclization, condensation and thionation of the said acids, anhydrides or their derivatives with 2-aminothiophenol, 2-aminobenzothiazole, p-toluidine and Lawesson’s reagent. As a result, together with the desired compounds, some unexpected products 8, 25, and 27 were obtained, and the structures and mechanisms for their formation have been proposed. Compounds 4, 9, and 25 showed higher antifungal and antibacterial activity compared to the standards caspofungin (MIC = 1.5 μg/mL) and kanamycin (MIC = 3.0 μg/mL), while compound 8 had comparable activities. In addition, compounds 6, 17, and 27 showed selective antifungal activity at MIC = 2.0, 0.25, and 1.0 μg/mL, respectively