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The synthesis of novel steroidal 3-cyano-2-aminopyridines using enaminonitrile and various primary amines was established under solvent-free condition. Structures of the new compounds were characterized by MS, 1H and 13C NMR data and the structure of 2-aminopyridine of the product 5b was further confirmed by X-ray analysis. The reaction mechanism was proposed on the basis of the key intermediate obtained...
Multicomponent assembly of steroidal dihydropyridinyl spirooxindoles from pregnenolone, isatins, malononitrile, and ammonium acetate is described, which involves the formation of two C–C bonds, two C–N bonds, and an all-carbon quaternary stereogenic center in a single operation. MTT assays showed that some of these compounds had moderate to excellent cytotoxicity against the tested cancer cell lines...
An efficient and practical base-promoted cascade reaction has been developed to access steroidal polysubstituted anilines from simple precursors. The protocol reported herein achieved the formation of a benzene ring as well as three continuous C–C bonds in a single operation. The reaction mechanism was proposed on the basis of the key intermediate obtained. Besides, this method could be potentially...
A series of novel steroidal spirooxindoles 3a–h were synthesized from pregnenolone in a high regioselective manner using the 1,3-dipolar cycloaddition as the key step. This protocol resulted in the formation of two C–C bonds, one C–N bond and the creation of one pyrrolidine ring and three contiguous stereocenters in a single operation. Biological evaluation showed that these synthesized steroidal...
A series of novel steroidal pyran–oxindole hybrids were efficiently synthesized in a single operation through the vinylogous aldol reaction of vinyl malononitrile 3 with substituted isatins involving the construction of C–C and C–O bonds. Some compounds displayed moderate to good cytotoxicity against T24, SMMC-7721, MCF-7 and MGC-803 cells. Compounds 4f and 4i were more potent than 5-Fu against T24...
Novel C6-cyclo secondary amine substituted purine steroid-nucleoside analogues (2–9) were efficiently synthesized through displacement of the C6 chloro on the purine ring of series 1 with versatile cyclic secondary amines, including pyrrolidines, piperidine, morpholine, and piperazines. All the newly-synthesized compounds were evaluated for their anticancer activity in vitro against Hela, PC-3 and...
Novel C6-piperazine substituted purine nucleoside analogues (2–9) bearing a modified pyranose-like D ring of the 4-azasteroid moiety were efficiently synthesized through nucleophilic substitution at C6 position of the steroid–nucleoside precursors (1) with versatile piperazines. All newly-synthesized compounds were evaluated for their anticancer activity in vitro against Hela, PC-3 and MCF-7 cell...
A series of steroidal[17,16-d]thiazole, steroidal[1,2-b]pyridine and steroidal[17,16-d]thiazole[2,1-b]imidazo products were synthesized through a convenient and productive method. Anti-proliferation activity against EC109 (human esophageal carcinoma), EC9706 (human esophageal carcinoma) and MGC-803 (human gastric carcinoma) cell lines was examined in vitro. Among the screened compounds, several highly...
Using dehydroepiandrosterone as the starting material, we have synthesized a series of steroid analogs possessing a D-ring fused with heterocycles which are pyridine, imidazo [2,1-b]thiazoles or substituted thiazole imines. All the final structures are first reported and identified by NMR and MS spectroscopys, the yields of these products are moderate to good and the reaction conditions are mild....
The stereoselective and metal-free protocol involving a cascade aldol/cyclization process for the synthesis of steroidal (E, E) dienamides from steroidal α, α-dicyanoalkene was reported. This protocol efficiently achieved the construction of CC bond and selective conversion of cyano group into carboxamide in one-pot procedure under mild condition. Further biological evaluation showed that some of...
A simple and practical method for synthesis of the D-ring modified steroidal dienamides (4a–k) from the steroidal α,α-dicyanoalkene 3 and aldehydes via vinylogous aldol reaction was first reported. By using NaOAc as a base, the desired products were obtained in moderate to good yields in ethanol under mild conditions. All the synthesized steroidal dienamides are new and are currently being evaluated...
The preparation of steroidal[17,16-d][1,2,4]triazolo[1,5-a]pyrimidines and their biological evaluation as potential anticancer agents are herein reported. These novel heterosteroids (2, 4) were prepared through the condensation reaction of 3-amino-1,2,4-triazole with 16-arylidene-17-ketosteroids (1, 3). All the synthesized compounds were evaluated for their anticancer activity in vitro against PC-3...
The preparation of novel steroidal heterocycles containing the 7-aryl-substituted 1,2,4-triazolo[1,5-a]pyrimidine moiety fused to the 16,17-positions of the steroid nucleus is described. The Aldol reaction of 4-aza-androst-3,17-dione (1a) and dehydroepiandrosterone (DHEA, 1b) with aromatic aldehydes was catalyzed by KF/Al 2 O 3 to give the corresponding 3-oxo-4-aza-5α- and 3β-hydroxy-5-en-16-arylidene-17-ketosteroids...
Microbial transformation of dehydroepiandrosterone (DHEA, 1) using Penicillium griseopurpureum Smith and Penicillium glabrum (Wehmer) Westling has been investigated. Neither fungi had been examined previously for steroid biotransformation. One novel metabolic product of DHEA (1) transformed with P. griseopurpureum Smith, 15α-hydroxy-17a-oxa-d-homo-androst-4-ene-3,17-dione (5), was reported for the...
A series of digoxin derivatives containing the γ-alkylidene butenolide moiety were synthesised by way of stereoselective vinylogous aldol reaction of the unactivated butenolide in simple conditions. The structures of compounds synthesised were characterised by infrared (IR), nuclear magnetic resonance (NMR) and HR-MS. Preliminary bioassay shows that some of them have cardiac functions, especially...
Fermentation of 5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one (4) with Trichoderma viride under aerobic condition yielded 3β,5α,6β-trihydroxy-16-pregnen-20-one (5) and 3β,5α,6β,15β-tetrahydroxy-16-pregnen-20-one (6). Each microbial metabolite was characterized by spectroscopic methods. Compounds 6 and 3β,5α,15β-trihydroxy-16-pregnen-6,20-dione (7) are reported for the first time.
Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization...
The biotransformations of a series of steroids by the fungus penicillium citreo-viride A.C.C.C. 0402 have been investigated, and the conversion to the same product testolactone (1) was observed from progesterone (2), dehydroepiandrosterone (3), 4-androstene-3, 17-dione (4), 5-androstene-3, 17-diol (5) with the exception of pregnenolone (6) and 3β-hydroxy-5, 16-pregnadien-20-one (7). The possible metabolic...
The fermentation of dehydroepiandrosterone synthesized from the starting material diosgenin using Mucor racemosus produced 7α-hydroxy-dehydroepiandrosterone and 7β-hydroxy-dehydroepiandrosterone. The bioactivity of the microbial metabolites is also discussed. The species M. racemosus was isolated by screening among stains from soil samples collected from various parts of China.
Treatment of 3β-hydroxyl-5-Δ steroids with anhydrous FeCl 3 in CH 2 Cl 2 afforded reasonable yields of the corresponding alkyl chlorides with a retention of configurations. The structures of the chlorine-exchanging products were determined by NMR and HRMS spectra. The absolute configurations were confirmed by X-ray crystal analysis of 3β-chloro-androst-5-en-17-one. The generality...
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