Preparation of 3-(6-Deoxy-β-D-glucopyranosyloxy) and 3-(6-Deoxy-α-L-mannopyranosyloxy)androstane Derivatives with Unsaturated Side Chain in Position 17β

1993 ◽  
Vol 58 (12) ◽  
pp. 3000-3008 ◽  
Author(s):  
Hana Chodounská ◽  
Vladimír Pouzar
Keyword(s):  
Side Chain ◽  
Unsaturated Ester ◽  
Silver Silicate ◽  
Derivatives Of ◽  
Androstane Derivatives ◽  
Steroidal Derivatives ◽  
Ester Chain

In our previous papers we described the preparation of 3-β-D-glucopyranosyloxy) and 3-β-D-galactopyranosyloxy) derivatives of steroids with an α,β-unsaturated ester chain in position 17β of androstane skeleton. In conection with this project we have studied silver silicate promoted glycosylation of some of above mentioned steroidal derivatives with 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl bromide and 2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl bromide.

Glucosylation of 5-androsten-3β-ol derivatives containing butenolide, furan or unsaturated ester moieties in the side chain

1984 ◽  
Vol 49 (4) ◽  
pp. 881-891 ◽  
Author(s):  
Ivan Černý ◽  
Vladimír Pouzar ◽  
Pavel Drašar ◽  
Miloš Buděšínský ◽  
Miroslav Havel
Keyword(s):  
Sodium Borohydride ◽  
Lactone Ring ◽  
Acetyl Derivative ◽  
Side Chain ◽  
Unsaturated Ester ◽  
Reaction Sequence ◽  
Silver Silicate

3-O-(Tetra-O-acetyl-β-D-glucopyranosyl) derivatives II, V, XV and XX were prepared from 5-androstene-3β,17β-diol 17-benzoate (I), (20R)-3β-hydroxy-21-nor-5,22-choladien-(24 -20)-olide (IV), 17β-(2-furyl)-5-androsten-3β-ol (XIV) and methyl (20E)-3β-hydroxy-5,20-pregnadiene-21-carboxylate (XIX), respectively, using tetra-O-acetyl-α-D-glucopyranosyl bromide and silver silicate. The furyl derivative XIV was obtained from methyl 3β-methoxymethyletienate VIII by reaction sequence in which the key reactions were alkylation of the keto sulfoxide IX with bromoacetate, cyclization of the obtained product with sodium borohydride and reduction of the mixture of lactones XI and XII with diisobutylaluminium hydride. The unsaturated ester XIX was prepared from 3β-acetoxy-5-androstene-17β-carbaldehyde (XVII) by treatment with diethyl methoxycarbonylmethylphosphonate and deacetylation of the formed acetyl derivative XVIII. Deacetylation of the acetyl derivatives II, XV and XX afforded the glucosides III,XVI and XXI, respectively; the deacetylation of V was accompanied by opening of the lactone ring under formation of the methyl 21-nor-20-oxo-5-cholen-24-oate derivative VI.

Synthesis, anti-oxidant activity, and cytotoxicity of salicyloyl derivatives of estra-1,3,5(10)-triene and androst-5-ene

2012 ◽  
Vol 66 (4) ◽  
Author(s):  
Katarina Gaši ◽  
Evgenija Djurendić ◽  
Sanja Dojčinović-Vujašković ◽  
Andrea Gaković ◽  
Suzana Jovanović-Šanta ◽  
...  
Keyword(s):  
Methyl Salicylate ◽  
Radical Scavenging ◽  
Carcinoma Cells ◽  
Steroid Dependent ◽  
Anti Oxidant ◽  
New Compounds ◽  
Derivatives Of ◽  
Dpph Radical Scavenging ◽  
Androstane Derivatives ◽  
Steroidal Derivatives

AbstractSince many estrane and androstane derivatives exhibit cytotoxic, anti-oxidant, or anti-hormone activity, new steroidal derivatives were synthesised from appropriate estrogen or androgen precursors in order to obtain potential therapeutics for the treatment of steroid-dependent diseases. Starting from estradiol (I), 6-oxo derivatives V and VII were prepared. 17β-Salicyloyl-6-oxo derivatives VI and VIII were synthesised by the reaction of compounds V or VII with methyl salicylate in the presence of sodium. 17β-Salicyloyloxy estradiol IX was prepared from estradiol. Beckmann fragmentation of 16-oxyimino alcohols XII and XIII with methyl salicylate yielded corresponding D-seco derivatives XIV and XV. Simultaneous fragmentation and acylation of compound XII resulted in 3β-salicyloyl-D-seco derivative XVI which was also obtained from compound XIV. Anti-oxidant assays of the newly synthesised compounds V-IX, XIV, and XVI indicated a stronger capacity for hydroxyl radical scavenging, and a weaker capacity for DPPH radical scavenging, compared with the standard anti-oxidants BHA and BHT. Compounds V, XIV, and XVI showed higher or the same activity as BHT. The cytotoxicity of new compounds was evaluated against human breast and prostate carcinoma cells. Compound VI exhibited strong cytotoxicity against MDA-MB-231 cells; compound XIV exhibited strong cytotoxicity against PC-3 cell line, while compound VII moderately inhibited the growth of PC-3 cells.

Synthesis of Some Steroidal Derivatives with Side Chain of 20- and 22- Hydrazone Aromatic Heterocycles and their Antiproliferative Activity

2017 ◽  
Vol 13 (4) ◽  
pp. 375-383 ◽  
Author(s):  
Chunfang Gan ◽  
Liang Liu ◽  
Jianguo Cui ◽  
Zhiping Liu ◽  
Haixin Shi ◽  
...  
Keyword(s):  
Antiproliferative Activity ◽  
Side Chain ◽  
Aromatic Heterocycles ◽  
Steroidal Derivatives

Absolute configuration at C(20) of the derivatives of 21-nor-5α-cholane-20,24-diol

1980 ◽  
Vol 45 (9) ◽  
pp. 2443-2451
Author(s):  
Vladimír Pouzar ◽  
Miroslav Havel
Keyword(s):  
Absolute Configuration ◽  
Side Chain ◽  
Chemical Correlation ◽  
The Absolute ◽  
Derivatives Of

Derivatives of 21-nor-5α-cholane-20,24-diol XI and XIX were prepared by stepwise construction of the side-chain in the position 17β. Their absolute configuration at C(20) was determined on the basis of chemical correlation with the derivatives of 21-nor-5α-cholan-20-ol, XVI and XXIV. The absolute configuration of alcohols XVI and XXIV was determined from the ratio of the yields in which they are formed during the reduction of ketone X and using the benzoate rule. To compounds XI-XVIII the configuration 20R and to compounds XIX-XXVI the configuration 20S has been assigned.

scholarly journals Synthesis of New Derivatives of BEDT-TTF: Installation of Alkyl, Ethynyl, and Metal-Binding Side Chains and Formation of Tris(BEDT-TTF) Systems

2021 ◽  
Vol 7 (8) ◽  
pp. 110
Author(s):  
Songjie Yang ◽  
Matteo Zecchini ◽  
Andrew Brooks ◽  
Sara Krivickas ◽  
Desiree Dalligos ◽  
...  
Keyword(s):  
Metal Binding ◽  
Tricarboxylic Acid ◽  
Metal Salts ◽  
Side Chain ◽  
Side Chains ◽  
Ethynyl Group ◽  
X Ray ◽  
Transition Metal Salts ◽  
Alkyl Side Chains ◽  
Derivatives Of

The syntheses of new BEDT-TTF derivatives are described. These comprise BEDT-TTF with one ethynyl group (HC≡C-), with two (n-heptyl) or four (n-butyl) alkyl side chains, with two trans acetal (-CH(OMe)2) groups, with two trans aminomethyl (-CH2NH2) groups, and with an iminodiacetate (-CH2N(CH2CO2−)2 side chain. Three transition metal salts have been prepared from the latter donor, and their magnetic properties are reported. Three tris-donor systems are reported bearing three BEDT-TTF derivatives with ester links to a core derived from benzene-1,3,5-tricarboxylic acid. The stereochemistry and molecular structure of the donors are discussed. X-ray crystal structures of two BEDT-TTF donors are reported: one with two CH(OMe)2 groups and with one a -CH2N(CH2CO2Me)2 side chain.

ChemInform Abstract: A GENERAL SYNTHESIS OF SIDE CHAIN DERIVATIVES OF Δ9-THC

1978 ◽  
Vol 9 (12) ◽  
Author(s):  
C. G. PITT ◽  
H. H. SELTZMAN ◽  
Y. SAYED ◽  
C. E. JUN. TWINE ◽  
D. L. WILLIAMS
Keyword(s):  
Side Chain ◽  
Derivatives Of ◽  
General Synthesis

Concise Synthesis of the Terpene Core Structure of Suaveolindole Through a Time-Economic Route

Synlett ◽  
2021 ◽  
Author(s):  
Hiroki Tanimoto ◽  
Kazuki Tojo ◽  
Tsumoru Morimoto ◽  
Kiyomi Kakiuchi
Keyword(s):  
Claisen Rearrangement ◽  
Core Structure ◽  
Side Chain ◽  
Unsaturated Ester ◽  
Synthetic Route ◽  
Carbon Side Chain

The terpene core structure of suaveolindoles was synthesized through a concise route in a time-economical manner. A scalable synthetic route from pulegone delivered the desired α,β,γ,δ-unsaturated ester in a brief period. By way of Eschenmoser-Claisen rearrangement, carbon side chain moiety at the crowded double-allylic position was introduced stereoselectively.

New 4-Hydroxypyridine and 4-Hydroxyquinoline Derivatives as Inhibitors of NADH-ubiquinone Reductase in the Respiratory Chain

1989 ◽  
Vol 44 (7-8) ◽  
pp. 609-616 ◽  
Author(s):  
Kun Hoe Chung ◽  
Kwang Yun Cho ◽  
Yasuko Asami ◽  
Nobutaka Takahashi ◽  
Shigeo Yoshida
Keyword(s):  
Electron Transport ◽  
Respiratory Chain ◽  
Side Chain ◽  
Pyridine Derivatives ◽  
Transport Function ◽  
Optimal Length ◽  
Structure Activity ◽  
Membrane Effect ◽  
Relationship Of ◽  
Derivatives Of

Many derivatives of 2,3-dim ethoxy-4-hydroxypyridine, which were designed from examination of the structure-activity relationship of piericidins, were tested for inhibition of NADH-UQ reductase. The lipophilic side chain of those compounds was indicated to be a key part for activity and its optimal length was conjectured. By the use of two different phases of assay material, intact mitochondria and submitochondria, the size of a membrane effect was shown to depend on the structure of the side chain. 4-Hydroxyquinoline derivatives were also tested for an analogous role in relation to the electron transport function of menaquinone, and they were proven to be inhibitors of NADH-UQ reductase as good as the pyridine derivatives.

New N.alpha.-Guanidinobenzoyl Derivatives of Hirudin-54-65 Containing Stabilized Carboxyl or Phosphoryl Groups on the Side Chain of Phenylalanine-63

1994 ◽  
Vol 37 (5) ◽  
pp. 625-629 ◽  
Author(s):  
Christophe Thurieau ◽  
Serge Simonet ◽  
Joseph Paladino ◽  
Jean-Francois Prost ◽  
Tony Verbeuren ◽  
...  
Keyword(s):  
Side Chain ◽  
Phosphoryl Groups ◽  
Derivatives Of
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