The synthesis of 5-methyl-19-nor-5β-pregna-9,16-diene-3,20-dione, 5-methyl-19-nor-5β-pregna-9,10-diene-3,6,20-trione and their analogues with annellated E ring

1991 ◽  
Vol 56 (12) ◽  
pp. 2892-2905 ◽  
Author(s):  
Jiří Polman ◽  
Alexander Kasal
Keyword(s):  
Biological Activity ◽  
Hydroxy Group ◽  
Skeletal Rearrangements ◽  
Key Steps

The synthesis of compounds VII, XVII, XXXIV and XXXVII is described, in which biological activity is assumed. The key steps of their preparation are the dehalogenation of compound XVIII and radicalic deoxygenation of the 6β-hydroxy group in compound XXX, which take place without skeletal rearrangements.

scholarly journals Tandem MS-Based Metabolite Profiling of 19,20-Epoxycytochalasin C Reveals the Importance of a Hydroxy Group at the C7 Position for Biological Activity

ACS Omega ◽  
2021 ◽  
Vol 6 (5) ◽  
pp. 3717-3726
Author(s):  
Manoj Kushwaha ◽  
Arem Qayum ◽  
Shreyans K. Jain ◽  
Jasvinder Singh ◽  
Amit Kumar Srivastava ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hydroxy Group ◽  
Metabolite Profiling ◽  
Tandem Ms

The flavonoid paradox: conjugation and deconjugation as key steps for the biological activity of flavonoids

2012 ◽  
Vol 92 (9) ◽  
pp. 1822-1825 ◽  
Author(s):  
Francisco Perez-Vizcaino ◽  
Juan Duarte ◽  
Celestino Santos-Buelga
Keyword(s):  
Biological Activity ◽  
Key Steps

Synthesis and Biological Activity of New 16,17-Secoestrone Derivatives

2000 ◽  
Vol 65 (1) ◽  
pp. 77-82 ◽  
Author(s):  
Suzana Jovanović-Šanta ◽  
Silvana Andrić ◽  
Radmila Kovačević ◽  
Vjera Pejanović
Keyword(s):  
Biological Activity ◽  
Hydroxy Group ◽  
Sodium Borohydride ◽  
Estrogenic Activity ◽  
Complete Loss ◽  
Borohydride Reduction ◽  
Experimental Animals ◽  
Biological Tests ◽  
Sodium Borohydride Reduction

Starting from estrone 3-benzyloxy-17β-hydroxyestra-1,3,5(10)-trien-16-one oxime (3b) was synthesized, which underwent Beckmann fragmentation giving the 3-benzyloxy-17-oxo- 16,17-secoestra-1,3,5(10)-triene-16-nitrile (4b). Sodium borohydride reduction of this compound afforded 3-benzyloxy-17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile (5b). The deprotection of the 3-hydroxy group was achieved by action of hydrogen upon derivatives 4b and 5b in presence of Pd/C as a catalyst, yielding 3-hydroxy-17-oxo-16,17-secoestra- 1,3,5(10)-triene-16-nitrile (4a) and 3,17-dihydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile (5a). In biological tests on experimental animals, compounds 4a, 4b, 5a and 5b showed virtually a complete loss of estrogenic activity, whereas compounds 4a, 5a and 5b exhibited moderate antiestrogenic effect.

Total Synthesis of Bis-anthraquinone Antibiotic BE-43472B

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2490-2515 ◽  
Author(s):  
Yu Yamashita ◽  
Yoichi Hirano ◽  
Akiomi Takada ◽  
Hiroshi Takikawa ◽  
Keisuke Suzuki
Keyword(s):  
Total Synthesis ◽  
Hydroxy Group ◽  
Three Dimensional ◽  
Crystal Structure Analysis ◽  
Aryl Group ◽  
Full Account ◽  
Ring Fusion ◽  
Enantiomerically Pure ◽  
Pinacol Rearrangement ◽  
Key Steps

This is a full account of our synthetic endeavor on the total synthesis of bis-anthraquinone antibiotic BE-43472B, an unusual octacyclic aromatic polyketide with a bis-anthraquinone scaffold. Three key steps enabled a facile access to the anthraquinone unit corresponding to the ABCF rings; (1) cyclo-condensation or -addition of benzonitrile oxides with cyclic enone derivatives, (2) benzoin cyclization for the stereoselective ring fusion with an angular hydroxy group, and (3) pinacol rearrangement for stereoselective installation of the angular aryl group. Other keys for the success include, (4) diastereoselective methylation of a lactol derivative, and (5) late-stage installation of the C3 hydroxy group through stereoselective oxirane ring formation via halohydrin derivatives. Whereas oxidation of the double bond in the enone with an adjacent 1,3-diketone moiety failed, the projected oxidation was achieved with the alkene keeping the isoxazole moiety intact as a 1,3-diketone equivalent. In the racemic total synthesis, X-ray crystal structure analysis of the target was achieved, proving the three-dimensional architecture for the first time. The asymmetric total synthesis was also achieved by exploiting a cycloadduct of the nitrile oxide and the enantiomerically pure cyclohexenone, which was convertible to the common intermediate via dehydrogenation followed by alkoxycarbonylation.

Moulting Hormones. LIII. the Synthesis and Biological Activity of Some Ecdysone Analogues

1981 ◽  
Vol 34 (12) ◽  
pp. 2607 ◽  
Author(s):  
M Galbraith ◽  
DS Horn ◽  
B Kelly ◽  
J Kinnear ◽  
M Martin ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hydroxy Group ◽  
Structural Changes ◽  
Mosquito Larvae ◽  
Moulting Hormones

A number of ecdysone analogues were prepared to study the effect of structural changes on biological activity. It was found that analogues with the 5α-configuration or a 3,5-cyclo structure were inactive, that a 3β-hydroxy group enhances activity but is not essential for activity, and that 3β-substituents decrease activity as follows: OMe (60%), OAc (25%) and OEt (10%). The keto diol (3), keto alcohol (9) and amide (36) were found to be highly toxic to mosquito larvae.

scholarly journals Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

2016 ◽  
Vol 12 ◽  
pp. 353-361 ◽  
Author(s):  
Charlotte Collet ◽  
Françoise Chrétien ◽  
Yves Chapleur ◽  
Sandrine Lamandé-Langle
Keyword(s):  
Hydroxy Group ◽  
Pet Imaging ◽  
Fluorine Atom ◽  
Biological Properties ◽  
Diastereoselective Synthesis ◽  
Different Types ◽  
Key Steps

Efficient routes were developed for the diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues. The key steps of the synthesis were the easy accessibility of different types of arms in term of configuration (myo and scyllo), the linking method and length, which could modulate the biological properties. These inositol derivatives, bearing an arm terminated either with a hydroxy group or a fluorine atom, could be interesting candidates for diastereoisomeric intermediates and biological evaluations, especially for PET imaging experiments.

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