New β-ketophosphonates for the synthesis of prostaglandin analogues. 2 Phosphonates with bicyclo[3.3.0]octene and bicyclo[3.3.0]octane scaffolds linked to the β-keto group

2020 ◽  
Vol 44 (46) ◽  
pp. 20405-20410
Author(s):  
Constantin I. Tănase ◽  
Constantin Drăghici ◽  
Miron Teodor Caproiu
Keyword(s):  
Keto Group ◽  
Prostaglandin Analogues

β-Ketophosphonates, with the keto group linked to a bicyclo[3.3.0]oct(a)ene fragment, were synthesized starting from two diacids.

scholarly journals β-Ketophosphonates with Pentalenofuran Scaffolds Linked to the Ketone Group for the Synthesis of Prostaglandin Analogs

2021 ◽  
Vol 22 (13) ◽  
pp. 6787
Author(s):  
Constantin I. Tănase ◽  
Constantin Drăghici ◽  
Miron Teodor Căproiu ◽  
Anamaria Hanganu ◽  
Gheorghe Borodi ◽  
...  
Keyword(s):  
Lithium Salt ◽  
Methyl Esters ◽  
Secondary Compounds ◽  
Molecular Structures ◽  
Keto Group ◽  
High Yield ◽  
Oxidation Reactions ◽  
Prostaglandin Analogues ◽  
X Ray ◽  
Oxidation Of Alcohols

β-Ketophosphonates with pentalenofurane fragments linked to the keto group were synthesized. The bulky pentalenofurane skeleton is expected to introduce more hindrance in the prostaglandin analogues of type III, greater than that obtained with the bicyclo[3.3.0]oct(a)ene fragments of prostaglandin analogues I and II, to slow down (retard) the inactivation of the prostaglandin analogues by oxidation of 15α-OH to the 15-keto group via the 15-PGDH pathway. Their synthesis was performed by a sequence of three high yield reactions, starting from the pentalenofurane alcohols 2, oxidation of alcohols to acids 3, esterification of acids 3 to methyl esters 4 and reaction of the esters 4 with lithium salt of dimethyl methanephosphonate at low temperature. The secondary compounds 6b and 6c were formed in small amounts in the oxidation reactions of 2b and 2c, and the NMR spectroscopy showed that their structure is that of an ester of the acid with the starting alcohol. Their molecular structures were confirmed by single crystal X-ray determination method for 6c and XRPD powder method for 6b.

Selective cyclization modes of methyl 3′-heteroarylamino-2′-(2,5-dichlorothiophene-3-carbonyl)acrylates. Synthesis of model (thienyl)pyrazolo- and triazolo[1,5-α]pyrimidines

2020 ◽  
Vol 75 (12) ◽  
pp. 1037-1042
Author(s):  
Nuha I. Sweidan ◽  
Mustafa M. El-Abadelah ◽  
Musa Z. Nazer ◽  
Wolfgang Voelter
Keyword(s):  
Spectral Data ◽  
The Other ◽  
Keto Group ◽  
Other Hand ◽  
Selective Displacement ◽  
New Compounds

AbstractInteraction of methyl 3-ethoxy-2-(2,5-dichloro-3-thenoyl)acrylate (I) with 3-aminopyrazole and 3-amino-1,2,4-triazole generated the respective pyrazolo[1,5-α]pyrimidine (4) and triazolo[1,5-α]pyrimidine (7). The formation of 4 entails selective and consecutive displacement of the 3-ethoxy and methoxy (ester) anions in I by 3-NH2 and 1-NH of 3-aminopyrazole. On the other hand, the formation of 7 implies selective displacement of 3-ethoxy in I by the ring-NH followed by cyclocondensation involving the keto group in I and 3-NH2 of aminotriazole. This latter selective displacement sequence is also followed by 3-amino-5-hydroxypyrazole in its reaction with I. The structures of the new compounds are supported by microanalytical and spectral data.

PROSTAGLANDIN ANALOGUES

InPharma ◽  
1981 ◽  
Vol 314 (1) ◽  
pp. 6-7
Keyword(s):  
Prostaglandin Analogues

FURTHER STUDIES ON A SOLUBLE ANDROGEN-MACROMOLECULAR COMPLEX FROM THE RAT VENTRAL PROSTATE

1970 ◽  
Vol 65 (3) ◽  
pp. 517-524 ◽  
Author(s):  
Olav Unhjem
Keyword(s):  
Hydrogen Atom ◽  
Keto Group ◽  
Ventral Prostate ◽  
Metabolic Inhibitors ◽  
Macromolecular Complex ◽  
Structural Requirements ◽  
Macromolecular Complexes ◽  
Rat Ventral Prostate

ABSTRACT The ability of various steroids and metabolic inhibitors to influence the binding of androgen to soluble macromolecules in the rat ventral prostate was evaluated in vitro. The results obtained revealed some structural requirements of steroids for binding to the macromolecules. An androstane skeleton with the α-configuration of the hydrogen atom at position 5 seemed to be essential for binding as well as a keto group at position 3. N-ethylmaleimide, Na-iodoacetate and p-hydroxymercuribenzoate inhibited the binding of androgen to macromolecules. The androgen-macromolecular complexes appeared to be rather stable at temperatures below 5°C.

Stopping prostaglandin analogues in uneventful cataract surgery

2004 ◽  
Vol 30 (12) ◽  
pp. 2644-2645 ◽  
Author(s):  
Muhammad A. Ahad ◽  
Hamish D.R. McKee
Keyword(s):  
Cataract Surgery ◽  
Prostaglandin Analogues

Beneficial effects on the reproductive performance of sows of administering prostaglandin analogues after farrowing

2009 ◽  
Vol 164 (26) ◽  
pp. 807-809 ◽  
Author(s):  
J. V. Lopez ◽  
M. Ptaszynska ◽  
P. Gonzalez ◽  
M. Jimenez ◽  
M. R. T. M. Martens
Keyword(s):  
Reproductive Performance ◽  
Prostaglandin Analogues ◽  
Beneficial Effects

ChemInform Abstract: 7-Substituted Prostaglandin Analogues: A New Synthetic Approach.

ChemInform ◽  
1987 ◽  
Vol 18 (6) ◽  
Author(s):  
W. DANIKIEWICZ ◽  
T. JAWORSKI ◽  
S. KWIATKOWSKI
Keyword(s):  
Synthetic Approach ◽  
Prostaglandin Analogues
Sign in / Sign up

Export Citation Format

Share Document