A new stable prostacyclin mimic, 7-oxo-PGI2

Kovács, Gábor; Simonidesz, V.; Tömösközi, I.; Körmöczy, P.Sz.; Szekely, Ivan J.; Papp‐Behr, A.; Stadler, István; Szekeres, L.; Papp, Gábor

doi:10.1021/jm00344a001

Cited by 19 publications

(1 citation statement)

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“…In the prostaglandin (PG) and prostaglandin analogs (PGs), the inactivation of PGs is mainly realized by enzyme oxidation of the 15α-OH to the 15-keto group via the 15-PGDH pathway. To slow down (retard) the 15α-OH oxidation, some structural modifications have been done: the introduction of a 15-OH,15-methyl group [1], like in arbaprostil [2], prostalene [3], tioprostanide [4], etc., a 16-OH, 16-methyl group at C 16 carbon atom, like in mexiprostil [5], two methyl groups at C 16 , like in nocloprost [6], gemeprost [7,8], cyclopentyl and cyclohexyl scafolds for a few prostacyclin and carbacyclin type compounds, like: ataprost [9,10], CH-5084 [11], SC-43350 [12] for the first, and taprostene [13], U-68215 [14], RS-93427 [15] for the second. Some prostaglandins substituted at the C 16 carbon atom with cycloalkyl, aryl, heterocyclyl [16], furyl [17], methylene-2-(2-thiophene) [18] or C 15 with 2-indanyl [19], aryl or heteroaryl scafolds [20] are claimed in patents.…”

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confidence: 99%

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

Tănase

Drăghici²,

Cãproiu³

et al. 2021

IJMS

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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.

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