1363375-27-2Relevant academic research and scientific papers
Synthesis and biological evaluation of fluorinated 1,5-diarylpyrrole-3-alkoxyethyl ether derivatives as selective COX-2 inhibitors endowed with anti-inflammatory activity
Di Capua, Angela,Sticozzi, Claudia,Brogi, Simone,Brindisi, Margherita,Cappelli, Andrea,Sautebin, Lidia,Rossi, Antonietta,Pace, Simona,Ghelardini, Carla,Di Cesare Mannelli, Lorenzo,Valacchi, Giuseppe,Giorgi, Gianluca,Giordani, Antonio,Poce, Giovanna,Biava, Mariangela,Anzini, Maurizio
, p. 99 - 106 (2016/01/15)
A series of substituted 1,5-diarylpyrrole-3-alkoxyethyl ethers were previously synthesized and the potential anti-inflammatory and antinociceptive activities of these compounds were evaluated in vivo. The compounds displayed a very good activity against b
1,5-Diaryl-2-alkylpyrrole-3-Substituted Nitro Esters, Selective COX-2 Inhibitors and Nitric Oxide Donors
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Paragraph 0275; 0296, (2013/07/05)
1,5-diaryl-2-alkylpyrrole-3-substituted nitro esters, of Formula (I) are provided. Such compounds are potent and selective COX-2 inhibitors which are able to release NO in concentrations that make it possible to counteract the side effects due to selective COX-2 inhibition, without giving rise to hypotensive effects. Formula (I) includes compounds wherein the groups R′ and R″ are: —H, —F, —Cl, —Br, —CH3, —CF3, —OCH3, —SCH3, R1 is methyl, ethyl, trifluoromethyl, hydroxymethyl, methoxymethyl and the substituent in position ?3 of the pyrrole ring is a chain, where the groups X, Y, Z, W and R2 are: X is a carbonyl or a group —(CHR3)—, Y is an oxygen atom or the group —NR3— and Z is a carbonyl or a group —(CHR3)—, or a [—CH(COOH)—] group, or a group —(NR3)—, W is an aliphatic chain substituted with one or two (—O—NO2) groups, R2 is: —H, —OH, —OCH3, or —NHR3. R3 is: —H, —CH3, —CH2CH3, [—CH2(CH3)2]. R′″ is methylsulphonyl or sulphonamido. Pharmaceutical formulations and methods of making an using such formulations are also provided.
Novel analgesic/anti-inflammatory agents: 1,5-Diarylpyrrole nitrooxyalkyl ethers and related compounds as cyclooxygenase-2 inhibiting nitric oxide donors
Anzini, Maurizio,Di Capua, Angela,Valenti, Salvatore,Brogi, Simone,Rovini, Michele,Giuliani, Germano,Cappelli, Andrea,Vomero, Salvatore,Chiasserini, Luisa,Sega, Alessandro,Poce, Giovanna,Giorgi, Gianluca,Calderone, Vincenzo,Martelli, Alma,Testai, Lara,Sautebin, Lidia,Rossi, Antonietta,Pace, Simona,Ghelardini, Carla,Di Cesare Mannelli, Lorenzo,Benetti, Veronica,Giordani, Antonio,Anzellotti, Paola,Dovizio, Melania,Patrignani, Paola,Biava, Mariangela
, p. 3191 - 3206 (2013/06/05)
A series of 3-substituted 1,5-diarylpyrroles bearing a nitrooxyalkyl side chain linked to different spacers were designed. New classes of pyrrole-derived nitrooxyalkyl inverse esters, carbonates, and ethers (7-10) as COX-2 selective inhibitors and NO donors were synthesized and are herein reported. By taking into account the metabolic conversion of nitrooxyalkyl ethers (9, 10) into corresponding alcohols, derivatives 17 and 18 were also studied. Nitrooxy derivatives showed NO-dependent vasorelaxing properties, while most of the compounds proved to be very potent and selective COX-2 inhibitors in in vitro experimental models. Further in vivo studies on compounds 9a,c and 17a highlighted good anti-inflammatory and antinociceptive activities. Compound 9c was able to inhibit glycosaminoglycan (GAG) release induced by interleukin-1β (IL-1β), showing cartilage protective properties. Finally, molecular modeling and 1H- and 13C-NMR studies performed on compounds 6c,d, 9c, and 10b allowed the right conformation of nitrooxyalkyl ester and ether side chain of these molecules within the COX-2 active site to be assessed.
L,5-DIARYL-2-ALKVLPVRROLE-3-SUBSTITUTED NITRO ESTERS, SELECTIVE COX-2 INHIBITORS AND NITRIC OXIDE DONORS
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Page/Page column 79, (2012/03/27)
The present invention relates to l,5-diaryl-2-alkylpyrrole-3-substituted nitro esters, of formula (I), which are potent and selective COX-2 inhibitors able to release NO in concentrations that make it possible to counteract the side effects due to selective COX-2 inhibition, without giving rise to hypotensive effects. (I). Where the groups R' and R" are: -H, -F, -CI, -Br, -CH3, -CF3, -OCH3, -SCH3, R1 is methyl, ethyl, trifluoromethyl, hydroxymethyl, methoxymethyl and the substituent in position -3 of the pyrrole ring is a chain, where the groups X, Y, Z, W and R2 are: X is a carbonyl or a group -(CHR3)-, Y is an oxygen atom or the group -NR3- and Z is a carbonyl or a group - (CHR3)-, or a [-CH(COOH)-] group, or a group -(NR3)-, W is an aliphatic chain substituted with one or two (-O-NO2) groups, R2 is: -H, -OH, -OCH3, or -NHR3. R3 is: -H, -CH3, -CH2CH3, [-CH2(CH3)2]. R'" is methylsulphonyl or sulphonamido. The purpose of the invention includes: preparation of the compounds of formula (I), the respective pharmaceutical formulations and use thereof for treating acute and chronic pain, for treating inflammatory disorders and for drug treatment of some forms of tumours.
