Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives
Sinteza i farmakološko ispitivanje novih derivata N-(2-nitrofenil) piperazina
2007
Autori
Andrić, DeanaTovilović, Gordana
Roglić, Goran
Vasković, Đurđica
Šoškić, Vukić
Tomic, Mirko
Kostić-Rajačić, Slađana
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Six newly synthesized heterocyclic (2-nitroplienyl)piperazines. with a specific structure of the heteroaryl group, which mimics the catechol moiety of dopamine (benzimidazoles and substituted benzimidazoles), were evaluated for their binding affinity to rat dopamine (DA), serotonin (5-HT) and alpha I receptors. All compounds with a benzimidazole group had a 5-HT2A/D-2 receptors binding ratio characteristic for atypical neuroleptics ( gt 1, pK(i) values). Compound 7e, 4-bromo-6-{2-[4-(2-nitrophenyl)piperazin-1-yl]etliyl}-1H-benziniidazole, expressed higher affinities for all receptor classes than clozapine. Also, it exhibited the best characteristic for atypical neuroleptics and presents a compound with the best profile for further in vivo investigations.
Sintetisano je šest heterocikličnih (2-nitrofenil)piperazina sa specifičnom heteroaril grupom, koja podražava kateholsku grupu dopamina (benzimidazoli i supstituisani benzimidazoli), i ispitan je njihov afinitet ka dopaminskim, serotoninskim i _1 receptorima. Sva jedinjenja sa benzimidazolskim grupama su pokazala 5-HT 1A/D2 odnos vezivanja karakterističan za atipične neuroleptike ( gt 1, pK i vrednosti). Jedinjenje 7c, 4-bromo-6-{2-_4-(2-nitrofenil)piperazin-1-il_etil}-1H-benzimidazol, pokazalo je izraženiji afinitet ka svim klasama receptora u poređenju sa klozapinom i takođe predstavlja jedinjenje sa najboljim karakteristikama za dalja in vivo istraživanja.
Ključne reči:
arylpiperazines / benzimidazoles / benzimidazoles / dopamine receptors / dopamine receptors / serotonin receptors / serotonin receptors / atypical antipsychotic / atypical antipsychoticIzvor:
Journal of the Serbian Chemical Society, 2007, 72, 5, 429-435Izdavač:
- Serbian Chemical Soc, Belgrade
Finansiranje / projekti:
- Sinteza i karakterizacija biološki aktivnih supstanci i kompjuterska simulacija bioloških sistema (RS-MESTD-MPN2006-2010-142009)
- Biomedicinska ispitivanja i razvoj nekih novih psihotropnih supstanci (RS-MESTD-MPN2006-2010-143032)
DOI: 10.2298/JSC0705429A
ISSN: 0352-5139
WoS: 000247579900002
Scopus: 2-s2.0-34447136382
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Andrić, Deana AU - Tovilović, Gordana AU - Roglić, Goran AU - Vasković, Đurđica AU - Šoškić, Vukić AU - Tomic, Mirko AU - Kostić-Rajačić, Slađana PY - 2007 UR - https://cherry.chem.bg.ac.rs/handle/123456789/845 AB - Six newly synthesized heterocyclic (2-nitroplienyl)piperazines. with a specific structure of the heteroaryl group, which mimics the catechol moiety of dopamine (benzimidazoles and substituted benzimidazoles), were evaluated for their binding affinity to rat dopamine (DA), serotonin (5-HT) and alpha I receptors. All compounds with a benzimidazole group had a 5-HT2A/D-2 receptors binding ratio characteristic for atypical neuroleptics ( gt 1, pK(i) values). Compound 7e, 4-bromo-6-{2-[4-(2-nitrophenyl)piperazin-1-yl]etliyl}-1H-benziniidazole, expressed higher affinities for all receptor classes than clozapine. Also, it exhibited the best characteristic for atypical neuroleptics and presents a compound with the best profile for further in vivo investigations. AB - Sintetisano je šest heterocikličnih (2-nitrofenil)piperazina sa specifičnom heteroaril grupom, koja podražava kateholsku grupu dopamina (benzimidazoli i supstituisani benzimidazoli), i ispitan je njihov afinitet ka dopaminskim, serotoninskim i _1 receptorima. Sva jedinjenja sa benzimidazolskim grupama su pokazala 5-HT 1A/D2 odnos vezivanja karakterističan za atipične neuroleptike ( gt 1, pK i vrednosti). Jedinjenje 7c, 4-bromo-6-{2-_4-(2-nitrofenil)piperazin-1-il_etil}-1H-benzimidazol, pokazalo je izraženiji afinitet ka svim klasama receptora u poređenju sa klozapinom i takođe predstavlja jedinjenje sa najboljim karakteristikama za dalja in vivo istraživanja. PB - Serbian Chemical Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives T1 - Sinteza i farmakološko ispitivanje novih derivata N-(2-nitrofenil) piperazina VL - 72 IS - 5 SP - 429 EP - 435 DO - 10.2298/JSC0705429A ER -
@article{ author = "Andrić, Deana and Tovilović, Gordana and Roglić, Goran and Vasković, Đurđica and Šoškić, Vukić and Tomic, Mirko and Kostić-Rajačić, Slađana", year = "2007", abstract = "Six newly synthesized heterocyclic (2-nitroplienyl)piperazines. with a specific structure of the heteroaryl group, which mimics the catechol moiety of dopamine (benzimidazoles and substituted benzimidazoles), were evaluated for their binding affinity to rat dopamine (DA), serotonin (5-HT) and alpha I receptors. All compounds with a benzimidazole group had a 5-HT2A/D-2 receptors binding ratio characteristic for atypical neuroleptics ( gt 1, pK(i) values). Compound 7e, 4-bromo-6-{2-[4-(2-nitrophenyl)piperazin-1-yl]etliyl}-1H-benziniidazole, expressed higher affinities for all receptor classes than clozapine. Also, it exhibited the best characteristic for atypical neuroleptics and presents a compound with the best profile for further in vivo investigations., Sintetisano je šest heterocikličnih (2-nitrofenil)piperazina sa specifičnom heteroaril grupom, koja podražava kateholsku grupu dopamina (benzimidazoli i supstituisani benzimidazoli), i ispitan je njihov afinitet ka dopaminskim, serotoninskim i _1 receptorima. Sva jedinjenja sa benzimidazolskim grupama su pokazala 5-HT 1A/D2 odnos vezivanja karakterističan za atipične neuroleptike ( gt 1, pK i vrednosti). Jedinjenje 7c, 4-bromo-6-{2-_4-(2-nitrofenil)piperazin-1-il_etil}-1H-benzimidazol, pokazalo je izraženiji afinitet ka svim klasama receptora u poređenju sa klozapinom i takođe predstavlja jedinjenje sa najboljim karakteristikama za dalja in vivo istraživanja.", publisher = "Serbian Chemical Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives, Sinteza i farmakološko ispitivanje novih derivata N-(2-nitrofenil) piperazina", volume = "72", number = "5", pages = "429-435", doi = "10.2298/JSC0705429A" }
Andrić, D., Tovilović, G., Roglić, G., Vasković, Đ., Šoškić, V., Tomic, M.,& Kostić-Rajačić, S.. (2007). Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 72(5), 429-435. https://doi.org/10.2298/JSC0705429A
Andrić D, Tovilović G, Roglić G, Vasković Đ, Šoškić V, Tomic M, Kostić-Rajačić S. Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives. in Journal of the Serbian Chemical Society. 2007;72(5):429-435. doi:10.2298/JSC0705429A .
Andrić, Deana, Tovilović, Gordana, Roglić, Goran, Vasković, Đurđica, Šoškić, Vukić, Tomic, Mirko, Kostić-Rajačić, Slađana, "Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives" in Journal of the Serbian Chemical Society, 72, no. 5 (2007):429-435, https://doi.org/10.2298/JSC0705429A . .