Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid
2015
Аутори
Dobričić, VladimirFrancuski, Bojana M.
Jaćević, Vesna
Rodić, Marko V.
Vladimirov, Sote
Čudina, Olivera
Francuski, Đorđe
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid (DF) was synthesized and its crystal structure characterized by the X-ray diffraction method. The crystal system is orthorhombic with space group P2(1)2(1)2(1) and cell constants a = 8.2969(3) angstrom, b = 18.9358(8) angstrom, c = 20.0904(6) angstrom, V = 3156.4(2) angstrom(3) and Z = 4. Ring A of the steroid nucleus and phenyl ring in the 17 beta-side chain are almost planar. Rings B and C have a slightly distorted chair conformation, whereas ring D has an envelope conformation. The packing of DF is characterized by a network of intermolecular hydrogen bonds involving the O4 atom from one side of the steroid nucleus and O1 and F1 atoms from the other side as hydrogen bond acceptors. Apart from the intermolecular hydrogen bonds in the crystal packing, there are also numerous intramolecular hydrogen bonds of the N-H center dot center dot center dot O, C-H center dot center dot center dot O and C-H cente...r dot center dot center dot F type. The local anti-inflammatory activity of DF was evaluated using the croton oil-induced ear oedema test. This derivative achieved maximal inhibition of ear oedema at significantly lower concentration in comparison with dexamethasone.
Кључне речи:
17 beta-carboxamide steroids / X-ray diffraction / biological activity / ear oedema testИзвор:
Journal of the Serbian Chemical Society, 2015, 80, 12, 1481-1488Издавач:
- Srpsko hemijsko društvo, Beograd
Финансирање / пројекти:
DOI: 10.2298/JSC150505067D
ISSN: 0352-5139
WoS: 000367186500003
Scopus: 2-s2.0-84957534849
Институција/група
PharmacyTY - JOUR AU - Dobričić, Vladimir AU - Francuski, Bojana M. AU - Jaćević, Vesna AU - Rodić, Marko V. AU - Vladimirov, Sote AU - Čudina, Olivera AU - Francuski, Đorđe PY - 2015 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2358 AB - The L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid (DF) was synthesized and its crystal structure characterized by the X-ray diffraction method. The crystal system is orthorhombic with space group P2(1)2(1)2(1) and cell constants a = 8.2969(3) angstrom, b = 18.9358(8) angstrom, c = 20.0904(6) angstrom, V = 3156.4(2) angstrom(3) and Z = 4. Ring A of the steroid nucleus and phenyl ring in the 17 beta-side chain are almost planar. Rings B and C have a slightly distorted chair conformation, whereas ring D has an envelope conformation. The packing of DF is characterized by a network of intermolecular hydrogen bonds involving the O4 atom from one side of the steroid nucleus and O1 and F1 atoms from the other side as hydrogen bond acceptors. Apart from the intermolecular hydrogen bonds in the crystal packing, there are also numerous intramolecular hydrogen bonds of the N-H center dot center dot center dot O, C-H center dot center dot center dot O and C-H center dot center dot center dot F type. The local anti-inflammatory activity of DF was evaluated using the croton oil-induced ear oedema test. This derivative achieved maximal inhibition of ear oedema at significantly lower concentration in comparison with dexamethasone. PB - Srpsko hemijsko društvo, Beograd T2 - Journal of the Serbian Chemical Society T1 - Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid VL - 80 IS - 12 SP - 1481 EP - 1488 DO - 10.2298/JSC150505067D ER -
@article{ author = "Dobričić, Vladimir and Francuski, Bojana M. and Jaćević, Vesna and Rodić, Marko V. and Vladimirov, Sote and Čudina, Olivera and Francuski, Đorđe", year = "2015", abstract = "The L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid (DF) was synthesized and its crystal structure characterized by the X-ray diffraction method. The crystal system is orthorhombic with space group P2(1)2(1)2(1) and cell constants a = 8.2969(3) angstrom, b = 18.9358(8) angstrom, c = 20.0904(6) angstrom, V = 3156.4(2) angstrom(3) and Z = 4. Ring A of the steroid nucleus and phenyl ring in the 17 beta-side chain are almost planar. Rings B and C have a slightly distorted chair conformation, whereas ring D has an envelope conformation. The packing of DF is characterized by a network of intermolecular hydrogen bonds involving the O4 atom from one side of the steroid nucleus and O1 and F1 atoms from the other side as hydrogen bond acceptors. Apart from the intermolecular hydrogen bonds in the crystal packing, there are also numerous intramolecular hydrogen bonds of the N-H center dot center dot center dot O, C-H center dot center dot center dot O and C-H center dot center dot center dot F type. The local anti-inflammatory activity of DF was evaluated using the croton oil-induced ear oedema test. This derivative achieved maximal inhibition of ear oedema at significantly lower concentration in comparison with dexamethasone.", publisher = "Srpsko hemijsko društvo, Beograd", journal = "Journal of the Serbian Chemical Society", title = "Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid", volume = "80", number = "12", pages = "1481-1488", doi = "10.2298/JSC150505067D" }
Dobričić, V., Francuski, B. M., Jaćević, V., Rodić, M. V., Vladimirov, S., Čudina, O.,& Francuski, Đ.. (2015). Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid. in Journal of the Serbian Chemical Society Srpsko hemijsko društvo, Beograd., 80(12), 1481-1488. https://doi.org/10.2298/JSC150505067D
Dobričić V, Francuski BM, Jaćević V, Rodić MV, Vladimirov S, Čudina O, Francuski Đ. Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid. in Journal of the Serbian Chemical Society. 2015;80(12):1481-1488. doi:10.2298/JSC150505067D .
Dobričić, Vladimir, Francuski, Bojana M., Jaćević, Vesna, Rodić, Marko V., Vladimirov, Sote, Čudina, Olivera, Francuski, Đorđe, "Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid" in Journal of the Serbian Chemical Society, 80, no. 12 (2015):1481-1488, https://doi.org/10.2298/JSC150505067D . .