TY - JOUR AU - Khdar, Zein Alabdeen AU - Le Minh, Tam AU - Szakonyi, Zsolt TI - Gibberellic Acid (GA3): a Versatile Chiral Building Block for Syntheses of Pharmaceutical Agents JF - CHEMISTRY & BIODIVERSITY J2 - CHEM BIODIVERS VL - 22 PY - 2025 IS - 1 PG - 9 SN - 1612-1872 DO - 10.1002/cbdv.202401823 UR - https://m2.mtmt.hu/api/publication/35416385 ID - 35416385 N1 - Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, Szeged, H-6720, Hungary HUN-REN–SZTE Stereochemistry Research Group of the Hungarian Academy of Sciences, Eötvös utca 6, Szeged, H-6720, Hungary Export Date: 18 November 2024 CODEN: CBHIA Correspondence Address: Szakonyi, Z.; Institute of Pharmaceutical Chemistry, Eötvös utca 6, Hungary; email: szakonyi.zsolt@szte.hu Chemicals/CAS: gibberellic acid, 77-06-5 Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, K138871 Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH Funding details: 7172 Funding text 1: We are grateful for financial support from the Hungarian Research Foundation (NKFI K138871). Project no. TKP2021\\u2010EGA\\u201032 has been implemented with the support provided by the Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund and also by University of Szeged Open Access Fund (grant No. 7172). AB - Gibberellic acid (GA3), an ent‐kaurene tetracyclic diterpene, has been considered to be a chiral pool for the chemical transformation of significant heterocyclic compounds. This chiral pool continues to influence modern synthetic chemistry as an inexpensive and versatile starting material since it is widely applied in agriculture. This review focuses on the stereoselective syntheses of bioactive agents with pharmaceutical potency prepared from Gibberellic acid. LA - English DB - MTMT ER - TY - JOUR AU - Khdar, Zein Alabdeen AU - Le Minh, Tam AU - Schelz, Zsuzsanna AU - Zupkó, István AU - Szakonyi, Zsolt TI - Aminodiols, aminotetraols and 1,2,3-triazoles based on allo-gibberic acid: stereoselective syntheses and antiproliferative activities JF - RSC ADVANCES J2 - RSC ADV VL - 14 PY - 2024 IS - 49 SP - 36698 EP - 36712 PG - 15 SN - 2046-2069 DO - 10.1039/D4RA07334G UR - https://m2.mtmt.hu/api/publication/35577548 ID - 35577548 N1 - Institute of Pharmaceutical Chemistry, Interdisciplinary Excellent Center, University of Szeged, Eötvös utca 6, Szeged, H-6720, Hungary HUN-REN-SZTE Stereochemistry Research Group, University of Szeged, Eötvös utca 6, Szeged, H-6720, Hungary Institute of Pharmacodynamics and Biopharmacy, Interdisciplinary Excellent Center, University of Szeged, Eötvös utca 6, Szeged, H-6720, Hungary Export Date: 9 December 2024 CODEN: RSCAC Correspondence Address: Szakonyi, Z.; Institute of Pharmaceutical Chemistry, Eötvös utca 6, Hungary; email: szakonyi.zsolt@szte.hu Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, K138871, TKP2021-EGA-32 Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA, TKP2021-EGA Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA Funding details: 7314 Funding text 1: We are grateful for financial support from the Hungarian Research Foundation (NKFI K138871). Project no. TKP2021-EGA-32 has been implemented with the support provided by the Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund, financed under the TKP2021-EGA funding scheme and also by the University of Szeged Open Access Fund (grant no. 7314). The high-resolution mass spectrometric analysis was performed by Robert Berkecz. AB - Various allo -gibberic acid modifications yielded aminodiols, aminotetraols, and triazoles. N -naphthyl aminotetraols and di- or tetrahydroxy triazoles with a diaminopyrimidine moiety showed optimal antiproliferative activity. LA - English DB - MTMT ER - TY - JOUR AU - Khdar, Zein Alabdeen AU - Le Minh, Tam AU - Schelz, Zsuzsanna AU - Zupkó, István AU - Szakonyi, Zsolt TI - Stereoselective synthesis and antiproliferative activity of allo-gibberic acid-based 1,3-aminoalcohol regioisomers JF - RSC MEDICINAL CHEMISTRY J2 - RSC MED CHEM VL - 15 PY - 2024 IS - 3 SP - 874 EP - 887 PG - 14 SN - 2632-8682 DO - 10.1039/D3MD00665D UR - https://m2.mtmt.hu/api/publication/34577084 ID - 34577084 AB - A new library of allo -gibberic acid-based aminoalcohol regioisomers was synthesised stereoselectively starting from commercially available gibberellic acid, which yields allo -gibberic acid under mild acidic conditions. The successful formation of hydroxymethyl... LA - English DB - MTMT ER - TY - CONF AU - Khdar, Zein Alabdeen TI - Allogibberic acid based 1,3-aminoalcohol regioisomers:stereoselective synthesis and biological applications T2 - XV. Clauder Ottó Emlékverseny 2023 PB - Magyar Gyógyszerésztudományi Társaság (MGYT) C1 - Budapest PY - 2023 SP - 38 EP - 38 PG - 1 UR - https://m2.mtmt.hu/api/publication/35198104 ID - 35198104 LA - English DB - MTMT ER - TY - JOUR AU - Khdar, Zein Alabdeen AU - Le Minh, Tam AU - Schelz, Zsuzsanna AU - Zupkó, István AU - Szakonyi, Zsolt TI - Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 23 PY - 2022 IS - 18 PG - 24 SN - 1661-6596 DO - 10.3390/ijms231810366 UR - https://m2.mtmt.hu/api/publication/33087002 ID - 33087002 AB - A series of gibberellic acid-based aminodiols was designed and synthesized from commercially available gibberellic acid. Exposure of gibberellic acid to hydrochloric acid under reflux conditions resulted in aromatization followed by rearrangement to form allo-gibberic acid. The key intermediate, ethyl allo-gibberate, was prepared according to literature methods. Epoxidation of key intermediate and subsequent ring-opening of the corresponding epoxide with different nucleophiles resulted in N-substituted aminodiols. The regioselective ring closure of N-benzyl-substituted aminodiol with formaldehyde was also investigated. All aminodiol derivatives were well characterized using modern spectroscopic techniques and evaluated for their antiproliferative activity against a panel of human cancer cell lines. In addition, structure–activity relationships were examined by assessing substituent effects on the aminodiol systems. The results indicated that aminodiols containing aromatic rings on their nitrogen substituents displayed significant cytotoxic effects. Among these agents, N-naphthylmethyl-substituted aminodiols were found to be the most potent candidates in this series. One of these molecules exhibited a modest cancer selectivity determined by non-cancerous fibroblast cells. A docking study was also made to exploit the observed results. LA - English DB - MTMT ER - TY - JOUR AU - Fawzi, Mourad AU - Oubella, Ali AU - Bimoussa, Abdoullah AU - Bamou Zahra, Fatima AU - Khdar, Zein Alabdeen AU - Auhmani, Aziz AU - Riahi, Abdelkhalek AU - Robert, Anthony AU - Morjani, Hamid AU - Itto, My Youssef Ait TI - Design, synthesis, evaluation of new 3-acetylisoxazolines and their hybrid analogous as anticancer agents: In vitro and in silico analysis JF - COMPUTATIONAL BIOLOGY AND CHEMISTRY J2 - COMPUT BIOL CHEM VL - 98 PY - 2022 PG - 11 SN - 1476-9271 DO - 10.1016/j.compbiolchem.2022.107666 UR - https://m2.mtmt.hu/api/publication/32925656 ID - 32925656 LA - English DB - MTMT ER - TY - JOUR AU - Bimoussa, Abdoullah AU - Oubella, Ali AU - Bamou Zahra, Fatima AU - Khdar, Zein Alabdeen AU - Fawzi, Mourad AU - Laamari, Yassine AU - Ait Itto, My Youssef AU - Morjani, Hamid AU - Auhmani, Aziz TI - New 1,3,4-thiadiazoles derivatives: synthesis, antiproliferative activity, molecular docking and molecular dynamics JF - FUTURE MEDICINAL CHEMISTRY J2 - FUTURE MED CHEM VL - 14 PY - 2022 IS - 12 SP - 881 EP - 897 PG - 17 SN - 1756-8919 DO - 10.4155/fmc-2022-0016 UR - https://m2.mtmt.hu/api/publication/32874321 ID - 32874321 LA - English DB - MTMT ER -