Catalyst free regiospecific amination, structural elucidation, and potential utilization of pyran-2,4-dione derivatives as novel antimicrobial agents

被引：0

作者：

Sarhan, Ahmed A. M. ^{[1
]}

Haukka, Matti ^{[2
]}

Soliman, Saied M. ^{[3
]}

Barakat, Assem ^{[4
]}

Boraei, Ahmed T. A. ^{[5
]}

机构：

[1] Arish Univ, Fac Sci, Chem Dept, Al Arish 45511, Egypt

[2] Univ Jyvaskyla, Dept Chem, POB 35, FI-40014 Jyvaskyla, Finland

[3] Alexandria Univ, Fac Sci, Chem Dept, POB 426, Ibrahimia 21321, Alexandria, Egypt

[4] King Saud Univ, Coll Sci, Chem Dept, POB 2455, Riyadh 11451, Saudi Arabia

[5] Suez Canal Univ, Fac Sci, Chem Dept, Ismailia 41522, Egypt

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2025年 / 1334卷

关键词：

Pyran-2,4-dione; 4-hydroxy-2-pyrones; Free catalyst; regiospecific amination; Antimicrobial agent; Gram-positive bacteria; NATURAL-PRODUCTS; ALPHA-PYRONES; POGOSTONE; SCAFFOLDS; 2-PYRONE;

D O I：

10.1016/j.molstruc.2025.141893

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Catalyst-free regiospecific amination at the C-4 position of 3-benzoyl-4-chloro-6-phenyl-2H-pyran-2-one precursor 3 was explored using various aminating agents such as ammonium acetate, primary aliphatic and aromatic amines in methanol. Structural investigation mainly based on NMR and X-ray single crystal analyses are presented. In addition, topology analysis of molecular packing was performed using Hirshfeld calculations. The antimicrobial activity of the newly synthesized aminated analogues compared to their (1-enamino-pyran2,4-dione isomers was assessed against S. aureus and C. albicans. In general, the (1-enamino-pyran-2,4-diones displayed better antimicrobial activity against S. aureus and C. albicans compared to their C4-aminated isomers and conventional medications (Neomycin, Streptomycin, and Amoxicillin + Co-amoxiclav).

引用

页数：11

共 40 条

[31] Design and characterization of Dendrimer of MNPs as a novel, heterogeneous and reusable nanomagnetic organometallic catalyst for one-pot synthesis of hydroxyl naphthalene-1,4-dione derivatives under solvent-free conditions
Mollazehi, Fouziyeh
Shaterian, Hamid Reza
APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (03)
[32] Synthesis and structure–activity relationship studies on novel 8-amino-3-[2-(4-fluorophenoxy)ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione derivatives as anticonvulsant agents
M. Madaiah
M. K. Prashanth
H. D. Revanasiddappa
B. Veeresh
Medicinal Chemistry Research, 2013, 22 : 2633 - 2644
[33] Design, synthesis, biological evaluation and in silico studies of novel 1,2,3- triazole linked benzoxazine-2,4-dione conjugates as potent antimicrobial, antioxidant and anti- inflammatory agents (vol 15, 104226, 2022)
Ben Hammouda, Manel
Ahmad, Iqrar
Hamdi, Assia
Dbeibia, Amal
Patel, Harun
Bouali, Nouha
Hamadou, Walid Sabri
Hosni, Karim
Ghannay, Siwar
Alminderej, Fahad
Noumi, Emira
Snoussi, Mejdi
Aouadi, Kaiss
Kadri, Adel
ARABIAN JOURNAL OF CHEMISTRY, 2023, 16 (09)
[34] Synthesis of Novel 1-(3′-CHLORO-1′,4′-DIOXO-1′,4′-Dihydronaphthalen-2′-YL)-5-Substitued-1H-Pyrimidine-2,4-Dione as Potential Antibacterial Agents
Siham A. Lahsasni
Pharmaceutical Chemistry Journal, 2014, 48 : 171 - 174
[35] Synthesis of Novel 1-(3'-CHLORO-1',4'-DIOXO-1',4'-Dihydronaphthalen-2'-YL)-5-Substitued-1H-Pyrimidine-2,4-Dione as Potential Antibacterial Agents
Lahsasni, Siham A.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 48 (03) : 171 - 174
[36] Synthesis and structure-activity relationship studies on novel 8-amino-3-[2-(4-fluorophenoxy)ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione derivatives as anticonvulsant agents
Madaiah, M.
Prashanth, M. K.
Revanasiddappa, H. D.
Veeresh, B.
MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (06) : 2633 - 2644
[37] Synthesis and pharmacological evaluation of new 5-(cyclo)alkyl-5-phenyl- and 5-spiroimidazolidine-2,4-dione derivatives. Novel 5-HT1A receptor agonist with potential antidepressant and anxiolytic activity
Czopek, Anna
Byrtus, Hanna
Kolaczkowski, Marcin
Pawlowski, Maciej
Dybala, Malgorzata
Nowak, Gabriel
Tatarczynska, Ewa
Wesolowska, Anna
Chojnacka-Wojcik, Ewa
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (04) : 1295 - 1303
[38] Catalyst-Free Synthesis of Novel 6-Phenyl-6H-chromeno [4, 3-b] quinoline Derivatives at RT: Their Further Structure Evaluation Leads to Potential Anti-cancer Agents
Kumar, Alleni Suman
Kumar, Rathod Aravind
Satyanarayana, Vavilaally
Reddy, Elala Pravardhan
Reddy, Boggu Jagan Mohan
Kumar, Duddukuri Nandan
Khurana, Amit
Chandraian, Godugu
Yadav, Jhillu Singh
NATURAL PRODUCT COMMUNICATIONS, 2017, 12 (07) : 1129 - 1132
[39] Ultrasound mediated catalyst free synthesis of 6H-1-benzopyrano [4,3-b]quinolin-6-ones leading to novel quinoline derivatives: Their evaluation as potential anti-cancer agents
Mulakayala, Naveen
Rambabu, D.
Raja, Mohan Rao
Chaitanya, M.
Kumar, Chitta Suresh
Kalle, Arunasree M.
Krishna, G. Rama
Reddy, C. Malla
Rao, M. V. Basaveswara
Pal, Manojit
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (02) : 759 - 768
[40] Structure-activity relationship studies of CNS agents.: Part 38 -: Novel 1,4-benzoxazin-3(4H)-one, 1,2-benzoxazolin-3-one and 1,3-benzoxazolin-2,4-dione arylpiperazine derivatives with different 5-HT1A and antagonistic 5-HT2A activities
Mokrosz, MJ
Kowalski, P
Kowalska, T
Majka, Z
Duszynska, B
Bojarski, AJ
Fruzinski, A
Karolak-Wojciechowska, J
Wesolowska, A
Klodzinska, A
Tatarczynska, E
Chojnacka-Wójcik, E
ARCHIV DER PHARMAZIE, 1999, 332 (11) : 373 - 379

← 1 2 3 4 →