Synthesis of 1-Hydroxypyrrolidin-2,5-dione Derivatives of the Phosphonic - Hydroxamic Acid Antibiotic SF-2312

2006 ◽  
Vol 59 (4) ◽  
pp. 283 ◽  
Author(s):  
Wamuyu Owotoki ◽  
Detlef Geffken ◽  
Thomas Kurz
Keyword(s):  
Hydroxamic Acid ◽  
Phosphonic Acids ◽  
Trialkyl Phosphites ◽  
Derivatives Of ◽  
Substituted 1 ◽  
Ring Position

Analogues of the antibiotic SF-2312 with a 3-substituted 1-hydroxypyrrolidine moiety have been prepared from 1-benzyloxy-3-bromopyrrolidin-2,5-dione (1) through Michaelis–Arbusov reaction with various trialkyl phosphites and subsequent alkylation of ring position 3. Cleavage of phosphonic esters 3 by TMSBr afforded the corresponding phosphonic acids 7, which were treated with ethanolamine to give the monosalts 8. Finally, hydrogenolysis furnished 1-hydroxypyrrolidin-2,5-diones 9.

Synthesis, characterization and biological activities of 1,3,4-oxadiazole derivatives of nalidixic acid and their copper complexes

2019 ◽  
Author(s):  
Chem Int
Keyword(s):  
Nalidixic Acid ◽  
Copper Complexes ◽  
Biological Activities ◽  
Bidentate Coordination ◽  
Antibacterial And Antifungal Activities ◽  
Elemental Analyses ◽  
Oxadiazole Derivatives ◽  
Antibacterial And Antifungal ◽  
Derivatives Of ◽  
Substituted 1

A series of novel 1, 3, 4-oxadiazole analogues was synthesized from cyclization of hydrazones of substituted 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carbohydrazides were prepared from nalidixic acid. The structures of synthesized oxadiazole derivatives and their copper complexes were elucidated on the basis of FTIR, elemental analyses, 1H-NMR and atomic absorption spectral analysis. It was observed from spectral data that metal ligand ratio was 1:1 in all copper complexes and they were bidentate, coordination was found to be done through oxygen of 4-oxo group and nitrogen of oxadiazole ring. The synthesized compounds were further evaluated with biological activities and compared with parent hydrazones. Copper complexes possess antibacterial and antifungal activities better than the oxadiazoles while they have better antioxidant activity then copper complexes. Parent hydrazones were better in all biological activities than synthesized oxadiazoles.

Synthesis of azaanthraquinones: homolytic substitution of pyridines

1982 ◽  
Vol 35 (7) ◽  
pp. 1451 ◽  
Author(s):  
DW Cameron ◽  
KR Deutscher ◽  
GI Feutrill ◽  
DE Hunt
Keyword(s):  
Ring Closure ◽  
Pyridine Derivatives ◽  
Derivatives Of ◽  
Substituted 1 ◽  
Homolytic Substitution

Synthesis of specific di- and tri-hydroxyazaanthraquinones by Friedel-Crafts procedures is limited by orientational ambiguity and by the lack of reactivity of pyridine derivatives in electrophilic acylation processes; however, suitable pyridines have been made to undergo radical benzoylation and benzylation at unsubstituted positions 2, 4 and 6. In particular, derivatives of pyridine-3-carbo-nitrile have been benzoylated at positions 2 and 4. Ring closure by intramolecular Houben-Hoesch reaction has then led to specifically substituted 1-and 2-azaanthraquinones and thence to the antibiotic bostrycoidin (1).

Synthesis and Biological Effects of N-(2-Phosphonomethoxyethyl) Derivatives of Deazapurine Bases

1993 ◽  
Vol 58 (6) ◽  
pp. 1419-1429 ◽  
Author(s):  
Hana Dvořáková ◽  
Antonín Holý
Keyword(s):  
Biological Effects ◽  
Sodium Hydride ◽  
Cesium Carbonate ◽  
Cytostatic Effect ◽  
Phosphonic Acids ◽  
Dna Viruses ◽  
Purine Bases ◽  
Heterocyclic Bases ◽  
L 1210 Leukemia ◽  
Derivatives Of

Analogs of antiviral 9-(2-phosphonomethoxyethyl)adenine (PMEA,II), containing modified purine bases 1-deazaadenine (VII, 3-deazapurine (XI), 7-deaza-7-cyanoadenine (XIIIb) and 3-deazaguanine (XXIb) were prepared by alkylation of the heterocyclic bases with bis(2-propyl) 2-chloroethoxymethylphosphonate (V) in dimethylformamide in the presence of sodium hydride or cesium carbonate. The obtained protected derivatives were deblocked with bromotrimethylsilane to give the phosphonic acids. 3-DeazaPMEG (XXIb) is active against DNA viruses and exhibits a marked cytostatic effect against L-1210 leukemia.

scholarly journals α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

2019 ◽  
Vol 15 ◽  
pp. 2524-2533 ◽  
Author(s):  
Shital K Chattopadhyay ◽  
Subhankar Ghosh ◽  
Sarita Sarkar ◽  
Kakali Bhadra
Keyword(s):  
Anticancer Drug ◽  
Hela Cells ◽  
Hydroxamic Acid ◽  
Suberoylanilide Hydroxamic Acid ◽  
Oxygen Species ◽  
Synthetic Route ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Terminal Alkene ◽  
Derivatives Of

An alternate synthetic route to the important anticancer drug suberoylanilide hydroxamic acid (SAHA) from its α,ß-didehydro derivative is described. The didehydro derivative is obtained through a cross metathesis reaction between a suitable terminal alkene and N-benzyloxyacrylamide. Some of the didehydro derivatives of SAHA were preliminarily evaluated for anticancer activity towards HeLa cells. The administration of the analogues caused a significant decrease in the proliferation of HeLa cells. Furthermore, one of the analogues showed a maximum cytotoxicity with a minimum GI50 value of 2.5 µg/mL and the generation of reactive oxygen species (ROS) as some apoptotic features.

scholarly journals Trends and Exceptions in the Interaction of Hydroxamic Acid Derivatives of Common Di- and Tripeptides with Some 3d and 4d Metal Ions in Aqueous Solution

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3941 ◽  
Author(s):  
Ozsváth ◽  
Bíró ◽  
Nagy ◽  
Buglyó ◽  
Sanna ◽  
...  
Keyword(s):  
Metal Ions ◽  
Hydroxamic Acid ◽  
Hydroxamic Acids ◽  
17O Nmr ◽  
Equilibrium Study ◽  
Sandwich Type ◽  
Uv Visible ◽  
First Time ◽  
Derivatives Of ◽  
Half Sandwich

By using various techniques (pH-potentiometry, UV-Visible spectrophotometry, 1H and 17O-NMR, EPR, ESI-MS), first time in the literature, solution equilibrium study has been performed on complexes of dipeptide and tripeptide hydroxamic acids—AlaAlaNHOH, AlaAlaN(Me)OH, AlaGlyGlyNHOH, and AlaGlyGlyN(Me)OH—with 4d metals: the essential Mo(VI) and two half-sandwich type cations, [(η6-p-cym)Ru(H2O)3]2+ as well as [(η5-Cp*)Rh(H2O)3]2+, the latter two having potential importance in cancer therapy. The tripeptide derivatives have also been studied with some biologically important 3d metals, such as Fe(III), Ni(II), Cu(II), and Zn(II), in order to compare these new results with the corresponding previously obtained ones on dipeptide hydroxamic acids. Based on the outcomes, the effects of the type of metal ions, the coordination number, the number and types of donor atoms, and their relative positions to each other on the complexation have been evaluated in the present work. We hope that these collected results might be used when a new peptide-based hydroxamic acid molecule is planned with some purpose, e.g. to develop a potential metalloenzyme inhibitor.

ChemInform Abstract: New Hydroxamic Acid Derivatives of Fluoroquinolones: Synthesis and Evaluation of Antibacterial and Anticancer Properties.

ChemInform ◽  
2014 ◽  
Vol 45 (27) ◽  
pp. no-no
Author(s):  
Gavara Govinda Rajulu ◽  
Halehatty Seephya Bhojya Naik ◽  
Abhilash Viswanadhan ◽  
Jayaraman Thiruvengadam ◽  
Kondodiyil Rajesh ◽  
...  
Keyword(s):  
Hydroxamic Acid ◽  
Anticancer Properties ◽  
Derivatives Of ◽  
Hydroxamic Acid Derivatives
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