scholarly journals SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE

2012 ◽  
Vol 12 (1) ◽  
pp. 70-76 ◽  
Author(s):  
Muhammad Idham Darussalam Mardjan ◽  
Retno Ambarwati ◽  
Sabirin Matsjeh ◽  
Tutik Dwi Wahyuningsih ◽  
Winarto Haryadi

Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives  in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.

Author(s):  
Gerhard Laus ◽  
Volker Kahlenberg ◽  
Thomas Gelbrich ◽  
Sven Nerdinger ◽  
Herwig Schottenberger

Mutual carboxyl–carboxyl O—H...O hydrogen bonds link the molecules of the title compound, C7H5BrO3, into centrosymmetric dimers which display a centralR22(8) ring motif. In addition, there is an intramolecular hydroxyl–carboxyl O—H...O interaction present. A comparison with the crystal structures of 59 other substituted derivatives of salicylic acid shows that both the centrosymmetric carboxyl–carboxyl O—H...O dimer and the stacking mode of molecules along the shortaaxis observed in the title structure are frequent packing motifs in this set.


10.26524/sa1 ◽  
2018 ◽  
Vol 7 (3) ◽  
pp. 01-07
Author(s):  
L Ilavarasan ◽  
A Ravi ◽  
M Ganapathi ◽  
E Subitchayini ◽  
K Sivasakthi ◽  
...  

Chalcone derivatives were synthesized by reaction of some benzaldehyde derivatives with acetophenone, then the products obtained were allowed to react withurea, thiourea and hydroxylamine, to give the heterocyclic derivatives of oxazine, thiazine and isoxazole, respectively.In this study, a series of chalcones and substituted pyrazole compounds were synthesized according to green chemistry methods of conventional and microwave irradiation by using substituted acetophenone, substituted benzaldehyde, hydrazine hydrate and PEG-400. The synthesized compounds were characterized by UV-Visible, FT-IR and 1H NMR spectral techniques. The purity of the synthesized compounds were monitored by TLC and tested for their antibacterial activity by Minimum Inhibitory Concentration (MIC) method against two different microorganisms Staphylococcus auras (MTCC3381), and Escherichia coli (MTCC739).


2011 ◽  
Vol 396-398 ◽  
pp. 2193-2197
Author(s):  
Bao Feng Lin ◽  
Wei Wang ◽  
Yan Ming Li ◽  
Xing Quan Liang ◽  
Yu Min Du

Different chitosan carboxylic salts were successfully prepared via a simple way using chitosan and oxalic, fumaric, salicylic acid for the first time. The characterizations of the salts were evaluated by FT-IR, 13C NMR, 1H NMR, elemental analysis, XRD. The solution properties and moisture absorption-retention abilities of the salts were compared with chitosan. The result indicated that chitosan and carboxylic acid were combined with salt bond. The properties of the salts were related to the type of carboxylic acid added and the formation of salt bond. The water-solubility, wetting effect and moisture-retention absorption abilities of the salts were better than chitosan. They therefore have the potential to substitute for chitosan for easy use as coating in food preservation.


2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.


2019 ◽  
Vol 16 (6) ◽  
pp. 478-484
Author(s):  
Kenia Barrantes ◽  
Mary Fuentes ◽  
Luz Chacón ◽  
Rosario Achí ◽  
Jorge Granados-Zuñiga ◽  
...  

Two ether and one ester derivatives of the 4-nitro-3-hydroxybenzoic acid were synthesized and characterized. The in vitro antimicrobial and cytotoxic activities of the three novel compounds were also evaluated. The aromatic derivatives showed antibacterial activity against one of the four microorganisms tested and two compounds (C8 and NOBA) had a lower IC50 in HeLa cells.


2021 ◽  
Vol 11 (3) ◽  
pp. 1180
Author(s):  
Kinga Paruch ◽  
Łukasz Popiołek ◽  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Malm ◽  
...  

Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.


1982 ◽  
Vol 35 (7) ◽  
pp. 1451 ◽  
Author(s):  
DW Cameron ◽  
KR Deutscher ◽  
GI Feutrill ◽  
DE Hunt

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).


2020 ◽  
Vol 18 (1) ◽  
pp. 890-897 ◽  
Author(s):  
Tin Myo Thant ◽  
Nanik Siti Aminah ◽  
Alfinda Novi Kristanti ◽  
Rico Ramadhan ◽  
Hnin Thanda Aung ◽  
...  

AbstractNew derivatives were obtained from natural nordentatin (1) previously isolated from the methanol fraction of Clausena excavata by an acylation method. Herein, we report ten new pyranocoumarin derivatives 1a–1j. Their structures were elucidated based on UV-vis, FT-IR, NMR, and DART-MS data. The α-glucosidase inhibition and anticancer activities of nordentatin (1) and its derivatives were also evaluated. The α-glucosidase inhibition assay exhibited that the derivatives 1b, 1d, 1e, 1f, 1h, 1i, and 1j possess higher inhibitory activity for α-glucosidase with IC50 values of 1.54, 9.05, 4.87, 20.25, 12.34, 5.67, and 2.43 mM, whereas acarbose was used as the positive control, IC50 = 7.57 mM. All derivatives exhibited a weak cytotoxicity against a cervical cancer (HeLa) cell line with the IC50 between 0.25 and 1.25 mM. They also showed moderate to low growth inhibition of a breast cancer (T47D) cell line with IC50 values between 0.043 and 1.5 mM, but their activity was lower than that of the parent compound, nordentatin (1) (IC50 = 0.041 mM).


ChemInform ◽  
2013 ◽  
Vol 44 (50) ◽  
pp. no-no
Author(s):  
Vilmaz Turgut ◽  
Murat Azizoglu ◽  
Asli Erdogan ◽  
Nevin Arslan ◽  
Halil Hosgoren

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