scholarly journals SYNTHESIS AND ANTIMICROBIAL EVALUATION OF QUINAZOLINONE PEPTIDE DERIVATIVES

2017 ◽  
Vol 10 (16) ◽  
pp. 7 ◽  
Author(s):  
Bhupinder Kapoor ◽  
Arshid Nabi ◽  
Reena Gupta ◽  
Mukta Gupta
Keyword(s):  
Antibacterial Activity ◽  
Amino Acid ◽  
Antimicrobial Agents ◽  
Methyl Esters ◽  
Standard Drug ◽  
Amino Acid Peptide ◽  
Chemical Structures ◽  
1H Nuclear Magnetic Resonance ◽  
Peptide Derivatives ◽  
Derivatives Of

  Objective: The increased microbial resistance against commercially available drugs initiated the development of novel and safe antimicrobial agents in last few decades. In this view, a series of amino acid/dipeptide derivatives of quinazolin-3(4H)-one was synthesized and was evaluated for their antimicrobial potential.Method: Synthesis of amino acid/peptide derivatives were carried out by coupling 5-(2-(2-chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-hydroxy benzoic acid with amino acid/dipeptide methyl esters in the presence of dicyclohexylcarbodiimide and N-methylmorpholine. The chemical structures of synthesized compounds were characterized by 1H nuclear magnetic resonance and infrared spectroscopy and were screened for antibacterial activity by disc diffusion method.Results: All the synthesized derivatives exhibited moderate to significant antibacterial activity against both Gram-positive and Gram-negative bacteria. The potency of compound 5d was comparable to standard drug ciprofloxacin in all the strains of bacteria used. The compound 5a was found to be more active against Streptococcus pyogenes and Staphylococcus aureus while compound 5c against Pseudomonas aeruginosa and Escherichia coli. Conclusion: Peptide derivatives of quinazolinone are promising antimicrobial agent and can be used for the synthesis of other novel compounds.

A convenient synthesis of novel amino acid derivatives with potential antibacterial activity using sustainable materials

2017 ◽  
Vol 41 (5) ◽  
pp. 280-286
Author(s):  
Mohamed S. Behalo
Keyword(s):  
Antibacterial Activity ◽  
Amino Acid ◽  
Low Cost ◽  
Amino Acid Derivatives ◽  
Standard Drug ◽  
Chemical Structures ◽  
Coupling Reagent ◽  
Convenient Synthesis ◽  
Weak Activity ◽  
High Yields

Following the principles of green chemistry, cardanol derivatives have been used as renewable, low-cost and easily available natural starting materials to construct a variety of protected and unprotected amino acid derivatives. The reaction of cardanol derivatives with different phthalylamino acids including glycine, alanine, phenylalanine and valine in the presence of N,N′-dicyclohexylcarbodiimide (DCC) as coupling reagent yielded the target compounds in high yields. Deprotection of phthalylamino acid derivatives was achieved by heating with hydrazine hydrate. The chemical structures of all products were confirmed by spectral (FTIR, MS, 1H NMR, 13C NMR) and elemental analyses. The synthesised products were evaluated for their antibacterial activity, and the compounds exhibited potent to weak activity in comparison with a standard drug.

Anticancer Properties of Amino Acid and Peptide Derivatives of Mycophenolic Acid

2020 ◽  
Vol 20 ◽  
Author(s):  
Agnieszka Siebert ◽  
Milena Deptuła ◽  
Mirosława Cichorek ◽  
Anna Ronowska ◽  
Grzegorz Cholewiński ◽  
...  
Keyword(s):  
Amino Acid ◽  
Cell Lines ◽  
Anticancer Agents ◽  
Mycophenolic Acid ◽  
Methyl Esters ◽  
Carboxylic Group ◽  
Anticancer Properties ◽  
Peptide Derivatives ◽  
Derivatives Of

Background: Although Mycophenolic Acid (MPA) is applied as prodrugs in clinic as immunosuppressant, it possesses also anticancer activity. MPA acts as Inosine-5’-Monophosphate Dehydrogenase (IMPDH) inhibitor, where carboxylic group at the end of the side chain interacts with Ser 276 of the enzyme via hydrogen bonds. Therefore, MPA derivatives with other polar groups indicated high inhibition too. On the other hand, potent anticancer agents like dacarbazine and cisplatin give numerous side-effects. Objective: Based on the literature data, MPA derivatives should be explored towards anticancer properties. Conversion of carboxylic group of MPA to amide could maintain antiproliferative activity. Therefore, we decided to investigate several amino acid and peptide derivatives of MPA against chosen cancer cell lines in vitro. Methods: Amides of MPA hold threonine and arginine amino acid unit. These amino acid derivatives were tested as L and D enantiomers and both in free acid and methyl esters forms. Additionally, MPA was modified with tuftsin or retro-tuftsin as biologically active peptides, which could act as a drug carrier. Results: Amino acid and peptide derivatives of MPA were investigated in vitro as potential anticancer agents on cell lines: Ab melanoma, A375 melanoma and SHSY5Y neuroblastoma. The activity of the tested compounds was compared to parent MPA and known chemotherapeutics: dacarbazine and cisplatin. Conclusion: Amino acid moiety and sequence of amino acids in peptide part influenced observed activity. The most active amino acid MPA analogues occurred to be D and L-threonine derivatives as methyl esters, probably due to better cell membrane penetration.

scholarly journals Novel Amino Acid Derivatives of Quinolines as Potential Antibacterial and Fluorophore Agents

2020 ◽  
Vol 88 (4) ◽  
pp. 57
Author(s):  
Oussama Moussaoui ◽  
Rajendra Bhadane ◽  
Riham Sghyar ◽  
El Mestafa El Hadrami ◽  
Soukaina El Amrani ◽  
...  
Keyword(s):  
Amino Acid ◽  
Methyl Esters ◽  
Amino Acid Derivatives ◽  
Bacterial Strains ◽  
Fluorescent Properties ◽  
Topoisomerase Iv ◽  
Microdilution Method ◽  
Hydrolysis Of ◽  
Derivatives Of

A new series of amino acid derivatives of quinolines was synthesized through the hydrolysis of amino acid methyl esters of quinoline carboxamides with alkali hydroxide. The compounds were purified on silica gel by column chromatography and further characterized by TLC, NMR and ESI-TOF mass spectrometry. All compounds were screened for in vitro antimicrobial activity against different bacterial strains using the microdilution method. Most of the synthesized amino acid-quinolines show more potent or equipotent inhibitory action against the tested bacteria than their correspond esters. In addition, many of them exhibit fluorescent properties and could possibly be utilized as fluorophores. Molecular docking and simulation studies of the compounds at putative bacterial target enzymes suggest that the antimicrobial potency of these synthesized analogues could be due to enzyme inhibition via their favorable binding at the fluoroquinolone binding site at the GyrA subunit of DNA gyrase and/or the ParC subunit of topoisomerase-IV.

ANTIMICROBIAL STUDIES OF NEWLY SYNTHESIZED 1H-BENZOTRIAZOLE-1-ACETYL-AMINO ACID METHYL ESTERS /PEPTIDE DERIVATIVES

INDIAN DRUGS ◽  
2013 ◽  
Vol 50 (12) ◽  
pp. 27-33
Author(s):  
K. Kaur ◽  
◽  
R Kaur ◽  
A. Kaur
Keyword(s):  
Amino Acid ◽  
1H Nmr Spectroscopy ◽  
Methyl Esters ◽  
Penicillium Expansum ◽  
Antimicrobial Compounds ◽  
Bacterial Strains ◽  
Antimicrobial Studies ◽  
Acid Methyl ◽  
Peptide Derivatives ◽  
Amino Acid Methyl Esters

Benzotriazole-1-acetic acid was coupled with amino acid methyl esters/ dipeptides/ tripeptides/tetrapeptides in the presence of DCC as a coupling agent and NMM as a base under continuous stirringfor 36 hrs. The reactions were monitored by TLC. The newly synthesized compounds were analyzedand the structures were confirmed by IR and 1H NMR spectroscopy. The synthesized compounds weretested against bacterial strains Bacillus subtilis, Staphylococcus aureus and Escherichia coli by usingciprofloxacin as standard in the concentration of 20?g/mL. All the compounds were also tested againstfungal strains Candida albicans, Aspergillus niger and Penicillium expansum by using fluconazole asstandard in the concentration of 10?g/mL. Compounds 1, 2, 3 and 4 were found to be more potent antimicrobial compounds.

Immunosuppressive properties of amino acid and peptide derivatives of mycophenolic acid

2020 ◽  
Vol 189 ◽  
pp. 112091
Author(s):  
Agnieszka Siebert ◽  
Grzegorz Cholewiński ◽  
Piotr Trzonkowski ◽  
Janusz Rachon
Keyword(s):  
Amino Acid ◽  
Mycophenolic Acid ◽  
Peptide Derivatives ◽  
Derivatives Of

scholarly journals Amino Acid and Peptide Derivatives of Kojic Acid and Their Antifungal Properties

1990 ◽  
Vol 54 (9) ◽  
pp. 2441-2442
Author(s):  
Hiroshi Kayahara ◽  
Norihisa Shibata ◽  
Koji Tadasa ◽  
Hideo Maeda ◽  
Takashi Kotani ◽  
...  
Keyword(s):  
Amino Acid ◽  
Kojic Acid ◽  
Antifungal Properties ◽  
Peptide Derivatives ◽  
Derivatives Of

Synthesis and Antimicrobial and Toxicological Studies of Amino Acid and Peptide Derivatives of Kanamycin A and Netilmicin

1995 ◽  
Vol 38 (23) ◽  
pp. 4710-4719 ◽  
Author(s):  
S. Kotretsou ◽  
M. P. Mingeot-Leclercq ◽  
V. Constantinou-Kokotou ◽  
R. Brasseur ◽  
M. P. Georgiadis ◽  
...  
Keyword(s):  
Amino Acid ◽  
Toxicological Studies ◽  
Peptide Derivatives ◽  
Derivatives Of

scholarly journals SECONDARY METABOLITES FROM A MARINE-DERIVED FUNGUS Penicillium chrysogenum 045-357-2

2018 ◽  
Vol 55 (1A) ◽  
pp. 65
Author(s):  
Phan Thi Hoai Trinh
Keyword(s):  
Antibacterial Activity ◽  
Penicillium Chrysogenum ◽  
Culture Medium ◽  
Antimicrobial Agents ◽  
Chemical Compounds ◽  
2D Nmr ◽  
Fungal Strain ◽  
Chemical Structures ◽  
High Antibacterial Activity ◽  
2D Nmr Spectra

Marine fungi represent a potential source for natural products in the future due to the incredible diversity of chemical compounds. In our previous investigation to search new antimicrobial agents from marine-derived fungi, we isolated fungal strain Penicillium chrysogenum 045-357-2 from a soft coral sample collected from Ca Na Bay, Ninh Thuan, Vietnam. The fungus showed high antibacterial activity and was selected for further study. By various chromatography separations, two compounds including andrastinA (1) and citreohybridonol (2) were obtained from the ethyl acetate extract of culture medium of this strain. Their chemical structures were determined by analysis of 1D and 2D NMR spectra and high-resolution mass spectroscopic data, as well as by comparison of the corresponding data to those previously reported in the literature. The compound 2 exhibited antibacterial activity towards Bacillus cereus ATCC 11778 and Streptoccocus faecalis ATCC 19433 with Minimal Inhibitory Concentration (MIC) values of 32 and 64 μg/ml, respectively; however, antibacterial activity was not detected in the compound 1. This is the first report on these compounds of marine fungal strain P. chrysogenum isolated in Vietnam.

scholarly journals Synthesis and properties of peptidyl derivatives of arginylfluoromethanes

1988 ◽  
Vol 256 (2) ◽  
pp. 481-486 ◽  
Author(s):  
H Angliker ◽  
P Wikström ◽  
P Rauber ◽  
S Stone ◽  
E Shaw
Keyword(s):  
Amino Acid ◽  
Amino Acid Sequence ◽  
Active Site ◽  
Relative Effectiveness ◽  
Serine Proteinases ◽  
Cysteine Proteinases ◽  
Peptide Derivatives ◽  
Guanidino Group ◽  
Derivatives Of

Two peptide derivatives of arginylfluoromethane (Arg-CH2F), namely Bz(benzoyl)-Phe-ArgCH2F and D-Phe-Pro-Arg-CH2F, have been synthesized by extension of available methods, i.e. the Dakin-West reaction [Rasnick (1985) Anal. Biochem. 149, 461-465] or synthesis of a phthaloyl-blocked C-terminal fluoromethane [Rauber, Angliker, Walker & Shaw (1986) Biochem. J. 239, 633-640; Angliker, Wikström, Rauber & Shaw (1987) Biochem. J. 241, 871-875] with subsequent elongation. The guanidino group of arginine was protected as the bis-Cbz (benzyloxycarbonyl) derivative. The products were examined as active-site-directed inhibitors of some trypsin-related serine proteinases as well as a pair of cysteine proteinases. The results extend previous observations that the rate of alkylation of serine proteinases by fluoromethanes may be considerably slower than by chloromethanes. As expected, the amino acid sequence of the inhibitors influenced their relative effectiveness. Thus the rate of inactivation of a number of trypsin-like proteinases by D-Phe-Pro-Arg-CH2F varied by more than two orders of magnitude.

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