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.

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.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

scholarly journals Novel 4,6-Disubstituted s-Triazin-2-yl Amino Acid Derivatives as Promising Antifungal Agents

2020 ◽  
Vol 6 (4) ◽  
pp. 237
Author(s):  
Rakia Abd Alhameed ◽  
Zainab Almarhoon ◽  
Essam N. Sholkamy ◽  
Salman Ali Khan ◽  
Zaheer Ul-Haq ◽  
...  
Keyword(s):  
Amino Acid ◽  
Antifungal Activity ◽  
Active Site ◽  
Antifungal Agents ◽  
Docking Studies ◽  
Amino Acid Derivatives ◽  
Active Site Residues ◽  
Standard Drug ◽  
Drug Compounds ◽  
Inhibition Zones

A novel series of 4,6-disubstituted s-triazin-2-yl amino acid derivatives was prepared and characterized. Most of them showed antifungal activity against Candida albicans compared to clotrimazole (standard drug). Compounds bearing aniline derivatives, piperidine and glycine on the triazine core showed the highest inhibition zones at concentrations of 50, 100, 200, and 300 μg per disc. In addition, docking studies revealed that all the compounds accommodated well in the active site residues of N-myristoltransferase (NMT) and exhibited complementarity, which explains the observed antifungal activity. Interestingly, none of these compounds showed antibacterial activity.

scholarly journals Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Kostiantyn O. Marichev ◽  
Kuiyong Dong ◽  
Lynée A. Massey ◽  
Yongming Deng ◽  
Luca De Angelis ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Coupling Reactions ◽  
Central Importance ◽  
Bond Forming ◽  
Donor Acceptor ◽  
High Yields ◽  
High Degree ◽  
Oxygen Bond ◽  
Steric Selectivity

AbstractCoupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon–oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereocontrol, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor–acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantiopurity of the original azetine.

Some N-acyl-D-amino acid derivatives having antibotulinal properties

1987 ◽  
Vol 33 (7) ◽  
pp. 577-582 ◽  
Author(s):  
A. Paquet ◽  
K. Rayman
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Aspartic Acid ◽  
Sodium Nitrite ◽  
Amino Acid Derivatives ◽  
Ester Method ◽  
Succinimidyl Ester ◽  
High Yields ◽  
Derivatives Of ◽  
Acyl Derivatives

Several N-acyl derivatives of D-tryptophan, D-alanine, D-methionine, D-valine, and D-aspartic acid were synthesized in high yields using the succinimidyl ester method and examined for their antibotulinal properties. In conjunction with 60 ppm of sodium nitrite, sorbyl-D-tryptophan, sorbyl-D-alanine, myristoyl-D-aspartic acid, and glycyl-D-alanine were highly inhibitory. In the absence of sodium nitrite, the N-acyl derivatives of the D-amino acids were not inhibitory. On its own, 60 ppm of sodium nitrite was only slightly inhibitory. Sorbyl-L-tryptophan and sorbyl-L-alanine had no effect in the presence or absence of 60 ppm of sodium nitrite.

scholarly journals Synthesis, Spectroscopic Studies and Antibacterial Activity of New Lauroyl Thiourea Amino Acid Derivatives

2016 ◽  
Vol 28 (3) ◽  
pp. 596-600 ◽  
Author(s):  
M.A. Kadir ◽  
R. Ramli ◽  
M.S.M. Yusof ◽  
N. Ismail ◽  
N. Ngah
Keyword(s):  
Antibacterial Activity ◽  
Amino Acid ◽  
Spectroscopic Studies ◽  
Amino Acid Derivatives

scholarly journals Synthesis of N-aryl β-amino acid derivatives via Cu(ii)-catalyzed asymmetric 1,4-reduction in air

RSC Advances ◽  
2019 ◽  
Vol 9 (16) ◽  
pp. 9187-9192
Author(s):  
Min Li ◽  
Hong-Feng Xia ◽  
Li-Yao Yang ◽  
Tao Hong ◽  
Lin-Jie Xie ◽  
...  
Keyword(s):  
Amino Acid ◽  
Precious Metal ◽  
Amino Acid Derivatives ◽  
High Yields

Non-precious metal copper-catalyzed asymmetric 1,4-hydrosilylation of β-aryl or β-alkyl-substituted N-aryl β-enamino esters proceeded in air in high yields and excellent enantioselectivities (26 examples, 90–98% ee).

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