Synthesis of Amino Acid Analogues of 5<i>H</i>‐Dibenz[<i>b,f</i>]azepine and Evaluation of their Radical Scavenging Activity

Kumar, Hemant; Gnanendra, C. R.; Naik, Nagaraja

doi:10.1155/2009/361490

Cited by 6 publications

(5 citation statements)

References 8 publications

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“…This may be due to the absence of a hydroxyl group. Among the synthesised conjugates, 1-(3-(5H-dibenz[ b , f ]azepine-5-yl)-3-oxopropyl)-3hydroxypyrolidine-2-carboxylic acid showed the highest activity with an IC 50 value of 4.1 ± 0.87 µM/mL, which might be due to the presence of a hydroxyl group of Hyp [ 111 ].…”

Section: Conjugated or Hybrid Moleculesmentioning

confidence: 99%

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Conjugation as a Tool in Therapeutics: Role of Amino Acids/Peptides-Bioactive (Including Heterocycles) Hybrid Molecules in Treating Infectious Diseases

et al. 2023

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Peptide-based drugs are gaining significant momentum in the modern drug discovery, which is witnessed by the approval of new drugs by the FDA in recent years. On the other hand, small molecules-based drugs are an integral part of drug development since the past several decades. Peptide-containing drugs are placed between small molecules and the biologics. Both the peptides as well as the small molecules (mainly heterocycles) pose several drawbacks as therapeutics despite their success in curing many diseases. This gap may be bridged by utilising the so called ‘conjugation chemistry’, in which both the partners are linked to one another through a stable chemical bond, and the resulting conjugates are found to possess attracting benefits, thus eliminating the stigma associated with the individual partners. Over the past decades, the field of molecular hybridisation has emerged to afford us new and efficient molecular architectures that have shown high promise in medicinal chemistry. Taking advantage of this and also considering our experience in this field, we present herein a review concerning the molecules obtained by the conjugation of peptides (amino acids) to small molecules (heterocycles as well as bioactive compounds). More than 125 examples of the conjugates citing nearly 100 references published during the period 2000 to 2022 having therapeutic applications in curing infectious diseases have been covered.

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Section: Conjugated or Hybrid Moleculesmentioning

confidence: 99%

“…The conjugation of Hyp (IC 50 = 4.1 ± 0.87 µM/mL) showed superior activity due to the presence of -OH group on pyrrolidine ring. Finally, the authors concluded that Hyp conjugate reported the highest activity among the synthesised derivatives [ 115 ].…”

Section: Conjugated or Hybrid Moleculesmentioning

confidence: 99%

Conjugation as a Tool in Therapeutics: Role of Amino Acids/Peptides-Bioactive (Including Heterocycles) Hybrid Molecules in Treating Infectious Diseases

et al. 2023

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“…[20] The scientific studies focused on amino acids and some of their derivatives revealed high antioxidant activity particularly their potential radical scavenging activities associated with cancer cells. [21] Glutathione synthesized in cells from its constituent amino acids (glutamate-cysteine-glycine) has antioxidant properties and capable of preventing damage to important cellular components caused by reactive oxygen species such as free radicals, peroxides, lipid peroxides, and heavy metals. [22] In addition, N,N'-dicyclohexylcarbodiimide (DCC) is a widely used reagent as a powerful dehydrating agent in the coupling of amino acids for the peptide synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…From the literature amino acids and some of their derivatives were also found to have antioxidant activity [20] . The scientific studies focused on amino acids and some of their derivatives revealed high antioxidant activity particularly their potential radical scavenging activities associated with cancer cells [21] …”

Section: Introductionmentioning

confidence: 99%

Amino acid and Dicyclohexylurea Linked Pyrazole Analogues: Synthesis, In Silico and In Vitro Studies

et al. 2023

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Pancreatic lipase (PL) inhibitors have received considerable attention by several researchers because of its ability to hydrolyse the triglycerides in the small intestine. This study reports the (i) synthesize of new pyrazole derivatives binding amino acid and Dicyclohexylurea (DCU), (ii) their pharmaceutical potentials-via enzyme inhibitory activity towards PL and antioxidant activities (using complementary antioxidant methods including FCR, FRAP and ORAC), (iii) the possible interactions between pyrazole compounds and PL enzyme through in silico studies, and the pharmacokinetic properties of the tetra-substituted pyrazole analogues by PreADMET. Enzyme activities with IC 50 values of the pyrazole analogues were found to be in a high range of 6.6 � 0.4 μM to 13.5 � 0.2 μM. However, antioxidant activities of the pyrazole analogues exhibited low binding affinities against FCR, FRAP, and ORAC. The pyrazole analogues with docking scores were in the range of À 7.3 to À 15.2 and their SAR analysis were demonstrated to highlight the importance of amino acid and DCU linked scaffolds. Two web tools were utilized for the purpose of predicting ADMET parameters of drugs and drug-like pyrazole analogues. These results suggested that the amino acid and DCU linked pyrazole analogues have potential as PL inhibitors.

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“…An effective anticonvulsant drug, 5H-dibenzo[b,f]azepine-5-carboxamide, was first synthesized by Schindler [13] in 1960 and since then it has become the most frequently prescribed first-line drug for the treatment of epilepsy. In addition, dibenzo[b,f]azepine derivatives are useful due to their antimicrobial [14], antioxidant [15,16], and antitubercular [17] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial, and Antioxidant Activities of N‐[(5′‐Substituted‐2′‐phenyl‐1H‐indol‐3′‐yl)methylene]‐5H‐dibenzo[b,f]azepine‐5‐carbohydrazide Derivatives

Saundane

Vijaykumar

Vaijinath³

2013

Journal of Chemistry

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The main aim of the present study was to synthesize new leads with potential antimicrobial and antioxidant activities. As a part of systematic investigation of synthesis and biological activity, some new indole compounds3a–cand4a–cwere prepared and screened for their antimicrobial and antioxidant activities. The antimicrobial evaluation of newly synthesized compounds was carried out by cup-plate method. Antimicrobial activity results revealed that compound4ashowed promising activity against bacteriaStaphylococcus aureus,Klebsiella pneumonia, andPseudomonas aeruginosaand exhibited maximum inhibition againstAspergillus niger,Aspergillus oryzae,Aspergillus terreus, andAspergillus flavus. The antioxidant activity was performed by three methods, namely, radical scavenging activity (RSA), ferric ions (Fe+3) reducing antioxidant power (FRAP), and metal chelating activity by using Hatano’s, Oyaizu’s, and Dinis' methods, respectively. Compound4ashowed promising RSA, FRAP, and metal chelating activity.

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Synthesis of Amino Acid Analogues of 5H‐Dibenz[b,f]azepine and Evaluation of their Radical Scavenging Activity

Cited by 6 publications

References 8 publications

Conjugation as a Tool in Therapeutics: Role of Amino Acids/Peptides-Bioactive (Including Heterocycles) Hybrid Molecules in Treating Infectious Diseases

Conjugation as a Tool in Therapeutics: Role of Amino Acids/Peptides-Bioactive (Including Heterocycles) Hybrid Molecules in Treating Infectious Diseases

Amino acid and Dicyclohexylurea Linked Pyrazole Analogues: Synthesis, In Silico and In Vitro Studies

Synthesis, Antimicrobial, and Antioxidant Activities of N‐[(5′‐Substituted‐2′‐phenyl‐1H‐indol‐3′‐yl)methylene]‐5H‐dibenzo[b,f]azepine‐5‐carbohydrazide Derivatives

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