Dodecanoic acid derivatives: Synthesis, antimicrobial evaluation and development of one-target and multi-target QSAR models

Sarova, Devinder; Kapoor, Archana; Narang, Rakesh; Judge, Vikramjeet; Narasimhan, Balasubramanian

doi:10.1007/s00044-010-9383-5

Cited by 14 publications

(4 citation statements)

References 40 publications

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“…In bioactivity studies, the honeybee Apis mellifera has been reported as producing the compounds associated with compounds 1, 7, 12, and 13, which are utilized in the queen fecal pheromones involved in nestmate recognition (Breed et al, 1992). Recently, the two laurates described as compounds 7 and 9 were evaluated for in vitro antimicrobial activity against the panel of Gram positive and Gram negative bacterial and fungal strains in quantitative structure activity relationship (QSAR) studies (Sarova et al, 2011). n-Hexyl Table 2 Constituent carboxylic acid and alcohol, and structures of fifteen esters from Anaulaciulus sp.…”

Section: Discussionmentioning

confidence: 99%

n-Hexyl Laurate and Fourteen Related Fatty Acid Esters: New Secretory Compounds from the Julid Millipede, Anaulaciulus sp.

et al. 2012

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A total of fifteen saturated fatty acid esters were newly identified from the secretions of an unidentified Anaulaciulus sp. (Julida: Julidae). The fatty acid components of the esters were composed of normal chain acids (from C(10) to C(14)) and of branched chain acids (from iso-C(12) to iso-C(15) and anteiso-C(15)). The alcohol moieties were all composed of normal chain alcohols varying from n-butanol to n-octanol. The most abundant component found in the total esters was n-hexyl laurate (64.7%). Novel compounds identified from the millipede secretion extracts include six branched iso- and anteiso-fatty esters, an odd-numbered C(11)-fatty acid ester, a C(13)-fatty acid ester, and a C(7)-alcohol ester, all of which were previously undescribed natural products. In addition, a characteristic mixture of benzoquinones, such as 2-methyl-1,4-benzoquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-methoxy-6-methyl-1,4-benzoquinone, and 2,3-dimethoxy-5-methyl-1,4-benzoquinone were identified from the secretions, together with trace amounts of 1,4-benzoquinone.

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Section: Discussionmentioning

confidence: 99%

n-Hexyl Laurate and Fourteen Related Fatty Acid Esters: New Secretory Compounds from the Julid Millipede, Anaulaciulus sp.

et al. 2012

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“…While in addition, the temperature was maintained at 0-10 0 C. The stirring was performed for 30min, and the precipitated amide was separated by filtration. The recrystallization of crude amide was done from alcohol 20 .…”

Section: Step 2: Formation Of Acid Chloridementioning

confidence: 99%

Design, Synthesis, Characterization and Biological Evaluation of Para-Amino Salicylic Acid (PAS) Analogues: An Approach to Repurpose

Kapoor

Thaiya

2023

Int J Life Sci Pharm Res

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The ever-emerging microbial resistance has imposed great challenges for the medicinal chemist in designing newer chemical entities, which is a lengthy and time-consuming process. An alternate approach of repurposing older drugs can be undertaken to accelerate the discovery of some newer derivatives with lesser side effects. The work reported in the present paper is an extension of the idea of repurposing older drugs. The study aimed to synthesize a series of ester and amide derivatives (P1-P28) of Para-amino salicylic acid. The antimicrobial evaluation of all the synthesized derivatives was performed via the serial dilution method. The Gram-positive bacteria: Staphylococcus aureus and Bacillus subtilis and Gram-negative bacteria: Escherichia coli and Pseudomonas aeruginosa were used for the antibacterial activity, and Candida albicans were used for the antifungal activity. Ciprofloxacin (antibacterial) and Fluconazole (antifungal) were the standard drugs. The antioxidant evaluation (ester derivatives, P1-P19) was carried out by using the DPPH scavenging method and BHA (butylated hydroxy anisole) was used as the reference. The derivative 5-acetamido-2-(propyl carbamoyl) phenyl acetate (P22) was the most effective antibacterial agent, which may be attributed to the presence of 3-carbon aliphatic alkyl chain. At the same time, 4-methoxy phenyl-4-amino-2-hydroxy benzoate (P15) and 2-chloro phenyl-4-amino-2-hydroxy benzoate (P16) displayed effective antifungal activity. Ethyl-4-amino-2-hydroxy benzoate (P2) demonstrated the most potent free radical scavenging activity. Further, the spectroscopic characterization and physicochemical characterization of the synthesized derivatives have been carried out and were found to be in accord with the assigned structures.

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“…Sarova et al [ 14 ] synthesized three dodecanoic acid derivatives 1 − 3 with yields of 59–61 % , starting from dodecanoic acid in two steps, chlorination with thionyl chloride and reaction with the corresponding aminopyridine ( Scheme 1 ). All compounds possessed good antibacterial activity against B. subtilis , S. aureus and E. coli and antifungal activity against A. niger and C. albicans .…”

Section: Synthesis Of Antimicrobial Compounds Containing Only Pyridin...mentioning

confidence: 99%

Pyridine Compounds with Antimicrobial and Antiviral Activities

Marinescu

Popa

2022

IJMS

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In the context of the new life-threatening COVID-19 pandemic caused by the SARS-CoV-2 virus, finding new antiviral and antimicrobial compounds is a priority in current research. Pyridine is a privileged nucleus among heterocycles; its compounds have been noted for their therapeutic properties, such as antimicrobial, antiviral, antitumor, analgesic, anticonvulsant, anti-inflammatory, antioxidant, anti-Alzheimer’s, anti-ulcer or antidiabetic. It is known that a pyridine compound, which also contains a heterocycle, has improved therapeutic properties. The singular presence of the pyridine nucleus, or its one together with one or more heterocycles, as well as a simple hydrocarbon linker, or grafted with organic groups, gives the key molecule a certain geometry, which determines an interaction with a specific protein, and defines the antimicrobial and antiviral selectivity for the target molecule. Moreover, an important role of pyridine in medicinal chemistry is to improve water solubility due to its poor basicity. In this article, we aim to review the methods of synthesis of pyridine compounds, their antimicrobial and antiviral activities, the correlation of pharmaceutical properties with various groups present in molecules as well as the binding mode from Molecular Docking Studies.

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Dodecanoic acid derivatives: Synthesis, antimicrobial evaluation and development of one-target and multi-target QSAR models

Cited by 14 publications

References 40 publications

n-Hexyl Laurate and Fourteen Related Fatty Acid Esters: New Secretory Compounds from the Julid Millipede, Anaulaciulus sp.

n-Hexyl Laurate and Fourteen Related Fatty Acid Esters: New Secretory Compounds from the Julid Millipede, Anaulaciulus sp.

Design, Synthesis, Characterization and Biological Evaluation of Para-Amino Salicylic Acid (PAS) Analogues: An Approach to Repurpose

Pyridine Compounds with Antimicrobial and Antiviral Activities

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