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1.
Molecules ; 23(4)2018 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-29641457

RESUMO

The article describes the use of facile one-pot, high-yielding reactions to synthesize substituted 3,4-dimethyl-1H-pyrrole-2-carboxamides 3a-m and carbohydrazide analogues 5a-l as potential antifungal and antimicrobial agents. The structural identity and purity of the synthesized compounds were assigned based on appropriate spectroscopic techniques. Synthesized compounds were assessed in vitro for antifungal and antibacterial activity. The compounds 5h, 5i and 5j were found to be the most potent against Aspergillusfumigatus, with MIC values of 0.039 mg/mL. The compound 5f bearing a 2, 6-dichloro group on the phenyl ring was found to be the most active broad spectrum antibacterial agent with a MIC value of 0.039 mg/mL. The mode of action of the most promising antifungal compounds (one representative from each series; 3j and 5h) was established by their molecular docking with the active site of sterol 14α-demethylase. Molecular docking studies revealed a highly spontaneous binding ability of the tested compounds in the access channel away from catalytic heme iron of the enzyme, which suggested that the tested compounds inhibit this enzyme and would avoid heme iron-related deleterious side effects observed with many existing antifungal compounds.


Assuntos
Antibacterianos/síntese química , Antifúngicos/síntese química , Hidrazinas/síntese química , Antibacterianos/química , Antibacterianos/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Aspergillus fumigatus/efeitos dos fármacos , Bacillus subtilis/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Hidrazinas/química , Hidrazinas/farmacologia , Klebsiella pneumoniae/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Simulação de Acoplamento Molecular , Estrutura Molecular , Pseudomonas aeruginosa/efeitos dos fármacos , Salmonella typhi/efeitos dos fármacos , Relação Estrutura-Atividade
2.
Bioorg Med Chem Lett ; 22(17): 5550-4, 2012 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-22850211

RESUMO

Benzoyl phenyl urea, a class of insect growth regulator's acts by inhibiting chitin synthesis. Carvacrol, a naturally occurring monoterpenoid is an effective antifungal agent. We have structurally modified carvacrol (2-methyl-5-[1-methylethyl] phenol) by introducing benzoylphenyl urea linkage. Two series of benzoylcarvacryl thiourea (BCTU, 4a-f) and benzoylcarvacryl urea (BCU, 5a-f) derivatives were prepared and characterized by elemental analysis, IR, (1)H and (13)C NMR and Mass spectroscopy. Derivatives 4b, 4d, 4e, 4f and 5d, 5f showed comparable insecticidal activity with the standard BPU lufenuron against Dysdercus koenigii. BCTU derivatives 4c, 4e and BCU 5c showed good antifungal activity against phytopathogenic fungi viz. Magnaporthe grisae, Fusarium oxysporum, Dreschlera oryzae; food spoilage yeasts viz. Debaromyces hansenii, Pichia membranifaciens; and human pathogens viz. Candida albicans and Cryptococcus neoformans. Compounds 5d, 5e and 5f showed potent activity against human pathogens. Moderate and selective activity was observed for other compounds. All the synthesized compounds were non-haemolytic. These compounds have potential application in agriculture and medicine.


Assuntos
Antifúngicos/química , Antifúngicos/farmacologia , Monoterpenos/química , Monoterpenos/farmacologia , Compostos de Fenilureia/química , Compostos de Fenilureia/farmacologia , Animais , Cimenos , Fungos/efeitos dos fármacos , Humanos , Insetos/efeitos dos fármacos , Inseticidas/química , Inseticidas/farmacologia , Testes de Sensibilidade Microbiana , Micoses/tratamento farmacológico , Tioureia/química , Tioureia/farmacologia
3.
J Environ Sci Health B ; 47(2): 136-43, 2012.
Artigo em Inglês | MEDLINE | ID: mdl-22251213

RESUMO

Insect-growth regulators (IGRs) have been receiving foremost attention as potential means of selective insect control. Benzoyl phenyl urea (BPU) is a well-known IGR having chitin synthesis inhibitor activity. Mimics of BPU have been synthesized by suitable derivatization of a naturally occurring monoterpenoid, thymol (2-isopropyl-5-methyl phenol) to form a = series of substituted benzoyl thymyl thioureas (BTTUs) [IVa-f] and benzoyl thymyl ureas (BTUs) [Va-f]. The synthesized compounds have been characterized by (1)H and (13)C NMR, LC-MS and elemental analysis. These derivatives have been screened for their effect on total haemocyte count of Dysdercus koenigii. It has been observed that the introduction of substituted benzoyl thiourea and urea linkage into a thymol ring via an amino group results in higher activity than the parent compound thymol and a comparable pattern of results with the standard insect-growth regulators, Penfluron. Urea [Va-f] compounds exhibited greater effect on Total Haemocyte Count (THC) than thiourea [IVa-f]. Fluoro substitution enhanced the effect on THC more than chloro substituted compounds, while ortho-substitution resulted in a better effect than para-substitution. The results described in this paper are promising and provide new array of synthetic chemicals that may be utilized as insect growth regulators.


Assuntos
Hemócitos/efeitos dos fármacos , Hormônios Juvenis/análise , Hormônios Juvenis/síntese química , Tioureia/análise , Animais , Heterópteros/efeitos dos fármacos , Controle de Insetos/métodos , Espectroscopia de Ressonância Magnética , Compostos de Fenilureia/análise , Compostos de Fenilureia/síntese química , Tioureia/análogos & derivados , Tioureia/síntese química
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