DESIGN, SYNTHESIS, BIOLOGICAL EVALUATION AND MOLECULAR MODELING STUDY OF NOVEL INDOLIZINE-1-CARBONITRILE DERIVATIVES AS POTENTIAL ANTI-MICROBIAL AGENTS

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FAGHIH MIRZAEI EHSAN; SEIFI MOHAMMAD; ABBASZADEH MEHDI; ZOMORODIAN KAMIAR; HELALI HELIA

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Journal: Iranian Journal of Pharmaceutical Research Year:2018 | Volume:17 | Issue:3 Page(s): 883-895

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Title

DESIGN, SYNTHESIS, BIOLOGICAL EVALUATION AND MOLECULAR MODELING STUDY OF NOVEL INDOLIZINE-1-CARBONITRILE DERIVATIVES AS POTENTIAL ANTI-MICROBIAL AGENTS

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Keywords

INDOLIZINE-1-CARBONITRILES

3-DIPOLAR CYCLOADDITION

ULTRASOUND IRRADIATION

ANTIFUNGAL ACTIVITY

ANTIBACTERIAL ACTIVITY

MOLECULAR DOCKING

Abstract

A novel one-pot two step tandem reaction for the synthesis of indolizine-1-carbonitrilederivatives (5a-i) was identified. The route comprises 1, 3-DIPOLAR CYCLOADDITION reaction of aromatic aldehyde derivatives (1a-i), malononitrile (2) and 1- (2- (4-bromophenyl) -2-oxoethyl) - 2-chloropyridin-1-ium (4) under ULTRASOUND IRRADIATION at room temperature in the presence of triethylamine at acetonitrile. The product compounds were tested against bacteria and fungi. It was revealed that compound 5b had the most ANTIFUNGAL ACTIVITY (range MICs=8–32 mg/mL) and compound 5g had the most ANTIBACTERIAL ACTIVITY (range MICs=16–256 mg/mL). MOLECULAR DOCKING of compounds (5a-i) into fungal 14α-demethylase and bacterial protein tyrosine phosphatase active sites were also performed and probable binding mode of compounds 5b and 5g were determined.

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APA: Copy

FAGHIH MIRZAEI, EHSAN, SEIFI, MOHAMMAD, ABBASZADEH, MEHDI, ZOMORODIAN, KAMIAR, & HELALI, HELIA. (2018). DESIGN, SYNTHESIS, BIOLOGICAL EVALUATION AND MOLECULAR MODELING STUDY OF NOVEL INDOLIZINE-1-CARBONITRILE DERIVATIVES AS POTENTIAL ANTI-MICROBIAL AGENTS. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), 17(3), 883-895. SID. https://sid.ir/paper/288751/en

Vancouver: Copy

FAGHIH MIRZAEI EHSAN, SEIFI MOHAMMAD, ABBASZADEH MEHDI, ZOMORODIAN KAMIAR, HELALI HELIA. DESIGN, SYNTHESIS, BIOLOGICAL EVALUATION AND MOLECULAR MODELING STUDY OF NOVEL INDOLIZINE-1-CARBONITRILE DERIVATIVES AS POTENTIAL ANTI-MICROBIAL AGENTS. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR)[Internet]. 2018;17(3):883-895. Available from: https://sid.ir/paper/288751/en

IEEE: Copy

EHSAN FAGHIH MIRZAEI, MOHAMMAD SEIFI, MEHDI ABBASZADEH, KAMIAR ZOMORODIAN, and HELIA HELALI, “DESIGN, SYNTHESIS, BIOLOGICAL EVALUATION AND MOLECULAR MODELING STUDY OF NOVEL INDOLIZINE-1-CARBONITRILE DERIVATIVES AS POTENTIAL ANTI-MICROBIAL AGENTS,” IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), vol. 17, no. 3, pp. 883–895, 2018, [Online]. Available: https://sid.ir/paper/288751/en

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