Synthesis and antifungal activity of noble 5-arylamino- and 6-arylthio-4,7-dioxobenzoselenazoles

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 3, 2005, Pages 679-682

  Ryu, Chung Kyu ^a   Han, Ja Young ^a   Jung, Ok Jai ^a   Lee, Su Kyung ^a   Lee, Jung Yoon ^a   Jeong, Seong Hee ^a  

^a Ewha Womans University   (South Korea)

Author keywords

4,7 Dioxobenzoselenazole; Antifungal; Antimicrobial compounds; Fungi; Substitution effects

Indexed keywords

ANTIFUNGAL AGENT; SELENAZOLE DERIVATIVE;

ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS; CANDIDA; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; NONHUMAN;

ANTIFUNGAL AGENTS; ASPERGILLUS; CANDIDA; HUMANS; MICROBIAL SENSITIVITY TESTS; ORGANOSELENIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

ASPERGILLUS; CANDIDA; FUNGI;

EID: 12444273595     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.11.027     Document Type: Article

References (17)

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13. 3 with TMS. High-resolution mass spectra (HRMS EI) were taken with Jeol JMS AX505 WA. 5-Methoxy-2-methyl-benzoselenazole (6) and other reagents were purchased from Aldrich Chemical Co
14. 3Se: 256.9591. Found: 256.9592. General procedure for synthesis of 5-arylamino-2-methyl-4,7- dioxobenzoselenazoles 4a-j: a solution of compound 9 (0.256 g, 1 mmol) in 20 mL of 95% EtOH was added to a solution of the arylamine (1.1 mmol) in 10 mL of 95% EtOH and then refluxed for 4-6 h. After the reaction mixture was kept overnight, the precipitate was collected by the filtration. The crude product was purified by silica gel column chromatography with EtOAc/n-hexane (1:2) or crystallized from 95% EtOH. Crystallization from aq EtOH afforded 5-arylamino-2-methyl-4,7- dioxobenzoselenazoles4a-j (Table 1). General procedure for synthesis of 6-arylthio-5-methoxy-2-methyl-4,7-dioxobenzoselenazoles 5a-g: a solution of compound 10 (0.256 g, 1 mmol) in 30 mL of 95% EtOH was added to a solution of the arylthiol (1.1 mmol) in 10 mL of 95% EtOH and then refluxed for 4-10 h. After the reaction mixture was kept overnight, the precipitate was collected by the filtration. The crude product was purified by silica gel column chromatography with EtOAc/n-hexane (1:2) or crystallized from 95% EtOH. Crystallization from aq EtOH afforded 6-arylthio-5-methoxy-2-methyl-4,7- dioxobenzoselenazoles 5a-g (Table 1)
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17. 14 All of the tested compounds did not show significant cytotoxic activity