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Volumn 1, Issue 4, 2010, Pages 155-159

Impact of absolute stereochemistry on the antiangiogenic and antifungal activities of itraconazole

Author keywords

angiogenesis; antifungal activity; diastereomers; Itraconazole; stereochemistry

Indexed keywords

ANGIOGENESIS INHIBITOR; ANTIFUNGAL AGENT; ITRACONAZOLE; ITRACONAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77955905585     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml1000068     Document Type: Article
Times cited : (43)

References (17)
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    • cis - and trans -Designations describe the geometrical relationship of triazolylmethyl (C-2) and oxymethyl (C-4) substituents, either on the same face (cis) or the opposite face (trans) of the dioxolane ring. While going from tosyl derivatives (11a ? d) all the way to itraconazole stereoisomers 1a ? h, the cis and trans relationship does not change. However, according to Cahn?Ingold?Prelog priority rules, the R and S notations corresponding to C-4 of the dioxolane ring do change. For example, cis -2 S,4 S tosylate derivative (11a) eventually leads to cis -2 S,4 R,2? S (1a) or cis -2 S,4 R,2? R (1b) itraconazole stereoisomers.
    • cis-and trans -Designations describe the geometrical relationship of triazolylmethyl (C-2) and oxymethyl (C-4) substituents, either on the same face (cis) or the opposite face (trans) of the dioxolane ring. While going from tosyl derivatives (11a ? d) all the way to itraconazole stereoisomers 1a ? h, the cis and trans relationship does not change. However, according to Cahn?Ingold?Prelog priority rules, the R and S notations corresponding to C-4 of the dioxolane ring do change. For example, cis -2 S,4 S tosylate derivative (11a) eventually leads to cis -2 S,4 R,2? S (1a) or cis -2 S,4 R,2? R (1b) itraconazole stereoisomers.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.