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Literature DB >> 11866589

Diazo group electrophilicity in kinamycins and lomaiviticin A: potential insights into the molecular mechanism of antibacterial and antitumor activity.

Abstract

Theoretical and chemical studies of the reactivity of isoprekinamycin, the kinamycins, and the lomaiviticins support the proposal that these natural products exhibit enhanced diazonium salt character and may owe their antitumor antibiotic properties to their ability to act as electrophilic azo-coupling agents in vivo.

Entities: Chemical

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Year: 2002 PMID： 11866589 DOI： 10.1021/ja0167809

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

16 in total

1. 11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

Authors: Seth B Herzon; Liang Lu; Christina M Woo; Shivajirao L Gholap
Journal: J Am Chem Soc Date: 2011-01-31 Impact factor: 15.419

2. Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

Authors: Hong Geun Lee; Jae Young Ahn; Amy S Lee; Matthew D Shair
Journal: Chemistry Date: 2010-11-22 Impact factor: 5.236

Diazo group electrophilicity in kinamycins and lomaiviticin A: potential insights into the molecular mechanism of antibacterial and antitumor activity.

1. 11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

2. Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

3. The Mechanism of Action of (-)-Lomaiviticin A.

Review 4. The re-emergence of natural products for drug discovery in the genomics era.

Review 5. Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.

Review 6. Diazo Compounds: Versatile Tools for Chemical Biology.

7. Analysis of diazofluorene DNA binding and damaging activity: DNA cleavage by a synthetic monomeric diazofluorene.

8. Natural products: DNA double whammy.

9. Development of enantioselective synthetic routes to (-)-kinamycin F and (-)-lomaiviticin aglycon.

10. Mechanism of the cytotoxicity of the diazoparaquinone antitumor antibiotic kinamycin F.