BU-4704

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Category Antibiotics
Catalog number BBF-02756
CAS
Molecular Weight 382.39
Molecular Formula C19H14N2O5S

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Description

BU-4704 is produced by the strain of Aspergillus sp. No. FA2692. It has anti-gram-positive bacteria, anti-gram-negative bacteria and cryptococcus neoformans activity. The IC50 of human colorectal cancer cells (HCT-16) and murine melanoma were 0.63 and 4.3 μg/mL, respectively.

Specification

Synonyms 4-[(1Z,3Z)-2,3-Diisocyano-4-(4-methoxyphenyl)-1,3-butadien-1-yl]phenyl hydrogen sulfate
IUPAC Name [4-[(1Z,3Z)-2,3-diisocyano-4-(4-methoxyphenyl)buta-1,3-dienyl]phenyl] hydrogen sulfate
Canonical SMILES COC1=CC=C(C=C1)C=C(C(=CC2=CC=C(C=C2)OS(=O)(=O)O)[N+]#[C-])[N+]#[C-]
InChI InChI=1S/C19H14N2O5S/c1-20-18(12-14-4-8-16(25-3)9-5-14)19(21-2)13-15-6-10-17(11-7-15)26-27(22,23)24/h4-13H,3H3,(H,22,23,24)/b18-12-,19-13-
InChI Key AFDVXUYMZKBPPT-BKHHGCLFSA-N

Properties

Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor)
Melting Point 165-170°C

Reference Reading

1. Induced production of N-formyl alkaloids from Aspergillus fumigatus by co-culture with Streptomyces peucetius
Karina M Zuck, Suzanne Shipley, David J Newman J Nat Prod. 2011 Jul 22;74(7):1653-7. doi: 10.1021/np200255f. Epub 2011 Jun 13.
Co-culture of the fungus Aspergillus fumigatus with the bacteria Streptomyces peucetius led to the induction of production of formyl xanthocillin analogues. This mixed fermentation yielded two new metabolites, fumiformamide (1) and N,N'-((1Z,3Z)-1,4-bis(4-methoxyphenyl)buta-1,3-diene-2,3-diyl)diformamide (2), together with two known N-formyl derivatives and the xanthocillin analogue BU-4704. The structures were determined by spectroscopic methods and by comparison with literature. Cytotoxic activity of all the analogues was tested on the NCI-60 cell line screen, and compound 2 exhibited significant activity against several cell lines. The analogues did not show antimicrobial activity.

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