O-Acetylbenzeneamidinocarboxylic acid

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O-Acetylbenzeneamidinocarboxylic acid
Category Antineoplastic
Catalog number BBF-05895
CAS 82744-16-9
Molecular Weight 206.20
Molecular Formula C10H10N2O3
Purity ≥95%

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Description

O-Acetylbenzeneamidinocarboxylic acid is isolated from Gibberella saubinetii with antitumor activity. It has weak inhibitory effect on tumor cells.

Specification

Synonyms Acetic acid, 2-[(2-acetylphenyl)amino]-2-imino-; [(2-Acetylphenyl)amino](imino)acetic acid
IUPAC Name 2-((2-acetylphenyl)amino)-2-iminoacetic acid
Canonical SMILES CC(=O)C1=CC=CC=C1N=C(C(=O)O)N
InChI InChI=1S/C10H10N2O3/c1-6(13)7-4-2-3-5-8(7)12-9(11)10(14)15/h2-5H,1H3,(H2,11,12)(H,14,15)
InChI Key HFLBXTVTCFCWID-UHFFFAOYSA-N

Properties

Appearance Needles
Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 365.0±44.0°C at 760 mmHg
Melting Point 175-175.5°C
Density 1.3±0.1 g/cm3

Reference Reading

1. [Isolation and identification of an endophytic fungus of Polygonatum cyrtonema and its antifungal metabolites]
Ying Wang, Guoping Wang, Liwei Wang, Xuhui Xu, Jing Xia, Xuefang Huang, Yougui Wu, Chulong Zhang Wei Sheng Wu Xue Bao. 2010 Aug;50(8):1036-43.
Objective: Endophytic fungi in medicinal plants produce a variety of bioactivity compounds. In this study, an endophytic fungus zjqy610 with antifungal activity was isolated from Polygonatum cyrtonema in Zhejiang Qingyuan Baishanzu Mountain nature reserve. Methods: Strain zjqy610 was identified as Penicillium canescens based on the morphology and its rDNA sequence analysis. Three antifungal compounds were isolated from the fermentation broth of zjqy610 through normal-phase silica gel column chromatography and gel (Sephadex LH-20) column chromatography, traced by ultraviolet light or iodine vapor with bioassay-guided fractionation. Results: These three compounds were elucidated as o-acetylbenzeneamidinocarboxylic acid (zjqy610B-g-3), griseofulvin (zjqy610D-4) and naphtho [1,2-b] furan-3-carboxylic acid, 4-hydroxy-5-methoxy-2-methyl-(zjqy610F-2) based on mass spectrometry and nuclear magnetic resonance spectroscopy. The antifungal activity assays showed that the three compounds had inhibitory to variety of plant pathogenic fungi. Compound zjqy610D-4 had strong antifungal activity against Botrytis cinerea, Colletotrichum orbiculare, Didymella bryoniae and Sclerotinia sclerotiorum. EC50 was 0.68, 0.38, 0.91 and 0.61 mg/L, respectively. Conclusion: Zjqy610D-4 is deserved to develop an agricultural antibiotics.

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