151271-53-3

Basic information

• Product Name: UK 1
• Synonyms: UK 1;2'-(2-Hydroxyphenyl)-[2,4'-bibenzoxazole]-4-carboxylic acid methyl ester;UK 1 (cytotoxin)
• CAS NO: 151271-53-3
• Molecular Formula: C₂₂H₁₄N₂O₅
• Molecular Weight: 386.362
• Mol File: 151271-53-3.mol

Chemical Properties

• Melting Point: 209-210℃
• Boiling Point: 558.2°Cat760mmHg
• Flash Point: 291.4°C
• Appearance: /
• Density: 1.423g/cm³
• Vapor Pressure: 1.71E-12mmHg at 25°C
• Refractive Index: 1.687
• Solubility: Soluble in DMSO;Soluble in dimethyl formamide
• PKA: 8.55±0.30(Predicted)
• CAS DataBase Reference: UK 1(CAS DataBase Reference)
• NIST Chemistry Reference: UK 1(151271-53-3)
• EPA Substance Registry System: UK 1(151271-53-3)

Safety Data

• Hazardous Substances Data: 151271-53-3(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
UK 1 is used as an antitumor agent for its ability to inhibit human topoisomerase II, which plays a crucial role in DNA replication and transcription. By targeting this enzyme, UK 1 can potentially disrupt cancer cell processes and exhibit antitumor activity.
Used in Pharmaceutical Industry:
UK 1 is used as an antibiotic and antifungal inhibitor of topoisomerase II for its potential to combat various diseases caused by bacteria and fungi. Its topoisomerase II inhibitory properties make it a valuable compound in the development of new drugs to treat infections.

Biological Activity

uk 1, an unusual bis-benzoxazole metabolite isolated from streptomyces sp. 517-02, is an inhibitor of topoisomerase ii (topo ii) and hepatitis c viral replication. it is an antifungal and an antibiotic, and displays a wide spectrum of potent anticancer activities against lymphoma, leukemia, and certain solid tumor-derived cell lines with ic50 values as low as 20 nm. however, uk 1 is devoid of antimicrobial activity and is inactive against pseudomonas aeruginosa and staphylococcus aureus, a methicillin-resistant strain of s. aureus. additionally, uk-1 can bind a wide variety of di- and tri-valent metal ions, particularly mg2+ ions, and form complexes with dna in the presence of mg2+ ions. topo ii are atp-dependent enzymes, which can simultaneously cut both strands of the dna helix to manage dna supercoils and tangles.

in vitro

uk 1 strongly blocked the growth of human epitheloid carcinoma hela, mouse melanoma b16, mouse leukemia p388 cells with ed50 values of 1.22 μg/ml, 1.17 μg/ml, and 0.11 μg/ml, respectively. uk 1 did not display any growth inhibitory activity against bacteria, fungi and yeasts up to 100 μg/ml [1].

references

[1]. ueki, m., ueno, k., miyadoh, s., abe, k., shibata, k., taniguchi, m., & oi, s. uk-1, a novel cytotoxic metabolite from streptomyces sp. 517-02. i. taxonomy, fermentation, isolation, physico-chemical and biological properties. the journal of antibiotics. 1993; 46(7): 1089-1094.

InChI:InChI=1/C22H14N2O5/c1-27-22(26)14-8-5-11-17-19(14)24-21(29-17)13-7-4-10-16-18(13)23-20(28-16)12-6-2-3-9-15(12)25/h2-11,23H,1H3/b20-12+

Upstream product

• 90-02-8 salicylaldehyde 
• 906095-21-4 2-(2-hydroxyphenyl)benzo[d]oxazole-4-carboxylic acid 
• 17672-21-8 2-amino-3-hydroxy-benzoic acid methyl ester 
• 548-93-6 3-hydroxyanthranilic acid 
• 119-36-8 methyl salicylate 
• 69-72-7 salicylic acid 
• 186501-21-3 2-(2-(benzyloxy)benzoylamino)-3-hydroxybenzoic acid methyl ester 
• 186501-24-6 methyl 2-(2-(benzyloxy)phenyl)benzo[d]oxazole-4-carboxylate 
• 186501-25-7 2-(2-(benzyloxy)phenyl)benzo[d]oxazole-4-carboxylic acid 
• 153373-42-3 2-(2-Benzyloxy-phenyl)-benzooxazole-4-carbonyl chloride 
• 55142-16-0 methyl 2-(benzyloxy)benzoate 
• 4349-62-6 2-benzyloxybenzoyl chloride 
• 14389-86-7 2-benzyloxybenzoic acid 
• 186501-26-8 methyl 3-hydroxy-2-{[2-(benzyloxyphenyl)-1,3-benzoxazol-4-yl]carbonyl}aminobenzoate 

Relevant articles and documents

Synthetic method of anticancer drug UK-1

The invention discloses a synthetic method of an anticancer drug UK-1. The method comprises the following steps: mixing a methyl 2-amino-3-hydroxybenzoate compound, an aldehyde and a molecular sieve to generate a mixture; performing heating reflux on the

Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles

Four classes of UK-1 analogues were synthesized and their cytotoxicity testing against human A-549, BFTC-905, RD, MES-SA, and HeLa carcinoma cell lines was determined. The results revealed that UK-1 and four of these analogues (15-18) are potent against the cancer cell lines. In particular, compound 16 is more potent than UK-1 against A-549 and HeLa cell lines, and compounds 15, 17, and 18 selectively exhibit potent cytotoxic activity against the BFTV-905 cells (IC50 9.6 μM), A-549 cells (IC50 6.6 μM), and MES-SA cells (IC50 9.2 μM), respectively.

UK-1 analogues: methods of preparation and use

The present invention includes a number of structural analogues of UK-1. A comparision of the anticancer activity of the UK-1 analogues with their ability to inhibit the growth of methicillin-sensitive and methicillin-resistant Staphylococcus aureus demon

Critical structural motif for the catalytic inhibition of human topoisomerase II by UK-1 and analogs

Three new analogs of UK-1 have been synthesized and their efficacies as topoisomerase II inhibitors have been determined. Results show that UK-1 and two of these analogs are catalytic inhibitors of topo II and identifies a critical structure motif necessa

Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1

UK-1 is a structurally unique bis(benzoxazole) natural product isolated from a strain of Streptomyces. UK-1 has been reported to possess anticancer activity but no activity against bacteria, yeast, or fungi. Previous work has also demonstrated the ability

The total synthesis of UK-1

A concise, five-step total synthesis of UK-1, a novel bis(benzoxazole) metabolite of Streptomyces sp. 517-02, was accomplished. The methyl ether of UK-1 was also synthesized in 3 steps using the same methodology. Both syntheses are accomplished by the seq