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115871-02-8 | L-Argininamide, L-phenylalanyl-N-2-naphthalenyl-
CAS No: 115871-02-8 Catalog No: AG000H0I MDL No:
Product Description
Catalog Number:
AG000H0I
Chemical Name:
L-Argininamide, L-phenylalanyl-N-2-naphthalenyl-
CAS Number:
115871-02-8
Molecular Formula:
C25H30N6O2
Molecular Weight:
446.5447
IUPAC Name:
(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-5-(diaminomethylideneamino)-N-naphthalen-2-ylpentanamide
InChI:
InChI=1S/C25H30N6O2/c26-21(15-17-7-2-1-3-8-17)23(32)31-22(11-6-14-29-25(27)28)24(33)30-20-13-12-18-9-4-5-10-19(18)16-20/h1-5,7-10,12-13,16,21-22H,6,11,14-15,26H2,(H,30,33)(H,31,32)(H4,27,28,29)/t21-,22-/m0/s1
InChI Key:
ZNHUFUZDUQRKBB-VXKWHMMOSA-N
SMILES:
NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)cccc2)NC(=O)[C@H](Cc1ccccc1)N
Properties
Complexity:
659
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
446.243g/mol
Formal Charge:
0
Heavy Atom Count:
33
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
5
Isotope Atom Count:
0
Molecular Weight:
446.555g/mol
Monoisotopic Mass:
446.243g/mol
Rotatable Bond Count:
10
Topological Polar Surface Area:
149A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2
Literature
| Title | Journal |
|---|---|
| Effects of efflux pump inhibitors on erythromycin, ciprofloxacin, and tetracycline resistance in Campylobacter spp. isolates. | Microbial drug resistance (Larchmont, N.Y.) 20121001 |
| Prevalence of efflux-mediated ciprofloxacin and levofloxacin resistance in recent clinical isolates of Pseudomonas aeruginosa and its reversal by the efflux pump inhibitors 1-(1-naphthylmethyl)-piperazine and phenylalanine-arginine-β-naphthylamide. | International journal of antimicrobial agents 20120101 |
| Synthesis and evaluation of inhibitors of bacterial drug efflux pumps of the major facilitator superfamily. | Bioorganic & medicinal chemistry 20111215 |
| The cyclohexane tolerance and Phe-Arg-β-naphtylamide susceptibility of multidrug-resistant Enterobacter cloacae clinical isolates, and the predominance of one PFGE clone in Hungary. | Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20110801 |
| Activity of the efflux pump inhibitor phenylalanine-arginine β-naphthylamide against the AdeFGH pump of Acinetobacter baumannii. | International journal of antimicrobial agents 20110501 |
| The role of RamA on the development of ciprofloxacin resistance in Salmonella enterica serovar Typhimurium. | PloS one 20110101 |
| Detection of the floR gene in a diversity of florfenicol resistant Gram-negative bacilli from freshwater salmon farms in Chile. | Zoonoses and public health 20100501 |
| Contribution of efflux pumps to clarithromycin resistance in Helicobacter pylori. | Journal of gastroenterology and hepatology 20100501 |
| Effects of efflux pump inhibitors phenyl-arginine-beta-naphthylamide and 1-(1-naphthylmethyl)-piperazine on the antimicrobial susceptibility of Pseudomonas aeruginosa isolates from cystic fibrosis patients. | Journal of chemotherapy (Florence, Italy) 20091101 |
| Treatment of multiresistant Acinetobacter baumannii infections. | Current opinion in investigational drugs (London, England : 2000) 20090201 |
| Effect of the efflux inhibitors 1-(1-naphthylmethyl)-piperazine and phenyl-arginine-beta-naphthylamide on antimicrobial susceptibility and virulence factor production in Vibrio cholerae. | The Journal of antimicrobial chemotherapy 20090101 |
| [Investigation of the effect of efflux pump inhibitors to MIC values of ciprofloxacin in clinical isolates of Pseudomonas aeruginosa, Escherichia coli, Acinetobacter baumannii and Staphylococcus aureus]. | Mikrobiyoloji bulteni 20081001 |
| Persistence of Campylobacter species, strain types, antibiotic resistance and mechanisms of tetracycline resistance in poultry flocks treated with chlortetracycline. | The Journal of antimicrobial chemotherapy 20080801 |
| Effect of putative efflux pump inhibitors and inducers on the antimicrobial susceptibility of Campylobacter jejuni and Campylobacter coli. | Journal of medical microbiology 20080701 |
| Acinetobacter baumannii bloodstream infection while receiving tigecycline: a cautionary report. | The Journal of antimicrobial chemotherapy 20070101 |
| High-level resistance to moxifloxacin and gatifloxacin associated with a novel mutation in gyrB in toxin-A-negative, toxin-B-positive Clostridium difficile. | The Journal of antimicrobial chemotherapy 20061201 |
| Multidrug efflux inhibition in Acinetobacter baumannii: comparison between 1-(1-naphthylmethyl)-piperazine and phenyl-arginine-beta-naphthylamide. | The Journal of antimicrobial chemotherapy 20060501 |
| Effect of 1-(1-naphthylmethyl)-piperazine, a novel putative efflux pump inhibitor, on antimicrobial drug susceptibility in clinical isolates of Enterobacteriaceae other than Escherichia coli. | The Journal of antimicrobial chemotherapy 20060201 |
| Effect of 1-(1-naphthylmethyl)-piperazine, a novel putative efflux pump inhibitor, on antimicrobial drug susceptibility in clinical isolates of Escherichia coli. | The Journal of antimicrobial chemotherapy 20060201 |
| Molecular basis of macrolide resistance in Campylobacter: role of efflux pumps and target mutations. | The Journal of antimicrobial chemotherapy 20050901 |
| Characterization of Salmonella spp. mutants with reduced fluoroquinolone susceptibility: importance of efflux pump mechanisms. | Chemotherapy 20050301 |
| Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats. | Journal of applied microbiology 20050101 |
| A multidrug efflux pump inhibitor reduces fluoroquinolone resistance in Pseudomonas aeruginosa isolates. | Chemotherapy 20040401 |
| [Investigation of the effects of efflux pump inhibitors on ciprofloxacin MIC values of high level fluoroquinolone resistant Escherichia coli clinical isolates]. | Mikrobiyoloji bulteni 20040101 |
| Conformationally-restricted analogues of efflux pump inhibitors that potentiate the activity of levofloxacin in Pseudomonas aeruginosa. | Bioorganic & medicinal chemistry letters 20030818 |
| Effect of an efflux pump inhibitor on the MIC of nalidixic acid for Acinetobacter baumannii and Stenotrophomonas maltophilia clinical isolates. | The Journal of antimicrobial chemotherapy 20020401 |
| Addressing the stability of C-capped dipeptide efflux pump inhibitors that potentiate the activity of levofloxacin in Pseudomonas aeruginosa. | Bioorganic & medicinal chemistry letters 20010312 |
| MC-207110 Daiichi Seiyaku/Microcide Pharmaceuticals. | Current opinion in investigational drugs (London, England : 2000) 20010201 |
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