Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity

In Vivo

Volumn 17, Issue 5, 2003, Pages 509-512

  Kawase, Masami ^a   Tanaka, Toru ^a   Sohara, Yoshitaka ^a   Tani, Satoru ^a   Sakagami, Hiroshi ^b   Hauer, Hermann ^c   Chatterjee, Shyam S ^c  

^a JOSAI UNIVERSITY   (Japan)

^b MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^c DR WILLMAR SCHWABE GMBH AND CO KG   (Germany)

Author keywords

Anti Helicobacter pylori; Coumarin derivatives; In vitro study; Structure activity; Urease

Indexed keywords

2,3 DIHYDRO 7 HYDROXY 8 METHOXYCYCLOPENTA[C][1]BENZOPYRAN 4(1H) ONE; 2,3 DIHYDRO 7,8 DIHYDROXYCYCLOPENTA[C][1]BENZOPYRAN 4(1H) ONE; 2,3 DIHYDRO 7,9 DIHYDROXYCYCLOPENTA[C][1]BENZOPYRAN 4(1H) ONE; 2,3 DIHYDRO 8 HYDROXY 7 METHOXYCYCLOPENTA[C][1]BENZOPYRAN 4(1H) ONE; 4 METHYLESCULETIN; 5,7 DIHYDROXYCYCLOPENTANOCOUMARIN; 6 HYDROXY 4 METHYLCOUMARIN; 6 HYDROXY 7 METHOXY 4 METHYLCOUMARIN; 6,7 DIHYDROXY 3,4 DIMETHYLCOUMARIN; 7 HYDROXY 3 METHYLCOUMARIN; 7 HYDROXY 3,4 DIMETHYLCOUMARIN; 7 METHOXY 4 METHYLCOUMARIN; 8 HYDROXY 7 METHOXY 3,4 DIMETHYLCOUMARIN; COUMARIN DERIVATIVE; ESCULETIN; HYDROXYL GROUP; HYMECROMONE; METRONIDAZOLE; SCOPOLETIN; UMBELLIFERONE; UMCKALIN; UNCLASSIFIED DRUG; UREASE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIUM CULTURE; CHEMICAL REACTION; COLONY FORMING UNIT; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG INHIBITION; DRUG POTENCY; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; HELICOBACTER PYLORI; IN VITRO STUDY; METHYLATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 0142198850     PISSN: 0258851X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Labigne JCA and Suerbaum S: Comparative ultrastructural and functional studies of Helicobacter pylori and Helicobacter mustelae flagellin mutants: Both flagellin subunits, FlaA and FlaB, are necessary for full motility in Helicobacter species. J Bacteriol 177: 3010-3020, 1995.
2. Blaser MJ: Helicobacter pylori: Its role in disease. Clin Infect Dis 15: 386-391, 1992.
3. Megraud F, Neman-Simha V and Brugmann D: Further evidence of the toxic effect of ammonia produced by Helicobacter pylori urease on human epithelial cells. Infect Immun 60: 1858-1863, 1992.
4. Larry KL and Tanaka SK: Therapy of Helicobacter pylori infections: Current status and future directions. Annu Rep Med Chem 30: 151-158, 1995.
5. Alarcon T, Domingo D and Lopez-Brea M: Antibiotic resistance problems with Helicobacter pylori. Int J Antimicrobial Agents 12: 1926, 1999.
6. Kawase M, Varu B, Shah A, Motohashi N, Tani S, Saito S, Debnath S, Mahapatra S, Dastidar SG and Chakrabarty AN: Antimicrobial activity of new coumarin derivatives. Arzneim.-Forsch/Drug Res 51: 67-71, 2001.
7. Von Pechmann H and Duisberg C: Uber die Verbindungen der Phenole mit Acetessigather. 16: 2119-2128, 1883.
8. Ahluwalia VK, Prakash C and Gupta MC: Structures of isofraxetin, umckalin, arsotin and 7-geranyloxy-5,6-dimethoxycoumarin. Indian J Chem Sect B 16B: 286-288, 1978.
9. Kessar SV, Gupta YP, Mohammad T, Goyal M and Sawal KK: Regioselective mono-O-alkylation of some pyrocatechoxide dianions. J Chem Soc Chem Commun 400-401, 1983.
10. Ahluwalia VK, Bhat K and Singh RP: Synthesis of 3-methylpsoralene and 3-methylxanthyletin. Indian J Chem Sect B 21B: 403-404, 1982.
11. Primofiore G and Valenti P: Synthesis and pharmacological profile of some 2-(6- and 7-cumarinoxymethyl)imidazolines. Atti Accad Sci Ist Bologna Cl Sci Fis Rend 3: 95-98, 1976. (Chem Abstr 88: 37696z).
12. Klopman G and Dimayuga ML: Computer-automated structure evaluation of flavonoids and other structurally related compounds as glyoxalase I enzyme inhibitors. Mol Pharmacol 34: 218-222, 1988.
13. Chatterjee SS, Noeldner M and Hauer H: Benzopyranones, a method for producing them and uses. Ger Offen DE 4,111,861 (C1. C07D311/16); US Patent (US 5428038) (Chem Abstr 118: 124397j).
14. Numao N, Iwahori A, Hirota Y, Sasatsu M, Kondo I, Onimura K, Sampe R, Yamane S, Itoh S, Katoh T and Kobayashi S: Antibacterial activity of two alkylamines integrated an indane scaffold: Mimicry of a complementary unit on magainin 2. Biol Pharm Bull 20: 800-804, 1997.
15. Dunn BE, Campbell GP, Perez-Perez GI and Blaser MJ: Purification and characterization of urease from Helicobacter pylori. J Biol Chem 265: 9464-9469, 1990.
16. Cesareo SD and Langton SR: Kinetic properties of Helicobacter pylori urease compared with jack bean urease. FEMS Microbiol Letters 99: 15-22, 1992.
17. Van Slyke DD and Archibald RM: Manomeric, titrimetric and colorimetric methods for measurement of urease activity. J Biol Chem 154: 623-642, 1944.
18. Tsutsui N, Taneike I, Ohara T, Goshi S, Kojio S, Iwakura N, Matsumaru H, Wakisaka-Saito N, Zhang H-M and Yamamoto TA: A novel action of the proton pump inhibitor rabeprazole and its thioether derivative against the motility of Helicobacter pylori. Antimicro Agents Chemother 44: 3069-3073, 2000.
19. Buiatli ED, Palli A, Decarli D, Amadori C, Avellini S, Bianchi R, Biserni F, Cipriani P, Cocco A, Giacosa E, Marubini R, Puntoni C, Vindigni J, Fraumeni Jr. and Blot W: A case-control study of gastric cancer and diet in Italy. Int J Cancer 44: 611-616, 1989.
20. Murray RDH, Mendez J and Brown SA: The Natural Coumarins: Occurrence, Chemistry and Biochemistry. John Wiley, New York, pp 282-289, 1982.