Design and synthesis of N-Aryl isothioureas as a novel class of gastric H+/K+-ATPase inhibitors

Archiv der Pharmazie

Volumn 346, Issue 12, 2013, Pages 891-900

  Ma, Chao ^a   Wu, Anhui ^a   Wu, Yongqi ^a   Ren, Xuhong ^a   Cheng, Maosheng ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

H+ K+ ATPase; N Aryl isothiourea; Synthesis

Indexed keywords

N (2 BROMOBENZYL) 2 (4 ETHOXYPYRIDYLMETHYL)ISOTHIOUREA; N (2 BROMOBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (2 CHLOROBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (2 ETHOXYBENZYL) 2 (4 ETHOXYPYRIDYLMETHYL)ISOTHIOUREA; N (2 ETHOXYBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (2 METHYLBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (2,6 DIMETHYLBENZYL) 2 (4 ETHOXYPYRIDYLMETHYL)ISOTHIOUREA; N (2,6 DIMETHYLBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (3 METHYLBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (3 TRIFLUOROMETHYLBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (4 BROMOBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (4 CHLOROBENZYL) 2 (4 ETHOXYPYRIDYLMETHYL)ISOTHIOUREA; N (4 CHLOROBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (4 ETHOXYBENZYL) 2 (4 ETHOXYPYRIDYLMETHYL)ISOTHIOUREA; N (4 ETHOXYBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (4 FLUOROBENZYL) 2 (4 ETHOXYPYRIDYLMETHYL)ISOTHIOUREA; N (4 FLUOROBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (4 METHOXYBENZYL) 2 (4 ETHOXYPYRIDYLMETHYL)ISOTHIOUREA; N (4 METHOXYBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; N (4 METHYLBENZYL) 2 [3 METHYL 4 (2',2',2' TRIFLUOROETHOXY)PYRIDYLMETHYL]ISOTHIOUREA; PANTOPRAZOLE; PANTOPRAZOLE MAGNESIUM; PROTON PUMP INHIBITOR; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPARATIVE MOLECULAR FIELD ANALYSIS; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFECT; DRUG SYNTHESIS; GUINEA PIG; MASS FRAGMENTOGRAPHY; MOLECULAR MODEL; NONHUMAN; PREDICTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REACTION TIME; SOLVENT EFFECT; STOMACH ACID SECRETION; STOMACH MUCOSA; TEMPERATURE;

H+/K+-ATPASE; N-ARYL ISOTHIOUREA; SYNTHESIS;

2-PYRIDINYLMETHYLSULFINYLBENZIMIDAZOLES; ANIMALS; COMPUTER SIMULATION; COMPUTER-AIDED DESIGN; DRUG DESIGN; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GASTRIC ACID; GASTRIC MUCOSA; GUINEA PIGS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PROTON PUMP INHIBITORS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA;

EID: 84889690068     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201300276     Document Type: Article

References (15)

1. M. Robinson, Int. J. Clin. Pract. 59, 2005, (6), 709-715.
2. a) E. Fellenius, T. Berglindh, G. Sachs, L. Olbe, B. Elander, S. E. Sjöstrand, B. Wallmark, Nature 1981, 290, 159-161
3. b) L. Olbe, T. Berglindh, B. Elander, H. Helander, E. Fellenius, S. E. Sjöstrand, G. Sundell, B. Wallmark, Scand. J. Gastroenterol. 1979, 14 (Suppl 55), 131-133.
4. a) H. Satoh, N. Inatomi, H. Nagaya, I. Inaba, A. Nohara, N. Nakamura, Y. Maki, J. Pharmacol. Exp. Ther. 1989, 248, 806-815
5. b) K. Kubo, K. Oda, T. Kaneko, H. Satoh, A. Nohara, Chem. Pharm. Bull. 1990, 38, 2853-2858.
6. B. Kohl, E. Sturm, J. Senn-Bilfinger, W. Alexander Simon, U. Krüger, H. Schaefer, G. Rainer, V. Figala, K. Kelemm, J. Med. Chem. 1986, 35, 1049-1057.
7. J. M. Shin, Y. M. Cho, G. Sachs, J. Am. Chem. Soc. 2004, 126 (25), 7800-7811.
8. a) S. Devi, A. Nayak, S. Mittra, J. Indian, Chem. Soc. 1984, 335-337
9. b) N. Sung, K. Jeong, Han'guk Nong hwa Hakoehchi 1995, 38 (2), 163-167.
10. a) A. L. Salzman, A. G. Denenberg, I. Ueta, Am. J. Phaysiol. 1996, 312 (3), 341-347
11. b) D. Jang, C. Szabo, G. A. C. Murrell, Eur. J. Pharmacol. 1996, 312 (3), 341-347.
12. M. Mittelbaeh, H. W. Schmidt, G. Uray, G. Uray, H. Junek, B. Lamm, K. Ankner, A. Brändström, R. Simonsson, Acta Chem. Scand. B 1988, 42 (8), 524-529.
13. B. Liu, H. Q. Gao, X. J. Zhou, Chemistry 1994, (5), 42-43.
14. S. W. Chen, M. W. Wang, Acta Pharm. Sin. 1994, 10 (1), 75-76.
15. R. X. Wang, Y. Gao, L. Liu, L. H. Lai, J. Mol. Model. 1998, 4 (8), 276-283.