Synthesis and biological evaluation of 3-(1H-indol-3-yl)pyrazole-5- carboxylic acid derivatives

Archives of Pharmacal Research

Volumn 34, Issue 3, 2011, Pages 343-355

  Zhang, Datong ^a   Wang, Guangtian ^a   Tan, Chubing ^b   Xu, Weiren ^b   Pei, Yuan ^b   Huo, Lingyan ^a  

^a SHANDONG POLYTECHNIC UNIVERSITY   (China)

^b TIANJIN INSTITUTE OF PHARMACEUTICAL RESEARCH   (China)

Author keywords

Antibacterial activity; Endothelin 1 antagonist activity; Indole; Pyrazole; Structure activity relationships (SAR)

Indexed keywords

1 (3,4 DIMETHOXYBENZYL) 3 (1 PROPYL 1H INDOL 3 YL) 1H PYRAZOLE 5 CARBOXYLIC ACID; 1 (4 METHOXYBENZYL) 3 (1 PROPYL 1H INDOL 3 YL) 1H PYRAZOLE 5 CARBOXYLIC ACID; 1 BENZYL 3 (1 BENZYL 1H INDOL 3 YL) 1H PYRAZOLE 5 CARBOXYLIC ACID; 1 BENZYL 3 (1 METHYL 1H INDOL 3 YL) 1H PYRAZOLE 5 CARBOXYLIC ACID; 1 BENZYL 3 (1H INDOL 3 YL) 1H PYRAZOLE 5 CARBOXYLIC ACID; 1 BUTYL 3 (1 BUTYL 1H INDOL 3 YL) 1H PYRAZOLE 5 CARBOXYLIC ACID; 1 PROPYL 3 (1 PROPYL 1H INDOL 3 YL) 1H PYRAZOLE 5 CARBOXYLIC ACID; 2 BENZYL 3 (1H INDOL 3 YL) 1H PYRAZOLE 5 CARBOXYLIC ACID; 3 (1H INDOL 3 YL)PYRAZOLE 5 CARBOXYLIC ACID DERIVATIVE; 3 [1 (3,4 DIMETHOXYBENZYL) 1H INDOL 3 YL] 1 PROPYL 1H PYRAZOLE 5 CARBOXYLIC ACID; 3 [1 (3,4 DIMETHOXYBENZYL) 1H INDOL 3 YL] 2 PROPYL 1H PYRAZOLE 5 CARBOXYLIC ACID; 3 [1 (4 FLUOROBENZYL) 1H INDOL 3 YL] 1 PROPYL 1H PYRAZOLE 5 CARBOXYLIC ACID; 3 [1 (4 METHOXYBENZYL) 1H INDOL 3 YL] 1 PROPYL 1H PYRAZOLE 5 CARBOXYLIC ACID; 3 [1 (CARBOXYMETHYL) 1H INDOL 3 YL] 1 (3, 4 DIMETHOXYBENZYL) 1H PYRAZOL 5 CARBOXYLIC ACID; AMPICILLIN; ANTIBIOTIC AGENT; BOSENTAN; ENDOTHELIN RECEPTOR ANTAGONIST; INDOLE DERIVATIVE; KANAMYCIN; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BACILLUS THURINGIENSIS; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; MALE; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; SUDDEN DEATH;

ANIMALS; ANTI-BACTERIAL AGENTS; AORTA, THORACIC; DEATH, SUDDEN; ENDOTHELIN-1; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MALE; MICE; MICE, INBRED ICR; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PYRAZOLES; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; VASOCONSTRICTION; VASODILATOR AGENTS;

EID: 79960015975     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-011-0301-2     Document Type: Article

References (21)

1. Abdel-Aziz, M., Abuo-Rahma, G., El-Din. A., and Hassan, A. A., Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur. J. Med. Chem., 44, 3480-3487 (2009).
2. Akbas, E., Berber, I., Sener, A., and Hasanov, B., Synthesis and antibacterial activity of 4-benzoyl-1-methyl-5-phenyl- 1H-pyrazole-3-carboxylic acid and derivatives. Farmaco, 60, 23-26 (2005). (Pubitemid 40126284)
3. Basavarajaiah, S. D. M. and Mruthyunjayaswamy, B. H. M., Synthesis and antimicrobial activity of some5-substituted- 3-phenyl-N?-(substituted-2-oxo-2H- pyrano[2, 3-b]quinoline- 3-carbonyl)-1H-indole-2-carboxyhydrazide. Chem. Pharm. Bull., 57, 557-560 (2009).
4. Brady, T., Vu, K., Barber, J. R., Ng, S. C., and Zhou, Y. F., Synthesis of novel 2, 3-substituted-2, 4-dihydro-pyrazolo [4, 3-d]pyrimidine-5, 7-diones. Tetrahedron Lett., 50, 6223-6227 (2009).
5. Clozel, M., Breu, V., Gray, G. A., Kalina, B., Löffler, B. M., Burri, K., Cassal, J. M., Hirth, G., Müller, M., and Neidhart, W., Pharmacological characterization of Bosentan, a new potent orally active nonpeptide endothelin receptor antagonist. J. Pharmacol. Exp. Ther., 270, 228-235 (1994). (Pubitemid 24229632)
6. EI-Sabbagh, O. I., Baraka, M. M., Ibrahim, S. M., Pannecouque, C., Andrei, G., Snoeck, R., Balzarini, J., and Rashad, A. A., Synthesis and antiviral activity of new pyrazole and thiazole derivatives. Eur. J. Med. Chem., 44, 3746-3753 (2009).
7. Gorbunova, V. P. and Suvorov, N. N., Indoles derivatives LXXXIX. Synthesis of some diketo esters of the indole series and of indolypyrazoles from them. Khim. Geterotsikl. Soedin., 11, 1519-1522 (1973).
8. Ihara, M., Noguchi, K., Saeki, T., Fukuroda, T., Tsuchida, S., Kimura, S., Fukami, T., Ishikawa, K., Nishikibe, M., and Yano, M., Biological profiles of highly potent novel endothelin antagonists selective for the ETA receptor. Life Sci., 50, 247-255 (1992).
9. Jaiswal, N., Lambrecht, G., Mutschler, E., Tacke, R., and Malik, K. U., Pharmacological characterization of the vascular muscarinic receptors mediating relaxation and contraction in Rabbit Aorta. J. Pharmacol. Exp. Ther., 258, 842-850 (1991).
10. Jaronczyka, M., Dobrowolski, J. C., and Mazureka, A. P., Theoretical studies on tautomerism and IR spectra of pyrazole derivatives. J. Mol. Struct. (Theochem), 673, 17-28 (2004).
11. Karthikeyan, K., Veenus, S. T., Lalitha, K. G., and Perumal, P. T., Synthesis and antinociceptive activity of pyrazolyl isoxazolines and pyrazolyl isoxazoles. Bioorg. Med. Chem. Lett., 19, 3370-3373 (2009).
12. Okumura, H., Ashizawa, N., Aotsuka, T., Asakura, R., Kobayashi, F., and Matsuura, A., Possible mechanisms of sudden death and hemoconcentration induced by endothelin-1 and big endothelin-1 in mice. Biol. Pharm. Bull., 17, 645-650 (1994). (Pubitemid 24186108)
13. Okumura, H., Ashizawa, N., Asakura, R., Aotsuka, T., Kobayashi, F., and Matsuura, A., Possible involvement of different mechanisms in sudden death induced by endothelin-1 and big endothelin-1. Biol. Pharm. Bull., 18, 18-23 (1995).
14. Papesch, V. and Dodson, R. M., Isomeric pyrazolo[4, 3- d]pyrimidinediones. J. Org. Chem., 30, 199-203 (1965).
15. Prasda, M. R. and Kishore, D. P., Multistep, microwave assisted, solvent free synthesis and antibacterial activity of 6-substituted-2, 3, 4-trihydropyrimido[1, 2-c]9, 10, 11, 12- tetrahydrobenzo[b]thieno[3, 2-e] pyrimidines. Chem. Pharm. Bull., 55, 776-779 (2007).
16. Raschack, M., Unger, L., Riechers, H., and Klinge, D., Receptor selectivity of endothelin antagonists and prevention of vasoconstriction and endothelin-induced sudden death. J. Cardiovasc. Pharmacol., 26 Suppl 3, S397-S399 (1995).
17. Rawson, D. J., Dack, K. N., Dickinson, R. P., and James, K., The design and synthesis of a novel series of indole derived selective ETA antagonists. Bioorg. Med. Chem. Lett., 12, 125-128 (2002). (Pubitemid 34037949)
18. Shawali1, A. S., Sherif, S. M., Darwish, M. A. A., and Elmerzabani, M. M., Synthesis and antitumor screening of new 1, 7-diphenyl-3-(1, 3-disubstituted-1H-pyrazole-4-carbonyl)-[ 1, 2, 4]triazolo[4, 3-a] pyrimidin-5(1H)-ones. Arch. Pharm. Res., 33, 647-654 (2010).
19. Singh, N., Bhati, S. K., and Kumar, A., Thiazolyl/oxazolyl formazanyl indoles as potent anti-inflammatory agents. Eur. J. Med. Chem., 43, 2597-2609 (2008).
20. Yamamoto, Y. and Kurazono, M., A new class of anti-MRSA and anti-VRE agents: preparation and antibacterial activities of indole-containing compounds. Bioorg. Med. Chem. Lett., 17, 1626-1628 (2007). (Pubitemid 46274339)
21. Zhang, J., Didierlaurent, S., Fortin, M., Lefrancois, D., Uridata, E., and Veverta, J. P., Potent nonpeptide endothelin antagonists: Synthesis and structure-activity relationships of pyrazole-5-carboxylic acids. Bioorg. Med. Chem. Lett., 10, 2575-2578 (2000).