Benzothieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines: Synthesis, characterization, antimicrobial activity, and incorporation into solid lipid nanoparticles

Archiv der Pharmazie

Volumn 344, Issue 6, 2011, Pages 358-365

  Panchamukhi, Shridhar I ^a   Mulla, Jameel Ahmed S ^b   Shetty, Nitinkumar S ^a   Khazi, Mohammed Iqbal A ^a   Khan, Ashraf Y ^a   Kalashetti, Mallikarjun B ^a   Khazi, Imitiyaz Ahmed M ^a  

^a KARNATAK UNIVERSITY   (India)

^b KLE College of Pharmacy   (India)

Author keywords

Antimicrobial activity; Gewald reaction; In vitro release study; Solid lipid nanoparticles; Triazolothienopyrimidines

Indexed keywords

3 (2 CHLORO PHENYL) 9,10,11,12 TETRAHYDRO[1]BENZOTHIENO[3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE; 3 (3 BENZYL) 9,10,11,12 TETRAHYDRO[1]BENZOTHIENO [3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE; 3 (3 METHYL FURAN 2 YL) 9,10,11,12 TETRAHYDRO[1]BENZOTHIENO[3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE; 3 (3 METHYL THIOPHEN 2 YL) 9,10,11,12 TETRAHYDRO[1]BENZOTHIENO[3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE; 3 (9H FLUOREN 9 YL) 9,10,11,12 TETRAHYDRO[1]BENZOTHIENO[3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE; 3 (9H XANTHEN 9 YL) 9,10,11,12 TETRAHYDRO[1]BENZOTHIENO[3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE; 3 (NAPHTHALEN 2 YL) 9,10,11,12 TETRAHYDRO[1]BENZOTHIENO[3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE; 3 (PYREN 1 YL) 9,10,11,12 TETRAHYDRO[1]BENZOTHIENO [3,2 E][1,2,4]TRIAZOLO[4,3 C]PYRIMIDINE; PYRIMIDINE DERIVATIVE; SOLID LIPID NANOPARTICLE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG RELEASE; DRUG STABILITY; DRUG SYNTHESIS; IN VITRO STUDY; NONHUMAN; PARTICLE SIZE; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; ZETA POTENTIAL;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CALORIMETRY, DIFFERENTIAL SCANNING; DELAYED-ACTION PREPARATIONS; LIPIDS; MICROSCOPY, ELECTRON, SCANNING; NANOPARTICLES; PARTICLE SIZE; PYRIMIDINES;

EID: 79958204030     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201000227     Document Type: Article

References (39)

1. R. V. Chambhare, B. G. Khase, A. S. Bobde, R. H. Bahekar, Eur. J. Med. Chem. 2003, 38, 89-100.
2. N. S. Shetty, R. S. Lamani, I. M. Khazi, J. Chem. Sci. 2009, 121, 1-7.
3. C. R. Petrie, H. B. Cottam, P. A. Mckernan, R. K. Robins, G. R. Revankar, J. Med. Chem. 1985, 28, 1010-1016.
4. M. N. Nasr, M. M. Gineinah, Arch. Pharm. 2002, 335, 289-295.
5. P. G. Baraldi, M. G. Pavani, M. C. Nunez, P. Brigidi, B. Vitali, R. Gambari, R. Romanoli, Bioorg. Med. Chem. 2002, 10, 449-456.
6. S. M. Sondhi, M. Johar, S. Rajvanshi, S. G. Dastidar, R. Shukla, R. Raghubir, J. William Lown, Australian J. Chem. 2001, 54, 69-74.
7. D. J. Brown, Pyrimidines and Their Benzo Derivatives, in Comprehensive Heterocyclic Chemistry (Eds.:, A. R. Katritzky, C. W. Rees,), Vol. III, Pergamon Press, Oxford 1984.
8. B. Roth, C. C. Cheng, Diaminopyrimidines, in Progress in Medicinal Chemistry (Eds.:, G.B. Ellisand, G.E. West,), Vol. IXX, Elsevier Biomedical Press, New York 1982.
9. M. S. El-Gaby, S. G. Abdel-Hamide, M. M. Ghorab, S. M. El-Sayed, Acta Pharm. 1999, 49, 149-158.
10. Z. H. Dong, S. X. Chang, J. H. Kai, H. Z. Chang, Biomaterials 2003, 24, 1781-1785.
11. R. H. Müller, K. Mäder, S. Gohla, Eur. J. Pharm. Biopharm. 2000, 50, 161-177.
12. R. H. Müller, M. Radtke, S. A. Wissing, Adv. Drug Delivery Rev. 2002, 54, 131-155.
13. M. Wolfgang, M. Karsten, Adv. Drug Delivery Rev. 2001, 47, 165-196.
14. Q. G. David, T. E. David, G. Q. Adriana, A. Eric, D. Eric, Eur. J. Pharm. Sci. 2005, 26, 211-218.
15. M. A. Schubert, C. C. Muller, Eur. J. Pharm. Biopharm. 2003, 55, 125-131.
16. Q. H. Fu, P. J. Sai, Z. D. Yong, Y. Hong, Q. Y. Yi, Z. Su, Biointerfaces 2005, 45, 167-173.
17. M. Zhinan, C. Huabing, W. Ting, Y. Yajiang, Y. Xiangliang, Eur. J. Pharm. Biopharm. 2003, 56, 189-196.
18. V. Vobalaboina, M. Kopparam, J. Controlled Release 2004, 95, 627-638.
19. B. Siekmann, K. Westesen, Pharm. Pharmacol. Lett. 1994, 3, 194-197.
20. R. H. Muller, W. Mehnert, J. S. Lucks, C. Schwarz, A. zur Muhlen, H. Weyhers, C. Freitas, D. Ruhl, Eur. J. Pharm. Biopharm. 1995, 41, 62-69.
21. R. W. Sabnis, D. W. Rangnekar, Dyes Pigm. 1989, 10, 295-302.
22. K. Gewald, E. Schinke, H. Bottcher, Chem. Ber. 1966, 99, 94-100.
23. rd ed., NCCLS, Tuscon 1996.
24. th ed., NCCLS, Tuscon 2009.
25. C. Olbrich, R. H. Muller, Int. J. Pharm. 1999, 180, 31-39.
26. H. Komatsu, A. Kitajima, S. Okada, Chem. Pharm. Bull. 1995, 43, 1412-1415.
27. M. Y. Levy, W. Schutze, C. Fuhrer, S. Benita, J. Microencapsulation 11, 1994, 79-92.
28. C. Schwarz, W. Mehnert, J. Microencapsulation 1999, 16, 205-213.
29. E. B. Souto, S. A. Wissing, C. M. Barbosa, R. H. Muller, Int. J. Pharm. 2004, 278, 71-77.
30. A. del Pozo-Rodriguez, M. A. Solinis, A. R. Gascon, J. L. Pedraz, Eur. J. Pharm. Biopharm. 2009, 71, 181-189.
31. R. Cavalli, O. Caputo, M. R. Gasco, Int. J. Pharm. 1997, 148, 47-54.
32. R. Cavalli, O. Caputo, M. R. Gasco, Eur. J. Pharm. Sci. 2000, 10, 305-309.
33. V. Jenning, A. F. Thunemann, S. H. Gohla, Int. J. Pharm. 2000, 199, 167-177.
34. V. Jenning, M. Schafer-Korting, S. Gohla, J. Controlled Release 2000, 66, 115-126.
35. A. Geze, M. C. Venier-Julienne, D. Mathieu, R. Filmon, R. Phan-Tan-Luu, J. P. Benoit, Int. J. Pharm. 1999, 178, 257-268.
36. N. Kun, P. Keun-Hong, W. K. Sung, H. B. You, J. Controlled Release 2000, 69, 225-236.
37. T. P. Maria, G. Ruxandra, M. Yoshiharu, D. Avi, L. Noah, L. Robert, J. Controlled Release 1997, 46, 223-231.
38. M. Maria, S. Chiara, V. Donatella, L. Giuseppe, M. F. Anna, Int. J. Pharm. 2002, 234, 237-248.
39. D. B. Chen, T. Z. Yang, W. L. Lu, Q. Zhang, Chem. Pharm. Bull. 2001, 49, 1444-1447.