Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Novel 6,7,8,9-Tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted Hydrazino Thiazolo (2,3-b) Quinazoline as Potent Antinociceptive and Anti-inflammatory Agents

  • Selvam, T. Panneer (Department of Pharmaceutical Chemistry, D.C.R.M. Pharmacy College) ;
  • Kumar, P. Vijayaraj (Department of Pharmacy, Island College of Technology)
  • Received : 2010.02.16
  • Accepted : 2010.09.15
  • Published : 2010.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

A series of 6,7,8,9-tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted hydrazino thiazolo (2,3-b) quinazolines have been synthesized to meet the structural requirements essential for anti-inflammatory and antinociceptive properties. The synthesized series of heterocycles, 6,7,8,9-tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted hydrazino thiazolo (2,3-b) quinazoline by the reaction of 6,7,8,9-tetrahydro-5H-5-hydroxy phenyl thiazolo (2,3-b) quinazolin-3(2H)-one with appropriate hydrazine hydrate and ketones/aldehydes in the presence of anhydrous sodium acetate and glacial acetic acid as presented in Scheme 1. Their antinociceptive activity were evaluated by tailflick technique, anti-inflammatory was evaluated by carrageenan-induced paw edema test and their ulcerogenicity index determined by reported protocol. The compounds exhibited the lowest ulcer index ($0.51{\pm}1.63$, $0.48{\pm}1.28$ and $0.50{\pm}1.53$, respectively. The 6,7,8,9-tetrahydro-5H-5-hydroxy phenylhydroxy-2-benzylidine-3-(N'-3-pentylidenehydrazino) thiazolo (2,3-b) quinazoline and 6,7,8,9-tetrahydro-5H-5-hydroxy phenyl-2-benzylidine-3-(N'-2-pentylidene-hydrazino) thiazolo (2,3-b) quinazoline exhibited the most potent antinociceptive and anti-inflammatory activities.

Keywords

References

  1. Alagarsamy, V.; Meena, S.; Revathi, R.; Vijayakumar, S.; Ramseshu, K. V. Pharmazie. 2003, 58, 233-236.
  2. Alagarsamy, V.; Thangathirupathy, A.; Mandal, S. C.; Rajasekaran, S.; Vijayakumar, S.; Revathi, R.; Anburaj, J.; Arunkumar, S.; Rajesh, S. Indian J. Pharm. Sci. 2006, 68, 108-111. https://doi.org/10.4103/0250-474X.22980
  3. Hitkari, A.; Bhalla, M.; Saxena, A. K.; Verma, M.; Gupta, M. P.; Shanker, K. Boll. Chim. Farm. 1995, 134, 609-615.
  4. Chao, Q.; Deng, L.; Shih, H.; Leoni, L. M.; Genini, D.; Carson, D. A.; Cottam, H. B. J. Med. Chem. 1999, 42, 3860-3873. https://doi.org/10.1021/jm9805900
  5. Alagarsamy, V.; Muthukumar, V.; Pavalarani, N.; Vasanthanathan, P.; Revathi, R. Biol. Pharm. Bull. 2003, 26, 557-559. https://doi.org/10.1248/bpb.26.557
  6. Zappal, M.; Grasso, S.; Micale, N.; Zuccal, G.; Menniti, F. S.; Ferreri, G.; De Sarro, G.; De Micheli, C. Bioorg. Med. Chem. Lett. 2003, 13, 4427-4430. https://doi.org/10.1016/j.bmcl.2003.09.032
  7. Alagarsamy, V.; Solomon, V. R.; Vanikavitha, G.; Paluchamy, V.; Chandran, M. R.; Sujin, A. A.; Thangathiruppathy, A.; Amuthalakshmi, S.; Revathi, R. Biol. Pharm. Bull. 2002, 25, 1432-1435. https://doi.org/10.1248/bpb.25.1432
  8. Alagarsamy, V.; Murugananthan, G.; Venkateshperumal, R. Biol. Pharm. Bull. 2003, 26, 1711-1714. https://doi.org/10.1248/bpb.26.1711
  9. Alagarsamy, V.; Rajesh, R.; Meena, R.; Vijaykumar, S.; Ramseshu, K. V.; Duraianandakumar, T. Biol. Pharm. Bull. 2004, 27, 652-656. https://doi.org/10.1248/bpb.27.652
  10. Alagarsamy, V.; Meena, S.; Ramaseshu, K. V.; Solomon, V. R.; Kumar, T. D.; Thirumurugan, K. Chem. Biol. Drug Des. 2007, 70, 254-260. https://doi.org/10.1111/j.1747-0285.2007.00548.x
  11. Alagarsamy, V.; Solomon, V. R.; Dhanabal, K. Bioorg. Med. Chem. 2007, 15, 235-241. https://doi.org/10.1016/j.bmc.2006.09.065
  12. Alagarsamy, V.; Dhanabal, K.; Parthiban, P.; Anjana, G.; Deepa, G.; Murugesan, B.; Rajkumar, S.; Beevi, A. J. J. Pharm. Pharmacol. 2007, 59, 669-677. https://doi.org/10.1211/jpp.59.5.0007
  13. Alagarsamy, V.; Shankar, D.; Murugan, M.; Siddiqui, A. A.; Rajesh, R. Arch Pharm. (Weinheim). 2007, 340, 41-46. https://doi.org/10.1002/ardp.200600189
  14. Alagarsamy, V.; Solomon, V. R.; Murugesan, S. Arzneimittelforschung. 2008, 58, 174-181.
  15. Quiroga, J.; Hernandez, P.; Insuassy, B. R.; Abonia, R.; Cobo, J.; Sanchez, A.; Nogueras, M.; Low, J. N. J. Chem. Soc. Perkin Trans. 2002, 1, 555-559.
  16. Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. R.; Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 2002, 45, 744-747. https://doi.org/10.1021/jm011025r
  17. Winter, C. A.; Risely, E. A.; Nuss, G. W. Exp. Biol. Med. 1962, 111, 544-547. https://doi.org/10.3181/00379727-111-27849
  18. Goel, R. K.; Chakrabarti, A.; Sanyal, A. K. Planta Med. 1985, 29, 85-88.
  19. Kulkarni, S. K. Life Sci. 1980, 27, 185-188. https://doi.org/10.1016/0024-3205(80)90136-8
  20. Sharma, R.; Kumar, S.; Pujari, H. K. Indian J. Chem. 1991, 30B, 425-426.
  21. Amour, R. E.; Smith, D. L. J. Pharmacol. Exp. Ther. 1941, 72, 74-78.
  22. Shay, M.; Komarov, S. A.; Fels, D.; Meranze, D.; Grunstein, H.; Siplet, H. Gastroenterology 1945, 5, 43-61.
  23. Ganguly, A. K.; Bhatnagar, O. P. Can. J. Physiol. Pharmacol. 1973, 51, 748-750. https://doi.org/10.1139/y73-113

Cited by

  1. ChemInform Abstract: Synthesis of Novel 6,7,8,9-Tetrahydro-5H-5-hydroxyphenyl-2-benzylidene-3-substituted Hydrazino Thiazolo(2,3-b)quinazoline as Potent Antinociceptive and Antiinflammatory Agents. vol.42, pp.13, 2011, https://doi.org/10.1002/chin.201113163
  2. Synthesis of thiazolo[2,3-b]quinazoline derivatives via base-promoted cascade bicyclization of o-alkenylphenyl isothiocyanates with propargylamines vol.17, pp.29, 2010, https://doi.org/10.1039/c9ob01098j
  3. Synthesis of Azoloquinazolines and Substituted Benzothiazepine as Antimicrobial Agents vol.20, pp.5, 2010, https://doi.org/10.2174/1389557519666190603091101