Table of Contents 
Organic Chemistry International
Volume 2016 (2016), Article ID 9589517, 10 pages
http://dx.doi.org/10.1155/2016/9589517
Research Article

Synthesis and Antiproliferative Activity of Some Quinoline and Oxadiazole Derivatives

Mohamed Jawed Ahsan,1 Sunil Shastri,1 Rita Yadav,1 Mohd. Zaheen Hassan,2 Mohammed Afroz Bakht,3 Surender Singh Jadav,4 and Sabina Yasmin4

1Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan 302 039, India
2School of Chemical Science, University Sains Malaysia, Penang 118 00, Malaysia
3Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, P.O. Box 11323, Al-Kharj, Saudi Arabia
4Department of Pharmaceutical Chemistry, Birla Institute of Technology, Mesra, Ranchi, Jharkhand 835 215, India

Received 21 July 2016; Revised 20 October 2016; Accepted 31 October 2016

Academic Editor: Kirpal Bisht

Copyright © 2016 Mohamed Jawed Ahsan et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. http://www.cancer.gov/.
  2. R. L. Siegel, K. D. Miller, and A. Jemal, “Cancer statistics, 2015,” CA: A Cancer Journal for Clinicians, vol. 65, no. 1, pp. 5–29, 2015. View at Publisher · View at Google Scholar · View at Scopus
  3. WHO World Cancer Report 2014, http://www.nydailynews.com/life-style/health/14-million-people-cancer-2012-article-1.1545738.
  4. N. Aydemir and R. Bilaloglu, “Genotoxicity of two anticancer drugs, gemcitabine and topotecan, in mouse bone marrow in vivo,” Mutation Research, vol. 537, no. 1, pp. 43–51, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. B. Heiniger, G. Gakhar, K. Prasain, D. H. Hua, and T. A. Nguyen, “Second-generation substituted quinolines as anticancer drugs for breast cancer,” Anticancer Research, vol. 30, no. 10, pp. 3927–3932, 2010. View at Google Scholar · View at Scopus
  6. O. Afzal, S. Kumar, M. R. Haider et al., “A review on anticancer potential of bioactive heterocycles quinoline,” European Journal of Medicinal Chemistry, vol. 97, pp. 871–910, 2015. View at Publisher · View at Google Scholar
  7. S. B. Marganakop, R. R. Kamble, T. Taj, and M. Y. Kariduraganvar, “An efficient one-pot cyclization of quinoline thiosemicarbazones to quinolines derivatized with 1,3,4-thiadiazole as anticancer and anti-tubercular agents,” Medicinal Chemistry Research, vol. 21, no. 2, pp. 185–191, 2012. View at Publisher · View at Google Scholar · View at Scopus
  8. S. B. Marganakop, R. R. Kamble, J. Hoskeri, D. J. Prasad, and G. Y. Meti, “Facile synthesis of novel quinoline derivatives as anticancer agents,” Medicinal Chemistry Research, vol. 23, no. 6, pp. 2727–2735, 2014. View at Publisher · View at Google Scholar · View at Scopus
  9. E. I. Aly, “Design, synthesis and in vitro cytotoxic activity of new 4-anilino-7-chloro quinoline derivatives targeting EGFR tyrosine kinase,” Journal of American Science, vol. 6, pp. 73–83, 2010. View at Google Scholar
  10. K. Kubo, T. Shimizu, S. I. Ohyama et al., “Novel potent orally active selective VEGFR-2 tyrosine kinase inhibitors: synthesis, structure-activity relationships, and antitumor activities of N-phenyl-N′-(4-(4-quinolyloxy)phenyl)ureas,” Journal of Medicinal Chemistry, vol. 48, no. 5, pp. 1359–1366, 2005. View at Google Scholar
  11. C.-H. Tseng, Y.-L. Chen, C.-Y. Hsu et al., “Synthesis and antiproliferative evaluation of 3-phenylquinolinylchalcone derivatives against non-small cell lung cancers and breast cancers,” European Journal of Medicinal Chemistry, vol. 59, pp. 274–282, 2013. View at Publisher · View at Google Scholar · View at Scopus
  12. M. I. El-Gamal, M. A. Khan, M. S. Abdel-Maksoud, M. M. G. El-Din, and C.-H. Oh, “A new series of diarylamides possessing quinoline nucleus: synthesis, in vitro anticancer activities, and kinase inhibitory effect,” European Journal of Medicinal Chemistry, vol. 87, pp. 484–492, 2014. View at Publisher · View at Google Scholar · View at Scopus
  13. S. Chakrabarty, M. S. Croft, M. G. Marko, and G. Moyna, “Synthesis and evaluation as potential anticancer agents of novel tetracyclic indenoquinoline derivatives,” Bioorganic & Medicinal Chemistry, vol. 21, no. 5, pp. 1143–1149, 2013. View at Publisher · View at Google Scholar · View at Scopus
  14. C.-T. Chen, M.-H. Hsu, Y.-Y. Cheng et al., “Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs,” European Journal of Medicinal Chemistry, vol. 46, no. 12, pp. 6046–6056, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. M. Abdel-Aziz, K. A. Metwally, A. M. Gamal-Eldeen, and O. M. Aly, “1,3,4-oxadiazole-2-thione derivatives; novel approach for anticancer and tubulin polymerization inhibitory activities,” Anti-Cancer Agents Medicinal Chemistry, vol. 16, no. 2, pp. 269–277, 2016. View at Google Scholar
  16. Salahuddin, M. Shaharyar, A. Majumdar, and M. J. Ahsan, “Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substitutedpheny)-[1, 3, 4]oxadiazol-2-ylmethyl]-1H-benzimidazole,” Arabian Journal of Chemistry, vol. 7, no. 4, pp. 418–424, 2014. View at Publisher · View at Google Scholar
  17. G. Karabanovich, J. Zemanová, T. Smutný et al., “Development of 3,5-dinitrobenzylsulfanyl-1,3,4-oxadiazoles and thiadiazoles as selective antitubercular agents active against replicating and nonreplicating Mycobacterium tuberculosis,” Journal of Medicinal Chemistry, vol. 59, no. 6, pp. 2362–2380, 2016. View at Publisher · View at Google Scholar
  18. H. Rajak, B. S. Thakur, A. Singh et al., “Novel limonene and citral based 2,5-disubstituted-1,3,4-oxadiazoles: a natural product coupled approach to semicarbazones for antiepileptic activity,” Bioorganic & Medicinal Chemistry Letters, vol. 23, no. 3, pp. 864–868, 2013. View at Publisher · View at Google Scholar · View at Scopus
  19. M. A. Bakht, M. S. Yar, S. G. Abdel-Hamid, S. I. Al Qasoumi, and A. Samad, “Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives,” European Journal of Medicinal Chemistry, vol. 45, no. 12, pp. 5862–5869, 2010. View at Publisher · View at Google Scholar
  20. M. U. Khan, T. Akhtar, N. A. Al-Masoudi, H. Stoeckli-Evans, and S. Hameed, “Synthesis, crystal structure and anti-HIV activity of 2-adamantyl/adamantylmethyl-5-aryl-1,3,4-oxadiazoles,” Medicinal Chemistry, vol. 8, no. 6, pp. 1190–1197, 2012. View at Google Scholar
  21. G. C. Ramaprasad, B. Kalluraya, B. Sunil Kumar, and S. Mallya, “Synthesis of new oxadiazole derivatives as anti-inflammatory, analgesic, and antimicrobial agents,” Medicinal Chemistry Research, vol. 22, no. 11, pp. 5381–5389, 2013. View at Publisher · View at Google Scholar · View at Scopus
  22. https://ncats.nih.gov/files/ZD4054.pdf.
  23. A. Kar, Advanced Practical Medicinal Chemistry, New Age International Publishers, New Delhi, India, 2004.
  24. M. J. Ahsan and J. P. Stables, “Psychomotor seizure test, neurotoxicity and in vitro neuroprotection assay of some semicarbazone analogues,” Central Nervous System Agents in Medicinal Chemistry, vol. 13, no. 2, pp. 141–147, 2013. View at Publisher · View at Google Scholar · View at Scopus
  25. F. W. Askar, N. K. Abood, and N. A. Jinzell, “Synthesis and characterization of new 2-aminopyridine derivatives,” Iraqi National Journal of Chemistry, vol. 52, pp. 453–465, 2013. View at Google Scholar
  26. J. N. Sangshetti, A. R. Chabukswar, and D. B. Shinde, “Microwave assisted one pot synthesis of some novel 2,5-disubstituted 1,3,4-oxadiazoles as antifungal agents,” Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 1, pp. 444–448, 2011. View at Publisher · View at Google Scholar · View at Scopus
  27. V. Vichai and K. Kirtikara, “Sulforhodamine B colorimetric assay for cytotoxicity screening,” Nature Protocols, vol. 1, no. 3, pp. 1112–1116, 2006. View at Publisher · View at Google Scholar · View at Scopus
  28. V. Prabhakar, R. Balasubramanium, P. Sathe, C. M. Krishna, and A. Juvekar, “In vitro anticancer activity of monosubstituted chalcone derivatives,” International Journal of Tumor Therapy, vol. 3, pp. 1–9, 2014. View at Google Scholar
  29. Development therapeutic program NCI/NIH, 2014, http://dtp.nci.nih.gov.
  30. A. Monks, D. Scudiero, P. Skehan et al., “Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines,” Journal of the National Cancer Institute, vol. 83, no. 11, pp. 757–766, 1991. View at Publisher · View at Google Scholar · View at Scopus
  31. M. R. Body and K. D. Paull, “Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen,” Drug Development Research, vol. 34, no. 2, pp. 91–109, 1995. View at Publisher · View at Google Scholar · View at Scopus
  32. R. H. Shoemaker, “The NCI60 human tumour cell line anticancer drug screen,” Nature Reviews Cancer, vol. 6, no. 10, pp. 813–823, 2006. View at Publisher · View at Google Scholar · View at Scopus
  33. M. Chauhan, G. Joshi, H. Kler et al., “Dual inhibitor of epidermal growth factor receptor and topoisomerase IIα derived from a quinoline scaffold,” RSC Advances, vol. 6, pp. 77717–77734, 2016. View at Google Scholar
  34. M. J. Ahsan, H. Khalilullah, S. Yasmin, S. S. Jadav, and J. Govindasamy, “Synthesis, characterisation, and in vitro anticancer activity of curcumin analogues bearing pyrazole/pyrimidine ring targeting EGFR tyrosine kinase,” BioMed Research International, vol. 2013, Article ID 239354, 14 pages, 2013. View at Publisher · View at Google Scholar · View at Scopus
  35. M. J. Ahsan, J. Sharma, S. Bhatia, P. K. Goyal, K. Shankhala, and M. Didel, “Synthesis of 2,5-disubstituted-1,3,4-oxadiazole analogs as novel anticancer and antimicrobial agents,” Letters in Drug Design & Discovery, vol. 11, no. 4, pp. 413–419, 2014. View at Publisher · View at Google Scholar · View at Scopus