Ravibabu VELPULA, Janardhan BANTHU, Rajitha GALI, Rajitha BAVANTULA, Yakaiah SARGAM

7089

One-pot and solvent-free synthesis of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5H-benzo[h]thiazolo[2,3-b]quinazolin-9-yl)-2H-chromen-2-ones and their antibacterial evaluation

One-pot and solvent-free synthesis of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5H-benzo[h]thiazolo[2,3-b]quinazolin-9-yl)-2H-chromen-2-ones and their antibacterial evaluation

Abstract: A series of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5H-benzo[h]thiazolo[2,3-b]quinazolin-9-yl)-2H-chromen-2-ones (5a-j) were synthesized by one-pot multicomponent reaction of 6-methoxy-1-tetralone, aryl aldehydes, and thiourea followed by cyclization with 3-(2-bromoacetyl)-2H-chromen-2-one in the presence of a Bronsted solid acid catalyst, poly(4-vinylpyridinium)hydrogen sulfate [P(4-VPH)HSO4] (0.015 g), under solvent-free conditions at 120 ∘C. All the synthesized compounds were characterized by spectral studies and screened for their in vitro antibacterial activity against S. aureus and B. thuringiensis (gram positive), and E. coli and K. pneumoniae (gram negative) bacterial strains. On comparing with the standard drug gentamicin, compounds derived from 4-methoxy and 3,4,5-trimethoxy benzaldehyde, i.e. 5g and 5h, showed broad spectrum antibacterial activity and the remaining compounds showed weak to moderate activity.
PDF

___

  • Ram, V. J.; Tripathi, B. K.; Srivastava, A. K. Bioorg. Med. Chem. 2003, 11, 2439–2444.
  • Xia, Y.; Yang, Z. Y.; Hour, M. J.; Kuo, S. C.; Xia, P.; Bastow, K. F.; Nakanishi, Y.; Nampoothiri, P.; Hackl, T.; Hamel, E.; et al. Bioorg. Med. Chem. Lett. 2001, 11, 1193–1196.
  • El-Sharief, A.; Ammar, Y. A.; Zahran, M. A.; Ali, A. H.; El-Gaby, M. Molecules 2001, 6, 267–278.
  • Kumar, K. S.; Ganguly, S.; Veerasamy, R.; Clercq, E. D. Eur. J. Med. Chem. 2010, 45, 5474–5479.
  • Malleshappa, N. N; Harun, M. Arabian J. Chem. 2013, 6, 35–48.
  • Ashok, K.; Chatrasal, S. Eur. J. Med. Chem. 2009, 44, 83–90.
  • El-Azab, A. S.; Eltahir, K. E. Bioorg. Med. Chem. Lett. 2012, 22, 327–333.
  • Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Pharm. Acta. Helv. 1999, 74, 11–17.
  • Sen Gupta, A. K.; Pandey, A. K. Pestic. Sci. 1989, 26, 41–49.
  • Wu, J.; Bai, S.; Yue, M.; Luo, L. J.; Shi, Q. C.; Ma, J.; Du, X. L.; Kang, S. H.; Hu, D.; Yang, S. Chem. Pap. 2014, 68, 969–975.
  • Shridhar, S. K.; Satyakam, S.; Janki, R. S.; Woon-Kai, L.; Tanaji, T. T. Eur. J. Med. Chem. 2012, 50, 264–273.
  • Testard, A.; Loge, C.; Leger, B.; Robert, J. M.; Lozach, O.; Blairvacq, M.; Meijer, L.; Thiery, V.; Besson, T. Bioorg. Med. Chem. Lett. 2006, 16, 3419–3423.
  • Guiles, J.; Sun, X.; Critchley, I. A.; Ochsner, U.; Tregay, M.; Stone, K.; Bertino, J.; Green, L.; Sabin, R.; Dean, F.; et al. Bioorg. Med. Chem. Lett. 2009, 19, 800.
  • Omar, K.; Geronikoki, A.; Zoumpoulakis, P.; Camoutsis, C.; Sokovic, M.; Ciric, A.; Glamoclija, J. Bioorg. Med. Chem. 2010, 18, 426–432.
  • Shiradkar, M. R.; Murahari, K. K.; Gangadasu, H. R.; Suresh, T.; Kalyan, C. A.; Panchal, D.; Kaur, R.; Burange, P.; Ghogare, J.; Mokale, V.; et al. Bioorg. Med. Chem. 2007, 15, 3997–4008.
  • Hassan, G. S.; El-Messery, S. M.; Al-Omary, F. A.; El-Subbagh, H. I. Bioorg. Med. Chem. Lett. 2012, 22, 6318–6323.
  • Bell, F. W.; Cantrell, A. S.; Hogberg, M.; Jaskunas, S. R.; Johansson, N. G.; Jordan, C. L.; Kinnick, M. D.; Lind, P.; Morin, J. M.; Noreen, R.; et al. J. Med. Chem. 1995, 38, 4929–4936.
  • Siddiqui, N.; Ahsan, W. Med. Chem. Res. 2011, 20, 261–268.
  • Shih, M. H.; Ke, F. Y. Bioorg. Med. Chem. 2004, 12, 4633–4643.
  • Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Pifferi, G. J. Pharm. Belg. 1994, 49, 308–314.
  • Oncu, M.; Punar, M.; Eraksoy, H. Chemotherapy 2004, 50, 98–100.
  • Arshad, A.; Osman, H.; Bagley, M. C.; Lam, C. K.; Mohamad, S.; Zahariluddin, A. S. M. Eur. J. Med. Chem. 2011, 46, 3788–3794.
  • Sashidhara, K. V.; Kumar, A.; Kumar, M.; Sarkar, J.; Sinha, S. Bioorg. Med. Chem. Lett. 2010, 20, 7205–7211.
  • Neyts, J.; De Clercq, E.; Singha, R.; Chang, Y. H.; Das, A. R.; Chakraborty, S. K.; Hong, S. C.; Tsay, S. C.; Hsu, M. H.; Hwu, J. R. J. Med. Chem. 2009, 52, 1486–1490.
  • Sashidhara, K. V.; Kumar, A.; Chatterjee, M.; Rao, K. B.; Singh, S.; Verma, A. K.; Palit, G. Bioorg. Med. Chem. Lett. 2011, 21, 1937–1941.
  • Tyagi, A. K.; Raj, H. G.; Vohra, P.; Gupta, G.; Kumari, R.; Kumar, P.; Gupta, R. K. Eur. J. Med. Chem. 2003, 40, 413–420.
  • Huang, L.; Yuon, X.; Yu, D.; Lee, K. H.; Chin, H. C. Virology 2005, 332, 623–628.
  • Ruszat, R.; Wyler, S.; Forster, T.; Reich, O.; Christian, G. S.; Thomas, C. G.; Sulser, T.; Bachmann, A. Eur. Assoc. Urol. 2006, 50, 675–683.
  • Zahradnik, M. The Production and Application of Fluorescent Brightening Agents; Wiley: New York, NY, USA, 1992.
  • Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry and Biochemistry; Wiley: New York, NY, USA, 1982.
  • Janardhan, B.; Manjulatha, K.; Srinivas, B.; Rajitha, B.; Muralikrishna, N.; Sadanandam, A. R. Soc. Chem. Adv. 2014, 4, 22866–22874.
  • Janardhan, B.; Srinivas, B.; Rajitha, Crooks, P. A. Tetrahedron Lett. 2014, 55, 224–226.
  • Janardhan, B.; Rajitha, B.; Crooks, P. A. J. Saudi Chem. Soc. 2012, http://dx.doi.org/10.1016/j.jscs.2012.10.007.
  • Tozkoparan, B.; Ertan, M.; Kelicen, P.; Demirdamar, R. Il Farmaco 1999, 54, 588–593.
  • Mohamed, S. F.; Flefel, E. M.; Amra, A. E.; Abd El-Shafy, D. N. Eur. J. Med. Chem. 2010, 45, 1494–1501.
  • Rashad, A. E.; Sayed, H. H.; Shamroukh, A. H. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 2767–2777.
  • El-Baih, F. E. M.; Al-Rasheed, H. H.; Al-Hazimi, H. M. J. Saudi Chem. Soc. 2005, 9, 575–596.
  • Flefel, E. E.; Salama, M. A.; El-Shahat, M. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1739–1756.
  • Abd El-Galil, E. A.; Maigali, S. S.; Abdulla, M. M. Monatsh. Chem. 2008, 139, 1409–1415.
  • Kolb, S.; Mondesert, O.; Goddard, M.-L.; Jullien, D.; Villoutreix, B. O.; Ducommun, B.; Garbay, C.; Braud, E. Chem. Med. Chem. 2009, 4, 633–648.
  • Kulakov, I. V.; Nurkenov, O. A.; Turdybekov, D. M.; Issabaeva, G. M.; Mahmutova, A. S.; Turdybekov, K. M. Chem. Heterocycl. Compd. 2009, 45, 856–859.
  • Abu-Hashem, A. A.; Youssef, M. M.; Hussein, H. A. R. J. Chin. Chem. Soc. 2011, 58, 41–48.
  • Kulakov, I. V. Chem. Heterocycl. Compd. 2009, 45, 1019–1021.
  • Khaligh, N. G. Ultrason. Sonochem. 2012, 19, 736–739.
  • Bauer, A. W.; Kirby, M. M.; Sherris, J. C.; Truck, M. Am. J. Clin. Pathol. 1966, 45, 493–496.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Arşiv
Sayıdaki Diğer Makaleler

Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones

Ikhlass ABBAS, Mahmoud ELASSER, Mohamed ELNEAIRY, Bazada MOBROUK

One-pot and solvent-free synthesis of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5$H$-benzo[$h$]thiazolo[2,3-$b$]quinazolin-9-yl)-2$H$-chromen-2-ones and their antibacterial evaluation

RAVIBABU VELPULA, JANARDHAN BANOTHU, RAJITHA GALI, YAKAIAH SARGAM, RAJITHA BAVANTULA

Green synthesis of 2-amino-7-hydroxy-4-aryl-4$H$-chromene-3-carbonitriles using ZnO nanoparticles prepared with mulberry leaf extract and ZnCl$_{2}$

AKBAR MOBINIKHALEDI, ATISA YAZDANIPOUR, MAJID GHASHANG

Synthesis of bis-thiazoles, bis-pyrazoles, bis-hydrazonates, and bis-triazolothiadiazoles based on bis-hydrazonoyl and bis-hydrazones

ABDELWAHED SAYED

Acid-free synthesis of S-nitrosothiols at neutral pH by shock-freezing in liquid nitrogen

DIMITRIOS TSIKAS, Dimitrios TSIKAS, ANKE BÖHMER, ARNE TRETTIN, ARSLAN ARINÇ KAYAÇELEBİ

Kinetics study and influence of water-soluble polymer on the electrodeposition of iron from a citrate-chloride electrolyte on the basis of Fe(III)

VYACHESLAV PROTSENKO, FELIX DANILOV

Characterization of a Cu2+-selective fluorescent probe derived from rhodamine B with 1,2,4-triazole as subunit and its application in cell imaging

Na LI, Jun ZHANG, Chunwei YU, Yuxiang JI

One-pot and solvent-free synthesis of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5H-benzo[h]thiazolo[2,3-b]quinazolin-9-yl)-2H-chromen-2-ones and their antibacterial evaluation

Ravibabu VELPULA, Janardhan BANTHU, Rajitha GALI, Rajitha BAVANTULA, Yakaiah SARGAM

Preparation and characterization of polyaniline microrods synthesized by using dodecylbenzene sulfonic acid and periodic acid

RECEP TAŞ, Recep TAŞ, MUZAFFER CAN, Muzaffer CAN, SAVAŞ SÖNMEZOĞLU

Synthesis, characterization, biological studies, and molecular modeling of mixed ligand bivalent metal complexes of Schiff bases based on N-aminopyrimidine-2-one/2-thione

Mehmet SÖNMEZ, İsmet BERBER, Feyza YILMAZ, Tuğba TOK TAŞKIN, Hatice Gamze SOĞUKÖMEROĞULLARI