Synthesis and Cytotoxicity Activity of Novel Benzotrizolyl Methyl[1,2,4-triazolo][3,4-b]thiadiazinyl Substituted Chromene 2-ones

S. Yakaiah; K. Durgaprasad; A.K.S. Bhujanga Rao; P. Baby Rani; S. Awantika; G. Buchappa; P. Aparna

doi:10.14233/ajchem.2016.19714

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Issue Published : February 29, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Cytotoxicity Activity of Novel Benzotrizolyl Methyl[1,2,4-triazolo][3,4-b]thiadiazinyl Substituted Chromene 2-ones

https://doi.org/10.14233/ajchem.2016.19714

S. Yakaiah

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

K. Durgaprasad

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

A.K.S. Bhujanga Rao

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

P. Baby Rani

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

S. Awantika

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

G. Buchappa

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

P. Aparna

Jawaharlal Nehru Technological University, Hyderabad-500 085, India

Corresponding Author(s) : S. Yakaiah

prasannasargam1984@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 6 (2016): Vol 28 Issue 6
Article Published : February 29, 2016

Abstract

The biological importance of the coumarins and triazolothiadiazines, prompted as to synthesize a series of novel benzotrizolyl methyl[1,2,4-triazolo][3,4-b]thiadiazinyl substituted chromene 2-ones applying simple experimental conditions with good yields. All the synthesized molecules were well characterized by physical, analytical and spectroscopic techniques. The novel synthesized molecules 5(a-k) were screened for the anticancer activity and some of the molecules exhibited moderate to good activity in vitro.

Keywords

Substituted 3-(2-bromoacetyl)coumarins Thiocarbohydrazide Anticancer activity Triazolothiadiazines

Yakaiah, S., Durgaprasad, K., Rao, A. B., Rani, P. B., Awantika, S., Buchappa, G., & Aparna, P. (2016). Synthesis and Cytotoxicity Activity of Novel Benzotrizolyl Methyl[1,2,4-triazolo][3,4-b]thiadiazinyl Substituted Chromene 2-ones. Asian Journal of Chemistry, 28(6), 1381–1384. https://doi.org/10.14233/ajchem.2016.19714

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References

N. Demirbas, S.A. Karaoglu, A. Demirbas and E. Çelik, ARKIVOC, 75 (2005); doi:10.3998/ark.5550190.0006.108.
N.S. Habib, R. Soliman, F.A. Ashour and M. El Taiebi, Pharmazie, 52, 844 (1997).
D.J. Sheehan, C.A. Hitchcock and C.M. Sibley, Clin. Microbiol. Rev., 12, 40 (1999).
S.M.I. Badr and R.M. Barwa, Bioorg. Med. Chem., 19, 4506 (2011); doi:10.1016/j.bmc.2011.06.024.
J.T. Witkowski, R.K. Robins, G.P. Khare and R.W. Sidwell, J. Med. Chem., 16, 935 (1973); doi:10.1021/jm00266a014.
P. Puthiyapurayil, B. Poojary, C. Chikkanna and S.K. Buridipad, Eur. J. Med. Chem., 57, 407 (2012); doi:10.1016/j.ejmech.2012.06.059.
A. Almasirad, S.A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); doi:10.1016/j.bmcl.2004.09.072.
8 B. Shivarama Holla, B. Veerendra, M.K. Shivananda and B. Poojary, Eur. J. Med. Chem., 38, 759 (2003); doi:10.1016/S0223-5234(03)00128-4.
K.S. Bhat, D.J. Prasad, B. Poojary and B.S. Holla, Phosphorus Sulfur Silicon Rel. Elem., 179, 1595 (2004); doi:10.1080/10426500490464186.
K. Walczak, A. Gondela and J. Suwinski, Eur. J. Med. Chem., 39, 849 (2004); doi:10.1016/j.ejmech.2004.06.014.
M. Amir and K. Shikha, Eur. J. Med. Chem., 39, 535 (2004); doi:10.1016/j.ejmech.2004.02.008.
M. Basanagouda, K. Shivashankar, M.V. Kulkarni, V.P. Rasal, H. Patel, S.S. Mutha and A.A. Mohite, Eur. J. Med. Chem., 45, 1151 (2010); doi:10.1016/j.ejmech.2009.12.022.
D. Lafitte, V. Lamour, P. Tsvetkov, A. Makarov, M. Klich, P. Deprez, D. Moras, C. Briand and R. Gilli, Biochemistry, 41, 7217 (2002); doi:10.1021/bi0159837.
P. Curir, F. Galeotti, M. Dolci, E. Barile and V. Lanzotti, J. Nat. Prod., 70, 1668 (2007); doi:10.1021/np070295v.
R. Frédérick, S. Robert, C. Charlier, J. de Ruyck, J. Wouters, B. Pirotte, B. Masereel and L. Pochet, J. Med. Chem., 48, 7592 (2005); doi:10.1021/jm050448g.
C.M. Lin, S.-T. Huang, F.-W. Lee, H.S. Kuo and M.-H. Lin, Bioorg. Med. Chem., 14, 4402 (2006); doi:10.1016/j.bmc.2006.02.042.
T. Taechowisan, C. Lu, Y. Shen and S. Lumyong, J. Cancer Res. Ther., 3, 86 (2007); doi:10.4103/0973-1482.34685.
A. Maucher and E. Von Angerer, J. Cancer Res. Clin. Oncol., 120, 502 (1994); doi:10.1007/BF01191806.
C. Kontogiorgis and D. Hadjipavlou-Litina, J. Enzyme Inhib. Med. Chem., 18, 63 (2003); doi:10.1080/1475636031000069291.
I. Kempen, D. Papapostolou, N. Thierry, L. Pochet, S. Counerotte, B. Masereel, J.M. Foidart, M.J. Reboud-Ravaux, A. Noel and B. Pirotte, Br. J. Cancer, 88, 1111 (2003); doi:10.1038/sj.bjc.6600856.
C. Spino, M. Dodier and S. Sotheeswaran, Bioorg. Med. Chem. Lett., 8, 3475 (1998); doi:10.1016/S0960-894X(98)00628-3.
M. Curini, F. Epifano, F. Maltese, M.C. Marcotullio, S.P. Gonzales and J.C. Rodriguez, Aust. J. Chem., 56, 59 (2003); doi:10.1071/CH02177.
T. Mosmann, J. Immunol. Methods, 65, 55 (1983); doi:10.1016/0022-1759(83)90303-4.
X. Chen, C. Liu, J. Wang and Y. Li, J. Heterocycl. Chem., 47, 1225 (2010); doi:10.1002/jhet.178.
I.F. Audrieth, E.S. Scott and P.S. Kippur, J. Org. Chem., 19, 733 (1954); doi:10.1021/jo01370a006.
A. Arshad, H. Osman, M.C. Bagley, C.K. Lam, S. Mohamad and A.S.M. Zahariluddin, Eur. J. Med. Chem., 46, 3788 (2011); doi:10.1016/j.ejmech.2011.05.044.

References

N. Demirbas, S.A. Karaoglu, A. Demirbas and E. Çelik, ARKIVOC, 75 (2005); doi:10.3998/ark.5550190.0006.108.

N.S. Habib, R. Soliman, F.A. Ashour and M. El Taiebi, Pharmazie, 52, 844 (1997).

D.J. Sheehan, C.A. Hitchcock and C.M. Sibley, Clin. Microbiol. Rev., 12, 40 (1999).

S.M.I. Badr and R.M. Barwa, Bioorg. Med. Chem., 19, 4506 (2011); doi:10.1016/j.bmc.2011.06.024.

J.T. Witkowski, R.K. Robins, G.P. Khare and R.W. Sidwell, J. Med. Chem., 16, 935 (1973); doi:10.1021/jm00266a014.

P. Puthiyapurayil, B. Poojary, C. Chikkanna and S.K. Buridipad, Eur. J. Med. Chem., 57, 407 (2012); doi:10.1016/j.ejmech.2012.06.059.

A. Almasirad, S.A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); doi:10.1016/j.bmcl.2004.09.072.

8 B. Shivarama Holla, B. Veerendra, M.K. Shivananda and B. Poojary, Eur. J. Med. Chem., 38, 759 (2003); doi:10.1016/S0223-5234(03)00128-4.

K.S. Bhat, D.J. Prasad, B. Poojary and B.S. Holla, Phosphorus Sulfur Silicon Rel. Elem., 179, 1595 (2004); doi:10.1080/10426500490464186.

K. Walczak, A. Gondela and J. Suwinski, Eur. J. Med. Chem., 39, 849 (2004); doi:10.1016/j.ejmech.2004.06.014.

M. Amir and K. Shikha, Eur. J. Med. Chem., 39, 535 (2004); doi:10.1016/j.ejmech.2004.02.008.

M. Basanagouda, K. Shivashankar, M.V. Kulkarni, V.P. Rasal, H. Patel, S.S. Mutha and A.A. Mohite, Eur. J. Med. Chem., 45, 1151 (2010); doi:10.1016/j.ejmech.2009.12.022.

D. Lafitte, V. Lamour, P. Tsvetkov, A. Makarov, M. Klich, P. Deprez, D. Moras, C. Briand and R. Gilli, Biochemistry, 41, 7217 (2002); doi:10.1021/bi0159837.

P. Curir, F. Galeotti, M. Dolci, E. Barile and V. Lanzotti, J. Nat. Prod., 70, 1668 (2007); doi:10.1021/np070295v.

R. Frédérick, S. Robert, C. Charlier, J. de Ruyck, J. Wouters, B. Pirotte, B. Masereel and L. Pochet, J. Med. Chem., 48, 7592 (2005); doi:10.1021/jm050448g.

C.M. Lin, S.-T. Huang, F.-W. Lee, H.S. Kuo and M.-H. Lin, Bioorg. Med. Chem., 14, 4402 (2006); doi:10.1016/j.bmc.2006.02.042.

T. Taechowisan, C. Lu, Y. Shen and S. Lumyong, J. Cancer Res. Ther., 3, 86 (2007); doi:10.4103/0973-1482.34685.

A. Maucher and E. Von Angerer, J. Cancer Res. Clin. Oncol., 120, 502 (1994); doi:10.1007/BF01191806.

C. Kontogiorgis and D. Hadjipavlou-Litina, J. Enzyme Inhib. Med. Chem., 18, 63 (2003); doi:10.1080/1475636031000069291.

I. Kempen, D. Papapostolou, N. Thierry, L. Pochet, S. Counerotte, B. Masereel, J.M. Foidart, M.J. Reboud-Ravaux, A. Noel and B. Pirotte, Br. J. Cancer, 88, 1111 (2003); doi:10.1038/sj.bjc.6600856.

C. Spino, M. Dodier and S. Sotheeswaran, Bioorg. Med. Chem. Lett., 8, 3475 (1998); doi:10.1016/S0960-894X(98)00628-3.

M. Curini, F. Epifano, F. Maltese, M.C. Marcotullio, S.P. Gonzales and J.C. Rodriguez, Aust. J. Chem., 56, 59 (2003); doi:10.1071/CH02177.

T. Mosmann, J. Immunol. Methods, 65, 55 (1983); doi:10.1016/0022-1759(83)90303-4.

X. Chen, C. Liu, J. Wang and Y. Li, J. Heterocycl. Chem., 47, 1225 (2010); doi:10.1002/jhet.178.

I.F. Audrieth, E.S. Scott and P.S. Kippur, J. Org. Chem., 19, 733 (1954); doi:10.1021/jo01370a006.

A. Arshad, H. Osman, M.C. Bagley, C.K. Lam, S. Mohamad and A.S.M. Zahariluddin, Eur. J. Med. Chem., 46, 3788 (2011); doi:10.1016/j.ejmech.2011.05.044.

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Synthesis and Cytotoxicity Activity of Novel Benzotrizolyl Methyl[1,2,4-triazolo][3,4-b]thiadiazinyl Substituted Chromene 2-ones

Corresponding Author(s) : S. Yakaiah

Abstract

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