Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Cytotoxic Studies of Pyrrolopyrimidine Derivatives
Corresponding Author(s) : Toreshettahally R. Swaroop
Asian Journal of Chemistry,
Vol. 33 No. 8 (2021): Vol 33 Issue 8, 2021
Abstract
The synthesis and in vitro cytotoxicity of new pyrrolopyrimidine derivatives is reported in this work. All the compounds were characterized by IR, NMR and MS. They are examined for cytotoxic activity against HeLa. Pyrrolopyrimidine derivatives of benzyl amine (8g) and 4-bromoaniline (8k) showed a potent activity, which is comparable to that of standard Sorafenib.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- D.M. Parkin, Int. J. Cancer, 118, 3030 (2006); https://doi.org/10.1002/ijc.21731
- J.S. Smith, L. Lindsay, B. Hoots, J. Keys, S. Franceschi, R. Winer and G.M. Clifford, Int. J. Cancer, 121, 621 (2007); https://doi.org/10.1002/ijc.22527
- F.X. Bosch, M.M. Manos, N. Munoz, M. Sherman, A.M. Jansen, J. Peto, M.H. Schiffman, V. Moreno, R. Kurman and K.V. Shan, J. Natl. Cancer Inst., 87, 796 (1995); https://doi.org/10.1093/jnci/87.11.796
- N. Ylitalo, P. Sorensen, A. Josefsson, M. Frisch, P. Sparen, J. Ponten and H.-O. Adami, Int. J. Cancer, 81, 357 (1999); https://doi.org/10.1002/(SICI)1097-0215(19990505)81:3<357::AIDIJC8>3.0.CO;2-1
- M.J. Thun, J.O. DeLancey, M.M. Center, A. Jemal and E.M. Ward, Carcinogenesis, 31, 100 (2010); https://doi.org/10.1093/carcin/bgp263
- T.-C. Chang, C.-H. Lai, J.-H. Hong, S. Hsueh, K.-G. Huang, H.-H. Chou, C.-J. Tseng, C.-S. Tsai, J.T. Chang, C.-T. Lin, H.-H. Chang, P.-J. Chao, K.-K. Ng, S.G.-J. Tang and Y.-K. Soong, J. Clin. Oncol., 18, 1740 (2000); https://doi.org/10.1200/JCO.2000.18.8.1740
- H.J. Long III, B.N. Bundy, E.C. Grendys Jr., J.A. Benda, D.S. McMeekin, J. Sorosky, D.S. Miller, L.A. Eaton and J.V. Fiorica, J. Clin. Oncol., 23, 4626 (2005); https://doi.org/10.1200/JCO.2005.10.021
- N.S. Girgis, M.A. Michael, D.F. Smee, H.A. Alaghamandan, R.K. Robins and H.B. Cottam, J. Med. Chem., 33, 2750 (1990); https://doi.org/10.1021/jm00172a011
- M. Trzoss, D.C. Bensen, X. Li, Z. Chen, T. Lam, J. Zhang, C.J. Creighton, M.L. Cunningham, B. Kwan, M. Stidham, K. Nelson, V. Brown-Driver, A. Castellano, K.J. Shaw, F.C. Lightstone, S.E. Wong, T.B. Nguyen, J. Finn and L.W. Tari, Bioorg. Med. Chem. Lett., 23, 1537 (2013); https://doi.org/10.1016/j.bmcl.2012.11.073
- M.S.A. El-Gaby, A.M. Gaber, A.A. Atalla and K.A. Abd Al-Wahab, Farmaco, 57, 613 (2002); https://doi.org/10.1016/S0014-827X(01)01178-8
- R. Roopashree, T.R. Swaroop, S. Jagadish, C.D. Mohan and K.S. Rangappa, Lett. Drug Des. Discov., 11, 1143 (2014); https://doi.org/10.2174/1570180811666140704171902
- S. Nagashima, T. Hondo, H. Nagata, T. Ogiyama, J. Maeda, H. Hoshii, T. Kontani, S. Kuromitsu, K. Ohga, M. Orita, K. Ohno, A. Moritomo, K. Shiozuka, M. Furutani, M. Takeuchi, M. Ohta and S. Tsukamoto, Bioorg. Med. Chem., 17, 6926 (2009); https://doi.org/10.1016/j.bmc.2009.08.021
- C. Shih, V.J. Chen, L.S. Gossett, S.B. Gates, W.C. MacKellar, L.L. Habeck, K.A. Shackelford, L.G. Mendelsohn, D.J. Soose and V.F. Patel, Cancer Res., 57, 1116 (1997).
- D.J. Calderwood, D.N. Johnston, R. Munschauer and P. Rafferty, Bioorg. Med. Chem. Lett., 12, 1683 (2002); https://doi.org/10.1016/S0960-894X(02)00195-6
- C.T. Brain, G. Thoma and M.J. Sung, Canadian Patent, WO 2007/140222 A3 (2007).
- M. Borland, C.T. Brain, S. Doshi, S. Kim, J. Ma, J. Murtie and H. Zhang, US Patent, WO/2011/130232 (2011).
- J.-Y. Le Brazidec, A. Pasis, B. Tam, C. Boykin, D. Wang, D.J. Marcotte, G. Claassen, J.-H. Chong, J. Chao, J. Fan, K. Nguyen, L. Silvian, L. Ling, L. Zhang, M. Choi, M. Teng, N. Pathan, S. Zhao, T. Li and A. Taveras, Bioorg. Med. Chem. Lett., 22, 4033 (2012); https://doi.org/10.1016/j.bmcl.2012.04.085
- Y. Oguro, N. Miyamoto, T. Takagi, K. Okada, Y. Awazu, H. Miki, A. Hori, K. Kamiyama and S. Imamura, Bioorg. Med. Chem., 18, 7150 (2010); https://doi.org/10.1016/j.bmc.2010.08.042
- C. Esteve, A. Nueda, J.L. Díaz, J. Beleta, A. Cárdenas, E. Lozoya, M.I. Cadavid, M.I. Loza, H. Ryder and B. Vidal, Bioorg. Med. Chem. Lett., 16, 3642 (2006); https://doi.org/10.1016/j.bmcl.2006.04.074
- J.T. Arcari, J.S. Beebe, M.A. Berliner, V. Bernardo, M. Boehm, G.V. Borzillo, T. Clark, B.D. Cohen, R.D. Connell, H.N. Frost, D.A. Gordon, W.M. Hungerford, S.M. Kakar, A. Kanter, N.F. Keene, E.A. Knauth, S.D. LaGreca, Y. Lu, L. Martinez-Alsina, M.A. Marx, J. Morris, N.C. Patel, D. Savage, C.I. Soderstrom, C. Thompson, G. Tkalcevic, N.J. Tom, F.F. Vajdos, J.J. Valentine, P.W. Vincent, M.D. Wessel and J.M. Chen, Bioorg. Med. Chem. Lett., 23, 3059 (2013); https://doi.org/10.1016/j.bmcl.2013.03.012
- R. Roopashree, C.D. Mohan, T.R. Swaroop, S. Jagadish and K.S. Rangappa, Asian J. Pharm. Clin. Res., 5, 309 (2014).
- R. Roopashree, C.D. Mohan, T.R. Swaroop, S. Jagadish, B. Raghava, K.S. Balaji, S. Jayarama, Basappa and K.S. Rangappa, Bioorg. Med. Chem. Lett., 25, 2589 (2015); https://doi.org/10.1016/j.bmcl.2015.04.010
- N. Ashwini, M. Garg, C.D. Mohan, J.E. Fuchs, S. Rangappa, S. Anusha, T.R. Swaroop, K.S. Rakesh, D. Kanojia, V. Madan, A. Bender, H.P. Koeffler, Basappa and K.S. Rangappa, Bioorg. Med. Chem., 23, 6157 (2015); https://doi.org/10.1016/j.bmc.2015.07.069
- K.S. Rakesh, S. Jagadish, K.S. Balaji, F. Zameer, T.R. Swaroop, C.D. Mohan, S. Jayarama and K.S. Rangappa, Inflammation, 39, 269 (2016); https://doi.org/10.1007/s10753-015-0247-5
- P.S. Devegowda, K.S. Balaji, D.S. Prasanna, T.R. Swaroop, S. Jayarama, L. Siddalingaiah and K.S. Rangappa, Asian J. Chem., 29, 896 (2017); https://doi.org/10.14233/ajchem.2017.20356
- S.D. Preethi, H.K. Vivek, K.S. Balaji, D.S. Prasanna, T.R. Swaroop, J. Shankar, S. Lokesh and K.S. Rangappa, Int. J. Curr. Res., 9, 46509 (2017).
- S.D. Preethi, K.S. Balaji, D.S. Prasanna, T.R. Swaroop, J. Shankar, K.S. Rangappa and S. Lokesh, Anticancer. Agents Med. Chem., 17, 1931 (2017); https://doi.org/10.2174/1871521409666170412120837
- K.B. Harsha, C.V. Kavitha, T.R. Swaroop, S. Rangappa and K.S. Rangappa, Asian J. Chem., 33, 1006 (2021); https://doi.org/10.14233/ajchem.2021.23103
- J.V. Calienni, G.P. Chen, B. Gong, P.K. Kapa and V. Saxena, Salt(s) of 7-Cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]-pyrimidine-6-carboxylic Acid Dimethylamide and Processes of making thereof, US Patent, US 9,193,732 B2 (2015).
- P. Rajendran, F. Li, M.K. Shanmugam, R. Kannaiyan, J.N. Goh, K.F. Wong, W. Wang, E. Khin, V. Tergaonkar, A.P. Kumar, J.M. Luk and G. Sethi, Cancer Prevent. Res., 5, 631 (2012); https://doi.org/10.1158/1940-6207.CAPR-11-0420
- C.V. Kavitha, M. Nambiar, C.S. Ananda Kumar, B. Choudhary, K. Muniyappa, K.S. Rangappa and S.C. Raghavan, Biochem. Pharmacol., 77, 348 (2009); https://doi.org/10.1016/j.bcp.2008.10.018
References
D.M. Parkin, Int. J. Cancer, 118, 3030 (2006); https://doi.org/10.1002/ijc.21731
J.S. Smith, L. Lindsay, B. Hoots, J. Keys, S. Franceschi, R. Winer and G.M. Clifford, Int. J. Cancer, 121, 621 (2007); https://doi.org/10.1002/ijc.22527
F.X. Bosch, M.M. Manos, N. Munoz, M. Sherman, A.M. Jansen, J. Peto, M.H. Schiffman, V. Moreno, R. Kurman and K.V. Shan, J. Natl. Cancer Inst., 87, 796 (1995); https://doi.org/10.1093/jnci/87.11.796
N. Ylitalo, P. Sorensen, A. Josefsson, M. Frisch, P. Sparen, J. Ponten and H.-O. Adami, Int. J. Cancer, 81, 357 (1999); https://doi.org/10.1002/(SICI)1097-0215(19990505)81:3<357::AIDIJC8>3.0.CO;2-1
M.J. Thun, J.O. DeLancey, M.M. Center, A. Jemal and E.M. Ward, Carcinogenesis, 31, 100 (2010); https://doi.org/10.1093/carcin/bgp263
T.-C. Chang, C.-H. Lai, J.-H. Hong, S. Hsueh, K.-G. Huang, H.-H. Chou, C.-J. Tseng, C.-S. Tsai, J.T. Chang, C.-T. Lin, H.-H. Chang, P.-J. Chao, K.-K. Ng, S.G.-J. Tang and Y.-K. Soong, J. Clin. Oncol., 18, 1740 (2000); https://doi.org/10.1200/JCO.2000.18.8.1740
H.J. Long III, B.N. Bundy, E.C. Grendys Jr., J.A. Benda, D.S. McMeekin, J. Sorosky, D.S. Miller, L.A. Eaton and J.V. Fiorica, J. Clin. Oncol., 23, 4626 (2005); https://doi.org/10.1200/JCO.2005.10.021
N.S. Girgis, M.A. Michael, D.F. Smee, H.A. Alaghamandan, R.K. Robins and H.B. Cottam, J. Med. Chem., 33, 2750 (1990); https://doi.org/10.1021/jm00172a011
M. Trzoss, D.C. Bensen, X. Li, Z. Chen, T. Lam, J. Zhang, C.J. Creighton, M.L. Cunningham, B. Kwan, M. Stidham, K. Nelson, V. Brown-Driver, A. Castellano, K.J. Shaw, F.C. Lightstone, S.E. Wong, T.B. Nguyen, J. Finn and L.W. Tari, Bioorg. Med. Chem. Lett., 23, 1537 (2013); https://doi.org/10.1016/j.bmcl.2012.11.073
M.S.A. El-Gaby, A.M. Gaber, A.A. Atalla and K.A. Abd Al-Wahab, Farmaco, 57, 613 (2002); https://doi.org/10.1016/S0014-827X(01)01178-8
R. Roopashree, T.R. Swaroop, S. Jagadish, C.D. Mohan and K.S. Rangappa, Lett. Drug Des. Discov., 11, 1143 (2014); https://doi.org/10.2174/1570180811666140704171902
S. Nagashima, T. Hondo, H. Nagata, T. Ogiyama, J. Maeda, H. Hoshii, T. Kontani, S. Kuromitsu, K. Ohga, M. Orita, K. Ohno, A. Moritomo, K. Shiozuka, M. Furutani, M. Takeuchi, M. Ohta and S. Tsukamoto, Bioorg. Med. Chem., 17, 6926 (2009); https://doi.org/10.1016/j.bmc.2009.08.021
C. Shih, V.J. Chen, L.S. Gossett, S.B. Gates, W.C. MacKellar, L.L. Habeck, K.A. Shackelford, L.G. Mendelsohn, D.J. Soose and V.F. Patel, Cancer Res., 57, 1116 (1997).
D.J. Calderwood, D.N. Johnston, R. Munschauer and P. Rafferty, Bioorg. Med. Chem. Lett., 12, 1683 (2002); https://doi.org/10.1016/S0960-894X(02)00195-6
C.T. Brain, G. Thoma and M.J. Sung, Canadian Patent, WO 2007/140222 A3 (2007).
M. Borland, C.T. Brain, S. Doshi, S. Kim, J. Ma, J. Murtie and H. Zhang, US Patent, WO/2011/130232 (2011).
J.-Y. Le Brazidec, A. Pasis, B. Tam, C. Boykin, D. Wang, D.J. Marcotte, G. Claassen, J.-H. Chong, J. Chao, J. Fan, K. Nguyen, L. Silvian, L. Ling, L. Zhang, M. Choi, M. Teng, N. Pathan, S. Zhao, T. Li and A. Taveras, Bioorg. Med. Chem. Lett., 22, 4033 (2012); https://doi.org/10.1016/j.bmcl.2012.04.085
Y. Oguro, N. Miyamoto, T. Takagi, K. Okada, Y. Awazu, H. Miki, A. Hori, K. Kamiyama and S. Imamura, Bioorg. Med. Chem., 18, 7150 (2010); https://doi.org/10.1016/j.bmc.2010.08.042
C. Esteve, A. Nueda, J.L. Díaz, J. Beleta, A. Cárdenas, E. Lozoya, M.I. Cadavid, M.I. Loza, H. Ryder and B. Vidal, Bioorg. Med. Chem. Lett., 16, 3642 (2006); https://doi.org/10.1016/j.bmcl.2006.04.074
J.T. Arcari, J.S. Beebe, M.A. Berliner, V. Bernardo, M. Boehm, G.V. Borzillo, T. Clark, B.D. Cohen, R.D. Connell, H.N. Frost, D.A. Gordon, W.M. Hungerford, S.M. Kakar, A. Kanter, N.F. Keene, E.A. Knauth, S.D. LaGreca, Y. Lu, L. Martinez-Alsina, M.A. Marx, J. Morris, N.C. Patel, D. Savage, C.I. Soderstrom, C. Thompson, G. Tkalcevic, N.J. Tom, F.F. Vajdos, J.J. Valentine, P.W. Vincent, M.D. Wessel and J.M. Chen, Bioorg. Med. Chem. Lett., 23, 3059 (2013); https://doi.org/10.1016/j.bmcl.2013.03.012
R. Roopashree, C.D. Mohan, T.R. Swaroop, S. Jagadish and K.S. Rangappa, Asian J. Pharm. Clin. Res., 5, 309 (2014).
R. Roopashree, C.D. Mohan, T.R. Swaroop, S. Jagadish, B. Raghava, K.S. Balaji, S. Jayarama, Basappa and K.S. Rangappa, Bioorg. Med. Chem. Lett., 25, 2589 (2015); https://doi.org/10.1016/j.bmcl.2015.04.010
N. Ashwini, M. Garg, C.D. Mohan, J.E. Fuchs, S. Rangappa, S. Anusha, T.R. Swaroop, K.S. Rakesh, D. Kanojia, V. Madan, A. Bender, H.P. Koeffler, Basappa and K.S. Rangappa, Bioorg. Med. Chem., 23, 6157 (2015); https://doi.org/10.1016/j.bmc.2015.07.069
K.S. Rakesh, S. Jagadish, K.S. Balaji, F. Zameer, T.R. Swaroop, C.D. Mohan, S. Jayarama and K.S. Rangappa, Inflammation, 39, 269 (2016); https://doi.org/10.1007/s10753-015-0247-5
P.S. Devegowda, K.S. Balaji, D.S. Prasanna, T.R. Swaroop, S. Jayarama, L. Siddalingaiah and K.S. Rangappa, Asian J. Chem., 29, 896 (2017); https://doi.org/10.14233/ajchem.2017.20356
S.D. Preethi, H.K. Vivek, K.S. Balaji, D.S. Prasanna, T.R. Swaroop, J. Shankar, S. Lokesh and K.S. Rangappa, Int. J. Curr. Res., 9, 46509 (2017).
S.D. Preethi, K.S. Balaji, D.S. Prasanna, T.R. Swaroop, J. Shankar, K.S. Rangappa and S. Lokesh, Anticancer. Agents Med. Chem., 17, 1931 (2017); https://doi.org/10.2174/1871521409666170412120837
K.B. Harsha, C.V. Kavitha, T.R. Swaroop, S. Rangappa and K.S. Rangappa, Asian J. Chem., 33, 1006 (2021); https://doi.org/10.14233/ajchem.2021.23103
J.V. Calienni, G.P. Chen, B. Gong, P.K. Kapa and V. Saxena, Salt(s) of 7-Cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]-pyrimidine-6-carboxylic Acid Dimethylamide and Processes of making thereof, US Patent, US 9,193,732 B2 (2015).
P. Rajendran, F. Li, M.K. Shanmugam, R. Kannaiyan, J.N. Goh, K.F. Wong, W. Wang, E. Khin, V. Tergaonkar, A.P. Kumar, J.M. Luk and G. Sethi, Cancer Prevent. Res., 5, 631 (2012); https://doi.org/10.1158/1940-6207.CAPR-11-0420
C.V. Kavitha, M. Nambiar, C.S. Ananda Kumar, B. Choudhary, K. Muniyappa, K.S. Rangappa and S.C. Raghavan, Biochem. Pharmacol., 77, 348 (2009); https://doi.org/10.1016/j.bcp.2008.10.018