Mass Spectrometry of Heterocyclic Compounds: Benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines

Samia Khakwani; Samina Aslam; Mehrzadi Noureen Shahi; Alice M. Rolim Bernardino; Misbahul Ain  Khan

doi:10.14233/ajchem.2016.19946

Issue

Vol. 28 No. 11 (2016): Vol 28 Issue 11

Issue Published : August 10, 2016

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

Mass Spectrometry of Heterocyclic Compounds: Benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines

https://doi.org/10.14233/ajchem.2016.19946

Samia Khakwani

Department of Chemistry, Women University Multan, Multan, Pakistan

Samina Aslam

Department of Chemistry, Women University Multan, Multan, Pakistan; Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Mehrzadi Noureen Shahi

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Alice M. Rolim Bernardino

Departamento de Quimica Organica, Instituto de Quimica, Universidade Federal Fluminense, Niteroi, RJ, 24020-150, Brazil

Misbahul Ain Khan

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan; Research and Development Labs, Shafi Reso, Ferozepur Road, Lahore, Pakistan

Corresponding Author(s) : Samia Khakwani

samiakhakwani@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 11 (2016): Vol 28 Issue 11
Article Published : August 11, 2016

Abstract

The mass spectra of a number of benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines are presented. The fragmentation involves elimination of CO molecule followed by other fragments, such as halogen (Cl, Br) or halogen acids (HCl, HBr) and HCN, etc.

Keywords

Fragmentations Pyrazoles Naphthyridines. Pyrazolo-[3,4-b]-pyridines

Khakwani, S., Aslam, S., Shahi, M. N., Rolim Bernardino, A. M., & Khan, M. A. (2016). Mass Spectrometry of Heterocyclic Compounds: Benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines. Asian Journal of Chemistry, 28(11), 2385–2387. https://doi.org/10.14233/ajchem.2016.19946

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References

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A.E.G. Hammam, M.A. Sharaf and N.A.A. El-Hafez, Indian J. Chem., 40B, 213 (2001).
A. Gangjee, Y. Zeng, J.J. McGuire and R.L. Kisliuk, J. Med. Chem., 45, 5173 (2002); doi:10.1021/jm0202369.
J.S. Skotnicki, 2-Amino-3-cyano-bicyclic pyridines/pyrazines as Inhibitors of Interleukin 1, U.S. Patent 4902685 (1990).
J. Blagg, M.J. Fray, M.L. Lewis, J.P. Mathias, M.H. Stefaniak and A. Stobie, WO Patent 2003076427 (2003).
T. Ohta, S. Komoriya, T. Yoshino, K. Uoto, Y. Nakamoto, H. Naito, A. Mochizuki, T. Nagata, H. Kanno, N. Haginoya, K. Yoshikawa, M. Nagamochi, S. Kobayashi and M. Ono, WO Patent 2004058715, (2004).
(a) A.D. Broom, J.L. Shim and G.L. Anderson, J. Org. Chem., 41, 1095 (1976); doi:10.1021/jo00869a003; (b) E.M. Grivsky, S. Lee, C.W. Sigel, D.S. Duch and C.A. Nichol, J. Med. Chem., 23, 327 (1980); doi:10.1021/jm00177a025.
(a) J. Matsumoto and S. Minami, J. Med. Chem., 18, 74 (1975); doi:10.1021/jm00235a017; (b) N. Suzuki, Chem. Pharm. Bull., 28, 761 (1980); doi:10.1248/cpb.28.761; (c) V. Oakes and H.N. Rydon, J. Chem. Soc., 4433 (1956); doi:10.1039/jr9560004433; (d) J.I. DeGraw, R.L. Kisliuk, Y. Gaumont and C.M. Baugh, J. Med. Chem., 17, 470 (1974); doi:10.1021/jm00250a026; (e) A.V. Zakharov, M.Yu. Gavrilov, G.N. Novoselova, M.I. Vakhrin and M.E. Konshin, Khim. Farm. Zh., 30, 39 (1996).
A.B. Deyanov, R.Kh. Niyazov, F.Ya. Nazmetdinov, B.Ya. Syropyatov, V.E. Kolla and M.E. Konshin, Khim. Farm. Zh., 25, 26 (1991).
R.E. Heckler and G.P. Jourdan, Eur. Pat. Appl. EP 414386A127 (1991); Chem. Abstr., 115, 71630 (1991).
A. Agarwal, Ramesh, Ashutosh, N. Goyal, P.M.S. Chauhan and S. Gupta, Bioorg. Med. Chem., 13, 6678 (2005); doi:10.1016/j.bmc.2005.07.043.
A.R. de Azevedo, I.C.P.P. Frugulhetti, M.A. Khan, S. Khakwani and A.M.R. Bernardino, Heterocycl. Commun., 8, 47 (2002); doi:10.1515/HC.2002.8.1.47.
Q.N. Porter and J. Baldas, in eds.: A. Weissbeger and E.C. Taylor, Mass Spectrometry of Heterocyclic Compounds, Wiley-Interscience, New York (1971).

References

(a) H.I. El-Subbagh, S.M. Abu-Zaid, M.A. Mahran, F.A. Badria and A.M. Al-Obaid, J. Med. Chem., 43, 2915 (2000); doi:10.1021/jm000038m; (b) R.R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari and D. Sriram, Bioorg. Med. Chem. Lett., 17, 6459 (2007); doi:10.1016/j.bmcl.2007.09.095; (c) N.V. Sviridenkova, S.Z. Vatsadze, M.A. Manaenkova and N.V. Zyk, Russ. Chem. Bull., 54, 2590 (2005); doi:10.1007/s11172-006-0161-y; (d) J. Krapcho and C.F. Turk, Ger. Offen. 31 (1974).

A.E.G. Hammam, M.A. Sharaf and N.A.A. El-Hafez, Indian J. Chem., 40B, 213 (2001).

A. Gangjee, Y. Zeng, J.J. McGuire and R.L. Kisliuk, J. Med. Chem., 45, 5173 (2002); doi:10.1021/jm0202369.

J.S. Skotnicki, 2-Amino-3-cyano-bicyclic pyridines/pyrazines as Inhibitors of Interleukin 1, U.S. Patent 4902685 (1990).

J. Blagg, M.J. Fray, M.L. Lewis, J.P. Mathias, M.H. Stefaniak and A. Stobie, WO Patent 2003076427 (2003).

T. Ohta, S. Komoriya, T. Yoshino, K. Uoto, Y. Nakamoto, H. Naito, A. Mochizuki, T. Nagata, H. Kanno, N. Haginoya, K. Yoshikawa, M. Nagamochi, S. Kobayashi and M. Ono, WO Patent 2004058715, (2004).

(a) A.D. Broom, J.L. Shim and G.L. Anderson, J. Org. Chem., 41, 1095 (1976); doi:10.1021/jo00869a003; (b) E.M. Grivsky, S. Lee, C.W. Sigel, D.S. Duch and C.A. Nichol, J. Med. Chem., 23, 327 (1980); doi:10.1021/jm00177a025.

(a) J. Matsumoto and S. Minami, J. Med. Chem., 18, 74 (1975); doi:10.1021/jm00235a017; (b) N. Suzuki, Chem. Pharm. Bull., 28, 761 (1980); doi:10.1248/cpb.28.761; (c) V. Oakes and H.N. Rydon, J. Chem. Soc., 4433 (1956); doi:10.1039/jr9560004433; (d) J.I. DeGraw, R.L. Kisliuk, Y. Gaumont and C.M. Baugh, J. Med. Chem., 17, 470 (1974); doi:10.1021/jm00250a026; (e) A.V. Zakharov, M.Yu. Gavrilov, G.N. Novoselova, M.I. Vakhrin and M.E. Konshin, Khim. Farm. Zh., 30, 39 (1996).

A.B. Deyanov, R.Kh. Niyazov, F.Ya. Nazmetdinov, B.Ya. Syropyatov, V.E. Kolla and M.E. Konshin, Khim. Farm. Zh., 25, 26 (1991).

R.E. Heckler and G.P. Jourdan, Eur. Pat. Appl. EP 414386A127 (1991); Chem. Abstr., 115, 71630 (1991).

A. Agarwal, Ramesh, Ashutosh, N. Goyal, P.M.S. Chauhan and S. Gupta, Bioorg. Med. Chem., 13, 6678 (2005); doi:10.1016/j.bmc.2005.07.043.

A.R. de Azevedo, I.C.P.P. Frugulhetti, M.A. Khan, S. Khakwani and A.M.R. Bernardino, Heterocycl. Commun., 8, 47 (2002); doi:10.1515/HC.2002.8.1.47.

Q.N. Porter and J. Baldas, in eds.: A. Weissbeger and E.C. Taylor, Mass Spectrometry of Heterocyclic Compounds, Wiley-Interscience, New York (1971).

Issue

Vol. 28 No. 11 (2016): Vol 28 Issue 11

Mass Spectrometry of Heterocyclic Compounds: Benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines

Corresponding Author(s) : Samia Khakwani

Abstract

Keywords

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