Mass Spectrometry of Pyrazolo[3,4-b]pyrido[2',3'-b]-1,6-naphthyridines and Dipyrazolo[3,4-b];3',4'-h]-1,6-naphthyridines

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

doi:10.14233/ajchem.2016.19947

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Issue Published : September 1, 2016

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

Mass Spectrometry of Pyrazolo[3,4-b]pyrido[2',3'-b]-1,6-naphthyridines and Dipyrazolo[3,4-b];3',4'-h]-1,6-naphthyridines

https://doi.org/10.14233/ajchem.2016.19947

Samia Khakwani

Department of Chemistry, The Women University Multan, Multan, Pakistan

Samina Aslam

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

Sara Mussadiq

Department of Chemistry, The Women University Multan, Multan, Pakistan

Mehrzadi Noureen Shahi

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

Najma Perveen

Department of Chemistry, Sadiq Government Women University, 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. 12 (2016): Vol 28 Issue 12
Article Published : September 2, 2016

Abstract

The mass spectra of several pyrazolo[3,4-b]pyrido[2',3'-b]-1,6-naphthyridines and dipyrazolo[3,4-b];3',4'-h]-1,6-naphthyridines are presented. The fragmentation is initiated by the elimination of CO molecule [m/z 28] followed by other fragments, such as halogen (Cl, Br) or halogen acid (HCl, HBr) and some proton loss is also observed in some cases. Successive loss of HCN (m/z 27) molecules also completes the scheme with the stable C₆H₅ fragment.

Keywords

Fragmentations Pyrazolo[3,4-b]pyrido[2',3'-b]-1,6-naphthyridines Dipyrazolo[3,4-b];3',4'-h]-1,6-naphthyridines

Khakwani, S., Aslam, S., Mussadiq, S., Shahi, M. N., Perveen, N., Rolim Bernardino, A. M., & Khan, M. A. (2016). Mass Spectrometry of Pyrazolo[3,4-b]pyrido[2’,3’-b]-1,6-naphthyridines and Dipyrazolo[3,4-b];3’,4’-h]-1,6-naphthyridines. Asian Journal of Chemistry, 28(12), 2601–2604. https://doi.org/10.14233/ajchem.2016.19947

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References

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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, 414386,A127 (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.

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, US Patent 4902685 (1990); Chem. Abstr., 113, 78372 (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. (Tokyo), 28, 761 (1980); doi:10.1248/cpb.28.761; (c) V. Oakes and H.N. Rydon, J. Chem. Soc., 4433-4438 (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, 414386,A127 (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. 12 (2016): Vol 28 Issue 12

Mass Spectrometry of Pyrazolo[3,4-b]pyrido[2',3'-b]-1,6-naphthyridines and Dipyrazolo[3,4-b];3',4'-h]-1,6-naphthyridines

Corresponding Author(s) : Samia Khakwani

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