Electrospray ionization tandem mass spectrometry of 3-phenyl-N-(3-(4- phenylpiperazin-1-yl)propyl)-1H-pyrazole-5-carboxamide derivatives: Unusual fragmentation involving loss of 11 u

Rapid Communications in Mass Spectrometry

Volumn 26, Issue 2, 2012, Pages 207-214

  Purna Chander, C ^a   Raju, G ^a   Mathai, George ^b   Srinivas, R ^a   Gaikwad, Hanmant K ^a   Bantu, Rajashekar ^a   Nagarapu, Lingaiah ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b SACRED HEART COLLEGE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSPRAY IONIZATION;

1H-PYRAZOLE; CARBOXAMIDES; ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY;

MASS SPECTROMETRY;

EID: 83755169639     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.5318     Document Type: Letter

References (17)

1. W. L. John, R. M. Patera, M. J. Plummer, B. P. Halling, D. A. Yuhas,. Synthesis, mechanism of action, and QSAR of herbicidal 3-substituted-2-aryl-4,5, 6,7-tetrahydroindazoles. Pest. Sci. 1994, 42, 29.
2. B. Cottineau, P. Toto, C. Marot, A. Pipaud, J. Chenault,. Synthesis and hypoglycemic evaluation of substituted pyrazole-4-carboxylic acids. J. Bioorg. Med. Chem. Lett. 2002, 12, 2105.
3. K. Y. Lee, J. M. Kim, J. N. Kim,. Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis-Hillman adducts. Tetrahedron Lett. 2003, 44, 6737.
4. Z. J. Jia, Y. Wu, W. Huang, P. Zhang, Y. Song, J. Woolfrey, U. Sinha, A. E. Arfsten, S. T. Edwards, A. Hutchaleelaha, S. J. Hollennbach, J. L. Lambing, R. M. Scarborough, B. Y. Zhu,. 1-(2-Naphthyl)-1H-pyrazole-5-carboxylamides as potent factor Xa inhibitors. Part 3: Design, synthesis and SAR of orally bioavailable benzamidine-P4 inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 1229.
5. M. J. Genin, C. Biles, B. J. Keiser, S. M. Poppe, S. M. Swaney, W. G. Tarpley, Y. Yagi, D. L. Romero,. Novel 1,5-Diphenylpyrazole Nonnucleoside HIV-1 Reverse Transcriptase Inhibitors with Enhanced Activity versus the Delavirdine-Resistant P236L Mutant: Lead Identification and SAR of 3- and 4-Substituted Derivatives. J. Med. Chem. 2000, 43, 1034.
6. H. Hashimoto, K. Imamura, J. I. Haruta, K. Wakitani,. 4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors: enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-5221. J. Med. Chem. 2002, 45, 1511.
7. A. G. Habeeb, P. N. P. Rao, E. E. Knaus,. Design and Synthesis of celecoxib and rofecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of sulfonamide and methylsulfonyl pharmacophores by an azido bioisostere. J. Med. Chem. 2001, 44, 3039.
8. M. L. P. Price, W. L. Jorgensen,. Analysis of binding affinities for celecoxib analogues with COX-1 and COX-2 from combined docking and Monte Carlo simulations and insight into the COX-2/COX-1 selectivity. J. Am. Chem. Soc. 2000, 122, 9455.
9. R. R. Ranatunge, R. A. Earl, D. S. Garvey, D. R. Janero, L. G. Letts, A. M. Martino, M. G. Murty, S. K. Richardson, D. J. Schwalb, D. V. Young, I. S. Zemtseva,. 3-(2-Methoxytetrahydrofuran-2-yl)pyrazoles: a novel class of potent, selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 6049.
10. S. M. Sakya, K. M. L. DeMello, M. L. Minich, B. Rast, A. Shavnya, R. J. Rafka, D. A. Koss, H. Cheng, J. Li, B. H. Jaynes, C. B. Ziegler, D. W. Mann, C. F. Petras, S. B. Seibel, A. M. Silvia, D. M. George, L. A. Lund, St. S. Denis, A. Hickman, L. Michelle, M. L. Haven, M. P. Lynch. 5-Heteroatom substituted pyrazoles as canine COX-2 inhibitors. Part 1: Structure-activity relationship studies of 5-alkylamino pyrazoles and discovery of a potent, selective, and orally active analog. Bioorg. Med. Chem. Lett. 2006, 16, 288.
11. L. Nagarapu, J. Mateti, H. K. Gaikwad, B. Rajashaker, M. Sheeba Rani, N. J. Prameela Subhashini,. Synthesis and anti-inflammatory activity of some novel 3-phenyl-N-[3-(4 phenylpiperazin-1yl)propyl]-1H-pyrazole-5-carboxamide derivatives. Bioorg. Med. Chem. Lett. 2011, 21, 4138.
12. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox,. Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford, CT, 2009.
13. + ion of hydrochlorothiazide. J. Mass Spectrom. 2009, 44, 1538.
14. 2O adduct formation and gas phase reactions in the collision cell. J. Am. Soc. Mass Spectrom. 2005, 16, 1291.
15. S. Beuck, T. Schwabe, S. Grimme, N. Schlorer, M. Kamber, W. Schanzer, M. Thevis,. Unusual mass spectrometric dissociation pathway of protonated isoquinoline-3-carboxamides due to multiple reversible water adduct formation in the gas phase. J. Am. Soc. Mass Spectrom. 2009, 20, 2034.
16. Z. Guan, L. M. Liesch,. Solvation of acylium fragment ions in electrospray ionization quadrupole ion trap and Fourier transform ion cyclotron resonance mass spectrometry. J. Mass Spectrom. 2001, 36, 264.
17. M. Thevis, M. Kohler, N. Schlorer, W. Schanzer,. Gas-phase reaction of substituted isoquinolines to carboxylic acids in ion trap and triple quadrupole mass spectrometers after electrospray ionization and collision-induced dissociation. J. Am. Soc. Mass Spectrom. 2008, 19, 151.