European Journal of Chemistry

Study on regioselective synthesis of bioactive bis-spiropyrazolines using molecular orbital calculations



Main Article Content

Thoraya Abd El-Reheem Farghaly
Ikhlass Mohamed Abbas
Walid Mohamed Ibrahim Hassan
Mai Samir Lotfy

Abstract

1,3-Dipolar cycloaddition reaction of (2E,2'E)-2,2'-(1,4-phenylene bis(methanylylidene)) bis(3,4-dihydronaphthalen-1(2H)-one) (3) and 2,2'-(1,4-phenylene bis(methanylylidene)) bis(1H-indene-1,3(2H)-dione) (8) with a variety of nitrilimines, generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl halides, (4) proceeded region-selectively and affording novel spiropyrazoline derivatives 5 and 10, respectively. The mechanisms of the reactions studied are discussed and the structures of the products were confirmed by spectral data and elemental analyses. Also, molecular orbital plots for HOMO and LUMO verify our suggested mechanism and stereo-selectivity of the reaction. The antimicrobial activity of the products was evaluated and promising results were obtained.

 


icon graph This Abstract was viewed 1635 times | icon graph Article PDF downloaded 1026 times

How to Cite
(1)
Farghaly, T. A. E.-R.; Abbas, I. M.; Hassan, W. M. I.; Lotfy, M. S. Study on Regioselective Synthesis of Bioactive Bis-Spiropyrazolines Using Molecular Orbital Calculations. Eur. J. Chem. 2014, 5, 577-583.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Berquist, P. R.; Wells, R. J. Chemical and Biological Perspectives, vol. 5, Academic Press, New York, 1993, pp. 1-50.

[2]. Encarnacion, R. D.; Sandoval, E.; Malmstrom, J.; Christophersen, C. J. Nat. Prod. 2000, 63, 874-875.
http://dx.doi.org/10.1021/np990489d

[3]. James, D. M.; Kunze, H. B.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 1137-1140.
http://dx.doi.org/10.1021/np50076a040

[4]. Girgis, A. S.; Ibrahim, Y. A.; Mishriky, N.; Lisgarten, J. N.; Potterc; B. S.; Palmer, R. A. Tetrahedron 2001, 57, 2015-2019.
http://dx.doi.org/10.1016/S0040-4020(01)00020-5

[5]. Fisera, L.; Sauter, F.; Frohlich, J.; Feng, Y.; Ertl, P.; Mereiter, K. Monatsh. Chem. 1994, 125, 553-563.
http://dx.doi.org/10.1007/BF00811848

[6]. Fisera, L.; Sauter, F.; Frohlich, J.; Feng, Y.; Mereiter, K. Monatsh. Chem. 1994, 125, 909-919.
http://dx.doi.org/10.1007/BF00812705

[7]. Strauss, A.; Otto, H. H. Helv. Chim. Acta, 1997, 80, 1823-1830.
http://dx.doi.org/10.1002/hlca.19970800606

[8]. Stverkova, S.; Zak, Z. J. Liebigs Ann. Chem. 1995, 477-480.
http://dx.doi.org/10.1002/jlac.199519950365

[9]. Riyadh, S. M.; Farghaly, T. A. Tetrahedron 2012, 68(44), 9056-9060.
http://dx.doi.org/10.1016/j.tet.2012.08.064

[10]. Padwa, A. 1,3-Dipolar cycloaddition reactions, Vol. 1, Wiley: New York, 1984, pp. 291.

[11]. Girgis, A. S.; Ibrahim, Y. A.; Mishriky, N.; Lisgarten, J. N.; Potter, B. S.; Palmer, R. A. Tetrahedron 2001, 57(10), 2015-2019.
http://dx.doi.org/10.1016/S0040-4020(01)00020-5

[12]. Lee, H. H.; Cain, B. F.; Denny, W. A. J. Org. Chem. 1989, 54, 428-431.
http://dx.doi.org/10.1021/jo00263a032

[13]. Claramunt, R. M.; Elguero. J. Org. Prep. Proced. Int. 1991, 23, 273-320.
http://dx.doi.org/10.1080/00304949109458208

[14]. Havaldar, F. H.; Fernandes, P. S. J. Indian Chem. Soc. 1988, 65, 691-694.

[15]. Sachchar, S. P.; Singh, A. K. J. Indian Chem. Soc. 1985, 62, 142-146.

[16]. Sangwan, N. K.; Dhindsa, K. S.; Malik, O. P.; Malik, M. S. Chim. Acta Turc. 1983, 11, 65-72.

[17]. Berenson, H. (American Cyanamid Co.), U. S. 3, 947, 583 (Cl. 242-273; A01N), 30 Mar. 1976; Chem. Abstr. 85, 1211 (1976).

[18]. Satti, N. K.; Suri, K. A.; Suri, O. P. Indian Drugs 1987, 24, 492-493.

[19]. Fauran, C.; Turin, M. G.; Pourrias, B. (Delalande, S. A.), Fr. Demande 2, 259, 590 (Cl. A61 K, C07D), 29 Aug. 1975; Chem. Abstr. 84, 59477 (1976).

[20]. Sawhney, S. N.; Dhindsa, G. S.; Vir, D. J. Indian Chem. Soc. 1988, 65, 643-645.

[21]. Reis, H.; Vilhuber, H. G.; Schulz, L.; Leuke, D. (BASF A. -G.), Ger. Offen. 2, 525, 024 (Cl. C07D403/12), 30 Dec. 1976; Chem. Abstr. 86, 140042 (1977).

[22]. Bruno, O.; Ranise, A.; Bondavalli, F.; Schenone, P. Farmaco 1992, 47, 1235-1248.

[23]. Vinge, E.; Bjoerkman, S. Acta Pharmacol. Toxicol. 1986, 59, 165-174.
http://dx.doi.org/10.1111/j.1600-0773.1986.tb00150.x

[24]. Bailey, D. M.; Hansen, P. E.; Hlavac, A. G.; Baizman, E. R.; Pearl, J.; De Felice, A. F.; Feigenson, M. E. J. Med. Chem. 1985, 28, 256-260.
http://dx.doi.org/10.1021/jm00380a020

[25]. Farghaly, T. A.; Abdallah, M. A.; Abdel Aziz, M. R. Molecules 2012, 17, 14625-14636.
http://dx.doi.org/10.3390/molecules171214625

[26]. Farghaly, T. A.; Gomha, S. M.; Abbas, E. M. H.; Abdalla, M. M. Arch. Pharm. Chem. Life Sci. 2012, 345, 117-122.
http://dx.doi.org/10.1002/ardp.201100212

[27]. Farghaly, T. A.; Hassaneen, H. M. E. Arch. Pharm. Res. 2013, 36, 564-572.
http://dx.doi.org/10.1007/s12272-013-0045-2

[28]. Farghaly, T. A.; Mahmoud, H. K. Arch. Pharm. Chem. Life Sci. 2013, 346, 392-402.
http://dx.doi.org/10.1002/ardp.201200486

[29]. Farghaly, T. A.; Riyadh, S. M.; Abdallah, M. A.; Ramadan, M. A. Acta. Chim. Slov. 2011, 58, 87-94.

[30]. Ariens, E. J.; Drug Design, Vol. 1., Ariens, E. J.; Editor. P. 1. Academic Press, New York, 1971.
http://dx.doi.org/10.1016/B978-0-12-060302-2.50008-7

[31]. Saint-Ruf, G.; Buu-Hoi, N. P.; Jacouignon, P. J. Chem. Soc. 1960, 35(8), 2690-2694.
http://dx.doi.org/10.1039/jr9600002690

[32]. Wolkoff, P. Can. J. Chem. 1975, 53(9), 1333-1335.
http://dx.doi.org/10.1139/v75-183

[33]. Hassaneen, H. M.; Hilal, R. H.; Elwan, N. M.; Harhash, A.; Shawali, A. S. J. Heterocyclic Chem. 1984, 21, 1013-1016.
http://dx.doi.org/10.1002/jhet.5570210417

[34]. Hassaneen, H. M.; Mousa, H. A. H.; Abed, N. M.; Shawali, A. S. Heterocycles 1988, 27, 695-706.
http://dx.doi.org/10.3987/COM-87-4381

[35]. Holder, I. A.; Boyce, S. T. Burns 1994, 20, 426‐429.
http://dx.doi.org/10.1016/0305-4179(94)90035-3

[36]. Agwa, H.; Aly, M. M.; Bonaly, R. J. Union Arab. Biol. 2000, 7, 62‐82.

[37]. Doughari, J. H. Trop. J. Pharm. Res. 2006, 5, 597‐603.

[38]. Midgley, G.; Clayton, Y.; Hay, J. Diagnosis in color medical mycology, international, UK. Mosby-Year Book, 1997, pp. 14‐17.

[39]. Shiriling, E. M.; Gottlieb, D. Int. J. Syst. Bact. 1966, 16, 313‐340.
http://dx.doi.org/10.1099/00207713-16-3-313

[40]. Girgis, A. S.; Osman, F. H.; El-Samahy, F. A.; Ahmed-Farag. I. S.; Chem. Pap. 2006, 60, 237-242.
http://dx.doi.org/10.2478/s11696-006-0042-8

[41]. Boudriga, S.; Askri, M.; Gharbi, R.; Rammah, M.; Ciamala, K. J. Chem. Res. (S) 2003, 2003, 204-207.

[42]. Girgis, A. S.; Ismail, N. S. M.; Farag, H.; George, R. F.; Eur. J. Med. Chem. 2010, 45, 4229-4238.
http://dx.doi.org/10.1016/j.ejmech.2010.06.018

[43]. Girgis, A. S.; Farag, H.; Ismail, N. S. M.; George, R. F. Eur. J. Med. Chem. 2011, 46, 4964-4969.
http://dx.doi.org/10.1016/j.ejmech.2011.07.058

[44]. Girgis, A. S.; Ibrahim, Y. A.; Farag, A. I. S.; Mishriky, N. J. Chem. Res. (S), 2000, 2000, 508-509.

[45]. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
http://dx.doi.org/10.1103/PhysRevA.38.3098

[46]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.

[47]. Johnson, B. G.; Frisch, M. J. Chem. Phys. Lett. 1993, 216, 133-140.
http://dx.doi.org/10.1016/0009-2614(93)E1238-C

[48]. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
http://dx.doi.org/10.1103/PhysRevB.37.785

[49]. McLean, A. D.; Chandler. G. S.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5648.
http://dx.doi.org/10.1063/1.438980

[50]. Raghavachari, K.; Binkley, J. S.; Seeger, R.; Pople.; J. A. J. Chem. Phys. 1980, 72, 650-654.

[51]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, Jr.; J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J. 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, Inc.; Wallingford CT, 2010.

[52]. GaussView, Version 5, R. Dennington, T. Keith, J. Millam, Semichem Inc.; Shawnee Mission KS, 2009.

Supporting Agencies

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).