European Journal of Chemistry 2017, 8(3), 240-247. doi:10.5155/eurjchem.8.3.240-247.1599

Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities


Ibrahim Ali Radini (1) , Hany Mostafa Hamed (2) , Mohammed Abdo Yahya Kharir (3) , Ashraf Hassan Fekry Abd Elwahab (4,*)

(1) Department of Chemistry, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(2) Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
(3) Department of Chemistry, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(4) Department of Chemistry, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(*) Corresponding Author

Received: 12 Jun 2017, Accepted: 12 Jul 2017, Published: 30 Sep 2017

Abstract


Synthesis of several new of benzochromenes (4-7), benzochromenopyrimidines (8 and 9), 14-(4-chlorophenyl)-12-(phenyldiazenyl)-14H-benzo[7,8]chromeno[3,2-e][1, 2, 4]triazolo[1, 5-c]pyrimidines, 4-amino-16-(4-chlorophenyl)-14-(phenyldiazenyl)-16H-benzo[7', 8']chro-meno[2',3':4,5]pyrimido[1,6-b][1,2,4]triazepine-3-carbonitrile (10a-e, 13) and 9-(benz-ylideneamino)-7-(4-chlorophenyl)-5-(phenyldiazenyl)-7, 9-dihydro-8H-benzo[7,8]chromeno [2,3-d]pyrimidin-8-imine (12), form starting from 2-amino-4-(p-chlorophenyl)-6-phenyl-diazenyl-4H-benzochromene-3-carbonitrile (3). The structure of these new compounds was confirmed using IR, 1H NMR and 13C NMR as well as MS spectroscopy. The structure activity relationship studies of the target compounds in agreement with the in vitro essays and confirmed higher potent antimicrobial activity against some of the tested microorganisms. The structure-activity relationship study revealed that the antimicrobial activity of benzochromenopyrimido triazepine nucleus was more beneficial than benzochromeno-triazolopyrimidine nucleus for antimicrobial activity.


Keywords


Benzochromene; Antimicrobial activities; Benzochromenopyrimidine; 4-Phenenyldiazenyl-1-naphthol; Benzochromenotriazolopyrimidine; Benzochromenopyrimidotriaziepine

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DOI: 10.5155/eurjchem.8.3.240-247.1599

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References

[1]. Wojciechowski, K.; Wyrebak, A.; Gumulak, J.; Dyes Pigments 2003, 56, 99-106.
https://doi.org/10.1016/S0143-7208(02)00130-4

[2]. Rudyk, H.; Knaggs, M. H.; Vasiljevic, S.; Hope, J.; Birkett, C.; Gilbert, I. H. Eur. J. Med. Chem. 2003, 38, 567-579.
https://doi.org/10.1016/S0223-5234(03)00081-3

[3]. Mittal, A.; Kurup, L.; Mittal, J. Materials 2007, 146, 243-248.

[4]. Wainwright, M. Dyes Pigments 2008, 76, 582-589.
https://doi.org/10.1016/j.dyepig.2007.01.015

[5]. Ahmed, A. E. I.; Hay, J. N.; Bushell, M. E.; Wardell, J. N.; Cavalli, G.; Reac. Funct. Polym. 2008, 68, 248-260.
https://doi.org/10.1016/j.reactfunctpolym.2007.09.004

[6]. Simu, G.; Chicu, S. A.; Morin, N.; Schmid, W.; Sisu, E. Turk. J. Chem. 2004, 28, 579-585.

[7]. Simu, G. M.; Hora, S. G.; Sisu, E.; Sisu, I. Rev. Roum. Chim. 2011, 56, 527-536.

[8]. Bae, S. J.; Freeman, H. S.; El-Shafei, A. Dyes Pigments 2003, 57, 121-129.
https://doi.org/10.1016/S0143-7208(02)00120-1

[9]. Hildenbrand, S.; Schmahl, F. W.; Wodarz, R.; Kimmel, R.; Dartsch, P. C. Int. Arch. Occup. Environ. Hlth. 1999, 72, 52-57.
https://doi.org/10.1007/PL00014217

[10]. Pinson, J.; Podyorica, F. Chem. Soc. Rev. 2005, 34, 429-444.
https://doi.org/10.1039/b406228k

[11]. Dabbagh, H. A.; Teimouri, A.; Chermahini, A. N. Azo Comp. Pigments 2007, 73, 239-244.
https://doi.org/10.1016/j.dyepig.2005.12.002

[12]. Murray, P. S.; Ralph, S. F. Electrochimica Acta 2006, 51, 2471-2476.
https://doi.org/10.1016/j.electacta.2005.07.029

[13]. Garg, H. G.; Praksh, C. J. J. Med. Chem. 1972, 15, 435-436.
https://doi.org/10.1021/jm00274a035

[14]. Browing, C. H.; Cohen, J. B.; Ellingworth, S.; Gulbransen, R. J. Storage 1926, 100, 293-325.

[15]. Khalid, A;, Arshad, M.; Crowley, D. E. Appl. Microbiol. Biotech. 2008, 78, 361-369.
https://doi.org/10.1007/s00253-007-1302-4

[16]. Pagga, U.; Brown, D. Chemosphere 1986, 15, 479-491.
https://doi.org/10.1016/0045-6535(86)90542-4

[17]. Farghaly, T. A.; Abdallah, Z. A. Arkivoc 2008, 17, 295-305.

[18]. El-Agrody, A. M.; Abd El-Latif, M. S.; El-Hady, N. A.; Fakery, A. H.; Bedair, A. H. Molecules 2001, 6, 519-527.
https://doi.org/10.3390/60600519

[19]. Bedair, A. H.; El-Hadd, N. A.; Abd El-Latif, M. S.; Fakery, A. H.; El-agrody, A. M. Il Farmaco 2000, 55, 708-714.
https://doi.org/10.1016/S0014-827X(00)00097-5

[20]. El-Agrody, A. M.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H.; El-Sayed, E. S. M.; El-Ghareab, K. A. Acta Pharm. 2000, 50, 111-120.

[21]. Abd El-Wahab, A. H. F. Pharmaceuticals 2012, 5, 745-757.
https://doi.org/10.3390/ph5070745

[22]. Bedair, A. H.; Emam, H. A.; El-Hady, N. A.; Ahmed, K. A. R.; El-Agrody, A. M. Il Farmaco 2001, 56, 965-973.
https://doi.org/10.1016/S0014-827X(01)01168-5

[23]. Khafagy, M. M.; Abd El-Wahab, A. H. F.; Eid, F. A.; El-Agrody, A. M. Il Farmaco 2002, 57, 715-722.
https://doi.org/10.1016/S0014-827X(02)01263-6

[24]. Foroumadi, A.; Emami, S.; Sorkhi, M.; Nakhjiri, M.; Nazarian, Z.;, Heydar, S.; Ardestani, S.; Poorrajab, F.; Shafiee, A.; Chem. Biol. Drug Des. 2010, 75, 590-596.
https://doi.org/10.1111/j.1747-0285.2010.00959.x

[25]. Narender, T.; Shweta, S. A.; Gupta, O. Org. Med. Chem. Lett. 2009, 14, 3913-3916.
https://doi.org/10.1016/j.bmcl.2004.05.071

[26]. Sabry, N. M.; Mohamed, H. M.; Khattab, E. S. A. E. H.; Motlaq, S. S.; El-Agrody, A. M. Eur. J. Med. Chem. 2011, 46, 765-777.
https://doi.org/10.1016/j.ejmech.2010.12.015

[27]. Rampa, A.; Bisi, A.; Belluti, F.; Gobbi, S.; Piazzi, L.; Valenti, P.; Zampiron, A.; Caputo, A.; Varani, K.; Borea, P. A.; Carrara M. Il Farmaco 2005, 60, 135-148.
https://doi.org/10.1016/j.farmac.2004.09.006

[28]. Magedov, I. V.; Manpadi, M.; Evdokimov, N. M.; Elias, E. M.; Rozhkova, E.; Ogasawara, M. A.; Bettale, J. D.; Przheval'skii, N. M.; Rogelj, S.; Kornienko, A. Bioorg. Med. Chem. Lett. 2007, 17, 3872-3876.
https://doi.org/10.1016/j.bmcl.2007.05.004

[29]. Singh, O. M.; Devi, N. S.; Thokchom, D. S.; Sharma, G. J. Eur. J. Med. Chem. 2010, 45, 2250-2257
https://doi.org/10.1016/j.ejmech.2010.01.070

[30]. Vukovic, N.; Sukdolak, S.; Solujic, S.; Niciforovic, N. Food Chem. 2010, 120, 1011-1018.
https://doi.org/10.1016/j.foodchem.2009.11.040

[31]. Tandon, V. K.; Vaish, M.; Jain, S.; Bhakuni, D. S.; Srimal, R. C. Indian J. Pharm. Sci. 1991, 53, 22-23.

[32]. Mahmoodi, M.; Aliabadi, A.; Emami, S.; Safavi, M.; Rajabalian, S.; Mohagheghi, M. A.; Khoshzaban, A.; Samzadeh, A. K.; Lamei, N.; Shafiee, A. Arch. Pharm. Chem. 2010, 343, 411-416.
https://doi.org/10.1002/ardp.200900198

[33]. Endo, S.; Matsunaga, T.; Kuwata, K.; Zhao, H. T.; El-Kabbani, O.; Kitade, Y.; Hara, A. Bioorg. Med. Chem. 2010, 18, 2485-2490.
https://doi.org/10.1016/j.bmc.2010.02.050

[34]. Tseng, T. H.; Chuang, S. H.; Hu, C. C.; Chang, C. F.; Huang, Y. C.; Lin, C. W.; Lee, Y. J. Tetrahedron 2010, 66, 1335-1340.
https://doi.org/10.1016/j.tet.2009.12.002

[35]. El-Agrody, A. M.; Fouda, A. M.; Khattab, E. S. A. E. H. Med. Chem. Res. 2013, 22, 6105-6120.
https://doi.org/10.1007/s00044-013-0602-8

[36]. Bruhlmann, C.; Ooms, F.; Carrupt, P.; Testa, B.; Catto, M.; Leonetti, F.; Altomare, C.; Cartti, A. J. Med. Chem. 2001, 44, 3195-3198.
https://doi.org/10.1021/jm010894d

[37]. Kesten, S. R.; Heffner, T. G.; Johnson, S. J.; Pugsley, T. A.; Wright, J. L.; Wise, D. L. J. Med. Chem. 1999, 42, 3718-3725.
https://doi.org/10.1021/jm990266k

[38]. Lee, K. S.; Khil, L. Y.; Chae, S. H.; Kim, D.; Lee, B. H.; Hwang, G. S.; Moon, C. H.; Chang, T. S.; Moon, C. K. Life Sci. 2006, 78, 1091-1097.
https://doi.org/10.1016/j.lfs.2005.06.017

[39]. Coudert, P.; Coyquelet, J. M.; Bastide, J.; Marion, Y.; Fialip, J. Ann. Pharm. Fr. 1988, 46, 91-96.

[40]. El-Sayed, A. T.; Ibrahim, M. A. J. Braz. Chem. 2010, 21, 1006-1007.

[41]. Narasimhan, B.; Kumar, P.; Sharma, D. Acta Pharm. Sci. 2010, 52, 169-180.

[42]. Keri, R. S.; Hosamani, K. M.; Shingalapur, R. V.; Hugar, M. H. Eur. J. Med. Chem. 2010, 45, 2597-2605.
https://doi.org/10.1016/j.ejmech.2010.02.048

[43]. Sashidhara, K. V.; Kumar, M.; Modukuri, R. K.; Srivastava, A.; Puri, A. Bioorg. Med Chem. Lett. 2011, 21, 6709-6713.
https://doi.org/10.1016/j.bmcl.2011.09.053

[44]. Hiramoto, K.; Nasuhara, A.; Michiloshi, K.; Kato, T.; Kikugawa, K. Mutat. Res. 1997, 395, 47-56.
https://doi.org/10.1016/S1383-5718(97)00141-1

[45]. Ibrahim, A. A.; Ashraf, H. F. A. Eur. J. Chem. 2016, 7(2), 230-237.
https://doi.org/10.5155/eurjchem.7.2.230-237.1432

[46]. European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID). Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by agar dilution. Clin. Microbiol. Infect. 2000, 6, 509-515.
https://doi.org/10.1046/j.1469-0691.2000.00142.x

[47]. National Committee for Clinical Laboratory Standards. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, 5th ed.; National Committee for Clinical Laboratory Standards (NCCLS): Wayne, PA, USA, 2000 Approved Standard M7-A5.


How to cite


Radini, I.; Hamed, H.; Kharir, M.; Elwahab, A. Eur. J. Chem. 2017, 8(3), 240-247. doi:10.5155/eurjchem.8.3.240-247.1599
Radini, I.; Hamed, H.; Kharir, M.; Elwahab, A. Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities. Eur. J. Chem. 2017, 8(3), 240-247. doi:10.5155/eurjchem.8.3.240-247.1599
Radini, I., Hamed, H., Kharir, M., & Elwahab, A. (2017). Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities. European Journal of Chemistry, 8(3), 240-247. doi:10.5155/eurjchem.8.3.240-247.1599
Radini, Ibrahim, Hany Mostafa Hamed, Mohammed Abdo Yahya Kharir, & Ashraf Hassan Fekry Abd Elwahab. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities." European Journal of Chemistry [Online], 8.3 (2017): 240-247. Web. 19 Sep. 2019
Radini, Ibrahim, Hamed, Hany, Kharir, Mohammed, AND Elwahab, Ashraf. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part II: Synthesis of some new benzochromens, benzochromenopyrimidines, benzochromenotriazolopyrimidines, benzochromenopyrimidotriazepine and antimicrobial activities" European Journal of Chemistry [Online], Volume 8 Number 3 (30 September 2017)

DOI Link: https://doi.org/10.5155/eurjchem.8.3.240-247.1599

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