World Journal of Organic Chemistry:

Home » Journal » WJOC » Archive » Volume 2, Issue 1

Article

Synthesis and Biological Evaluation of Novel Sulfone Derivatives Containing 1,3,4-Oxadiazole Moiety

1State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Devel-opment Center for Fine Chemicals, Guizhou University, Guiyang, China


World Journal of Organic Chemistry. 2014, 2(1), 18-27
DOI: 10.12691/wjoc-2-1-3
Copyright © 2014 Science and Education Publishing

Cite this paper:
Shihu Su, Xia Zhou, Yan Zhou, Guoping Liao, Li Shi, Xia Yang, Xian Zhang, Linhong Jin. Synthesis and Biological Evaluation of Novel Sulfone Derivatives Containing 1,3,4-Oxadiazole Moiety. World Journal of Organic Chemistry. 2014; 2(1):18-27. doi: 10.12691/wjoc-2-1-3.

Correspondence to: Linhong  Jin, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Devel-opment Center for Fine Chemicals, Guizhou University, Guiyang, China. Email: linhong_j@126.com

Abstract

A series of novel sulfone derivatives containing 1,3,4-oxadiazole moiety were synthesized. All the target com-pounds were characterized by 1H and 13C nuclear magnetic resonance, infrared spectroscopy and elemental analysis. Their antifungal activities were tested in vitro with six important phytopathogenic fungi, namely, Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica, Phytophthora infestans, Paralepetopsis sasakii and Sclerotinia sclerotiorum using the mycelium growth inhibition method. Their antibacterial activities were tested in vitro with two important phytopathogenic bacteria, namely, Xanthomonas oryzae and Ralstonia solanacearum from tobacco bacterial by the turbid meter test. Remarkably, compounds 5h, 5j, 5u and 5v exhibited the most potent inhibition against R. solanacearum and X. oryzae with 50% inhibition concentration (EC50) from 1.97 to 7.75 μg/mL and 0.45 to 0.52 μg/mL, respectively. Their antifungal tests indicated that among target compounds exhibited good antifungal activities against six kinds of fungi, especially against S. sclerotiorum with EC50 from 3.71 to 17.44 μg/mL. In vivo antibacterial activities tests demonstrated that the controlling effect of compounds 5u (81.9%) against rice bacterial leaf blight were better than that of bismerthiazol (50.8%) and thiodiazole-copper (44.7%). Our results also demonstrated that com-pounds 5h, 5u and 5v have a better antifungal and antibacterial activity, with good characteristics of broad spectrum. The structure−activity relationship (SAR) was also discussed.

Keywords

References

[[[[[[[[[[[[[[[[
[[1]  Hayward, C. “Biology and Epidemiology of Bacterial Wilt Caused by Pseudomonas Solanacearum”. Annu. Rev. Phytopathol. 29, 65-87. 1991.
 
[[2]  Hiromichi, I.; Masakazu, T.; Ten, U.; Seiichi, K. “Preparation of disulfonylthiadiazoles and their use as agrochemical microbicides”. JP 94116252, 1994. [Chem. Abstr. 1994, 121, 127847].
 
[[3]  Fitzjohn, S.; Robinson, M. P. “Benzoxazole and Benzothiazole Derivatives”. WO 9406783, 1994 [Chem. Abstr. 1994, 121, 9394f].
 
[[4]  Richter, H. G. F.; Angehrn, P.; Hubschwerlen, C.; Kania, M.; Page, M. G. P.; Specklin, J. L.; Winkler, F. K. “Design, Synthesis, and Evaluation of 2β-Alkenyl Penam Sulfone Acids as Inhibitors of β-Lactamases”. J. Med. Chem., 39, 3712-3722. 1996
 
[[5]  Andrew, P.; Jutta, E. B.; Janice, B.; Timothy, D. S. “Isoxazoline derivatives and their use as herbicides” WO 2006024820, 2006.
 
Show More References
[6]  Kang, W.; Du, X. Q.; Wang, L. Z.; Hu, L. J.; Dong, Y. H.; Bian, Y. Q.; Li, Y. “Design, Synthesis, and Evaluation of 2β-Alkenyl Penam Sulfone Acids as Inhibitors of β-Lactamases”. Chin. J. Chem., 31, 1305-1314, 2013.
 
[7]  Tai, X. S.; Yin, X. H.; Tan, M. Y. “Crystal Structure and Antitumor Activity of Tri[2-[N-(4-methyl-benzylsulfonyl)amino]ethyl]-amine”. Chin. J. Struc. Chem., 22, 411-414, 2003.
 
[8]  Zhang, Q.; Deng, C. L.; Fang, L. S.; Xu, W. W.; Zhao, Q.; Zhang, J. G.; Wang, Y. P.; Lei, X. S. “Synthesis and Evaluation of the Analogues of Penicillide against Cholesterol Ester Transfer Protein”. Chin. J. Chem., 31, 355-370, 2013.
 
[9]  Gong, P.; Chai, H. F.; Zhao, Y. F.; Zhao, C. S. “Synthesis and in vitro anti-hepatitis B virus activities of some ethyl 5-hydroxy-1H-indole-3-carboxylates”. Bioorg. Med. Chem., 14, 2552-2558, 2006.
 
[10]  Fang, S. H.; Padmavathi, V.; Rao, Y. K.; Subbaiah, D. R. C.; Thriveni, P.; Geethangili, M.; Padaja, A.; Tzeng, Y. M. “Biological evaluation of sulfone derivatives as anti-inflammatory and tumor cells growth inhibitory agents”. Int. Immunopharmacol., 6, 1699-1705, 2006.
 
[11]  Somani, R. R.; Shirodksar, P. Y.; Kadam, V. J. “Synthesis and Antibacterial Activity of Some New 2,5-Disubstituted-1,3,4-oxadiazole Derivatives”. Chin. J. Chem., 26, 1727-1731, 2008.
 
[12]  Dogan, H. N.; Duran, A.; Rollas, S.; Sener, G.; Uysal, M. K.; Gülen, D. “Synthesis of new 2,5-Disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial”. Bioorg. Med. Chem., 10, 2893-2898, 2002.
 
[13]  Girt, S.; Singh, H.; Yadav, L. D. S. “Studies in Oxadiazoles Synthesis of Some 2-Mercapto-1, 3, 4-oxadiazoles and Related Compounds as Potential Fungicides”. Agr. Biol. Chem., 40, 17-21, 1976.
 
[14]  Kleefeld, G.; Diehr, H. J.; Haas, W.; Dehne, H. W.; Brandes, W. “Fungicidal agents based on heterocyclically substituted sulphones”. US 5166165, 1992 [Chem. Abstr. 1992, 84: 121736n].
 
[15]  Yuan, D. K.; Li, Z. M.; Zhao, W. G.; Chen, H. S. “Synthesis and bioactivity of 2-substituted amino-5-pyrazolyl-1,3,4-oxadiazoles” Chin. J. Appl. Chem., 20, 624-628, 2003.
 
[16]  Xu, W. M.; He, J.; He, M.; Han, F.; Chen, X.; Pan, Z.; Wang, J.; Tong, M. “Synthesis and Antifungal Activity of Novel Sulfone Derivatives Containing 1,3,4-Oxadiazole Moieties”. Molecules., 16, 9129-9141, 2011.
 
[17]  Xu, W. M.; Han, F. F.; He, M.; Hu, D. Y.; He, J.; Yang, S.; Song, B. A. “Inhibition of tobacco bacterial wilt with sulfone derivatives containing an 1,3,4-oxadiazole moiety”. J. Agric. Food. Chem., 60, 1036-1041, 2012
 
[18]  Chen, C. J.; Song, B. A.; Yang, S.; Xu, G. F.; Bhadury, P. S.; Jin, L. H.; Hu, D. Y.; Li, Q. Z.; Liu, F.; Xue, W.; Lu, P.; Chen, Z. “Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives”. Bioorg. Med. Chem., 15, 3981-3989, 2007
 
[19]  Liu, F.; Luo, X. Q.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y. “Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety”. Bioorg. Med. Chem., 16, 3632-3640, 2008.
 
[20]  Xiao, Y.; Li, H. X.; Li, C.; Wang, J. X.; Li, J.; Wang, M. H.; Ye, Y. H. “Antifungal screening of endophytic fungi from Ginkgo biloba for discovery of potent anti-phytopathogenic fungicides”. FEMS. Microbiol. Lett., 339, 130-136, 2013.
 
[21]  Paw, D.; Thomas, R.; Laura, K.; Karina, N.; Thomas, A. M. “Estimation of bacterial growth rates from turbidimetric and viable count data”. Int. J. Food. Microbiol., 23, 391-404, 1994.
 
Show Less References

Article

Synthesis, Reactions and Biological Evaluation of Some Novel 5-Bromobenzofuran-Based Heterocycles

1Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt


World Journal of Organic Chemistry. 2014, 2(1), 9-17
DOI: 10.12691/wjoc-2-1-2
Copyright © 2014 Science and Education Publishing

Cite this paper:
Ahmed Hamdy Halawa. Synthesis, Reactions and Biological Evaluation of Some Novel 5-Bromobenzofuran-Based Heterocycles. World Journal of Organic Chemistry. 2014; 2(1):9-17. doi: 10.12691/wjoc-2-1-2.

Correspondence to: Ahmed  Hamdy Halawa, Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt. Email: ahmedhalawa_79@yahoo.com

Abstract

Condensation of 2-acetyl-5-bromobenzofuran with hydrazine derivatives 2a,b afforded hydrazone derivatives 3a,b, which reacted with alkyl halides4a,b to yield ethylidene derivatives 5a,b. Also, 3a reacted with hydrazonyl halides6a,b to give 1,3,4-thiadiazole derivatives 9a,b. Thiosemicarbazone3b was reacted with acetic anhydride and halogenated compounds to afford the corresponding heterocyclic derivatives 10, 11a,b, 12-17 and 18a,b.Moreover, interaction of 16 with tetracyanoethylene and salicyldehyde derivatives furnished 24 and 26a,b, respectively. Finally, reaction of 16 with DMF-DMA afforded enaminone29, which on treatment with different heterocyclic amines yielded 31 and 33 respectively. Some of the newly synthesized compounds showed promising antimicrobial activity.

Keywords

References

[[[[[[[[[[[[[[[[[[[[[[[[[[[
[[1]  Keay, B. A.; Dibble, P. W.; In Comprehensive Heterocyclic Chemistry II-A Review of the Literature 1982-1995; Pergamon: New York, 1996, 2, 413-436.
 
[[2]  A) Powers, L. J.; J. Med. Chem. 1976, 19, 57-62. (B) Lambert, C. M.; Ple, P.; PCT Int. Appl. WO 0230, 924; Chem. Abstr. 2002, 136, 325553d.
 
[[3]  Hayakawa, I.; Shioya, R.; Agatsuma, T.; Furukawa, H.; Sugano, Y.; Bioorg. Med. Chem. Lett. 2004, 14, 3411-3414.
 
[[4]  Santana, L.; Teijeira, M.; Uriarte, E.; Teran, C.; Linares, B.; Villar, R.; Laguna, R.; Cano, E.; Eur. J. Pharm. Sci. 1999, 7, 161-166.
 
[[5]  Sangapure, S.; Basawaraj, R.; Indian J. Pharm. Sci. 2004, 66, 221-225.
 
Show More References
[6]  Findlay, J.; Buthetezi, S.; Seveck, M.; Miller, J.; J. Nat. Prod. 1997, 60, 1214-1215.
 
[7]  Masubuchi, M.; Ebiike, H.; Kawasaki, K.; Sogabe, S.; Morikami, K.; Shiratori, Y.; Tsujii, S.; Fujii, T.; Sakata, K.; Hayase, M.; Shindoh, H.; Aoki, Y.; Ohtsuka, T.; Shimma, N.; Bioorg. Med. Chem. 2003, 11, 4463-4478.
 
[8]  Richardson, D.R.; Iron chelators as therapeutic agents for the treatment of cancer, Crit. Rev. Oncol. Hematol. 2002, 42, 267-281.
 
[9]  Lovejoy, D.B.; Richardson, D.R.; Novel “hybrid” iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells, Blood. 2002, 100, 666-676.
 
[10]  Belicchi-Ferrari, M.; Isceglie, F.; Casoli, C.; Durot, S.; Morgenstern-Badarau, I.; Pelosi, G.; Pilotti, E.; Pinelli, S.; Tarasconi, P.; Copper (II) and Cobalt (III) pyridoxal thiosemicarbazone complexes with nitroprusside as counterion: syntheses, electronic properties, and antileukemic activity, J. Med. Chem. 2005, 48, 1671-1675.
 
[11]  Greenbaum, D.C.; Mackey, Z.; Hansell, E.; Doyle, P.; Gut, J.; Caffrey, C.R.; Lehrman, J.; Rosenthal, P.J.; McKerrow, J.H.; Chibale, K.; J. Med. Chem. 2004, 47, 3212-3219.
 
[12]  Pirrung, M.C.; Pansare, S.V., Sarma, K.D.; Keith, K.A.; Kern, E.R.; J. Med. Chem. 2005, 48, 3045-3050.
 
[13]  Oh, C. H.; Cho, H. W.; Baek, D.; Cho, J. H. Eur. J. Med. Chem. 2002, 37, 743.
 
[14]  Holla, B. S.; Malini, K. V.; Rao, B. S.; Sarojini, B. K.; Kumari, N. S. Eur. J. Med. Chem. 2003, 38, 313.
 
[15]  Kritsanida, M.; Mouroutsou, A.; Marakos, P.; Pouli, N.; Papakonstantinou-Garoufalias, S.; Pannecouque, C.; Witvrouw, M.; Clercq, E. D. IL Farmaco 2002, 57, 253.
 
[16]  Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.;Rambaldi, M. Eur. J. Med. Chem. 2001, 36, 743.
 
[17]  Foroumadi, A.; Asadipour, A.; Mirzaei, M.; Karimi, J.; Emami, S. IL Farmaco 2002, 57, 765.
 
[18]  Gu, X. H.; Wan, X. Z.; Jiang, B. Bioorg. Med. Chem. Lett. 1999, 9, 569.
 
[19]  Jiang, B.; Gu, X. H. Bioorg. Med. Chem. 2000, 8, 363.
 
[20]  Bolos, C. A.; Papazisis, K. T.; Kortsaris, A. H.; Voyatzi, S.; Zambouli, D.; Kyriakidis, D. A. J. Inorg. Biochem. 2002, 88, 25.
 
[21]  Tapia, R. A.; Alegria, L.; Pessoa, C. D.; Salas, C.; Corte´s, M. J.; Valderrama, J. A.; Sarciron, M. E.; Pautet, F.; Walchshofer, N.; Fillion, H. Bioorg. Med. Chem. 2003, 11, 2175.
 
[22]  Ijichi, K.; Fujiwara, M.; Nagano, H.; Matsumoto, Y.; Hanasaki, Y.; Ide, T.; Katsuura, K.; Takayama, H.; Shirakawa, S.; Aimi, N.; Shigeta, S.; Konno, K.; Matsushima, M.; Yokota, T.; Baba, M. Antiviral Res. 1996, 31, 87.
 
[23]  Bedair, A. H. ; Abd el-wahab, A. H. F. ; El-agrody, A. M. ; Ali, F. M. ; Halawa, A. H. and El-sherbiny, G. M. ; J. Serb. Chem. Soc. 2006, 71 (5) 459-469.
 
[24]  Abd el-wahab, A. H. F. ; Al-Fifi, Z. A. ; Bedair, A. H. ; Ali, F. M. ; Halawa, A. H. and El-agrody, A. M. ; Molecules 2011, 16, 307-318.
 
[25]  Hanamanthsa, S. B. and Virupax, V. B.; J. Heterocycl. Chem 1982, 19, 69.
 
[26]  Klayman, D. L.; Bartosevichm, J. F.; Gtiffin, T. S. ; Mason, C. J. and Scovill, J. P.; J. of Med. Chem. 1979, 22, 855.
 
[27]  Shawali, A. S.; Abdelhamid, A. O.; Bulletin of the chemical society of Japan. 1976, 49, 321.
 
[28]  Sommen G.; Comel A.; and Kirsch G., Tetrahedron lett., 2002, 43, 257.
 
[29]  Röhrkasten, R.; Raatz, P.;kreher, R. P. And Balaszkewicz, M.; Z. Nature-forsch, 1997, 52b, 1526.
 
[30]  Hafiz, I. S.;Z. Naturforsch, 2000, 55b, 321.
 
[31]  European Committee for Antimicrobial SusceptibilityTesting (EUCAST) of the European Society of Clinical Microbiology andInfectious Diseases (ESCMID). Clinical Microbiology and Infection, Vol. 6 Number 9, September 2000, pp: 509.
 
[32]  National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 5th edn.Approved Standard M7-A5.Wayne, PA: NCCLS, 2000.
 
Show Less References

Article

A Convenient Synthesis of Ethyl 1-Amino-3-(Substituted Phenyl)-2-Cyano-3H-Benzo[4,5]Thiazolo-[3,2-a]Pyridine-4-Carboxylate Derivatives and Some of their Reactions

1Chemistry Department, Faculty of Medicine, Jazan University, Jazan, Saudi Arabia

2Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt


World Journal of Organic Chemistry. 2014, 2(1), 1-8
DOI: 10.12691/wjoc-2-1-1
Copyright © 2014 Science and Education Publishing

Cite this paper:
Hany M. Mohamed. A Convenient Synthesis of Ethyl 1-Amino-3-(Substituted Phenyl)-2-Cyano-3H-Benzo[4,5]Thiazolo-[3,2-a]Pyridine-4-Carboxylate Derivatives and Some of their Reactions. World Journal of Organic Chemistry. 2014; 2(1):1-8. doi: 10.12691/wjoc-2-1-1.

Correspondence to: Hany  M. Mohamed, Chemistry Department, Faculty of Medicine, Jazan University, Jazan, Saudi Arabia. Email: hanysm83@yahoo.com

Abstract

The titled compounds were prepared by interaction of ethyl 2-(benzo[d]thazol-2-yl)acetate (3) with different arylidinemalononitrile derivatives (4a-c) in EtOH/TEA solution at room temperature. When 3 was treated with 2-(ethoxymethylene)-malononitrile (4f) under same reaction conditions, the ethyl iminothiazolopyridine-4-carboxylate (6) was obtained. Ethyl (amino(methoxy)methyl)-3-(substitutedphenyl)-1-oxo-1H-benzo[4,5]thiazole[3,2-a]pyridine-4-carboxylate (8a,b) was obtained from reaction of 3 with different cyanoacrylate derivatives (7a,b) in MeOH/TEA at room temperature, while the diethyl thiazolo[3,2-a]pyridine-4-carboxylate derivative (8c) was obtained under same reaction conditions. The amino-imino derivative (10) was also prepared and used to synthesis new pyrido[3,2-e][1,2,4]triaziolo[1,5-c]pyrimidine-5-carboxylate derivatives (12). The structures of all the newly synthesized compounds were confirmed based on their elemental analysis and spectroscopic data.

Keywords

References

[[[[[[[[[[[[[[[[[[[[[[[[[[[[[[
[[1]  D. Shi, T. Bradshaw, S. Wrigley, C. McCall, P. Lalieveld, I. Fichhtner and M. Stevens, J. Med. Chem, 39, 3375, 1996.
 
[[2]  S. Choi, H. Park, S. Lee, S. Kim, G. Han and H. Choo, Bioorg.& Med. Chem., 14, 1229, 2006.
 
[[3]  H. A. Bhuva, S. G. Kini, J. Mole. Graph. Mod., 29, 32, 2010.
 
[[4]  C. G. Mortimer, G. Wells, J. P. Crochard, E. L. Stone, T. D. Bradshaw, M. F. G. Stevens and A. D. West well, J. Med. Chem, 49, 179, 2006.
 
[[5]  G. Alang, R. Kaur, A. Singh, P. Budhlakoti, A. Singh and R. Sanwal, Inter. J. Pharma. & Biolo. Arch., 1(1), 56, 2010.
 
Show More References
[6]  S. H. Suresh, R. J. Venkateshwara, K. N. Jayaveera, Res. J. Pharma., Biolo.Chem. Sci., 1(4), 635, 2010.
 
[7]  A. Yadav, P. Sharma, V. ranjeeta, S. Sunder and U. Nagaich, The Pharma Res., 1, 182, 2009.
 
[8]  K. M. Basavaraja, B. Somashekhar and B. Shivakumar, Inter. J. Pharm Tech Res., 2(2), 1139, 2010.
 
[9]  M. Maharan, S. William, F. Ramzy and A. Sembel, Molecules, 12, 622, 2007.
 
[10]  P. Venkatesh and S. N. Pandeya, Inter. J. Chem Tech Res., 1(4), 1354, 2009.
 
[11]  D. Shashank, T. Vishawanth, M. A. Prasha, V. Balasubramaniam, A. Nagendra, P. Perumal and R. Suthakaran, Inter. J. Chem Tech Res., 1(4), 1224, 2009.
 
[12]  H. Kaur, S. Kumar, I. Singh, K. K. Saxena and A. Kumar, Dig. J. Nanomat. Biostru., 5(1), 67, 2010.
 
[13]  V. Kumar, T. S. Ngaraja, H. Shameer, E. Jayachandran and G. M. Sreenivasa, J. Pharma. Sci. Res., 2, 83, 2009.
 
[14]  N. Siddiqui, S. N. Pandeya, S. Khan, J. Stables, A. Rana, M. Alam, M. Arshad and M. Bhat, Bioorg.& Med. Chem. Lett., 17, 255, 2007.
 
[15]  N. Amnerkar and K. P. Bhusari, Euro .J. Med. Chem., 45, 149, 2010.
 
[16]  S. R. Pattan, Ch. Suresh, V. D. Pujar, V. V. K. Reddy, V. P. Rasal and B. C. Koti, Ind. J. Chem., 44B, 2404, 2005.
 
[17]  C. Micael, V. Zandt, M. Jones, D. Gunn, L. Geraci, J. Jones, D. SAwicki, J. Sredy, J. Jacot, A. T. DiCioccio, T. Petrova, A. Mitschler and A. D. Podjarny, J. Med. Chem., 48, 3141, 2005.
 
[18]  P. Arora, S. Das, M. S. Ranawat, N. Arora and M. M. Gupta, J. Chem. and Pharm. Res., 2(4), 317, 2010.
 
[19]  M. S. S.Yar and Z. H. Ansari, Act. Polon. Pharm.-Drug Res., 66(4), 387, 2009.
 
[20]  S. Rostamizadeh and S. A. G. Housaini, Phosphorus, Sulfur, and Silicon, 180, 1321, 2005.
 
[21]  S. S. Patil and V. D. Bobade, Synt. comm., 40, 206, 2010.
 
[22]  V. P. DevmurariandT. J. Ghodasara, Arch. App. Sci. Res., 2(1), 198, 2010.
 
[23]  D. L. Boger, J. Org. Chem., 43, 2296, 1978.
 
[24]  R. H. Tale, Org. Lett., 4(10), 1641, 2002.
 
[25]  G. EvindarandR. A. Batey, J. Org. Chem., 71, 1802, 2006.
 
[26]  V. Rey, S. Castro, J. Arguello and A. Penenory, Tetra. Lett., 50, 4720, 2009.
 
[27]  A. M. El-Agrody, F. A. Eid, H. A. Emam, H. M. Mohamed and A. H. Bedair,Z. Naturforsch. Teil B, 57, 579, 2002.
 
[28]  F. A. Eid, A. H. Bedair, H. A. Emam, H. M. Mohamed and A. M. El-Agrody,Al-Azhar Bull. Sci., 14, 311, 2003.
 
[29]  A. S. Abd-El-Aziz, H. M. Mohamed, S. Z. S. Mohammed, A. Ata, A. H. Bedair, A. M. El-Agrody and P. D. Harvey, J. Heterocycl. chem., 44, 1287, 2007.
 
[30]  N. M. Sabry, H. M. Mohamed, E. Sh. Khattab, S. S. Motlaq and A. M. El-Agrody, Eur. J. Med. Chem., 46, 765, 2011.
 
[31]  A. H. F. Abd El-wahab, H. M. Mohamed, A. M. El-Agrody, A. H. Bedair, F. A. Eid, M. M. Khafagy and K. A. Abd-El-Rehem, Amer. J. Chem., 1(1), 1, 2011.
 
[32]  H. M. Mohamed, A. H. F. Abd El-Wahab, K. A. Ahmed,A. M. El-Agrody, A. H. Bedair, F. A. Eid and M. M. Khafagy, Molecules, 17, 971, 2012.
 
[33]  A. H. F. A. El-Wahab, H. M. Mohamed, A. M. El-Agrody, M. A. El-Nassag and A. H. Bedair, Eur. J. Chem., 4(1), 10, 2013.
 
[34]  H. M. Mohamed, I. A. Radini, A. M. El-Agrody and A. M. Al-Ghamdi, LDDD, 10, 758, 2013.
 
[35]  A.Abbotto, S.Bradamante, A.Facchetti, and G. A. Pagani, J. Org. Chem., 67, 5753, 2002.
 
Show Less References
comments powered by Disqus