Generic placeholder image

Letters in Organic Chemistry

Author(s): Marina Soselia*, Medea Lomidze, Tamar Tabatadze, Davit Zurabishvili, Marina Trapaidze and Shota Samsoniya

DOI: 10.2174/1570178617999200812134408

DownloadDownload PDF Flyer Cite As
Synthesis of Novel N-(R)-2-(1-Adamantyl)-1H-Benzimidazole-5(6)- Carboxamide, Carbohydrazide and 1,3,4-Oxadiazole Derivatives

Page: [490 - 499] Pages: 10

  • * (Excluding Mailing and Handling)

Abstract

A novel series of benzimidazole-5(6)-carboxamide 3a-g, carbohydrazide 5a-e and 1,3,4- oxadiazole 6a-g derivatives bearing adamantane moiety were synthesized. The synthesis of benzimidazole heterocycle was performed by direct condensation/cyclization reaction of 1- adamantanecarboxylic acid with methyl 3,4-diaminobenzoate in Trimethylsilyl Polyphosphate (PPSE). The obtained Methyl 2-(1-adamantyl)-1H-benzimidazole-5(6)-carboxylate was converted to desired carboxamide and carbohydrazide derivatives in two different ways. In the first case, the synthesized ester after hydrolysis was converted to an acid chloride and subsequently coupled with different aromatic and heterocycle amines to give carboxamide derivatives. In the second case, treatment with hydrazine hydrate gave corresponding 2-(1-adamantyl)-1H-benzimidazole-5(6)-carbohydrazide which was coupled with some acyl chlorides to give appropriate carbohydrazide derivatives and with some aromatic acids to give 1,3,4-oxadiazole derivatives.

Keywords: Adamantane, benzimidazole, 1, 3, 4-oxadiazoles, annulation reaction, nitrogen heterocycles, carboxamides, carbohydrazides.

Graphical Abstract

[1]
Anand, K.; Wakode, S. Int. J. Chem. Stud., 2017, 5(2), 350-362.
[2]
Ajani, O.O.; Aderohunmu, D.V.; Ikpo, C.O.; Adedapo, A.E.; Olanrewaju, I.O. Arch. Pharm. Chem. Life Sci., 2016, 349, 1-32.
[http://dx.doi.org/10.1002/ardp.201500464]
[3]
Ganie, A.M.; Dar, A.M.; Khan, F.A.; Dar, B.A. Mini Rev. Med. Chem., 2019, 19(16), 1292-1297.
[http://dx.doi.org/10.2174/1381612824666181017102930] [PMID: 30332950]
[4]
Marinescu, M. Chemistry and Applications of Benzimidazole and its Derivatives, Ed; IntechOpen. , 2019.
[5]
Tahlan, S.; Kumar, S.; Narasimhan, B. BMC Chemistry, 2019, 13(101), 1-21.
[PMID: 31355363]
[6]
Hadole, C.; Rajput, J.; Bendre, R. Org. Chem. Curr. Res., 2018, 7(3), 1-9.
[7]
Wanka, L.; Iqbal, K.; Schreiner, P. R. ChemRev., 2013, 8(113), 5- 3516-3604.
[8]
Liu, J.; Obando, D.; Liao, V.; Lifa, T.; Codd, R. Eur. J. Med. Chem., 2011, 46(6), 1949-1963.
[http://dx.doi.org/10.1016/j.ejmech.2011.01.047] [PMID: 21354674]
[9]
Spilovska, K.; Zemek, F.; Korabecny, J.; Nepovimova, E.; Soukup, O.; Windisch, M.; Kuca, K. Curr. Med. Chem., 2016, 23(29), 3245- 3266-3288.
[10]
Artsimovich, N.G.; Galushina, T.S.; Fadeeva, T.A. Int. J. Immun., 2000, 2(1), 54-60.
[11]
DeGrado, W. F.; Wang, J.; Wang, J.; Jo, H. WO 2013086131 A1 20130613, 2013.
[12]
Al-Wahaibi, L.H.; Hassan, H.M.; Abo-Kamar, A.M.; Ghabbour, H.A.; El-Emam, A.A. Molecules, 2017, 22(710), 1-12.
[13]
Vlachou, M.; Siamidi, A.; Diamantidi, E.; Iliopoulou, A.; Papanastasiou, I.; Ioannidou, V.; Kourbeli, V.; Foscolos, A.S.; Vocat, A.; Cole, S.T.; Karalis, V.; Kellici, T.; Mavromoustakos, T.; Vlachou, M. Drug Res. (Stuttg.), 2017, 67(8), 447-450.
[http://dx.doi.org/10.1055/s-0042-121491] [PMID: 28561241]
[14]
Joubert, J.; Geldenhuys, W.J.; Van der Schyf, C.J.; Oliver, D.W.; Kruger, H.G.; Govender, T.; Malan, S.F. ChemMedChem, 2012, 7(3), 375-384.
[http://dx.doi.org/10.1002/cmdc.201100559] [PMID: 22307951]
[15]
Morozov, I.S.; Ivanova, I.A.; Lukicheva, T.A. Pharm. Chem. J., 2001, 35(5), 235-238.
[http://dx.doi.org/10.1023/A:1011905302667]
[16]
Štimac, A.; Šekutor, M.; Mlinarić-Majerski, K.; Frkanec, L.; Frkanec, R. Molecules, 2017, 22(2), 297, 1-14.
[17]
Lamoureux, G.; Artavia, G. Curr. Med. Chem., 2010, 17(26), 2967-2978.
[http://dx.doi.org/10.2174/092986710792065027] [PMID: 20858176]
[18]
Grillaud, M.; Bianco, A. Pept. Sci., 2014. Special Issue Review
[http://dx.doi.org/10.1002/psc.2719]
[19]
Banie, H.; Sinha, A.; Thomas, R.J.; Sircar, J.C.; Richards, M.L. J. Med. Chem., 2007, 50(24), 5984-5993.
[http://dx.doi.org/10.1021/jm0704907] [PMID: 17973358]
[20]
Ludwig, J.W.; Richards, M.L. Curr. Top. Med. Chem., 2006, 6(2), 165-178.
[http://dx.doi.org/10.2174/156802606775270314] [PMID: 16454765]
[21]
Richards, M.L.; Lio, S.C.; Sinha, A.; Tieu, K.K.; Sircar, J.C. J. Med. Chem., 2004, 47(26), 6451-6454.
[http://dx.doi.org/10.1021/jm049288j] [PMID: 15588078]
[22]
Richards, M.L. Eur. J. Med. Chem., 2006, 41, 950-969.
[http://dx.doi.org/10.1016/j.ejmech.2006.03.014] [PMID: 16647159]
[23]
Sircar, J.C. United States Patent: US 6,303,645 B1, 2001, 130
[24]
Sircar, J. C. Benzimidazole Derivatives Asmodulators of Ige. WO99/61019, 1999.
[25]
Sircar, J. C.; Richards, M. L. Use of Benzimidazole Analogs in the Treatment of Cell Proliferation. WO 03/082186 A2, 2003.
[26]
Cruz Lio, Sh.; Johnson, J.; Chatterjee, A.; Millis, D.; Banie, H.; Sircar, J.C.; Sinha, A.; Richards, M.L. Cancer Chemother. Pharmacol., 2008, 61, 1045-1058.
[http://dx.doi.org/10.1007/s00280-007-0564-y] [PMID: 17690881]
[27]
Sircar, J. C.; Richards, M. L.; Major, M. W. Benzimidazole Compounds for Modulating Ige and Inhibiting Cellular Proliferation. WO 02/072090 Al, 2002.
[28]
Haruno, A.; Miyoshi, K.; Oda, N.; Hagiwara, Y.; Yamashita, T.; Konno, Y.; Kazuno, H. WO 2006070806 A1 20060706, 2006.
[29]
Lee, K.; Goo, J.; Jung, H.Y.; Kim, M.; Boovanahalli, S.K.; Park, H.R.; Kim, M.O.; Kim, D.H.; Lee, H.S.; Choi, Y. Bioorg. Med. Chem. Lett., 2012, 15(22), 24-, 7456-7460.
[30]
Pitasse-Santos, P.; Sueth-Santiago, V.; Lima, M.E.F. J. Braz. Chem. Soc., 2018, 29(3), 435-456.
[31]
Chawla, G.; Naaz, B.; Siddiqui, A.A. Mini Rev. Med. Chem., 2018, 18(3), 216-233.
[32]
Spink, E.; Ding, D.; Peng, Z.; Boudreau, M.A.; Leemans, E.; Lastochkin, E.; Song, W.; Lichtenwalter, K.; O’Daniel, P.I.; Testero, S.A.; Pi, H.; Schroeder, V.A.; Wolter, W.R.; Antunes, N.T.; Suckow, M.A.; Vakulenko, S.; Chang, M.; Mobashery, S. J. Med. Chem., 2015, 58(3), 1380-1389.
[http://dx.doi.org/10.1021/jm501661f] [PMID: 25590813]
[33]
Bajaj, S.; Roy, P.P.; Singh, J. Anti-Cancer Agen. Med. Chem., 2017, 17(15), 1869-1883.
[34]
Kerimov, İ.; Ayhan-Kilcigil, G.; Özdamar, E.D.; Can-Eke, B.; Çoban, T.; Özbey, S.; Kazak, C. Arch. Pharm. (Weinheim), 2012, 345(7), 549-556.
[http://dx.doi.org/10.1002/ardp.201100440] [PMID: 22467524]
[35]
Soselia, M.; Gogolashvili, I.; Zurabishvili, D.; Samsoniya, S. Bull. Geo. Nat. Acad. Sci., 2017, 11(3), 98-105.
[36]
Filimonov, D.A.; Druzhilovskiy, D.S.; Lagunin, A.A.; Gloriozova, T.A.; Rudik, A.V.; Dmitriev, A.V.; Pogodin, P.V.; Poroikov, V.V. Biomed. Chem. Res. Meth., 2018, 1(1), 1-21.
[http://dx.doi.org/10.18097/BMCRM00004]