Synthesis, reactions and applications of naphthofurans: A review

Ashraf Hassan Fekry Abdelwahab; Salma Ashraf Hassan Fekry

doi:10.5155/eurjchem.12.3.340-359.2126

PDF

Published: Sep 30, 2021

DOI: https://doi.org/10.5155/eurjchem.12.3.340-359.2126

Keywords:

Synthesis, Naphthol, Naphthofuran, Salicylaldehyde, Biological activity, 2-Hydroxy-1-naphthaldehyde

Section

Review Article

Issue

Vol. 12 No. 3 (2021): September 2021

Dates

Received 2021-05-11
Accepted 2021-06-17
Published 2021-09-30

Ashraf Hassan Fekry Abdelwahab

Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Saudi Arabia

https://orcid.org/0000-0001-9400-9396

Salma Ashraf Hassan Fekry

Faculty of pharmacy, German university, in Cairo (GUC), Cairo, Egypt

https://orcid.org/0000-0002-8199-9885

Abstract

Considering the highly important biological and medicinal properties of naphthofurans, the synthesis of these heterocycles has attracted the interest of medicinal and organic chemists. This review aims to describe the different strategies developed so far for the synthesis of naphthofurans and their applications and the literature reports for the period of 2000 to early 2020. After a brief introduction of the types of naphthofurans and their biological activities, the different synthetic approaches such as chemical and photochemical, methods are described and organized on the basis of the catalysts and the other reagents employed in the syntheses. Some of the reactions have been applied successfully to the synthesis of biologically important compounds.

This Abstract was viewed 1171 times |

Article PDF downloaded 1237 times

How to Cite

(1)

Abdelwahab, A. H. F.; Fekry, S. A. H. Synthesis, Reactions and Applications of Naphthofurans: A Review. Eur. J. Chem. 2021, 12, 340-359.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Vagdevi, H. M.; Latha, K. P.; Vaidya, V. P.; Vijaya Kumar, M. L.; Pai, K. S. R. Indian J. Pharm. Sci. 2001, 63 (4), 286-391.

[2]. Ravindra, K. C.; Vagdevi, H. M.; Vaidya, V. P.; Padmashali, B. Indian J. Chem. 2006, 45, 2506-2511.

[3]. Mahadevan, K. M., Vaidya, V. P. J. Indian Council of Chem. 2001, 18 (2), 78-82.

[4]. Mahadevan, K. M., Vaidya V.P. Indian J. Pharm. Sci. 2003, 65 (2), 128-134.

[5]. Bohlmann, F.; Zdero, C. Chem. Ber. 1977, 110 (2), 487-490.
https://doi.org/10.1002/cber.19771100211

[6]. de Olive-ira, A. B.; de Oliveira, G. G.; Carazza, F.; Filho, R. B.; Bacha, C. T. M.; Bauer, L.; de A.B. Silva, G. A.; Siqueira, N. C. S. Tetrahedron Lett. 1978, 19 (30), 2653-2654.
https://doi.org/10.1016/S0040-4039(01)91566-7

[7]. Miles, D. H.; Lho, D. S.; De la Cruz, A. A.; Gomez, E. D.; Weeks, J. A.; Atwood, J. L. J. Org. Chem. 1987, 52 (13), 2930-2932.
https://doi.org/10.1021/jo00389a053

[8]. Zubaidha, P. K.; Chavan, S. P.; Racherla, U. S.; Ayyangar, N. R. Tetrahedron 1991, 47 (30), 5759-5768.
https://doi.org/10.1016/S0040-4020(01)86527-3

[9]. Irie, H.; Matsumoto, R.; Nishimura, M.; Zhang, Y. Chem. Pharm. Bull. (Tokyo) 1990, 38 (7), 1852-1856.
https://doi.org/10.1248/cpb.38.1852

[10]. Ishiguro, K.; Ohira, Y.; Oku, H. J. Nat. Prod. 1998, 61 (9), 1126-1129.
https://doi.org/10.1021/np9704718

[11]. Einhorn, J.; Lamotte, G.; Buisson, J. P.; Royer, R. Eur. J. Med. Chem. 1984, 19 (3), 143-147.

[12]. Nagarsha, K. M.; Latha, K. P.; Ramesh, D.; Kumaraswamy, M. N.; Ramesh, D. R. Int. J. Pharm. Chem. Bio. Sci. 2017, 7 (4), 388-392.

[13]. Chiarini, A.; Cavrini, V.; Giovanninetti, G.; Mannini Palenzona, A.; Baserga, M. Chem. Inf. 1979, 10 (24). Farmaco Sci. 1979, 34 (2), 125-131.
https://doi.org/10.1002/chin.197924205

[14]. Gach, K.; Modranka, J.; Szymański, J.; Pomorska, D.; Krajewska, U.; Mirowski, M.; Janecki, T.; Janecka, A. Eur. J. Med. Chem. 2016, 120, 51-63.
https://doi.org/10.1016/j.ejmech.2016.05.002

[15]. Mahadevan, K. M.; Padmashali, B.; Vaidya, V. P. Indian J. Het. Chem. 2001, 11, 15-20.

[16]. Mazlan, N. W.; Clements, C.; Edrada-Ebel, R. Mar. Drugs 2020, 18 (12), 661-682.
https://doi.org/10.3390/md18120661

[17]. Arciniegas, A.; Pérez-Castorena, A. L.; Nieto-Camacho, A.; Villaseñor, J. L.; Vivar Romo de, A. J. Braz. Chem. Soc. 2013, 24 (1), 92-99.
https://doi.org/10.1590/S0103-50532013000100013

[18]. Naya, K.; Miyoshi, Y.; Mori, H.; Takai, K.; Nakanishi, M. Chem. Lett. 1976, 5 (1), 73-76.
https://doi.org/10.1246/cl.1976.73

[19]. Okuyama, E.; Umeyama, K.; Ohmori, S.; Yamazaki, M.; Satake, M. Chem. Pharm. Bull. (Tokyo) 1994, 42 (10), 2183-2186.
https://doi.org/10.1248/cpb.42.2183

[20]. Abdo, D.; Bernardi, M.; Marinoni, G.; Mellerio, G.; Samaniego, S.; Vidari, G.; Finzi, P. V. Phytochemistry 1992, 31, 3937-3941.
https://doi.org/10.1016/S0031-9422(00)97558-7

[21]. Jakupovic, J.; Pathak, V. P.; Grenz, M.; Banerjee, S.; Wolfrum, C.; Baruah, R. N.; Bohlmann, F. Phytochemistry 1987, 26 (4), 1049-1052.
https://doi.org/10.1016/S0031-9422(00)82348-1

[22]. Bohlmann, F.; Bapuji, M. Phytochemistry 1982, 21 (3), 681-683.
https://doi.org/10.1016/0031-9422(82)83165-8

[23]. Bohlmann, F.; Zdero, C. Chem. Ber. 1978, 111 (9), 3140-3145.
https://doi.org/10.1002/cber.19781110915

[24]. Liu, Q.; Shen, L.; Wang, T.-T.; Chen, C.-J.; Qi, W.-Y.; Gao, K. Food Chem. 2010, 122 (1), 55-59.
https://doi.org/10.1016/j.foodchem.2010.01.069

[25]. Ito, C.; Katsuno, S.; Kondo, Y.; Tan, H. T.; Furukawa, H. Chem. Pharm. Bull. (Tokyo) 2000, 48 (3), 339-343.
https://doi.org/10.1248/cpb.48.339

[26]. Stipanovic, R. D.; Bell, A. A.; Howell, C. R. Phytochemistry 1975, 14 (8), 1809-1811.
https://doi.org/10.1016/0031-9422(75)85299-X

[27]. Tatum, J.; A. Baker, R.; E. Berry, R. Phytochemistry 1987, 26 (9), 2499-2500.
https://doi.org/10.1016/S0031-9422(00)83863-7

[28]. Correa, J.; Romo, J. Tetrahedron 1966, 22 (2), 685-691.
https://doi.org/10.1016/0040-4020(66)80038-8

[29]. Nagano, H.; Kanda, M.; Yamada, H.; Hanai, R.; Gong, X.; Kuroda, C. Helv. Chim. Acta 2010, 93 (10), 1945-1952.
https://doi.org/10.1002/hlca.201000266

[30]. Doe, M.; Hirai, Y.; Kinoshita, T.; Shibata, K.; Haraguchi, H.; Morimoto, Y. Chem. Lett. 2004, 33 (6), 714-715.
https://doi.org/10.1246/cl.2004.714

[31]. Sutton, D. C.; Gillan, F. T.; Susic, M. Phytochemistry 1985, 24 (12), 2877-2879.
https://doi.org/10.1016/0031-9422(85)80018-2

[32]. Yamashita, M.; Kaneko, M.; Tokuda, H.; Nishimura, K.; Kumeda, Y.; Iida, A. Bioorg. Med. Chem. 2009, 17 (17), 6286-6291.
https://doi.org/10.1016/j.bmc.2009.07.039

[33]. Zani, C. L.; De Oliveira, A. B. Phytochemistry 1991, 30 (7), 2379-2381.
https://doi.org/10.1016/0031-9422(91)83653-3

[34]. Ribeiro-Rodrigues, R.; dos Santos, W. G.; Oliveira, A. B.; Snieckus, V.; Zani, C. L.; Romanha, A. J. Bioorg. Med. Chem. Lett. 1995, 5 (14), 1509-1512.
https://doi.org/10.1016/0960-894X(95)00248-R

[35]. UNDP. Tropical Diseases Progress in Research, 1989-1990; Tenth Programme Report of the UNDP World Bank WHO Special Programme for Research and Training in Tropical Diseases (TDR); Who, 1991.

[36]. Lumb, J.-P.; Trauner, D. J. Am. Chem. Soc. 2005, 127 (9), 2870-2871.
https://doi.org/10.1021/ja042375g

[37]. Horikawa, M.; Noguchi, T.; Takaoka, S.; Kawase, M.; Sato, M.; Tsunoda, T. Tetrahedron 2004, 60 (5), 1229-1234.
https://doi.org/10.1016/j.tet.2003.11.061

[38]. Heltzel, C. E.; Leslie Gunatilaka, A. A.; Glass, T. E.; Kingston, D. G. I. Tetrahedron 1993, 49 (31), 6757-6762.
https://doi.org/10.1016/S0040-4020(01)80419-1

[39]. Hetzel, C. E.; Gunatilaka, A. A.; Glass, T. E.; Kingston, D. G.; Hoffmann, G.; Johnson, R. K. J. Nat. Prod. 1993, 56 (9), 1500-1505.
https://doi.org/10.1021/np50099a008

[40]. Gunatilaka, A. A. L.; Kingston, D. G. I.; Johnson, R. K. Pure Appl. Chem. 1994, 66 (10-11), 2219-2222.
https://doi.org/10.1351/pac199466102219

[41]. Vernon, A. A. Rifamycin Antibiotics, with a Focus on Newer Agents; Rom, W. N., Garay, S. M., Eds.; Lippincott Williams & Wilkins: Philadelphia, PA, 2003; Vol. 71, p 759.

[42]. Badr, M. Z. A.; El-Dean, A. M. K.; Moustafa, O. S.; Zaki, R. M. J. Chem. Res. 2006, 2006 (11), 748-752.
https://doi.org/10.3184/030823406779173433

[43]. Fabbenind, I. G.; George Kalischer, A. G., Scheyer, H.; Keller, K. 1927, Ger 514, 415.

[44]. Fabbenind, I. G.; George Kalischer, A. G.; Keller, K. 1928, Ger. 519, 806.

[45]. Lindemann, H.; Könitzer, H.; Romanoff, S. Justus Liebigs Ann. Chem. 1927, 456 (1), 284-311.
https://doi.org/10.1002/jlac.19274560117

[46]. Gao, W.; Zhang, C.; Li, Y. J. Braz. Chem. Soc. 2010, 21 (5), 806-812.
https://doi.org/10.1590/S0103-50532010000500007

[47]. Saidi, M. R.; Firouzezare, M. J. Sc. I. R. Iran 1994, 5, 39-45.

[48]. Bell, D.; Davies, M. R.; Geen, G. R.; Mann, I. S. Synthesis (Mass.) 1995, 1995 (06), 707-712.
https://doi.org/10.1055/s-1995-3977

[49]. Satoh, T.; Tsuda, T.; Kushino, Y.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61 (19), 6476-6477.
https://doi.org/10.1021/jo9610873

[50]. Mathiyazhagan, K.; Arjun, P.; Vennila, S. Int. J. Pharm. Chem. 2016, 6 (9), 200-208.

[51]. Loader, C. E.; Timmons, C. J. J. Chem. Soc. C 1967, 1677-1681.
https://doi.org/10.1039/j39670001677

[52]. Abd El-Wahab, A.; H Bedair, A.; M Ali A, F.; HA Halawa, A.; M El-Agrody, A. J. Anal. Pharm. Res. 2018, 7 (4), 394-402.
https://doi.org/10.15406/japlr.2018.07.00257

[53]. Gewald, K.; Schinke, E.; Böttcher, H. Chem. Ber. 1966, 99 (1), 94-100.
https://doi.org/10.1002/cber.19660990116

[54]. Trofimov, B.; Mikhaleva, A.; Ivanov, A.; Skital'tseva, E.; Ushakov, I.; Vasil'tsov, A. Synthesis (Mass.) 2009, 2009 (04), 587-590.
https://doi.org/10.1055/s-0028-1083312

[55]. El-Wahab, A. H. F. A.; Al-Fifi, Z. I. A.; Bedair, A. H.; Ali, F. M.; Halawa, A. H. A.; El-Agrody, A. M. Molecules 2011, 16 (1), 307-318.
https://doi.org/10.3390/molecules16010307

[56]. Abd El-Wahab, A.; Ali, F.; Bedair, A.; Halawa, A.; El-Agrody, A.; El-Sherbiny, G. Al-Azhar Bull. Sci. 2007, 18 (2-A), 141-157.
https://doi.org/10.21608/absb.2007.11126

[57]. Prakash, M. S.; Vaidya, V. P.; Mahadevan, K. M.; Shivananda, M. K.; Vijayakumar, G. R. J. Pharm. Sci. Tech. 2012, 3 (9), 1004-1010.

[58]. Badr, M. Z. A.; Kamal El-Dean, A. M.; Moustafa, O. S.; Zaki, R. M. J. Chin. Chem. Soc. 2007, 54 (4), 1045-1052.
https://doi.org/10.1002/jccs.200700151

[59]. Kodihalli, C. R.; Hosadu, M. V.; Vijayvithal, P. V. Arkivoc 2008, 2008 (11), 1.

[60]. Ashour, F. A.; Habib, N. S.; el Taibbi, M.; el Dine, S.; el Dine, A. S. Farmaco 1990, 45 (12), 1341-1349.

[61]. Tarasov, E. V.; Morzherin, Y. Y.; Volkova, N. N.; Bakulev, V. A. Chem. Heterocycl. Compd. (N. Y.) 1996, 32 (8), 971-974.
https://doi.org/10.1007/BF01176975

[62]. Shukurov, S. S.; Kukaniev, M. A.; Nasyrov, M. I. Russ. Chem. Bull. 1995, 44 (10), 1957-1958.
https://doi.org/10.1007/BF00707236

[63]. Gundibasappa K. N.; Marlingaplara, N. K.; Vijayavittala, P. V.; Kittappa, M. M. Arkivoc 2006, 2006 (10), 211-219.
https://doi.org/10.3998/ark.5550190.0007.a24

[64]. Prakash, M. S.; Suchetan, P. A.; Krishnaswamy, G. J. App. Chem. 2018, 7 (5), 1158-1165.

[65]. Kumaraswamy, M. N.; Chandrashekhar, C.; Shivakumar, H.; Mathias, D. A.; Mahadevan, K. M.; Vaidya V. P. Indian J. Pharm. Sci. 2008, 70 (6), 715-720.

[66]. Nagaraja, G. K.; Prakash, G. K.; Kumaraswamy, M. N.; Vaidya, V. P.; Mahadevan, K. M. Arkivoc 2007, 2006 (15), 160-168.
https://doi.org/10.3998/ark.5550190.0007.f19

[67]. Veena, K. M.; Ramaiah, M.; Shashikaladevi, K.; Avinash, S. T.; Vaidya, P. V. J. Chem. Pharm. Res. 2011, 3 (5), 130-135.

[68]. Vagdevi, H. M.; Vaidya, V. P.; Latha, K. P.; Padmashali, B. Indian J. Pharm. Sci. 2006, 68 (6), 719-725.
https://doi.org/10.4103/0250-474X.31002

[69]. Prakash, M. S.; Vaidya, V. P.; Mahadevan, K. M.; Shivananda, K. M.; Suchetan, A. P.; Nirmala, B.; Sunitha, M. J. Chem. Pharm. Res. 2012, 4 (2), 1179-1184.

[70]. Thriveni, K. S.; Padmashali, B.; Siddesh, M. B.; Sandeep, C.; Nagesh, H. K.; Mallikarjun, S. M. Univ. J. Pharm. 2013, 2 (4), 129-134.

[71]. Sharda, M.; Acharya, D. G. Der Pharma Chemica 2015, 7 (8), 25-29.

[72]. Gaikwad Sanjeevan, S.; Suryawanshi Venkat, S. Rasayan J. Chem. 2012, 5 (1), 63-66.

[73]. Haidar, S.; Marminon, C.; Aichele, D.; Nacereddine, A.; Zeinyeh, W.; Bouzina, A.; Berredjem, M.; Ettouati, L.; Bouaziz, Z.; Le Borgne, M.; Jose, J. Molecules 2019, 25 (1), 97.
https://doi.org/10.3390/molecules25010097

[74]. Mahadevan, K. M.; Vaidya, V. P.; Vagdevi, H. V. Indian J. Chem. B 2003, 42, 1931-1936.

[75]. Padmashali, B.; Vaidya, V. P.; Kumar, M. L. Indian. J. Heterocyclic Chem. 2002, 12 (2), 89-94.

[76]. Kumaraswamy, M. N.; Vaidya, V. P. Indian J. Heterocyclic Chem. 2005, 14 (3), 193-196.

[77]. Vaidya, V. P.; Vagdevi, H. M.; Mahadevan, K. M.; Shreedhara, C. S. Indian J. Chem. B 2004. 43 (7), 1537-1543.

[78]. Rashid, S.; Bhat, B. A.; Mehta, G. Tetrahedron Lett. 2019, 60 (16), 1122-1125.
https://doi.org/10.1016/j.tetlet.2019.03.037

[79]. Olyaei, A.; Sadeghpour, M. RSC Adv. 2020, 10 (10), 5794-5826.
https://doi.org/10.1039/C9RA09987E

[80]. Kamboj, V. P.; Chandra, H.; Setty, B. S.; Kar, A. B. Contraception 1970, 1 (1), 29-45.
https://doi.org/10.1016/0010-7824(70)90004-1

[81]. Touati, E.; Krin, E.; Quillardet, P.; Hofnung, M. Carcinogenesis 1996, 17 (12), 2543-2550.
https://doi.org/10.1093/carcin/17.12.2543

[82]. Vagdevi, H. M.; Vaidya, V. P. Indian J. Heterocyclic Chem. 2001, 10 (4), 253-260.

[83]. Lee, K.-H.; Huang, B.-R. Eur. J. Med. Chem. 2002, 37 (4), 333-338.

[84]. Hranjec, M.; Grdisa, M.; Pavelic, K.; Boykin, D. W.; Karminski-Zamola, G. Farmaco 2003, 58 (12), 1319-1324.
https://doi.org/10.1016/S0014-827X(03)00197-6

[85]. Starcevic, K.; Kralj, M.; Piantanida, I.; Suman, L.; Pavelić, K.; Karminski-Zamola, G. Eur. J. Med. Chem. 2006, 41 (8), 925-939.
https://doi.org/10.1016/j.ejmech.2006.03.012

[86]. Kirilmiş, C.; Koca, M.; Servi̇, S.; Gür, S. Turk. J. Chem. 2009, 33 (3), 375-384.

[87]. Srivastava, V.; Negi, A. S.; Kumar, J. K.; Faridi, U.; Sisodia, B. S.; Darokar, M. P.; Luqman, S.; Khanuja, S. P. S. Bioorg. Med. Chem. Lett. 2006, 16 (4), 911-914.
https://doi.org/10.1016/j.bmcl.2005.10.105

[88]. Sumathi, R. B.; Halli, M. B. Bioinorg. Chem. Appl. 2014, 2014, 942162.
https://doi.org/10.1155/2014/942162

[89]. Mahadevan, K. M.; Nandeshwarappa, B. P.; Kiran, B. M.; Sherigara, B. S.; Aruna Kumar, D. B.; Prakash, G. K. Indian J. Pharm. Sci. 2006, 68 (6), 809-813.
https://doi.org/10.4103/0250-474X.31024

[90]. Hranjec, M.; Starcević, K.; Piantanida, I.; Kralj, M.; Marjanović, M.; Hasani, M.; Westman, G.; Karminski-Zamola, G. Eur. J. Med. Chem. 2008, 43 (12), 2877-2890.
https://doi.org/10.1016/j.ejmech.2008.02.010

[91]. Kotoku, N.; Higashimoto, K.; Kurioka, M.; Arai, M.; Fukuda, A.; Sumii, Y.; Sowa, Y.; Sakai, T.; Kobayashi, M. Bioorg. Med. Chem. Lett. 2014, 24 (15), 3389-3391.
https://doi.org/10.1016/j.bmcl.2014.05.083

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).

Article Sidebar

Main Article Content

Abstract

Article Details

Downloads

Metrics