Chromone Containing Hybrid Analogs: Synthesis and Applications in Medicinal Chemistry.
Bioactive scaffolds
chromone
drug discovery
hybrid analogs
molecular hybridization
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Aug 2023
Aug 2023
Historique:
received:
24
04
2023
accepted:
17
06
2023
medline:
24
8
2023
pubmed:
19
6
2023
entrez:
18
6
2023
Statut:
ppublish
Résumé
The use of privileged scaffolds has proven beneficial for generating novel bioactive scaffolds in drug discovery program. Chromone is one such privileged scaffold that has been exploited for designing pharmacologically active analogs. The molecular hybridization technique combines the pharmacophoric features of two or more bioactive compounds to avail a better pharmacological activity in the resultant hybrid analogs. The current review summarizes the rationale and techniques involved in developing hybrid analogs of chromone, which show potential in fields of obesity, diabetes, cancer, Alzheimer's disease and microbial infections. Here the molecular hybrids of chromone with various pharmacologically active analogs or fragments (donepezil, tacrine, pyrimidines, azoles, furanchalcones, hydrazones, quinolines, etc.) are discussed with their structure-activity relationship against above-mentioned diseases. Detailed methodologies for the synthesis of corresponding hybrid analogs have also been described, with suitable synthetic schemes. The current review will shed light on various strategies utilized for the design of hybrid analogs in the field of drug discovery. The importance of hybrid analogs in various disease conditions is also illustrated.
Identifiants
pubmed: 37332056
doi: 10.1002/cbdv.202300587
doi:
Substances chimiques
Chromones
0
Donepezil
8SSC91326P
Tacrine
4VX7YNB537
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300587Subventions
Organisme : Birla Institute of Technology and Science, Pilani (BITS, Pilani), Pilani Campus, Rajasthan (India)
Organisme : DST-INSPIRE
ID : DST/INSPIRE/03/2019/000570
Informations de copyright
© 2023 Wiley-VHCA AG, Zurich, Switzerland.
Références
M. L. Bolognesi, A. Cavalli, ChemMedChem 2016, 11, 1190-1192.
N. Kumar, Curr. Sci. 2014, 107, 1367.
A. S. Reddy, S. Zhang, Expert Rev. Clin. Pharmacol. 2013, 6, 41-47.
Shaveta, S. Mishra, P. Singh, Eur. J. Med. Chem. 2016, 124, 500-536.
V. Ivasiv, C. Albertini, A. E. Gonçalves, M. Rossi, M. L. Bolognesi, Curr. Top. Med. Chem. 2019, 19, 1694-1711.
C. Viegas-Junior, E. J. Barreiro, C. A. M. Fraga, Curr. Med. Chem. 2007, 14, 1829-1852.
A. Gaspar, M. J. Matos, J. Garrido, E. Uriarte, F. Borges, Chem. Rev. 2014, 114, 4960-4992.
R. S. Keri, S. Budagumpi, R. K. Pai, R. G. Balakrishna, Eur. J. Med. Chem. 2014, 78, 340-374.
J. Ungwitayatorn, C. Wiwat, W. Samee, P. Nunthanavanit, N. Phosrithong, J. Mol. Struct. 2011, 1001, 152-161.
M. Kuroda, S. Uchida, K. Watanabe, Y. Mimaki, Phytochemistry 2009, 70, 288-293.
R. Larget, B. Lockhart, P. Renard, M. Largeron, Bioorg. Med. Chem. Lett. 2000, 10, 835-838.
M. Kidwai, S. Saxena, M. K. R. Khan, S. S. Thukral, Bioorg. Med. Chem. Lett. 2005, 15, 4295-4298.
T. Al Nakib, V. Bezjak, M. Meegan, R. Chandy, Eur. J. Med. Chem. 1990, 25, 455-462.
A. Nohara, T. Umetani, Y. Sanno, Tetrahedron Lett. 1973, 14, 1995-1998.
“Cancer Fact sheet,” can be found under https://www.who.int/news-room/fact-sheets/detail/cancer, n.d.
Y. Zhang, Z. Lv, H. Zhong, D. Geng, M. Zhang, T. Zhang, Y. Li, K. Li, Eur. J. Med. Chem. 2012, 53, 356-363.
R. Jiao, F. Xu, X. Huang, H. Li, W. Liu, H. Cao, L. Zang, Z. Li, H. Hua, D. Li, J. Enzyme Inhib. Med. Chem. 2020, 35, 759-772.
R. Merugu, S. Garimella, D. Balla, K. Sambaru, Int. J. PharmTech Res. 2015, 8, 88-93.
Z. Önal, E. Saripinar, I. Ö. Ilhan, J. Heterocycl. Chem. 2001, 38, 397-402.
J. Lal, S. K. Gupta, D. Thavaselvam, D. D. Agarwal, Bioorg. Med. Chem. Lett. 2012, 22, 2872-2876.
D. Russowsky, L. K. Kohn, Bioorg. Chem. 2006, 34, 173-182.
I. Leizerman, R. Avunie-masala, M. Elkabets, A. Fich, L. Gheber, Cell. Mol. Life Sci.2004, 61, 2060-2070.
A. Kantankar, Y. Jayaprakash Rao, G. Mallikarjun, Y. Hemasri, R. R. Kethiri, J. Mol. Struct. 2021, 1239, 130502.
S. Ç. Yavuz, S. Akkoç, B. Tüzün, O. Şahin, E. Saripinar, Synth. Commun. 2021, 51, 2135-2159.
A. Y. Shaw, C. Y. Chang, H. H. Liau, P. J. Lu, H. L. Chen, C. N. Yang, H. Y. Li, Eur. J. Med. Chem. 2009, 44, 2552-2562.
R. Kaplánek, M. Jakubek, J. Rak, Z. Kejík, M. Havlík, B. Dolenský, I. Frydrych, M. Hajdúch, M. Kolář, K. Bogdanová, J. Králová, P. Džubák, V. Král, Bioorg. Chem. 2015, 60, 19-29.
O. S. Reddy, C. V. Suryanarayana, K. J. P. Narayana, V. Anuradha, B. H. Babu, Med. Chem. Res. 2015, 24, 1777-1788.
B. China Raju, R. Nageswara Rao, P. Suman, P. Yogeeswari, D. Sriram, T. B. Shaik, S. V. Kalivendi, Bioorg. Med. Chem. Lett. 2011, 21, 2855-2859.
Q. H. Chen, K. Yu, X. Zhang, G. Chen, A. Hoover, F. Leon, R. Wang, N. Subrahmanyam, E. Addo Mekuria, L. Harinantenaina Rakotondraibe, Bioorg. Med. Chem. Lett. 2015, 25, 4553-4556.
S. S. Shatokhin, V. A. Tuskaev, S. C. Gagieva, A. A. Markova, D. I. Pozdnyakov, E. K. Melnikova, B. M. Bulychev, E. T. Oganesyan, J. Mol. Struct. 2022, 1249, 131683.
J. H. Powers, Clin. Microbiol. Infect. Suppl. 2004, 10, 23-31.
R. C. Moellering, Int. J. Antimicrob. Agents 2011, 37, 2-9.
G. Bérubé, Expert Opin. Drug Discovery 2016, 11, 281-305.
V. Padmavathi, G. Sudhakar Reddy, A. Padmaja, P. Kondaiah, Ali-Shazia, Eur. J. Med. Chem. 2009, 44, 2106-2112.
Z. Xu, X. F. Song, Y. Q. Hu, M. Qiang, Z. S. Lv, Eur. J. Med. Chem. 2017, 138, 66-71.
N. Boechat, V. F. Ferreira, S. B. Ferreira, M. D. L. G. Ferreira, F. D. C. Da Silva, M. M. Bastos, M. D. S. Costa, M. C. S. Lourenço, A. C. Pinto, A. U. Krettli, A. C. Aguiar, B. M. Teixeira, N. V. Da Silva, P. R. C. Martins, F. A. F. M. Bezerra, A. L. S. Camilo, G. P. Da Silva, C. C. P. Costa, J. Med. Chem. 2011, 54, 5988-5999.
P. K. Kadaba, J. Med. Chem. 1988, 31, 196-203.
W. L. Dong, Z. X. Liu, X. H. Liu, Z. M. Li, W. G. Zhao, Eur. J. Med. Chem. 2010, 45, 1919-1926.
M. De La Rosa, H. W. Kim, E. Gunic, C. Jenket, U. Boyle, Y. hyo Koh, I. Korboukh, M. Allan, W. Zhang, H. Chen, W. Xu, S. Nilar, N. Yao, R. Hamatake, S. A. Lang, Z. Hong, Z. Zhang, J. L. Girardet, Bioorg. Med. Chem. Lett. 2006, 16, 4444-4449.
L. Labanauskas, E. Udrenaite, P. Gaidelis, A. Brukštus, Farmaco 2004, 59, 255-259.
G. Wang, Z. Peng, J. Wang, X. Li, J. Li, Eur. J. Med. Chem. 2017, 125, 423-429.
M. H. Shaikh, D. D. Subhedar, M. Arkile, V. M. Khedkar, N. Jadhav, D. Sarkar, B. B. Shingate, Bioorg. Med. Chem. Lett. 2016, 26, 561-569.
V. Nalla, A. Shaikh, S. Bapat, R. Vyas, M. Karthikeyan, P. Yogeeswari, D. Sriram, M. Muthukrishnan, R. Soc. Open Sci. 2018, 5, 171750.
P. A. Cano, A. Islas-Jácome, Á. Rangel-Serrano, F. Anaya-Velázquez, F. Padilla-Vaca, E. Trujillo-Esquivel, P. Ponce-Noyola, A. Martínez-Richa, R. Gámez-Montaño, Molecules 2015, 20, 12436-12449.
E. García, J. C. Coa, E. Otero, M. Carda, I. D. Vélez, S. M. Robledo, W. I. Cardona, Med. Chem. Res. 2018, 27, 497-511.
J. C. Coa, E. García, M. Carda, R. Agut, I. D. Vélez, J. A. Muñoz, L. M. Yepes, S. M. Robledo, W. I. Cardona, Med. Chem. Res. 2017, 26, 1405-1414.
N. Pathan, P. Ali, A. Rahatgaonkar, K. Al-Mousa, J. Heterocycl. Chem. 2021, 58, 1675-1689.
V. Arango, J. J. Domínguez, W. Cardona, S. M. Robledo, D. L. Muñoz, B. Figadere, J. Sáez, Med. Chem. Res. 2012, 21, 3445-3454.
E. Otero, S. Vergara, S. M. Robledo, W. Cardona, M. Carda, I. D. Vélez, C. Rojas, F. Otálvaro, Molecules 2014, 19, 13251-13266.
T. R. Mhyre, R. Nw, J. T. Boyd, G. Hall, C. Room, Subcell. Biochem. 2012, 389-455.
A. Husain, A. Balushi K, M. J. Akhtar, S. A. Khan, J. Mol. Struct. 2021, 1241, 130618.
P. Kapková, V. Alptüzün, P. Frey, E. Erciyas, U. Holzgrabe, Bioorg. Med. Chem. 2006, 14, 472-478.
P. Sharma, A. Tripathi, P. N. Tripathi, S. K. Prajapati, A. Seth, M. K. Tripathi, P. Srivastava, V. Tiwari, S. Krishnamurthy, S. K. Shrivastava, Eur. J. Med. Chem. 2019, 167, 510-524.
S. Abdpour, L. Jalili-Baleh, H. Nadri, H. Forootanfar, S. N. A. Bukhari, A. Ramazani, S. E. S. Ebrahimi, A. Foroumadi, M. Khoobi, Bioorg. Chem. 2021, 110, 104750.
J. C. Shih, K. Chen, M. J. Ridd, Annu. Rev. Neurosci. 1999, 22, 197-217.
G. D. Mellick, D. D. Buchanan, S. J. McCann, K. M. James, A. G. Johnson, D. R. Davis, N. Liyou, D. Chan, D. G. Le Couteur, Mov. Disord. 1999, 14, 219-224.
O. Bar-Am, T. Amit, O. Weinreb, M. B. H. Youdim, S. Mandel, J. Alzheimer′s Dis. 2010, 21, 361-371.
M. Yogev-Falach, O. Bar-Am, T. Amit, O. Weinreb, M. B. H. Youdim, M. Yogev-Falach, O. Bar-Am, T. Amit, O. Weinreb, M. B. H. Youdim, FASEB J. 2006, 20, 2177-2179.
L. J. Legoabe, A. Petzer, J. P. Petzer, Eur. J. Med. Chem. 2012, 49, 343-353.
A. Gaspar, F. Teixeira, E. Uriarte, N. Milhazes, A. Melo, M. N. D. S. Cordeiro, F. Ortuso, S. Alcaro, F. Borges, ChemMedChem 2011, 6, 628-632.
X. B. Wang, F. C. Yin, M. Huang, N. Jiang, J. S. Lan, L. Y. Kong, RSC Med. Chem. 2020, 11, 225-233.
G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherstone, Biochem. Pharmacol. 1961, 7, 88-95.
I. Pachón-Angona, B. Refouvelet, R. Andrýs, H. Martin, V. Luzet, I. Iriepa, I. Moraleda, D. Diez-Iriepa, M. J. Oset-Gasque, J. Marco-Contelles, K. Musilek, L. Ismaili, J. Enzyme Inhib. Med. Chem. 2019, 34, 479-489.
H. Moini, L. Packer, N. E. L. Saris, Toxicol. Appl. Pharmacol. 2002, 182, 84-90.
L. Holmquist, G. Stuchbury, K. Berbaum, S. Muscat, S. Young, K. Hager, J. Engel, G. Münch, Pharmacol. Ther. 2007, 113, 154-164.
L. Jalili-Baleh, H. Nadri, H. Forootanfar, T. T. Küçükkılınç, B. Ayazgök, M. Sharifzadeh, M. Rahimifard, M. Baeeri, M. Abdollahi, A. Foroumadi, M. Khoobi, DARU J. Pharm. Sci. 2021, 29, 23-38.
L. Monjas, J. Rademann, J. Med. Chem. 2012, 55, 1303-1317.
S. Bhagat, P. Shah, S. K. Garg, S. Mishra, P. Kamal Kaur, S. Singh, A. K. Chakraborti, MedChemComm 2014, 5, 665-670.
K. R. Valasani, G. Hu, M. O. Chaney, S. S. Yan, Chem. Biol. Drug Des. 2013, 81, 238-249.
F. R. Atherton, C. H. Hassall, R. W. Lambert, J. Med. Chem. 1986, 29, 29-40.
S. Thaslim Basha, H. Sudhamani, S. Rasheed, N. Venkateswarlu, T. Vijaya, C. Naga Raju, Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 1339-1343.
S. Shaikh, P. Dhavan, M. M. V. Ramana, B. L. Jadhav, Mol. Diversity 2021, 25, 811-825.
M. P. Jorge, C. Madjarof, A. L. T. G. Ruiz, A. T. Fernandes, R. A. F. Rodrigues, I. M. de Oliveira Sousa, M. A. Foglio, J. E. de Carvalho, J. Ethnopharmacol. 2008, 118, 361-366.
Y. C. Chooi, C. Ding, F. Magkos, Metabolism. 2019, 92, 6-10.
P. G. Kopelman, Nature 2000, 404, 635-643.
A. L. Handlon, H. Zhou, J. Med. Chem. 2006, 49, 4017-4022.
T. Högberg, T. M. Frimurer, P. K. Sasmal, Bioorg. Med. Chem. Lett. 2012, 22, 6039-6047.
J. K. Lynch, J. C. Freeman, A. S. Judd, R. Iyengar, M. Mulhern, G. Zhao, J. J. Napier, D. Wodka, S. Brodjian, B. D. Dayton, D. Falls, C. Ogiela, R. M. Reilly, T. J. Campbell, J. S. Polakowski, L. Hernandez, K. C. Marsh, R. Shapiro, V. Knourek-Segel, B. Droz, E. Bush, M. Brune, L. C. Preusser, R. M. Fryer, G. A. Reinhart, K. Houseman, G. Diaz, A. Mikhail, J. T. Limberis, H. L. Sham, C. A. Collins, P. R. Kym, J. Med. Chem. 2006, 49, 6569-6584.
R. R. Iyengar, J. K. Lynch, M. M. Mulhern, A. S. Judd, J. C. Freeman, J. Gao, A. J. Souers, G. Zhao, D. Wodka, H. Doug Falls, S. Brodjian, B. D. Dayton, R. M. Reilly, S. Swanson, Z. Su, R. L. Martin, S. T. Leitza, K. A. Houseman, G. Diaz, C. A. Collins, H. L. Sham, P. R. Kym, Bioorg. Med. Chem. Lett. 2007, 17, 874-878.
S. R. Joshi, E. Standl, N. Tong, P. Shah, S. Kalra, R. Rathod, Expert Opin. Pharmacother. 2015, 16, 1959-1981.
R. A. Rane, S. Karunanidhi, K. Jain, M. Shaikh, G. Hampannavar, R. Karpoormath, Curr. Top. Med. Chem. 2016, 16, 1262-1289.
F. A. Khan, A. Maalik, Trop. J. Pharm. Res. 2015, 14, 1937-1942.
C. Xie, L. M. Tang, F. N. Li, L. P. Guan, C. Y. Pan, S. H. Wang, Med. Chem. Res. 2014, 23, 2161-2168.
Z. Xie, G. Wang, J. Wang, M. Chen, Y. Peng, L. Li, B. Deng, S. Chen, W. Li, Molecules 2017, 22, 659.
X. M. Zhang, H. Guo, Z. S. Li, F. H. Song, W. M. Wang, H. Q. Dai, L. X. Zhang, J. G. Wang, Eur. J. Med. Chem. 2015, 101, 419-430.
T. R. Bal, B. Anand, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 2005, 15, 4451-4455.
F. Rahim, F. Malik, H. Ullah, A. Wadood, F. Khan, M. T. Javid, M. Taha, W. Rehman, A. Ur Rehman, K. M. Khan, Bioorg. Chem. 2015, 60, 42-48.
F. Rahim, M. Taha, N. Iqbal, S. Hayat, F. Qureshi, I. Uddin, K. Zaman, A. Rab, A. Wadood, N. Uddin, M. Nawaz, S. A. A. Shah, K. M. Khan, J. Mol. Struct. 2020, 1222, 128922.
G. Wang, J. Wang, D. He, X. Li, J. Li, Z. Peng, Chem. Biol. Drug Des. 2017, 89, 456-463.
G. Wang, M. Chen, J. Qiu, Z. Xie, A. Cao, Bioorg. Med. Chem. Lett. 2018, 28, 113-116.
G. Wang, M. Chen, J. Wang, Y. Peng, L. Li, Z. Z. Xie, B. Deng, S. Chen, W. Li, Bioorg. Med. Chem. Lett. 2017, 27, 2957-2961.