Amalgamating Isatin/Indole/Nitroimidazole with 7-chloroquinolines via azide-alkyne cycloaddition: Synthesis, anti-plasmodial, and cytotoxic evaluation.
7-chloroquinoline-based conjugates
anti-plasmodial activity
azide-alkyne cycloaddition
cytotoxicity
Journal
Chemical biology & drug design
ISSN: 1747-0285
Titre abrégé: Chem Biol Drug Des
Pays: England
ID NLM: 101262549
Informations de publication
Date de publication:
12 2020
12 2020
Historique:
received:
01
03
2020
revised:
23
04
2020
accepted:
24
05
2020
pubmed:
10
6
2020
medline:
18
8
2021
entrez:
10
6
2020
Statut:
ppublish
Résumé
The present paper describes the synthesis, anti-plasmodial, and cytotoxic evaluation of 7-chloroquinoline-based conjugates with isatins/indoles/ nitroimidazoles, obtained via Cu-promoted 1,3-dipolar cycloadditions. On contemplating SAR of the synthesized series, the inclusion of indole and nitroimidazole-core improved the anti-plasmodial activities while the isatin seemed to have a lesser effect. The conjugate with a nitroimidazole-core and hexyl chain length as a spacer between the two pharmacophores was found to be most potent among the synthesized series and displayed an IC
Substances chimiques
Alkynes
0
Antimalarials
0
Azides
0
Indoles
0
Nitroimidazoles
0
Quinolones
0
Isatin
82X95S7M06
Types de publication
Letter
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1355-1361Informations de copyright
© 2020 John Wiley & Sons A/S.
Références
Aneja, B., Kumar, B., Jairajpuri, M. A., & Abid, M. (2016). A structure guided drug-discovery approach towards identification of Plasmodium inhibitors. RSC Advances, 6, 18364-18406. https://doi.org/10.1039/C5RA19673F
Beteck, R. M., Smit, F. J., Haynes, R. K., & N’Da, D. D. (2014). Recent progress in the development of anti-malarial quinolones. Malar. J., 13, 339.
Brancale, A., & Silvestri, R. (2007). Indole, a core nucleus for potent inhibitors of tubulin polymerization. Medicinal Research Reviews, 27, 209-238.
De Andrade-Neto, V. F., Pohlit, A. M., Pinto, A. C. S., Silva, E. C. C., Nogueira, K. L., Melo, M. R. S., … Vieir, P. P. R. (2007). In vitro inhibition of Plasmodium falciparum by substances isolated from Amazonian antimalarial plants. Memorias do Instituto Oswaldo Cruz, 102, 359-365. https://doi.org/10.1590/S0074-02762007000300016
Dondorp, A. M., Nosten, F., Yi, P., Das, D., Phyo, A. P., Tarning, J., … White, N. J. (2009). Artemisinin resistance in Plasmodium falciparum malaria. New England Journal of Medicine, 361, 455-467.
Dondorp, A. M., Yeung, S., White, L., Nguon, C., Day, N. P. J., Socheat, D., & von Seidlein, L. (2010). Artemisinin resistance: Current status and scenarios for containment. Nature Reviews Microbiology, 8, 272-280.
Dousson, C., Alexandre, F.-R., Amador, A., Bonaric, S., Bot, S., Caillet, C., … Standring, D. (2016). Discovery of the Aryl-phospho-indole IDX899, a highly potent anti-HIV non1087 nucleoside reverse transcriptase inhibitor. Journal of Medicinal Chemistry, 59, 1891-1898.
Estevao, M. S., Carvalho, L. C., Ribeiro, D., Couto, D., Freitas, M., Gomes, A., … Marques, M. M. B. (2010). Antioxidant activity of unexplored indole derivatives: Synthesis and screening. European Journal of Medicinal Chemistry, 45, 4869-4878.
Gemma, S., Camodeca, C., Brindisi, M., Brogi, S., Kukreja, G., Kunjir, S., … Butini, S. (2012). Mimicking the intramolecular hydrogen bond: Synthesis, biological evaluation, and molecular modeling of benzoxazines and quinazolines as potential antimalarial agents. Journal of Medicinal Chemistry, 55, 10387-10404. https://doi.org/10.1021/jm300831b
Gobbi, F., Buonfrate, D., Menegon, M., Lunardi, G., Angheben, A., Severini, C., … Bisoffi, Z. (2016). Failure of dihydroartemisinin-piperaquine treatment of uncomplicated Plasmodium falciparum malaria in a traveller coming from Ethiopia. Malar J., 15, 525.
Gomha, S. M., & Riyadh, S. M. (2011). Synthesis under microwave irradiation of [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazoles and other diazoles bearing indole moieties and their antimicrobial evaluation. Molecules, 16, 8244-8256. https://doi.org/10.3390/molecules16108244
Guantai, E. M., Ncokazi, K., Egan, T. J., Gut, J., Rosenthal, P. J., Bhampidipati, R., … Chibale, K. (2011). Enone- and chalcone-chloroquinoline hybrid analogues: In silico guided design, synthesis, antiplasmodial activity, in vitro metabolism, and mechanistic studies. Journal of Medicinal Chemistry, 54, 3637-3649. https://doi.org/10.1021/jm200149e
Jensen, J. B. (2002). In vitro culture of plasmodium parasites. In D. L. Doolan (Ed.), Malaria methods and protocols (pp. 477-488). Totowa, NJ: Humana.
Kondaparla, S., Manhas, A., Dola, V. R., Srivastava, K., Puri, S. K., & Katti, S. B. (2018). Design, synthesis and antiplasmodial activity of novel imidazole derivatives based on 7-chloro-4-aminoquinoline. Bioorganic Chemistry, 80, 204-211.
Kumar, S., Saini, A., Gut, J., Rosenthal, P. J., Raj, R., & Kumar, V. (2017). 4-Aminoquinoline-chalcone/-N-acetylpyrazoline conjugates: Synthesis and antiplasmodial evaluation. European Journal of Medicinal Chemistry, 138, 993-1001.
Leang, R., Taylor, W. R. J., Bouth, D. M., Song, L., Tarning, J., Char, M. C., … Menard, D. (2015). Evidence of Plasmodium falciparum Malaria Multidrug Resistance to Artemisinin and Piperaquine in Western Cambodia: Dihydroartemisinin-Piperaquine Open-Label Multicenter Clinical Assessment. Antimicrobial Agents and Chemotherapy, 59, 4719-4726. https://doi.org/10.1128/AAC.00835-15
Mandalapu, D., Kushwaha, B., Gupta, S., Singh, N., Shukla, M., Kumar, J., … Sharma, V. L. (2016). 2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas: Design, synthesis, biology and 3D-QSAR study. European Journal of Medicinal Chemistry, 124, 820-839. https://doi.org/10.1016/j.ejmech.2016.09.006
Manohar, S., Rajesh, U. C., Khan, S. I., Tekwani, B. L., & Rawat, D. S. (2012). Novel 4-aminoquinoline-pyrimidine based hybrids with improved in vitro and in vivo antimalarial activity. ACS Med. Chem. Lett., 3, 555-559.
Nomura, S., Yamamoto, Y., Matsumura, Y., Ohba, K., Sakamaki, S., Kimata, H., … Tsuda-Tsukimoto, M. (2014). Novel Indole- N -glucoside, TA-1887 as a sodium glucose Cotransporter 2 inhibitor for treatment of type 2 diabetes. ACS Med. Chem. Lett., 5, 51-55.
Perez, B. C., Teixeira, C., Albuquerque, I. S., Gut, J., Rosenthal, P. J., Gomes, J. R., … Gomes, P. (2013). N-cinnamoylated chloroquine analogues as dual-stage antimalarial leads. Journal of Medicinal Chemistry, 56, 556-567.
Pesic, D., Starcevic, K., Toplak, A., Herreros, E., Vidal, J., Almela, M. J., … Peric, M. (2012). Design, synthesis, and in vitro activity of novel 2'-O-substituted 15-membered azalides. Journal of Medicinal Chemistry, 55, 3216-3227.
Praveen, C., Ayyanar, A., & Perumal, P. T. (2011). Practical synthesis, anticonvulsant, and antimicrobial activity of N-allyl and N-propargyl di(indolyl)indolin-2-ones. Bioorganic & Medicinal Chemistry Letters, 21, 4072-4077.
Raj, R., Gut, J., Rosenthal, P. J., & Kumar, V. (2014). 1H-1,2,3-Triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates: Synthesis and antimalarial evaluation. Bioorganic & Medicinal Chemistry Letters, 24, 756-759.
Raj, R., Saini, A., Gut, J., Rosenthal, P. J., & Kumar, V. (2015). Synthesis and in vitro antiplasmodial evaluation of 7-chloroquinoline-chalcone and 7-chloroquinoline-ferrocenylchalcone conjugates. European Journal of Medicinal Chemistry, 95, 230-239.
Rani, A., Kumar, S., Legac, J., Adeniyi, A. A., Awolade, P., Singh, P., … Kumar, V. (2019). Design, synthesis, heme binding and density functional theory studies of isoindoline-dione-4-aminoquinolines as potential antiplasmodials. Future Med. Chem. https://doi.org/10.4155/fmc-2019-0260
Rani, A., Singh, A., Gut, J., Rosenthal, P. J., & Kumar, V. (2018). Microwave-promoted facile access to 4-aminoquinoline-phthalimides: Synthesis and anti-plasmodial evaluation. European Journal of Medicinal Chemistry, 143, 150-156.
Ray, S., Madrid, P. B., Catz, P., LeValley, S. E., Furniss, M. J., Rausch, L. L., … Mirsalis, J. C. (2010). Development of a new generation of 4-aminoquinoline antimalarial compounds using predictive pharmacokinetic and toxicology models. Journal of Medicinal Chemistry, 53, 3685-3695.
Rottmann, M., McNamara, C., Yeung, B. K. S., Lee, M. C. S., Zou, B., Russell, B., … Diagana, T. T. (2010). Spiroindolones, a potent compound class for the treatment of malaria. Science, 329, 1175-1180. https://doi.org/10.1126/science.1193225
Samosorn, S., Tanwirat, B., Muhamad, N., Casadei, G., Tomkiewicz, D., Lewis, K., … Bremner, J. B. (2009). Antibacterial activity of berberine-NorA pump inhibitor hybrids with a methylene ether linking group. Bioorganic & Medicinal Chemistry, 17, 3866-3872.
Shalini, L. J., Adeniyi, A. A., Kisten, P., Rosenthal, P. J., Singh, P., & Kumar, V.(2020). Functionalized naphthalimide-4-aminoquinoline conjugates as promising antiplasmodials, with mechanistic insights. ACS Med. Chem. Lett., 11, 154-161. https://doi.org/10.1021/acsmedchemlett.9b00521
Singh, A., Gut, J., Rosenthal, P. J., & Kumar, V. (2017). 4-Aminoquinoline-ferrocenyl-chalcone conjugates: Synthesis and anti-plasmodial evaluation. European Journal of Medicinal Chemistry, 125, 269-277.
Singh, A., & Rosenthal, P. J. (2001). Comparison of efficacies of cysteine protease inhibitors against five strains of Plasmodium falciparum. Antimicrobial Agents and Chemotherapy, 45, 949-951.
Stec, J., Onajole, O. K., Lun, S., Guo, H., Merenbloom, B., Vistoli, G., … Kozikowski, A. P. (2016). Indole-2-carboxamide-based MmpL3 inhibitors show exceptional antitubercular activity in an animal model of tuberculosis infection. Journal of Medicinal Chemistry, 59, 6232-6247.
Thakur, R. K., Joshi, P., Baranwal, P., Sharma, G., Shukla, S. K., Tripathi, R., & Tripathi, R. P. (2018). Synthesis and antiplasmodial activity of glyco-conjugate hybrids of phenylhydrazono-indolinones and glycosylated 1,2,3-triazolylmethyl-indoline-2,3-diones. European Journal of Medicinal Chemistry, 155, 764-771.
Verma, M., Tripathi, M., Saxena, A., & Shanker, K. (1994). Antiinflammatory activity of novel indole derivatives. European Journal of Medicinal Chemistry, 29, 941-946.
Weng, J.-R., Tsai, C.-H., Kulp, S. K., & Chen, C.-S. (2008). Indole-3-carbinol as a chemopreventive and anti-cancer agent. Cancer Letters, 262, 153-163.
World Malaria Report, World Health Organization (2018). Online, http://apps.who.int/iris/bitstream/handle/10665/275867/9789241565653-eng.pdf?ua=1
Yadav, R. R., Khan, S. I., Singh, S., Khan, I. A., Vishwakarma, R. A., & Bharate, S. B. (2015). Synthesis, antimalarial and antitubercular activities of meridianin derivatives. European Journal of Medicinal Chemistry, 98, 160-169.
Zhang, M.-Z., Jia, C.-Y., Gu, Y.-C., Mulholland, N., Turner, S., Beattie, D., … Clough, J. (2017). Synthesis and antifungal activity of novel indole-replaced streptochlorin analogues. European Journal of Medicinal Chemistry, 126, 669-674.