References
- Abdullah, A. H., Zahra, J. A., El-Abadelah, M. M., Sabri, S. S., Khanfar, M. A., Matar, S. A., & Voelter, W. (2016). Synthesis and antibacterial activity of N1-(carbazol-3-yl)amidrazones incorporating piperazines and related congeners. Zeitschrift Für Naturforschung B, 71(8), 857–867. https://doi.org/https://doi.org/10.1515/znb-2016-0043
- Alzheimer’s Association (2015). 2015 Alzheimer’s disease facts and figures. Alzheimer's & Dementia, 11(3), 332–384. https://doi.org/https://doi.org/10.1016/j.jalz.2015.02.003
- Bachurin, S. O., Shevtsova, E. F., Makhaeva, G. F., Grigoriev, V. V., Boltneva, N. P., Kovaleva, N. V., Lushchekina, S. V., Shevtsov, P. N., Neganova, M. E., Redkozubova, O. M., Bovina, E. V., Gabrelyan, A. V., Fisenko, V. P., Sokolov, V. B., Aksinenko, A. Y., Echeverria, V., Barreto, G. E., & Aliev, G. (2017). Novel conjugates of aminoadamantanes with carbazole derivatives as potential multitarget agents for AD treatment. Scientific Reports, 7(July 2016), 45627–45615. https://doi.org/https://doi.org/10.1038/srep45627
- Baell, J. B., & Holloway, G. A. (2010). New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays. Journal of Medicinal Chemistry, 53(7), 2719–2740. https://doi.org/https://doi.org/10.1021/jm901137j
- Bajda, M., Więckowska, A., Hebda, M., Guzior, N., Sotriffer, C. A., & Malawska, B. (2013). Structure-based search for new inhibitors of cholinesterases. International Journal of Molecular Sciences, 14(3), 5608–5632. https://doi.org/https://doi.org/10.3390/ijms14035608
- Bandgar, B. P., Adsul, L. K., Chavan, H. V., Jalde, S. S., Shringare, S. N., Shaikh, R., Meshram, R. J., Gacche, R. N., & Masand, V. (2012). Synthesis, biological evaluation, and docking studies of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines as potent anti-inflammatory and antioxidant agents. Bioorganic & Medicinal Chemistry Letters, 22(18), 5839–5844. https://doi.org/https://doi.org/10.1016/j.bmcl.2012.07.080
- Bashir, M., Bano, A., Ijaz, A. S., & Chaudhary, B. A. (2015). Recent developments and biological activities of n-substituted carbazole derivatives: A review. Molecules (Basel, Switzerland), 20(8), 13496–13517. https://doi.org/https://doi.org/10.3390/molecules200813496
- Biamonte, M. A., Wanner, J., & Le Roch, K. G. (2013). Recent advances in malaria drug discovery. Bioorganic & Medicinal Chemistry Letters, 23(10), 2829–2843. https://doi.org/https://doi.org/10.1016/j.bmcl.2013.03.067
- Brus, B., Košak, U., Turk, S., Pišlar, A., Coquelle, N., Kos, J., Stojan, J., Colletier, J. P., & Gobec, S. (2014). Discovery, biological evaluation, and crystal structure of a novel nanomolar selective butyrylcholinesterase inhibitor. Journal of Medicinal Chemistry, 57(19), 8167–8179. https://doi.org/https://doi.org/10.1021/jm501195e
- Choubdar, N., Golshani, M., Jalili-Baleh, L., Nadri, H., Küçükkilinç, T. T., Ayazgök, B., Moradi, A., Moghadam, F. H., Abdolahi, Z., Ameri, A., Salehian, F., Foroumadi, A., & Khoobi, M. (2019). New classes of carbazoles as potential multi-functional anti-Alzheimer's agents. Bioorganic Chemistry, 91 (July), 103164. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.103164
- Deardorff, W. J., Feen, E., & Grossberg, G. T. (2015). The use of cholinesterase inhibitors across all stages of Alzheimer's disease. Drugs & Aging, 32(7), 537–547. https://doi.org/https://doi.org/10.1007/s40266-015-0273-x
- Dvir, H., Silman, I., Harel, M., Rosenberry, T. L., & Sussman, J. L. (2010). Acetylcholinesterase: From 3D structure to function. Chemico-Biological Interactions, 187(1–3), 10–22. https://doi.org/https://doi.org/10.1016/j.cbi.2010.01.042
- Ellman, G. L., Courtney, K. D., Andres, V., & Feather-Stone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7 (2), 88–95. https://doi.org/https://doi.org/10.1016/0006-2952(61)90145-9
- El-Sayed, N. F., El-Hussieny, M., Ewies, E. F., Fouad, M. A., & Boulos, L. S. (2020). New phosphazine and phosphazide derivatives as multifunctional ligands targeting acetylcholinesterase and β-Amyloid aggregation for treatment of Alzheimer's disease. Bioorganic Chemistry, 95, 103499. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.103499
- Ghobadian, R., Nadri, H., Moradi, A., Bukhari, S. N. A., Mahdavi, M., Asadi, M., Akbarzadeh, T., Khaleghzadeh-Ahangar, H., Sharifzadeh, M., & Amini, M. (2018). Design, synthesis, and biological evaluation of selective and potent carbazole-based butyrylcholinesterase inhibitors. Bioorganic Medicinal Chemistrt, 26(17), 4952–4962. https://doi.org/https://doi.org/10.1016/j.bmc.2018.08.035
- Giacobini, E. (2003). Cholinesterases: New roles in brain function and in Alzheimer’s disease. Neurochemical Research, 28 (3-4), 515–522. https://doi.org/https://doi.org/10.1023/A:1022869222652
- Greig, N. H., Lahiri, D. K., & Sambamurti, K. (2002). Butyrylcholinesterase: An important new target in Alzheimer’s disease therapy. International Psychogeriatrics, 14(S1), 77–91. https://doi.org/https://doi.org/10.1017/S1041610203008676
- Grosdidier, A., Zoete, V., & Michielin, O. (2011). SwissDock, a protein-small molecule docking web service based on EADock DSS. Nucleic Acids Research, 39(Suppl), W270–277. https://doi.org/https://doi.org/10.1093/nar/gkr366
- Indumathi, T., Fronczek, F. R., & Rajendra Prasad, K. J. (2012). Synthesis of 2-amino-8-chloro-4-phenyl-5,11-dihydro-6H-pyrido[2,3-a] carbazole-3-carbonitrile: Structural and biological evaluation. Journal of Molecular Structure, 1016, 134–139. https://doi.org/https://doi.org/10.1016/j.molstruc.2012.01.032
- Joshi, A. J., Gadhwal, M. K., & Joshi, U. J. (2014). A combined approach based on 3D pharmacophore and docking for identification of new aurora A kinase inhibitors. Medicinal Chemistry Research, 23(3), 1414–1436. https://doi.org/https://doi.org/10.1007/s00044-013-0747-5
- Kantevari, S., Yempala, T., Surineni, G., Sridhar, B., Yogeeswari, P., & Sriram, D. (2011). Synthesis and antitubercular evaluation of novel dibenzo[b,d]furan and 9-methyl-9H-carbazole derived hexahydro-2H-pyrano[3,2-c]quinolines via Povarov reaction. European Journal of Medicinal Chemistry, 46(10), 4827–4833. https://doi.org/https://doi.org/10.1016/j.ejmech.2011.06.014
- Karaaslan, C., Ince, E., Gurer-Orhan, H., Tavakkoli, M., Firuzi, O., Saso, L., & Suzen, S. (2019). Behaviour of 9-Ethyl-9H-carbazole hydrazone derivatives against oxidant systems: Protective effect on amyloid β-induced damage. Croatica Chemica Acta, 92(1), 87–94. https://doi.org/https://doi.org/10.5562/cca3481
- Kryger, G., Silman, I., & Sussman, J. L. (1999). Structure of acetylcholinesterase complexed with E2020 (Aricept): Implications for the design of new anti-Alzheimer drugs. Structure (London, England: 1993), 7(3), 297–307. https://doi.org/https://doi.org/10.1016/S0969-2126(99)80040-9
- Kumar, A., Pintus, F., Di Petrillo, A., Medda, R., Caria, P., Matos, M. J., Viña, D., Pieroni, E., Delogu, F., Era, B., Delogu, G. L., & Fais, A. (2018). Novel 2-pheynlbenzofuran derivatives as selective butyrylcholinesterase inhibitors for Alzheimer’s disease. Scientific Reports, 8(1), 1–12. https://doi.org/https://doi.org/10.1038/s41598-018-22747-2
- Lejczak, B., Kafarsk, P., Sztajer, H., & Mastalerz, P. (1986). Antibacterial activity of phosphono dipeptides related to alafosfalin. Journal of Medicinal Chemistry, 29(11), 2212–2217. https://doi.org/https://doi.org/10.1021/jm00161a014
- Liu, K., & Zhang, S. (2015). Highly efficient synthesis of 1,3-dihydroxy-2-carboxycarbazole and its neuroprotective effects. ACS Medicinal Chemistry Letters, 6(8), 894–897. https://doi.org/https://doi.org/10.1021/acsmedchemlett.5b00158
- Makhaeva, G. F., Kovaleva, N. V., Boltneva, N. P., Lushchekina, S. V., Rudakova, E. V., Stupina, T. S., Terentiev, A. A., Serkov, I. V., Proshin, A. N., Radchenko, E. V., Palyulin, V. V., Bachurin, S. O., & Richardson, R. J. (2020). Conjugates of tacrine and 1,2,4-thiadiazole derivatives as new potential multifunctional agents for Alzheimer's disease treatment: Synthesis, quantum-chemical characterization, molecular docking, and biological evaluation. Bioorganic Chemistry, 94, 103387. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.103387
- Markesbery, W. R. (1997). Oxidative stress hypothesis in Alzheimer’s disease. Free Radical Biology & Medicine, 23(1), 134–147. https://doi.org/https://doi.org/10.1016/S0891-5849(96)00629-6
- Mulla, S. A. R., Pathan, M. Y., Chavan, S. S., Gample, S. P., & Sarkar, D. (2014). Highly efficient one-pot multi-component synthesis of α-aminophosphonates and bis-α-aminophosphonates catalyzed by heterogeneous reusable silica supported dodecatungstophosphoric acid (DTP/SiO2) at ambient temperature and their antitubercular evaluation. RSC Advances, 4(15), 7666–7672. https://doi.org/https://doi.org/10.1039/c3ra45853a
- Narayana Reddy, P., & Padmaja, P. (2015). Applications of aminocarbazoles in heterocyclic synthesis. 2015(1), 244–268. https://doi.org/https://doi.org/10.3998/ark.5550190.p008.822
- Salthouse, T. A. (2004). What and when of cognitive aging. Current Directions in Psychological Science, 13(4), 140–144. https://doi.org/https://doi.org/10.1111/j.0963-7214.2004.00293.x
- Shaikh, S., Dhavan, P., Pavale, G., Ramana, M. M. V., & Jadhav, B. L. (2020a). Design, synthesis and evaluation of pyrazole bearing α-aminophosphonate derivatives as potential acetylcholinesterase inhibitors against Alzheimer's disease. Bioorganic Chemistry, 96, 103589. https://doi.org/https://doi.org/10.1016/j.bioorg.2020.103589
- Shaikh, S., Dhavan, P., Ramana, M. M. V., & Jadhav, B. L. (2020b). Design, synthesis and evaluation of new chromone-derived aminophosphonates as potential acetylcholinesterase inhibitor. Molecular Diversity. https://doi.org/https://doi.org/10.1007/s11030-020-10060-y
- Shi, D. H., Min, W., Song, M. q., Si, X. X., Li, M. C., Zhang, Z. y., Liu, Y. W., & Liu, W. W. (2020). Synthesis, characterization, crystal structure and evaluation of four carbazole-coumarin hybrids as multifunctional agents for the treatment of Alzheimer’s disease. Journal of Molecular Structure, 1209, 127897. https://doi.org/https://doi.org/10.1016/j.molstruc.2020.127897
- Sieńczyk, M., & Oleksyszyn, J. (2009). Irreversible inhibition of serine proteases—Design and in vivo activity of diaryl alpha-aminophosphonate derivatives. Current in Medicinal Chemistry, 16(13), 1673–1687. https://doi.org/https://doi.org/10.2174/092986709788186246
- Singla, S., & Piplani, P. (2016). Coumarin derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies. Bioorganic & Medicinal Chemistry, 24(19), 4587–4599. https://doi.org/https://doi.org/10.1016/j.bmc.2016.07.061
- Sudileti, M., Chintha, V., Nagaripati, S., Gundluru, M., Yasmin, S. H., Wudayagiri, R., & Cirandur, S. R. (2019). Green synthesis, molecular docking, anti-oxidant and anti-inflammatory activities of α-aminophosphonates. Medicinal Chemistry Research, 28(10), 1740–1754. https://doi.org/https://doi.org/10.1007/s00044-019-02411-8
- Sussman, J., Harel, M., Frolow, F., Oefner, C., Goldman, A., Toker, L., & Silman, I. (1991). Atomic structure of acetylcholinesterase from Torpedo californica: A prototypic acetylcholine-binding protein. Science (New York, NY), 253(5022), 872–879. https://doi.org/https://doi.org/10.1126/science.1678899
- Thiratmatrakul, S., Yenjai, C., Waiwut, P., Vajragupta, O., Reubroycharoen, P., Tohda, M., & Boonyarat, C. (2014). Synthesis, biological evaluation and molecular modeling study of novel tacrine-carbazole hybrids as potential multifunctional agents for the treatment of Alzheimer's disease. European Journal of Medicinal Chemistry, 75, 21–30. https://doi.org/https://doi.org/10.1016/j.ejmech.2014.01.020
- Wang, J., Zheng, Y., Efferth, T., Wang, R., Shen, Y., & Hao, X. (2005). Indole and carbazole alkaloids from Glycosmis montana with weak anti-HIV and cytotoxic activities. Phytochemistry, 66 (6), 697–701. https://doi.org/https://doi.org/10.1016/j.phytochem.2005.02.003
- Xie, D., Zhang, A., Liu, D., Yin, L., Wan, J., Zeng, S., & Hu, D. (2017). Synthesis and antiviral activity of novel a-aminophosphonates containing 6-fluorobenzothiazole moiety. Phosphorus, Sulfur, and Silicon and the Related Elements, 192 (9), 1061–1067. https://doi.org/https://doi.org/10.1080/10426507.2017.1323895
- Xu, Y., Zhang, Z., Jiang, X., Chen, X., Wang, Z., Alsulami, H., Qin, H. L., & Tang, W. (2019). Discovery of δ-sultone-fused pyrazoles for treating Alzheimer's disease: Design, synthesis, biological evaluation and SAR studies. European Journal of Medicinal Chemistry, 181, 111598. https://doi.org/https://doi.org/10.1016/j.ejmech.2019.111598
- Zhang, X., Wang, Y., Wang, S. N., Chen, Q., He, Tu, Y., Lin, Yang, X., Hong, Chen, J. k., Yan, J. w., Pi, R. b., & Wang, Y. (2018). Discovery of a novel multifunctional carbazole–aminoquinoline dimer for Alzheimer’s disease: Copper selective chelation, anti-amyloid aggregation, and neuroprotection. Medicinal Chemistry Research, 27(3), 777–784. https://doi.org/https://doi.org/10.1007/s00044-017-2101-9