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References
- 1. S. K. Sridhar and A. Ramesh, Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives, Biol. Pharm. Bull. 24 (2001) 1149–1152; https://doi.org/10.1248/bpb.24.114910.1248/bpb.24.114911642321
- 2. M. Verma, S. N. Pandeya, K. N. Singh and J. P. Stables, Anticonvulsant activity of Schiff bases of isatin derivatives, Acta Pharm. 59 (2004) 49–56.
- 3. A. K. Ádám, S. Grzegorz, J. B. Andrzej and M. K. György, Spiro[pyrrolidine-3,3′-oxindoles] and their indoline analogs as new 5-HT6 receptor chemotypes, Molecules 22 (2017) Article ID 2221; https://doi.org/10.3390/molecules2212222110.3390/molecules22122221614975129240714
- 4. E. Siddalingamurthy, K. M. Mahadevan, N. M. Jagadeesh and M. N. Kumara, Synthesis and docking study of 3-(N-alkyl/aryl piperidyl) indoles with serotonin-5HT, H1 and CCR2 antagonist receptors, Int. J. Pharm. Pharm. Sci. 6 (2014) 475–482.
- 5. N. Karal, A. Gursoy, F. Kandemirli, N. Shvets, F. B. Kaynak, S. Ozbey, V. Kovalishyn and A. Dimoglo, Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives, Bioorg. Med. Chem. 15 (2007) 5888–5904; https://doi.org/10.1016/j.bmc.2007.05.06310.1016/j.bmc.2007.05.06317561405
- 6. Q. Xu, L. Huang, J. Liu, L. Ma, T. Chen, J. Chen, F. Peng, D. Cao, Z. Yang, N. Qiu, J. Qiu, G. Wang, X. Liang, A. Peng, M. Xiang, Y. Wei and L. Chen, Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes, Eur. J. Med. Chem. 52 (2012) 70–81; https://doi.org/10.1016/j.ejmech.2012.03.00610.1016/j.ejmech.2012.03.00622483089
- 7. A. I. Hashem, A. S. Youssef, K. A. Kandeel and W. S. Abou-Elmagd, Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity, Eur. J. Med. Chem. 42 (2007) 934–939; https://doi.org/10.1016/j.ejmech.2006.12.03210.1016/j.ejmech.2006.12.03217321008
- 8. P. Kumar, S. Singh and M. R. F. Pratama, Synthesis of some novel 1H-indole derivatives with antibacterial activity and antifungal activity, Lett. App. NanoBioSci. 9 (2020) 961–967; https://doi.org/10.33263/LIANBS92.96196710.33263/LIANBS92.961967
- 9. R. V. Singh, N. Fahmi and M. K. Biyala, Coordination behavior and biopotency of N and S/O donor ligands with their palladium(II) and platinum(II) complexes, J. Iranian Chem. Soc. 40 (2005) 40–46; https://doi.org/https://doi.org/10.1007/BF0324577810.1007/BF03245778
- 10. K. Meenakshi, G. Sammaiah, M. Sarangapani and R. J. Venkateswar, Synthesis and antimicrobial activity of 1-N-piperidinomethyl isatin-3-[N-(quinolin-8-yloxy) acetyl] hydrazones, Indian J. Heterocycl. Chem. 16 (2006) 21–24.
- 11. W. Hong, J. Li, Z. Chang, X. Tan, H. Yang, Y. Ouyang, Y. Yang, S. Kaur, I. C. Paterson, Y. F. Ngeow and H. Wang, Synthesis and biological evaluation of indole core-based derivatives with potent antibacterial activity against resistant bacterial pathogens, J. Antibiot. 70 (2017) 832–844; https://doi.org/10.1038/ja.2017.5510.1038/ja.2017.5528465626
- 12. M. Taha, E A. J. Aldhamin, N. B. Almandil, El H. Anouar, N. Uddin, M. Alomari, F. Rahim, B. Adalat, M. Ibrahim, F. Nawaz, N. Iqbal, B. Alghanem, A. Altolayyan and K. M. Khan, Synthesis of indole based acetohydrazide analogs: Their in vitro and in silico thymidine phosphorylase studies, Bioorg. Chem. 98 (2020) Article ID 103745; https://doi.org/10.1016/j.bioorg.2020.10374510.1016/j.bioorg.2020.10374532200327
- 13. T. Tokunaga, H. W. Ewan, T. Umezome, K. Okazaki, Y. Ueki, K. Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji, H. Noguchi and R. Nagata, Oxindole derivatives as orally active potent growth hormone secretagogues, J. Med. Chem. 44 (2001) 4641–4649; https://doi.org/10.1021/jm010376310.1021/jm010376311741481
- 14. T. Tokunaga, H. W. Ewan, J. Nagamine and R. Nagata, Structure-activity relationships of the oxindole growth hormone secretagogues, Bioorg. Med. Chem. Lett. 15 (2005) 1789–1792; https://doi.org/10.1016/j.bmcl.2005.02.04210.1016/j.bmcl.2005.02.042
- 15. P. E. Romo, B. Insuasty, R. Abonia, M. del Pilar Crespo and J. Quiroga, Synthesis of new oxindoles and determination of their antibacterial properties, Heteroatom Chem. 2020 (2020) Article ID 8021920 (9 pages); https://doi.org/10.1155/2020/802192010.1155/2020/8021920
- 16. K. N. Aneesrahman, K. Ramaiah, G. Rohini, G. P. Stefy, N. S. P. Bhuvanesh and A. Sreekanth, Synthesis and characterisations of copper(II) complexes of 5-methoxyisatin thiosemicarbazones: Effect of N-terminal substitution on DNA/protein binding and biological activities, Inorg. Chim. Acta 492 (2019) 131–141; https://doi.org/10.1016/j.ica.2019.04.01910.1016/j.ica.2019.04.019
- 17. A. A. El-Gendy and A. M. Ahmed, Synthesis and antimicrobial activity of some new 2-indolinone derived oximes and spiro-isoxazolines, Arch. Pharm. Res. 23 (2000) 310–314; https://doi.org/10.1007/bf0297543910.1007/BF02975439
- 18. A. L. Davis, D. R. Smith and T. J. McCord, Synthesis and microbiological properties of 3-amino-1-hydroxy-2-indolinone and related compounds, J. Med. Chem. 16 (1973) 1043–1045; https://doi.org/10.1021/jm00267a02010.1021/jm00267a020
- 19. O. Sureyya and O. Z. Semiha, A Study of 3-substituted benzylidene-1,3-dihydro-indoline derivatives as antimicrobial and antiviral agents, Z. Naturforsch. C 64c (2009) 155–162; https://doi.org/10.1515/znc-2009-3-40110.1515/znc-2009-3-401
- 20. C. K. Ryu, J. Y. Lee, R. E. Park, M. Y. Ma and J. H. Nho, Synthesis and antifungal activity of 1H-indole-4,7-diones, Bioorg. Med. Chem. Lett. 17 (2007) 127–131; https://doi.org/10.1016/j.bmcl.2006.09.07610.1016/j.bmcl.2006.09.076
- 21. R. Hoessel, S. Leclerc, J. A. Endicott, M. E. Nobel, A. Lawrie, P. Tunnah, M. Leost, E. Damiens, D. Marie, D. Marko, E. Niederberger, W. Tang, G. Eisenbrand and L. Meijer, Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases, Nat. Cell Biol. 60 (1999) 60–67; https://doi.org/10.1038/903510.1038/9035
- 22. R. Han, Highlight on the studies of anticancer drugs derived from plants in China, Stem Cells 12 (1994) 53–63; https://doi.org/10.1002/stem.553012011010.1002/stem.5530120110
- 23. H. P. Zhang, Y. Kamano, Y. Ichihara, H. Kizu, K. Komiyama, H. ltokawa and G. R. Pettit, Isolation and structure of convolutamydines B – D from marine bryozoan Amathia convolute, Tetrahedron 51 (1995) 5523–5528; https://doi.org/10.1016/0040-4020(95)00241-Y10.1016/0040-4020(95)00241-Y
- 24. A. Abdel-Rahman, E. Keshk, M. Hanna and S. El-Bady, Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents, Bioorg. Med. Chem. 12 (2004) 2483–2488; https://doi.org/10.1016/j.bmc.2003.10.06310.1016/j.bmc.2003.10.06315080944
- 25. S. Rajeev, S. P. Siva, K. Leena, K. Shilpi and C. J. Subhash, Design and synthesis of spiro[indolethiazolidine]spiro[indole-pyrans] as antimicrobial agents, Bioorg. Med. Chem. Lett. 21 (2011) 5465–5469; https://doi.org/10.1016/j.bmcl.2011.06.12110.1016/j.bmcl.2011.06.12121782421
- 26. P. Maryam, A. Sakineh, and M. Mojtaba, Synthesis and antibacterial evaluation of novel spiro[indole-pyrimidine]ones, J. Heterocycl. Chem. 55 (2018) 173–180; https://doi.org/10.1002/jhet.302110.1002/jhet.3021
- 27. T. Kitayama, R. Iwabuchi, S. Minagawa, S. Sawada, R. Okumura, K. Hoshino, J. Cappiello and R. Utsumi, Synthesis of a novel inhibitor against MRSA and VRE: preparation from zerumbone ring opening material showing histidine-kinase inhibition, Bioorg. Med. Chem. Lett. 17 (2007) 1098–1101; https://doi.org/10.1016/j.bmcl.2006.11.01510.1016/j.bmcl.2006.11.01517157007
- 28. A. M. Stock, V. L. Robinson and P. N. Goudreau, Two-component signal transduction, Annu. Rev. Biochem. 69 (2000) 183–215; https://doi.org/10.1146/annurev.biochem.69.1.18310.1146/annurev.biochem.69.1.18310966457
- 29. R. Gao, and A. M. Stock, Biological insights from structures of two-component proteins, Annu. Rev. Microbiol. 63 (2009) 133–154; https://doi.org/10.1146/annurev.micro.091208.07321410.1146/annurev.micro.091208.073214364527419575571
- 30. K. E. Wilke and E. E. Carlson, All signals lost, Sci. Transl. Med. 5 (2013) Article ID 203ps12; https://doi.org/10.1126/scitranslmed.300667010.1126/scitranslmed.3006670448037024048521
- 31. A. E. Bem, N. Velikova, M. T. Pellicer, P. V. Baarlen, A. Marina and J. M. Wells, Bacterial histidine kinases as novel antibacterial drug targets, ACS Chem Biol. 10 (2015) 213–224; https://doi.org/10.1021/cb500713510.1021/cb500713525436989
- 32. A. A. Radwan and W. Abdel-Mageed, In silico studies of quinoxaline-2-carboxamide 1,4-di-n-oxide derivatives as antimycobacterial agents, Molecules 19 (2014) 2247–2260; https://doi.org/10.3390/molecules1902224710.3390/molecules19022247627188224566302
- 33. A. A. Radwan, F. K. Alanazi and M. H. Al-Agami, 1,3,4-Thiadiazole and 1,2,4-triazole-3(4H)-thione bearing salicylate moiety: synthesis and evaluation as anti-Candida albicans, Braz. J. Pharm. Sci. 53 (2017) e15239; https://doi.org/10.1590/s2175-9790201700011523910.1590/s2175-97902017000115239
- 34. T. Abul-Fadl, A. A. Radwan, H. A. Abdel-Aziz, B. Mohamed, I. A. Mohamad, K. Adnan, Novel Schiff bases of indoline-2,3-dione and nalidixic acid hydrazide: synthesis, in vitro antimycobacterial and in silico Mycobacterium tuberculosis (mtb) DNA gyrase inhibitory activity, Dig. J. Nanomater. Bios. 7 (2012) 329–336.
- 35. T. Aboul-Fadl, A. A. Radwan, M. I. Attia, A. Al-Dhfyan and H. A. Abdel-Aziz, Schiff bases of indoline-2,3-dione (isatin) with potential antiproliferative activity, Chem. Cent. J. 6 (2012) Article ID 49; https://doi.org/10.1186/1752-153X-6-4910.1186/1752-153X-6-49
- 36. A. A. Radwan, Structure-based virtual screening for novel EGFR kinase inhibitors using the zinc database, Lat. Am. J. Pharm. 34 (2015) 1107–1112.
- 37. A. A. Radwan, F. Al-Mohanna, F. K. Alanazi, P. S. Manogaran and A. Al-Dhfyan, Bioorg. Med. Chem. Lett. 26 (2016) 1664–1670; https://doi.org/10.1016/j.bmcl.2016.02.06410.1016/j.bmcl.2016.02.064
- 38. A. A. Radwan and F. K. Alanazi, In silico studies on novel inhibitors of MERS-CoV: Structure-based pharmacophore modeling, database screening and molecular docking, Trop. J. Pharm. Res. 17 (2018) 513–517; https://doi.org/http://dx.doi.org/10.4314/tjpr.v17i3.1810.4314/tjpr.v17i3.18
- 39. M. Kuroda, T. Ohta, I. Uchiyama, T. Baba, H. Yuzawa, I. Kobayashi, L. Cui, A. Oguchi, K. Aoki, Y. Nagai, J.-Q. Lian, T. Ito, M. Kanamori, H. Matsumaru, A. Maruyama, H. Murakami, A. Hosoyama, Y. Mizutani-Ui and K. Hiramatsu, Whole genome sequencing of methicillin resistant Staphylococcus aureus, Lancet 357 (2001) 1225–1240; https://doi.org/10.1016/S0140-6736(00)04403-210.1016/S0140-6736(00)04403-2
- 40. C. Camacho, G. Coulouris, V. Avagyan, N. Ma, J. Papadopoulos, K. Bealer and T. L. Madden, BLAST+: architecture and applications, BMC Bioinform. 10 (2009) 421–430; https://doi.org/10.1186/1471-2105-10-42110.1186/1471-2105-10-421
- 41. F. András and A. Sali, Modeller: generation and refinement of homology-based protein structure models, Meth. Enzymol. 374 (2003) 461–491; https://doi.org/10.1016/S0076-6879(03)74020-810.1016/S0076-6879(03)74020-8
- 42. P. T. Lang, S. R. Brozell, S. Mukherjee, E. F. Pettersen, E. C. Meng, V. Thomas, R. C. Rizzo, D. A. Case, T. L. James and I. D. Kuntz, DOCK 6: combining techniques to model RNA-small molecule complexes, RNA 15 (2009) 1219–1230; https://doi.org/10.1261/rna.156360910.1261/rna.1563609268551119369428
- 43. Y. Cai, M. Su, A. Ahmad, X. Hu, J. Sang, L. Kong, X. Chen, C. Wang, J. Shuai and A. Han, Conformational dynamics of the essential sensor histidine kinase WalK, Acta Crystallogr. D 73 (2017) 793–803; https://doi.org/10.1107/S205979831701304310.1107/S2059798317013043563390528994408
- 44. E. Geisinger, E. A. George, J. Chen, T. W. Muir and R. P. Novick, Identification of ligand specificity determinants in AgrC, the Staphylococcus aureus quorum-sensing receptor, J. Biol. Chem. 283 (2008) 8930–8938; https://doi.org/10.1074/jbc.M71022720010.1074/jbc.M710227200227637118222919