Click Here

Details



REVIEW ON ISATIN (PREPARATION, REACTIONS, BIOLOGICAL APPLICATIONS, BIO-USES)

Dr. Nagham Mahmood Aljamali, Mohammed Alaa Abdulzahra, Widad Hashim Yahya Almuhana, Dr. Amal Saadoon Majeed

30-39

Vol 11, Jan-Jun, 2020

Date of Submission: 2020-03-16 Date of Acceptance: 2020-04-19 Date of Publication: 2020-04-25

Abstract

This Review touched on the Bio-chemical compound known as isatin, which is known for its Bio-importance and properties in many well-known drugs and pharmacies, as it is considered a basic substance in many bio- compounds and the basic nucleus in bacterial, fungicidal antibodies to its composition derived from the heterocyclic compound indole. Also this survey involved alternative method of preparation ,reactions ,some of its applications in many fields like in drugs, in bacteriology field ,other Bio-applications.

References

  1. Chiyanzu, I. (2003). 'Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain'. Bioorg. Med. Chem. Lett. 13(20): 3527–30. doi:10.1016/S0960-894X(03)00756-X. PMID 14505663
  2. Mallamo, J.P. (2006). 'Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis'. Bioorg. Med. Chem. Lett. 16 (8): 2158–62. doi:10.1016/j.bmcl.2006.01.063. PMID 16460933
  3. He, Y. (2006). 'Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors'. Bioorg. Med. Chem. Lett. 16(8): 2109–12. doi:10.1016/j.bmcl.2006.01.066
  4. He, Y. (2006). 'Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors'. Bioorg. Med. Chem. Lett. 16(8): 2109–12. doi:10.1016/j.bmcl.2006.01.066
  5. Bin-Jubair, F.A.S. (2010). 'Anti-Tubercular activity of Isatin and Derivatives'. Int. J. Res. Pharm. Sci. 1: 113
  6. Vuzquez de Agredos-Pascual, M.L. (2011). 'From Maya Blue to 'Maya Yellow': A Connection between Ancient Nanostructured Materials from the Voltammetry of Microparticles'. Angew. Chem. Int. Ed. 50 (25): 5741–4. doi:10.1002/anie.201100921. PMID 21557419
  7. Sandmeyer, T. (1919). 'ÜberIsonitrosoacetanilide und derenKondensationzuIsatinen'. Helv. Chim. Acta. 2: 234. doi:10.1002/hlca.19190020125.
  8. Ji, S.J. (2014). 'I2/TBHP-Catalyzed Chemoselective Amination of Indoles'. Org. Lett. 16: 3094–3097.
  9. Kirsch, S.F. (2015). 'Synthesis of Isatins through Direct Oxidation of Indoles with IBX-SO3K/NaI'. Synthesis. 47 (13): 1937–1943. doi:10.1055/s-0034-1380517.
  10. Wei, W.T. (2018). 'Synthesis of Indoline-2,3-diones by Radical Coupling of Indolin-2-ones with tert-Butyl Hydroperoxide'. Synlett. 29 (2): 215–218. doi:10.1055/s-0036-1589106.
  11. Majumder, Arpi; Gupta, Ragini; Mandal, Mrinmay; Babu, Madhu; Chakraborty, Debashis (2015). 'Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C–N and C–O coupling reactions'. Journal of Organometallic Chemistry. 781: 23–34. doi:10.1016/j.jorganchem.2014.11.018.
  12. Donald, James R.; Unsworth, William P. ( 2017). 'Ring-Expansion Reactions in the Synthesis of Macrocycles and Medium-Sized Rings'. Chemistry - A European Journal. 23 (37): 8780–8799.
  13. Poomathi, Nataraj; Mayakrishnan, Sivakalai; Muralidharan, Doraiswamy; Srinivasan, Rajagopal; Perumal, Paramasivan T. (2015). 'Reaction of isatins with 6-amino uracils and isoxazoles: isatin ring-opening vs. annulations and regioselective synthesis of isoxazole fused quinoline scaffolds in water'. Green Chemistry. 17 (6): 3362–3372. doi:10.1039/c5gc00006h.
  14. Shi, Rong-Guo; Wang, Xiao-Hua; Liu, Ruzhang; Yan, Chao-Guo (2016). 'Two-carbon ring expansion of isatin: a convenient construction of a dibenzo[b,d]azepinone scaffold'. Chemical Communications. 52 (37): 6280–6283. doi:10.1039/c6cc00525j. PMID 27079548
  15. Bergman, Jan; Stålhandske, Claes; Vallberg, Hans (1997). 'Studies of the Reaction between Indole-2,3-diones (Isatins) and Secondary Aliphatic Amines'(PDF). ActaChemicaScandinavica. 51: 753–759
  16. Yang, Shuangshuang; Li, Xishuai; Hu, Fangfang; Li, Yinlong; Yang, Yunyun; Yan, Junkai; Kuang, Chunxiang; Yang, Qing ( 2013). 'Discovery of Tryptanthrin Derivatives as Potent Inhibitors of Indoleamine 2,3-Dioxygenase with Therapeutic Activity in Lewis Lung Cancer (LLC) Tumor-Bearing Mice'. Journal of Medicinal Chemistry. 56 (21): 8321–8331. doi:10.1021/jm401195n. PMID 24099220.
  17. Bao, Yajie; Yan, Yizhe; Xu, Kun; Su, Jihu; Zha, Zhenggen; Wang, Zhiyong2015). 'Copper-Catalyzed Radical Methylation/C–H Amination/Oxidation Cascade for the Synthesis of Quinazolinones'. The Journal of Organic Chemistry. 80(9): 4736–4742. doi:10.1021/acs.joc.5b00191. PMID 25849218.
  18. Wang, Cuiling; Yan, Jiaxu; Du, Mo; Burlison, Joseph A.; Li, Chi; Sun, Yanni; Zhao, Danqing; Liu,Jianli (2017). 'One step synthesis of indirubins by reductive coupling of isatins with KBH 4'. Tetrahedron. 73 (19): 2780–2785. doi:10.1016/j.tet.2017.03.077
  19. Nagham Mahmood Aljamali., 'The Various Preparation Methods in Synthetic Chemistry'.,1Edt., Evincepub Publishing house, 2019., ISBN :978-93-88277-82-2.
  20. Nagham Mahmood Aljamali. 'Reactions and Mechanisms'.,1 Edt., IJMRA Publication ,2018 .,ISBN : 978- 93-87176-25-6 .
  21. Matheus ME, de Almeida Violante F, Garden SJ. Isatins inhibit cyclooxygenase-2 and inducible nitric oxide synthase in a mouse macrophage cell line. Eur J Pharmacol. 2007; 556 :200–6.
  22. Nagham Mahmood Aljamali .'Experimental Methods for Preparation of Mannich Bases, Formazan, Normal and Cyclic Sulfur Compounds', 1st edition Evince pub Publishing House;2018, ISBN: 978-93-87905-19-1.
  23. Nagham Mahmood Aljamali. 2016. 'Synthesis and Biological Study of Hetero (Atoms and Cycles) Compounds', Der PharmaChemica, 8,6, 40-48.
  24. Imad Kareem Alwan Alsabri, Hasaneen Kudhair Abdullabass, Nagham Mahmood Aljamali., Invention of (Gluta.Sulfazane-Cefixime) Compounds as Inhibitors of Cancerous Tumors., Journal of Cardiovascular Disease Research, 2020,11, 2., 44-55 ., DOI: 10.31838/jcdr.2020.11.02.09 .
  25. Aseel Mahmood Jawad, Nagham Mahmood Aljamali, Saher Mahmood Jwad., Development and Preparation of ciprofloxacin Drug Derivatives for Treatment of Microbial Contamination in Hospitals and Environment, Indian Journal of Forensic Medicine & Toxicology, 2020,14, 2, p:1115-1122.
  26. Mawatari K, Segawa M, Masatsuka R. Fluorimetric determination of isatin in human urine and serum by liquid chromatography postcolumnphotoirradiation. Analyst. 2001;126:33–6.
  27. Medvedev AE, Adamik A, Glover V, et al. Cyclic GMP excretion blocked by isatin administration under conditions of fluid overload. BiochemPharmacol. 2001;62:225–7.
  28. Nagham Mahmood Aljamali., 2015. Synthesis and Chemical Identification of Macro Compounds of (Thiazol and Imidazol)'., Research J. Pharm. and Tech, 8,1, 78-84., DOI: 10.5958/0974-360X.2015.00016.5
  29. 29. Medvedev A, Buneeva O, GnedenkoO .Isatin interaction with glyceraldehydes-3-phosphate dehydrogenase, a putative target of neuroprotective drugs: partial agonism with deprenyl. J Neural Transm. 2006;71(Suppl):97–103
  30. Medvedev A,Byssygina O, Pyatakova N. Effect of isatin on nitric oxide-stimulated soluble guanylatecyclase from human platelets. Biochem Pharmacol. 2002;63:763–6.
  31. Nagham Mahmood Aljamali, Imad Kareem Alwan Alsabri., Development of Trimethoprim Drug and Innovation of Sulfazane-Trimethoprim Derivatives as Anticancer Agents., Biomedical & Pharmacology Journal, March 2020., Vol. 13, (2), p. 613-625 ., http://dx.doi.org/10.13005/bpj/1925 .
  32. Mestaf M, Nawfel Muhammed Baqer Muhsin., NeuroQuantology, 2019.,17,11, 11-16.,10.14704/nq.2019. 17.11.NQ19108.
  33. Miad Mohmed, Nagham Mahmood Aljamali, Sabreen Ali Abdalrahman.,Wassan Ala Shubber ., 'Formation of Oxadiazole Derivatives Ligands from Condensation and Imination Reaction with References To Spectral Investigation, Thermal and Microbial Assay'., Biochem. Cell. Arch., 2018 ,18, 1, pp. 847-853.
  34. Nagham Mahmood Aljamali.,Synthesis of Antifungal Chemical Compounds from Fluconazole with (Pharma-Chemical) Studying, Research journal of Pharmaceutical, biological and chemical sciences, 2017, 8 (3), 564 -573.
  35. Mehta SL, Manhas N, Raghubiz R. Molecular targets in cerebral ischemia for developing novel therapeutics . Brain Res Rev. 2007;54:34–66
  36. Nawfel Muhammed Baqer Muhsin, Hayder H K, Noor H D, Nagham Mahmood Aljamali., 'Preparation of Chemical Inhibitors to Treat the Corrosion and Erosion of Machines', International Journal of Engineering, Applied and Management Sciences Paradigms.,2019, 54,3,89-93
  37. Meaad M, Nagham Mahmood Aljamali, Nadheema A A .,'Preparation, Spectral Investigation, Thermal Analysis, Biochemical Studying of New (Oxadiazole -Five Membered Ring)-Ligands'.,Journal of Global Pharmacy Technology,2018;10,1,20-29.
  38. Ramasubbu N, Parthasarathy R. Short S…O contacts: structure of 2,5-bis(p-methoxyphenylhydroxymethyl)thiophene. ActaCrystallogr C. 1989;45:457–460. doi: 10.1107/S0108270188010728
  39. Pirrung MC, Panasare SV, Sarma KD, et al. Combinatorial optimization of isatin-beta-thiosemicarbazones as anti-poxvirus agents. J Med Chem. 2005;48:3045–50.
  40. Potter DE, Russell KR, Manhiani M. Bremazocine increases C-type natriuretic peptide levels in aqueous humor and enhances outflow facility. J PharmacolExpTher. 2004;309:548–53
  41. Potter LR, Abbey-Hosch S, Dickey DM. Natriuretic peptides, their receptors, and cyclic guanosine monophosphate-dependent signaling functions. Endocrine Rev. 2006;27:47–72
  42. Reeve JL, Duffy AM, O’Brien T, et al. Don’t lose heart – therapeutic value of apoptosis prevention in the treatment of cardiovascular disease. J Cell Mol Med. 2005;9:609–22
  43. Reinoso RF, Telfer BA, Rowland M. Tissue water content in rats measured by desiccation. J PharmacolToxicol Methods. 1997;38:87–92
  44. Rose CD, Martin TM. Caspase recruitment domain 15 mutations and rheumatic diseases. CurrOpinRheumatol . 2005;17:579–85
  45. Rowell EA, Wells AD. The role of cyclin-dependent kinases in T-cell development, proliferation, and function. Crit Rev Immunol. 2006;26:189–212
  46. Sandler M, Przyborowska A, Halket J, et al. Urinary but not brain isatin levels are reduced in germ-free rats. J Neurochem. 1991;57:1074–5
  47. Senderowicz AM. Novel small molecule cyclin-dependent kinases modulators in human clinical trials. Cancer BiolTher. 2003;2:S84–95
  48. Shimizu T, Uehara T, Nomura Y. Possible involvement of pyruvate kinase in acquisition of tolerance to hypoxic stress in glial cells. J Neurochem. 2004;91:167–75
  49. Shuttleworth SJ, Nasturica D, Gervais CM, et al. Parallel synthesis of isatin-based serine protease inhibitors. Bioorg Med Chem Let. 2000;10:2501–4
  50. Siegel RM. Caspases at the crossroads of immune-cell life and death. Natl Rev Immunol. 2006;6:308–17
  51. Silberbach M, Roberts CT., Jr Natriuretic peptide signalling: molecular and cellular pathways to growth regulation. Cell Signal. 2001;13:221–31
  52. Nagham Mahmood Aljamali, Rabab Mahdi Ubaid Mahmood, Rana Neama Atiya ,Fatimah A. Wannas, Rabab M U M . Review on preparation methods & application fields of oxadiazole., International Journal of Chemical Synthesis and Chemical Reactions, 2020, 6, 1.
  53. Nagham Mahmood Aljamali.,'Review on (Azo, Formazane, Sulfazane)-Compounds', International Journal of Innovations in Scientific Engineering, Vol. 11, Issue.,2020.
  54. Sriram D, Bal TR, Yogeeswari P. Design, synthesis and biological evaluation of novel non-nucleoside HIV-1 reverse transcriptase inhibitors with broad-spectrum chemotherapeutic properties. Bioorg Med Chem. 2004;12:5865–73
  55. Sriram D, Bal TR, Yogeeswari Pl. Aminopyrimidiniminoisatin analogues: Design of novel nonnucleoside HIV-1 reverse transcriptase inhibitors with broad-spectrum chemotherapeutic properties. J Pharm Pharmaceut Sci. 2005;8:565–77.
  56. Usami K, Kitahara K, Ishikura S, et al. Characterization of a major form of human isatin reductase and the reduced metabolite. Eur J Biochem. 2001; 268:5755–63.
  57. Verma M, Pandeya SN, Singh KN, et al. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharm. 2004; 54:49–56
  58. Vermeulen K, Van Bockstaele DR, Beznerman ZN. Apoptosis: mechanisms and relevance in cancer. Ann Hematol. 2005;84:627–39.
  59. Nemah SMH, Kadhium AJ, Wannas FA, Nagham Mahmood Aljamali, Nemah Sahib Mohammed Husien,. (2020). Novel Formazane Reagents and Ligands (Preparation, Spectral Characterization, Scanning Microscopy, Chromatographic Separation). Prensa Med Argent, Volume 106, 6, 303.
  60. Vértessy BG, Bánkfalvi D, Kovács J, et al. Piruvate kinase as a microtubule destabilizing factor in vitro. Biochem Biophys Res Commu. 1999;254:420–35
  61. Wanga QM, Chen SH. Human rhinovirus 3C protease as a potential target for the development of antiviral agents. Curr Protein Pept Sci. 2007;8:19–27
  62. Watkins P, Clow A, Glover V, et al. Isatin, regional distribution in rat brain and tissues. Neurochem Int. 1990;17:321–3.
  63. Webber SE, Tikhe J, Wozland ST, et al. Design, synthesis and evaluation of nonpeptidic inhibitors of human rhinovirus 3C protease. J Med Chem. 1996;39:5072–82.
  64. Wells AD. Cyclin-dependent kinases: molecular switches controlling anergy and potential therapeutic targets for tolerance. Seminars in Immunology. 2007;19:173–9
  65. Wiedemann K, Jahn H, Kellner M. Effects of natriuretic peptides upon hypothalamo–pituitary–adrenocortical system activity and anxiety behaviour. ExpClinEndocrinol Diabetes. 2000;108:5–13
  66. Nagham Mahmood Aljamali, Rabab Mahdi Ubaid Mahmood, Radhiyahabdul Baqialdujaili, Rana Neama Atiya. Review on Preparation and Application Fields of Triazole & Tetrazole Derivatives. International Journal of Analytical and Applied Chemistry. 2020; 6(1): 50–60p.
  67. Yamada K, Noguchi T. Nutrient and hormonal regulation of pyruvate kinase gene expression. Biochem J. 1999;337:1–11
  68. Yang XM, Downey JM, Cohen MV. Atrial natriuretic peptide administered just prior to reperfusion limits infarction in rabbit hearts. Basic Res Cardiol. 2006;101:311–18
  69. Yi M-K, Schultz DE, Lemon SM. Functional significance of the interaction of hepatitis A virus RNA with glyceraldehyde 3-phosphate dehydrogenase (GAPDH): Opposing effects of GAPDH and polypyrimidine tract binding protein on internal ribosome entry site function. J Virol. 2000;74:6459–68
  70. Yost C, Torres M, Miller JR, et al. The axis-inducing activity, stability and subcellular distribution of beta-catenin is regulated in Xenopus embryos by glycogen synthase kinase 3. Genes Dev. 1996;10:1443–54.
  71. Yuan J, Yankner BA. Apoptosis in the nervous system. Nature. 2000; 407:802–9
  72. Yury EC, Kabouridis PS, Abba A, et al. Increased ubiquitination and reduced expression of LCK in T lymphocytes from patients with systemic lupus erythematosus. Arthritis Rheum. 2003;48:1343–54
  73. Anand-Srivastava MB, Trachte GJ. Atrial natriuretic factor receptors and signal transduction mechanisms. Pharmacol Rev. 1993;45:455–97.
  74. Benford HL, McGavan NW, Helfrich MH, et al. Visualization of bisphosphonate-induced caspase-3 activity in apoptotic osteoclasts in vitro. Bone. 2001;28:465–73.
  75. Berry MD. Glyceradehyde-3-phosphate dehydrogenase as a target for small-molecule disease-modifying therapies in human neurodegenerative disorders. J Psychiatry Neurosci. 2004;29:337–45
  76. Bhattacharya SK, Chakrabati A, Sandler M, et al. Effects of some anxiogenic agents on rat brain monoamine oxidase (MAO) A and B inhibitory (tribulin) activity. Indian J Exp Biol. 1996a;34:1190–3
  77. Bhattacharya SK, Chakrabati A, Sandler M, et al. Anxiolytic activity of intraventriculary administered atrial natriuretic peptide in the rat. Neuropsychopharmacology. 1996b;15:199–206
Download PDF
Back