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Yıl 2021, Cilt 8, Sayı 4, 1089 - 1098, 30.11.2021
https://doi.org/10.18596/jotcsa.962260

Öz

Kaynakça

  • 1. Prudhomme M. Advances in Anticancer Agents in Medicinal Chemistry. [Internet]. Sharjah: Bentham Science Publishers; 2013 [cited 2021 Sep 24]. .
  • 2. Cândido-Bacani P de M, Reis MB dos, Serpeloni JM, Calvo TR, Vilegas W, Varanda EA, et al. Mutagenicity and genotoxicity of isatin in mammalian cells in vivo. Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 2011 Feb;719(1–2):47–51. .
  • 3. Silva JFM da, Garden SJ, Pinto AC. The chemistry of isatins: a review from 1975 to 1999. J Braz Chem Soc. 2001 Jun;12(3):273–324.
  • 4. Borad MA, Bhoi MN, Prajapati NP, Patel HD. Review of Synthesis of Multispiro Heterocyclic Compounds from Isatin. Synthetic Communications. 2014 Apr 18;44(8):1043–57.
  • 5. Ramakrishna Reddy K, Mahendra K. N. Synthesis of 3-[(Z)-5-Amino-1, 3, 3-trimethyl cyclohexyl methylimino]-1, 3-dihydroindol-2-one as a novel Schiff base. Molbank. 2006 Dec 1;2006(6):M517.
  • 6. Singh GS, Desta ZY. Isatins As Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks. Chem Rev. 2012 Nov 14;112(11):6104–55.
  • 7. Varun V, Sonam S, Kakkar R. Isatin and its derivatives: a survey of recent syntheses, reactions, and applications. Med Chem Commun. 2019;10(3):351–68.
  • 8. Khan FA, Maalik A. Advances in Pharmacology of Isatin and its Derivatives: A Review. Trop J Pharm Res. 2015 Nov 6;14(10):1937.
  • 9. Chiyanzu I, Hansell E, Gut J, Rosenthal PJ, McKerrow JH, Chibale K. Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain. Bioorganic & Medicinal Chemistry Letters. 2003 Oct;13(20):3527–30.
  • 10. Ali R, Gilani A-H, Choudhary M, Aftab K, Sener B, Turkoz S. Isolation of Antihypertensive Alkaloids from the Rhizomes of Veratrum album. Planta Med. 1993 Dec;59(06):569–71.
  • 11. Kapadia GJ, Shukla YN, Basak SP, Sokoloski EA, Fales HM. The melosatins—a novel class of alkaloids from melochia tomentosa. Tetrahedron. 1980 Jan;36(17):2441–7.
  • 12. Shaaban KA, Shaaban M, Nair V, Schuhmann I, Win HY, Lei L, et al. Structure elucidation and synthesis of hydroxylated isatins from Streptomycetes. Zeitschrift für Naturforschung B. 2016 Dec 1;71(12):1191–8.
  • 13. Benkendorff K, Bremner J, Davis A. Indole Derivatives from the Egg Masses of Muricid Molluscs. Molecules. 2001 Jan 16;6(12):70–8.
  • 14. Mamedova YV, Hasanova AE, Gasimova SZ, Huseynova RA, Mamedov IG. Some isatin based synthesis. New Materials, Compounds and Applications. 2020;4(1):16–9.
  • 15. Kumar M, Ramasamy K, Mani V, Mishra RK, Majeed ABA, Clercq ED, et al. Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides. Arabian Journal of Chemistry. 2014 Sep;7(4):396–408.
  • 16. Havrylyuk D, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R. Synthesis of New 4-Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity. J Med Chem. 2012 Oct 25;55(20):8630–41.
  • 17. Raj R, Singh P, Singh P, Gut J, Rosenthal PJ, Kumar V. Azide-alkyne cycloaddition en route to 1 H -1,2,3-triazole-tethered 7-chloroquinoline-isatin chimeras: Synthesis and antimalarial evaluation. European Journal of Medicinal Chemistry. 2013 Apr;62:590–6.
  • 18. Paul BK, Ray D, Guchhait N. Unraveling the binding interaction and kinetics of a prospective anti-HIV drug with a model transport protein: results and challenges. Phys Chem Chem Phys. 2013;15(4):1275–87.
  • 19. Kiran G, Maneshwar T, Rajeshwar Y, Sarangapani M. Microwave-Assisted Synthesis, Characterization, Antimicrobial and Antioxidant Activity of Some New Isatin Derivatives. Journal of Chemistry. 2013;2013:1–7.
  • 20. Prakash CR, Raja S, Saravanan G. Design and synthesis of 4-(1-(4-chlorobenzyl)-2,3-dioxoindolin-5-yl)-1-(4-substituted/unsubstituted benzylidene) semicarbazide: Novel agents with analgesic, anti-inflammatory and ulcerogenic properties. Chinese Chemical Letters. 2012 May;23(5):541–4.
  • 21. Khan KM, Karim A, Ambreen N, Saied S, Rasheed S, Perveen S, et al. Synthesis of benzoxazoles derivatives: Antiglycation activity. Journal of Pharmacy Research. 2012;5(1):664–5.
  • 22. Medvedev A, Buneeva O, Gnedenko O, Fedchenko V, Medvedeva M, Ivanov Y, et al. Isatin interaction with glyceraldehyde-3-phosphate dehydrogenase, a putative target of neuroprotective drugs: partial agonism with deprenyl. In: Parvez H, Riederer P, editors. Oxidative Stress and Neuroprotection [Internet]. Vienna: Springer Vienna; 2006 [cited 2021 Sep 24]. p. 97–103. (Journal of Neural Transmission. Supplementa; vol. 71). .
  • 23. Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, et al. New isatin derivatives with antioxidant activity. European Journal of Medicinal Chemistry. 2010 Apr;45(4):1374–8.
  • 24. Kumar K, Carrère-Kremer S, Kremer L, Guérardel Y, Biot C, Kumar V. 1 H -1,2,3-Triazole-Tethered Isatin–Ferrocene and Isatin–Ferrocenylchalcone Conjugates: Synthesis and in Vitro Antitubercular Evaluation. Organometallics. 2013 Oct 28;32(20):5713–9.
  • 25. Jarrahpour A, Khalili D, De Clercq E, Salmi C, Brunel J. Synthesis, Antibacterial, Antifungal and Antiviral Activity Evaluation of Some New bis-Schiff Bases of Isatin and Their Derivatives. Molecules. 2007 Aug 7;12(8):1720–30.
  • 26. Saravanan G, Alagarsamy V, Dineshkumar P. Anticonvulsant activity of novel 1-(morpholinomethyl)-3-substituted isatin derivatives. Bulletin of Faculty of Pharmacy, Cairo University. 2014 Jun;52(1):115–24.
  • 27. Rane RA, Napahde S, Bangalore PK, Sahu NU, Shah N, Kulkarni YA, et al. Synthesis and Evaluation of Novel Marine Bromopyrrole Alkaloid-Based Derivatives as Potential Antidepressant Agents. Chem Biol Drug Des. 2014 Nov;84(5):593–602.
  • 28. Ibrahim S, Elsaman T. Cytotoxic and Anticancer Activities of Indoline-2,3-dione (Isatin) and Its Derivatives. JPRI. 2018 Feb 27;21(2):1–19.
  • 29. Lelyukh M, Havrylyuk D, Lesyk R. Synthesis and anticancer activity of isatin, oxadiazole and 4-thiazolidinone based conjugates. Chemistry & Chemical Technology. 2015;9(1):29–36. .
  • 30. Thakur RK, Joshi P, Upadhyaya K, Singh K, Sharma G, Shukla SK, et al. Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents. European Journal of Medicinal Chemistry. 2019 Jan;162:448–54.
  • 31. Quraishi MA, Ahamad I, Singh AK, Shukla SK, Lal B, Singh V. N-(Piperidinomethyl)-3-[(pyridylidene)amino]isatin: A new and effective acid corrosion inhibitor for mild steel. Materials Chemistry and Physics. 2008 Dec;112(3):1035–9.
  • 32. Prakash CR, Raja S. Design, synthesis and antiepileptic properties of novel 1-(substituted benzylidene)-3-(1-(morpholino/piperidino methyl)-2,3-dioxoindolin-5-yl)urea derivatives. European Journal of Medicinal Chemistry. 2011 Dec;46(12):6057–65.
  • 33. Kang I-J, Wang L-W, Hsu T-A, Yueh A, Lee C-C, Lee Y-C, et al. Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors. Bioorganic & Medicinal Chemistry Letters. 2011 Apr;21(7):1948–52.
  • 34. Medvedev A, Igosheva N, Crumeyrolle-Arias M, Glover V. Isatin: Role in stress and anxiety: Review. Stress. 2005 Jan;8(3):175–83.
  • 35. Kandasamy R, Park SJ, Boyapalle S, Mohapatra S, Hellermann GR, Lockey RF, et al. Isatin down-regulates expression of atrial natriuretic peptide receptor A and inhibits airway inflammation in a mouse model of allergic asthma. International Immunopharmacology. 2010 Feb;10(2):218–25.
  • 36. Bogdanov AV, Zaripova IF, Voloshina AD, Sapunova AS, Kulik NV, Bukharov SV, et al. Synthesis and Biological Evaluation of New Isatin‐Based QACs with High Antimicrobial Potency. ChemistrySelect. 2019 May 31;4(20):6162–6.
  • 37. Blumenthal GM, Cortazar P, Zhang JJ, Tang S, Sridhara R, Murgo A, et al. FDA Approval Summary: Sunitinib for the Treatment of Progressive Well‐Differentiated Locally Advanced or Metastatic Pancreatic Neuroendocrine Tumors. The Oncologist. 2012 Aug;17(8):1108–13.
  • 38. Houk BE, Bello CL, Kang D, Amantea M. A Population Pharmacokinetic Meta-analysis of Sunitinib Malate (SU11248) and Its Primary Metabolite (SU12662) in Healthy Volunteers and Oncology Patients. Clin Cancer Res. 2009 Apr 1;15(7):2497–506.
  • 39. Ristovska N, Anastasova F, Stefova M. N"-[(3Z)-1-Acetyl-5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]thiocarbonohydrazide. Molbank. 2013 Apr 16;2013(2):M798.
  • 40. Gassman P, Cue, Jr. B, Luh T-Y. A General Method for the Synthesis of Isatins. J Org Chem. 1977;42(8):1344–8. .
  • 41. Klein LL, Tufano MD. Synthesis of substituted isatins. Tetrahedron Letters. 2013 Feb;54(8):1008–11. .
  • 42. Mathur G, Nain S. Recent advancement in synthesis of isatin as anticonvulsant agents: a review. Med Chem. 2014;4(4):417–27.
  • 43. Raghavender Reddy M, Nageswara Rao N, Ramakrishna K, Meshram HM. I2–DMSO promoted intramolecular oxidative cyclization of 2-(aryl or alkyl amino)-acetophenones for the synthesis of isatins. Tetrahedron Letters. 2014 Aug;55(34):4758–62.
  • 44. Sonawane RP, Tripathi RR. The chemistry and synthesis of 1H-indole-2, 3-dione (Isatin) and its derivatives. International Letters of Chemistry, Physics and Astronomy. 2013;7.
  • 45. Rewcastle GW, Sutherland HS, Weir CA, Blackburn AG, Denny WA. An improved synthesis of isonitrosoacetanilides. Tetrahedron Letters. 2005 Dec;46(50):8719–21.
  • 46. Vandana K, Marathakam A, Thushara B, Rajitha K. A Review on Isatin Derivatives With Diverse Biological Activites. World Journal of Pharmaceutical Research. 2017;6:318–32.
  • 47. Demchuk DV, Elinson MN, Nikishin GI. ‘On water’Knoevenagel condensation of isatins with malononitrile. Mendeleev Communications. 2011;4(21):224–5.
  • 48. Khorshidi A, Tabatabaeian K. An ultrasound-promoted green approach for the synthesis of 3-(indol-3-yl)-3-hydroxyindolin-2-ones catalyzed by Fe(III). J Serb Chem Soc. 2011;76(10):1347–53.
  • 49. Elinson MN, Merkulova VM, Ilovaisky AI, Barba F, Batanero B. Electrocatalytic tandem Knoevenagel–Michael addition of barbituric acids to isatins: Facile and efficient way to substituted 5,5′-(2-oxo-2,3-dihydro-1H-indole-3,3-diyl)bis(pyrimidine-2,4,6-(1H,3H,5H)-trione) scaffold. Electrochimica Acta. 2011 Oct;56(24):8219–23.
  • 50. Meshram HM, Ramesh P, Sanjeeva Kumar A, Swetha A. An efficient and environmentally friendly DABCO catalyzed Henry reaction of isatins. Tetrahedron Letters. 2011 Nov;52(44):5862–4.
  • 51. Yu F, Yan S, Hu L, Wang Y, Lin J. Cascade Reaction of Isatins with Heterocyclic Ketene Aminals: Synthesis of Imidazopyrroloquinoline Derivatives. Org Lett. 2011 Sep 16;13(18):4782–5.

Synthesis of Isatin and its derivatives containing heterocyclic compounds

Yıl 2021, Cilt 8, Sayı 4, 1089 - 1098, 30.11.2021
https://doi.org/10.18596/jotcsa.962260

Öz

Isatin or 1H-indole-2,3-dione or 2,3-dioxindole is an indole derivative. Isatin and its analogs are synthetically useful substances where they may be utilized for the production of a broad range of heterocyclic molecules, which are depicting a wide reach of biological and pharmacological activities, as well as anticancer, anti-inflammatory, antiviral, anticonvulsant, anti-TB, antidiabetic, anti-microbial, antitumor, antimalarial, anti-HIV, antibacterial, anti-analgesic, and antiplasmodial activities. Isatin is a precursor for many synthesized therapeutic molecules that are amenable to pharmacological action and have excellent biological potential. Isatin has a magnificent scaffold for both the natural and synthetic construction of molecules. These molecules are being used in drug therapy such as anticancer, antibiotic, and antidepressant drugs and have many more clinical applications. Due to its privileged scaffolding, the synthetic versatility of isatin has produced many structurally diverse derivatives, including the substitution of mono-, di- and tri- substitution of the aryl rings A and those derived by derivation of isatin nitrogen and C2 and C3 carbon moieties. As a result, improving and expediting access to isatin-related molecules is a challenging study in synthetic organic chemistry.

Kaynakça

  • 1. Prudhomme M. Advances in Anticancer Agents in Medicinal Chemistry. [Internet]. Sharjah: Bentham Science Publishers; 2013 [cited 2021 Sep 24]. .
  • 2. Cândido-Bacani P de M, Reis MB dos, Serpeloni JM, Calvo TR, Vilegas W, Varanda EA, et al. Mutagenicity and genotoxicity of isatin in mammalian cells in vivo. Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 2011 Feb;719(1–2):47–51. .
  • 3. Silva JFM da, Garden SJ, Pinto AC. The chemistry of isatins: a review from 1975 to 1999. J Braz Chem Soc. 2001 Jun;12(3):273–324.
  • 4. Borad MA, Bhoi MN, Prajapati NP, Patel HD. Review of Synthesis of Multispiro Heterocyclic Compounds from Isatin. Synthetic Communications. 2014 Apr 18;44(8):1043–57.
  • 5. Ramakrishna Reddy K, Mahendra K. N. Synthesis of 3-[(Z)-5-Amino-1, 3, 3-trimethyl cyclohexyl methylimino]-1, 3-dihydroindol-2-one as a novel Schiff base. Molbank. 2006 Dec 1;2006(6):M517.
  • 6. Singh GS, Desta ZY. Isatins As Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks. Chem Rev. 2012 Nov 14;112(11):6104–55.
  • 7. Varun V, Sonam S, Kakkar R. Isatin and its derivatives: a survey of recent syntheses, reactions, and applications. Med Chem Commun. 2019;10(3):351–68.
  • 8. Khan FA, Maalik A. Advances in Pharmacology of Isatin and its Derivatives: A Review. Trop J Pharm Res. 2015 Nov 6;14(10):1937.
  • 9. Chiyanzu I, Hansell E, Gut J, Rosenthal PJ, McKerrow JH, Chibale K. Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain. Bioorganic & Medicinal Chemistry Letters. 2003 Oct;13(20):3527–30.
  • 10. Ali R, Gilani A-H, Choudhary M, Aftab K, Sener B, Turkoz S. Isolation of Antihypertensive Alkaloids from the Rhizomes of Veratrum album. Planta Med. 1993 Dec;59(06):569–71.
  • 11. Kapadia GJ, Shukla YN, Basak SP, Sokoloski EA, Fales HM. The melosatins—a novel class of alkaloids from melochia tomentosa. Tetrahedron. 1980 Jan;36(17):2441–7.
  • 12. Shaaban KA, Shaaban M, Nair V, Schuhmann I, Win HY, Lei L, et al. Structure elucidation and synthesis of hydroxylated isatins from Streptomycetes. Zeitschrift für Naturforschung B. 2016 Dec 1;71(12):1191–8.
  • 13. Benkendorff K, Bremner J, Davis A. Indole Derivatives from the Egg Masses of Muricid Molluscs. Molecules. 2001 Jan 16;6(12):70–8.
  • 14. Mamedova YV, Hasanova AE, Gasimova SZ, Huseynova RA, Mamedov IG. Some isatin based synthesis. New Materials, Compounds and Applications. 2020;4(1):16–9.
  • 15. Kumar M, Ramasamy K, Mani V, Mishra RK, Majeed ABA, Clercq ED, et al. Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides. Arabian Journal of Chemistry. 2014 Sep;7(4):396–408.
  • 16. Havrylyuk D, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R. Synthesis of New 4-Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity. J Med Chem. 2012 Oct 25;55(20):8630–41.
  • 17. Raj R, Singh P, Singh P, Gut J, Rosenthal PJ, Kumar V. Azide-alkyne cycloaddition en route to 1 H -1,2,3-triazole-tethered 7-chloroquinoline-isatin chimeras: Synthesis and antimalarial evaluation. European Journal of Medicinal Chemistry. 2013 Apr;62:590–6.
  • 18. Paul BK, Ray D, Guchhait N. Unraveling the binding interaction and kinetics of a prospective anti-HIV drug with a model transport protein: results and challenges. Phys Chem Chem Phys. 2013;15(4):1275–87.
  • 19. Kiran G, Maneshwar T, Rajeshwar Y, Sarangapani M. Microwave-Assisted Synthesis, Characterization, Antimicrobial and Antioxidant Activity of Some New Isatin Derivatives. Journal of Chemistry. 2013;2013:1–7.
  • 20. Prakash CR, Raja S, Saravanan G. Design and synthesis of 4-(1-(4-chlorobenzyl)-2,3-dioxoindolin-5-yl)-1-(4-substituted/unsubstituted benzylidene) semicarbazide: Novel agents with analgesic, anti-inflammatory and ulcerogenic properties. Chinese Chemical Letters. 2012 May;23(5):541–4.
  • 21. Khan KM, Karim A, Ambreen N, Saied S, Rasheed S, Perveen S, et al. Synthesis of benzoxazoles derivatives: Antiglycation activity. Journal of Pharmacy Research. 2012;5(1):664–5.
  • 22. Medvedev A, Buneeva O, Gnedenko O, Fedchenko V, Medvedeva M, Ivanov Y, et al. Isatin interaction with glyceraldehyde-3-phosphate dehydrogenase, a putative target of neuroprotective drugs: partial agonism with deprenyl. In: Parvez H, Riederer P, editors. Oxidative Stress and Neuroprotection [Internet]. Vienna: Springer Vienna; 2006 [cited 2021 Sep 24]. p. 97–103. (Journal of Neural Transmission. Supplementa; vol. 71). .
  • 23. Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, et al. New isatin derivatives with antioxidant activity. European Journal of Medicinal Chemistry. 2010 Apr;45(4):1374–8.
  • 24. Kumar K, Carrère-Kremer S, Kremer L, Guérardel Y, Biot C, Kumar V. 1 H -1,2,3-Triazole-Tethered Isatin–Ferrocene and Isatin–Ferrocenylchalcone Conjugates: Synthesis and in Vitro Antitubercular Evaluation. Organometallics. 2013 Oct 28;32(20):5713–9.
  • 25. Jarrahpour A, Khalili D, De Clercq E, Salmi C, Brunel J. Synthesis, Antibacterial, Antifungal and Antiviral Activity Evaluation of Some New bis-Schiff Bases of Isatin and Their Derivatives. Molecules. 2007 Aug 7;12(8):1720–30.
  • 26. Saravanan G, Alagarsamy V, Dineshkumar P. Anticonvulsant activity of novel 1-(morpholinomethyl)-3-substituted isatin derivatives. Bulletin of Faculty of Pharmacy, Cairo University. 2014 Jun;52(1):115–24.
  • 27. Rane RA, Napahde S, Bangalore PK, Sahu NU, Shah N, Kulkarni YA, et al. Synthesis and Evaluation of Novel Marine Bromopyrrole Alkaloid-Based Derivatives as Potential Antidepressant Agents. Chem Biol Drug Des. 2014 Nov;84(5):593–602.
  • 28. Ibrahim S, Elsaman T. Cytotoxic and Anticancer Activities of Indoline-2,3-dione (Isatin) and Its Derivatives. JPRI. 2018 Feb 27;21(2):1–19.
  • 29. Lelyukh M, Havrylyuk D, Lesyk R. Synthesis and anticancer activity of isatin, oxadiazole and 4-thiazolidinone based conjugates. Chemistry & Chemical Technology. 2015;9(1):29–36. .
  • 30. Thakur RK, Joshi P, Upadhyaya K, Singh K, Sharma G, Shukla SK, et al. Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents. European Journal of Medicinal Chemistry. 2019 Jan;162:448–54.
  • 31. Quraishi MA, Ahamad I, Singh AK, Shukla SK, Lal B, Singh V. N-(Piperidinomethyl)-3-[(pyridylidene)amino]isatin: A new and effective acid corrosion inhibitor for mild steel. Materials Chemistry and Physics. 2008 Dec;112(3):1035–9.
  • 32. Prakash CR, Raja S. Design, synthesis and antiepileptic properties of novel 1-(substituted benzylidene)-3-(1-(morpholino/piperidino methyl)-2,3-dioxoindolin-5-yl)urea derivatives. European Journal of Medicinal Chemistry. 2011 Dec;46(12):6057–65.
  • 33. Kang I-J, Wang L-W, Hsu T-A, Yueh A, Lee C-C, Lee Y-C, et al. Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors. Bioorganic & Medicinal Chemistry Letters. 2011 Apr;21(7):1948–52.
  • 34. Medvedev A, Igosheva N, Crumeyrolle-Arias M, Glover V. Isatin: Role in stress and anxiety: Review. Stress. 2005 Jan;8(3):175–83.
  • 35. Kandasamy R, Park SJ, Boyapalle S, Mohapatra S, Hellermann GR, Lockey RF, et al. Isatin down-regulates expression of atrial natriuretic peptide receptor A and inhibits airway inflammation in a mouse model of allergic asthma. International Immunopharmacology. 2010 Feb;10(2):218–25.
  • 36. Bogdanov AV, Zaripova IF, Voloshina AD, Sapunova AS, Kulik NV, Bukharov SV, et al. Synthesis and Biological Evaluation of New Isatin‐Based QACs with High Antimicrobial Potency. ChemistrySelect. 2019 May 31;4(20):6162–6.
  • 37. Blumenthal GM, Cortazar P, Zhang JJ, Tang S, Sridhara R, Murgo A, et al. FDA Approval Summary: Sunitinib for the Treatment of Progressive Well‐Differentiated Locally Advanced or Metastatic Pancreatic Neuroendocrine Tumors. The Oncologist. 2012 Aug;17(8):1108–13.
  • 38. Houk BE, Bello CL, Kang D, Amantea M. A Population Pharmacokinetic Meta-analysis of Sunitinib Malate (SU11248) and Its Primary Metabolite (SU12662) in Healthy Volunteers and Oncology Patients. Clin Cancer Res. 2009 Apr 1;15(7):2497–506.
  • 39. Ristovska N, Anastasova F, Stefova M. N"-[(3Z)-1-Acetyl-5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]thiocarbonohydrazide. Molbank. 2013 Apr 16;2013(2):M798.
  • 40. Gassman P, Cue, Jr. B, Luh T-Y. A General Method for the Synthesis of Isatins. J Org Chem. 1977;42(8):1344–8. .
  • 41. Klein LL, Tufano MD. Synthesis of substituted isatins. Tetrahedron Letters. 2013 Feb;54(8):1008–11. .
  • 42. Mathur G, Nain S. Recent advancement in synthesis of isatin as anticonvulsant agents: a review. Med Chem. 2014;4(4):417–27.
  • 43. Raghavender Reddy M, Nageswara Rao N, Ramakrishna K, Meshram HM. I2–DMSO promoted intramolecular oxidative cyclization of 2-(aryl or alkyl amino)-acetophenones for the synthesis of isatins. Tetrahedron Letters. 2014 Aug;55(34):4758–62.
  • 44. Sonawane RP, Tripathi RR. The chemistry and synthesis of 1H-indole-2, 3-dione (Isatin) and its derivatives. International Letters of Chemistry, Physics and Astronomy. 2013;7.
  • 45. Rewcastle GW, Sutherland HS, Weir CA, Blackburn AG, Denny WA. An improved synthesis of isonitrosoacetanilides. Tetrahedron Letters. 2005 Dec;46(50):8719–21.
  • 46. Vandana K, Marathakam A, Thushara B, Rajitha K. A Review on Isatin Derivatives With Diverse Biological Activites. World Journal of Pharmaceutical Research. 2017;6:318–32.
  • 47. Demchuk DV, Elinson MN, Nikishin GI. ‘On water’Knoevenagel condensation of isatins with malononitrile. Mendeleev Communications. 2011;4(21):224–5.
  • 48. Khorshidi A, Tabatabaeian K. An ultrasound-promoted green approach for the synthesis of 3-(indol-3-yl)-3-hydroxyindolin-2-ones catalyzed by Fe(III). J Serb Chem Soc. 2011;76(10):1347–53.
  • 49. Elinson MN, Merkulova VM, Ilovaisky AI, Barba F, Batanero B. Electrocatalytic tandem Knoevenagel–Michael addition of barbituric acids to isatins: Facile and efficient way to substituted 5,5′-(2-oxo-2,3-dihydro-1H-indole-3,3-diyl)bis(pyrimidine-2,4,6-(1H,3H,5H)-trione) scaffold. Electrochimica Acta. 2011 Oct;56(24):8219–23.
  • 50. Meshram HM, Ramesh P, Sanjeeva Kumar A, Swetha A. An efficient and environmentally friendly DABCO catalyzed Henry reaction of isatins. Tetrahedron Letters. 2011 Nov;52(44):5862–4.
  • 51. Yu F, Yan S, Hu L, Wang Y, Lin J. Cascade Reaction of Isatins with Heterocyclic Ketene Aminals: Synthesis of Imidazopyrroloquinoline Derivatives. Org Lett. 2011 Sep 16;13(18):4782–5.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya, Organik
Bölüm DERLEME MAKALELER
Yazarlar

Pratibha MİSHRA
Dr. Harisingh Gour Central University Sagar M.P. India
0000-0003-0927-2857
India


Arunesh MİSHRA
Dr. Harisingh Gour Central University Sagar M.P. India
0000-0003-2862-3384
India


Anıl Kumar BAHE
Dr. Harisingh Gour Central University Sagar M.P. India
0000-0001-5733-1685
India


Atish ROY
Dr. Harisingh Gour Central University Sagar M.P. India
0000-0001-8612-5696
India


Ratnesh DAS (Sorumlu Yazar)
Dr. Harisingh Gour Central University Sagar M.P. India
0000-0002-5575-8359
India

Yayımlanma Tarihi 30 Kasım 2021
Başvuru Tarihi 4 Temmuz 2021
Kabul Tarihi 22 Eylül 2021
Yayınlandığı Sayı Yıl 2021, Cilt 8, Sayı 4

Kaynak Göster

Vancouver Mishra P. , Mishra A. , Bahe A. K. , Roy A. , Das R. Synthesis of Isatin and its derivatives containing heterocyclic compounds. Journal of the Turkish Chemical Society Section A: Chemistry. 2021; 8(4): 1089-1098.
J. Turk. Chem. Soc., Sect. A: Chem.