PharmaTutor (May - 2018)
ISSN: 2347 - 7881
(Volume 6, Issue 5)
Received On: 02/04/2018; Accepted On: 04/04/2018; Published On: 01/05/2018
AUTHORS:
D.Visagaperumal*, Justin Ebuka Ezekwem, Hemaprasad Munji, Vineeth Chandy
Department of Pharmaceutical Chemistry,
T. John College of Pharmacy,
Bangalore, Karnataka, India.
vishak_dr@yahoo.co.in
ABSTRACT
The review article is focused on studies of Isatin-based Schciff Bases and their biological and pharmacological activities. Isatin-based Schiff base are generally synthesized by condensation of the keto group of Isatin with different aromatic primary amines carrying imine or azomethine (–C=N–) functional group. Isatin Schciff Base possesses numerous biological properties like antitumor, antimicrobial, anti-inflammatory, anticonvulsant, antiviral, anti HIV, antioxidant, CNS depressant activities.
How to cite this article: Visagaperumal D, Ezekwem JE, Munji H, Chandy V; Isatin Schiff Base -An Overview; PharmaTutor; 2018; 6(5); 38-47; http://dx.doi.org/10.29161/PT.v6.i5.2018.38
[ABSTRACT WITH CITATION] [VIEW AS HTML]
REFERENCES:
1. Aboul-Fadl T., Mohammed F. A., and Hassan E. A. Synthesis, antitubercular activity and pharmacokinetic studies of some Schiff bases derived from 1- alkylisatin and isonicotinic acid hydrazide (INH), Arch. Pharm. Res. 2003; 26; 778–784.
2. Alam M., Younas M., Zafar M.A., Naeem. Scientific study and development meat barian a tradesnal food product Pak. J. Sci. Ind. Res. 1989; 32; 246.
3. Ali S. M. M., Abul Kalam Azad M., Jesmin M. et al., In vivo anticancer activity of Vanillin semicarbazone, Asian. Pac. J. Trop. Biomed. 2012; 2; 438–442.
4. Aliasghar J., Dariush K., Erik D.C., Chanaz S. Jean Michel Brunel Synthesis, Antibacterial, Antifungal and Antiviral Activity Evaluation of Some New bis-Schiff Bases of Isatin and Their Derivatives. Molecules. 2007; 12; 1720-1730.
5. Ashraf H. Abadi , Sahar M. Abou-Seri, Doaa Abdel-Rahman E. Christian Klein Olivier Lozach, Laurent Meijer. The synthesis of 3-substituted-2-oxoindoles and their evaluation as kinase inhibitors, anticancer and antiangiogenic agents. Eur. J. Med. Chem. 2006; 41; 294-305.
6. Avaji P. G., Vinod Kumar C. H., Patil S. A., Shivananda K. N., and Nagaraju C. Synthesis, spectral characterization, in-vitro microbiological evaluation and cytotoxic activities of novel macrocyclic bis hydrazone, Euro. J. Med. Chem. 2009; 44; 3552–3559.
7. Bergman J., Lindstrom J.O., Tilstam U. The structure and properties of some indolic constituents in Couroupita guianensis aubl. Tetrahedron. 1985; 41; 2879–2881.
8. Bhattacharya A., Purohit V. C., and Rinaldi F. Environmentally friendly solvent-free processes: novel dual catalyst system in Henry reaction, Org. Process. Res. Dev. 2003; 7; 254–258.
9. Breinholt J., Demuth H., Heide M., Jensen G.W., Moeller I.L., Nielsen R.I., Olsen C.E., Rosendahl C.N. Prenisatin (5-(3-methyl-2-butenyl) indole-2, 3-dione): an antifungal isatin derivative from Chaetomium globosum. Acta Chem. Scand. 1996; 50; 443.
10. Chandramouli C., Shivanand M. R., Nayanbhai T. B., Bheemachari B., and Udupi R. H. Synthesis and biological screening of certain new triazole schiff bases and their derivatives bearing substituted benzothiazole moiety, J. . Chem. Pharm. Res. 2012; 4; 1151-1159.
11. Chaubey A. K. and Pandeya S. N. Synthesis & anticonvulsant activity (Chemo Shock) of Schiff and Mannich bases of Isatin derivatives with 2-Amino pyridine (mechanism of action), Int. J. PharmTech. Res. 2012; 4; 590–598.
12. Chhajed S.S., Padwal M.S. Antimicrobial Evaluation of Some novel Schiff and Mannich bases of Isatin and its derivatives with quinoline. Int. J. ChemTech. Res. 2010; 2; 209-213.
13. Chinnasamy R. P., Sundararajan R., and Govindaraj S. Synthesis, characterization, and analgesic activity of novel schiff base of isatin derivatives, J. Adv. Pharm. Tech. Res. 2010; 3; 342–347.
14. Chohan Z. H., Praveen M., and Ghaffar A. Structural and biological behaviour of Co(II), Cu(II) and Ni(II) metal complexes of some amino acid derived Schiff-bases, Metal-Based Drugs 1997; 4; 267–272.
15. Dhar D. N. and Taploo C. L. Schiff bases and their application. J. Sci. Ind. Res. 1982; 41; 501-506.
16. Dharmarajan S., Tanushree R.B., Perumal Y. Aminopyrimidinimino isatin analogues: Design of novel nonnucleosideMHIV-1 reverse transcriptase inhibitors with broadspectrum chemotherapeutic properties. J. Pharm. Pharmaceut. Sci. 2005; 8; 565-577.
17. Durga P.B., Vasanthi R., Kanth B.C., Prabhakar D., Mohan R. Synthesis, characterization and anti-inflammatory activity of isatin derivatives. Int. J. Bio. Pharm. Res. 2012; 3; 182- 187.
18. Ershad S., Sagathforoush, Karim-Nezhad G., and Kangari S. Electrochemical behavior of N2SO Schiff-base Co(II) complexes in non-aqueous media at the surface of solid electrodes, Int. J. Electrochem. Sci. 2009; 4; 846–854.
19. Eshbha N.H, Salama H.M. 5-(2-Oxo-3-indolinylidene) thiazolidine-2, 4-dione-1, 3-diMannich base derivatives: Synthesis and evaluation for antileukemic activity, Pharmazie. 1985; 40; 320–322.
20. Grafe U., Radics L. Isolation and structure elucidation of 6-(3'- methylbuten-2'-yl)isatin, an unusual metabolite from Streptomyces albus. J. Antibiotics. 1986; 39; 162– 163.
21. Gummadi S.B., Nanam R., Puttireddy S.M., Bethi S., Umasankar K., Jupally V.R. Synthesis, characterization and evaluation of novel N-(1Hbenzimidazol-2-yl)-2-Isatinylidene hydrazine carboxamide derivatives as anti-inflammatory agents. Der. Pharma. Chemica. 2010; 2; 196-204.
22. Guo Y., Chen F. TLC-UV-spectrophotometric and TLC scanning determination of isatin in leaf of Isatis. Zhongcaoyao. 1986;17; 8-11.
23. Hoyun L., Solomon V.R., Changkun H. Hybrid pharmacophore design and synthesis of isatin– Chemistry. Bioorg. Med. Chem. 2009; 17; 7585-7592.
24. Ischia M., Palum M.A., Prota G. Adrenalin oxidation revisited. New products beyond the adrenochrome stage. Tetrahedron. 1988;44; 6441-6446.
25. Jarrahpour A., Khalili D., De Clercq E., Salmi C., and Brunel J. M. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives, Molecules. 2007; 12; 1720–1730.
26. Jnyanaranjan P. Synthesis of some Antibacterial, Analgesic and Anti-inflammatory agents containing isatin nucleus. Int. J. Pharm. Sci. 2012; 4; 2304-2313.
27. Joaquim F.M., Da Silva, Simon J. Garden, Angelo C. Pinto. The Chemistry of Isatin. J. Braz. Chem. Soc. 2001; 12; 273-324.
28. Kapadia G.J., Shukla B.K., Chowdhury S.P., Basak H.M., Falesm E.A. Phenylpel isatins: a novel class of alkaloids from Melochia tomentosa. J. Chem. Soc., Chem. Comm. 1977; 15; 535–536.
29. Kapadia G.J., Shukla Y.N., Basak S.P., Sokoloski E.A., Fales H.M. The melo- satins a novel class of alkaloids from Melochia tomentosa. Tetrahedron. 1980; 36; 2441–2447.
30. Li S., Chen S., Lei S., Ma H., Yu R., and Liu D. Investigation on some Schiff bases as HCl corrosion inhibitors for copper, Corrosion Sci. 1999; 41; 1273–1287.
31. Maharaj P., Blessi P.K., Uresh R., Shobaran B., Sammaiah G. Synthesis and characterization of new isatin derivatives for anti-inflammatory activity. Int. Pharm. Pharmaceut. Sci. 2012; 4; 248-251.
32. Manju P., Neeraj K., Sharma P., Jha K.K. Synthetic and biological multiplicity of isatin: A Review. J. Adv. Sci. Res. 2011; 2; 35-44.
33. Marvel C.S., Hiers G. S. Organic Syntheses Coll. 1941;Vol. 1: p.327 & 1925;Vol. 5; p.71.
34. Miri R., Razzaghi-asl N., and Mohammadi M. K., QM study and conformational analysis of an isatin Schiff base as a potential cytotoxic agent, J. Mol. Model. 2013; 19; 727–735.
35. Mounika K., Anupama B., Pragathi J., and Gyanakumari C. Synthesis, characterization and biological activity of a Schiff base derived from 3-ethoxy salicylaldehyde and 2-amino benzoic acid and its transition metal complexes, J. Sci. Res. 2010; 2; 513–524.
36. Otto Linne Erdmann. Untersuchungen uber den Indigo. Journal fur Praktische Chemie (1840);19 (1); 321-362.
37. Ozlen G., Nilgun K., Aydın S. Synthesis and antituberculosis activity of 5- methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives. Bioorg. Med. Chem. 2008; 16; 8976-8987.
38. Palumbo A., Ischia M.D., Misuraca Prota G. A new look at the rearrangement of adrenochrome under biomimetic conditions. Biochim. Biophys. Acta. 1989; 990; 297–302.
39. Pandey A., Dewangan D., Verma S., Mishra A., and. Dubey R. D. Synthesis of schiff bases of 2-amino-5-aryl-1,3,4-thiadiazole and its analgesic, anti-inflammatory, anti-bacterial and antitubercular activity, Int. J. ChemTech. Res. 2011; 3; 178-184.
40. Pandeya S.N., Senthil R., Stables J.P. Synthesis of isatin semicarbazones as novel anticonvulsants – role of hydrogen bonding. J. Pharm. Pharm. Sci. 2002; 5; 266–271.
41. Pandeya S.N., Sriram D., Nath G., Clercq E.D. Synthesis, antibacterial, antifungal and anti HIV activity of Schiff and Mannich bases of isatin with N-6-chlorobenzthiazol-2-ylthiosemicarbazide. Indian. J. Pharm. Sci. 1999; 61; 358-361.
42. Pandeya S.N., Yogeeswari P., Sriram D. Nath G. Synthesis and antimicrobial activity of NMannich bases of 3-_N'-sulphadoximino- isatin and its methyl derivative. Boll. Chim. Farm. 1998; 137; 321–324.
43. Perumal P., Ravi S.R., Kumarasamy M.N, Ramesh K. Synthesis, analgesic, antiinflammatory and antimicrobial activities of some novel Schiff’s bases of 5-subsituted Isatin. Der. Pharm. Chem. 2010; 2; 28-37.
44. Prakash C.R., Raja S., Saravanan G., Dinesh K.P., Panneer S. Synthesis and evaluation of antioxidant activities of some novel isatin derivatives and analogs. Asian. J. Res. Pharm. Sci. 2011; 1; 140-143.
45. Prince P.S., Pandeya S.N., Roy R.K., Anurag Verma K., Gupta S. Synthesis and anticonvulsant activity of some novel isatin schiff’s bases. Int. J. Chem. Tech. Res. 2009; 1; 758-763.
46. Ramachandran S. Synthesis and antimicrobial evaluation of some novel Schiff and Mannich bases of isatin derivatives. Int. J. Res. Pharm. Chem. 2011; 1; 289-294.
47. Sammaiah G., Brahmeshwari G.M., Sarangapani. Synthesis and biological activity of 2- aminobezoic acid (2-oxo-1, 2 dihydro-indol-3-ylidene)-hydrazides, J. Adv. Pharm. Sci 2011; 476-52.
48. Sandeep K.G., Shyam S.P. Synthesis and evaluation of antitubercular activity of some thiobenzimidazolyl derivatives. Der. Pharm. Chem. 2011; 3; 274-279.
49. Sandmeyer T. Helv uber Isonitrosoacetanilide und deren Kondensation zu Isatinen. Chimica. Acta. 1919;2 (1) ; 234–242.
50. Sangamesh A.P., Manjunatha M., Udaykumar V.K., Prema S.B. Synthesis, spectral characterization and biological evaluation Co(II), Ni(II), Cu(II) and Mn(II) metal complexes of novel Isatin schiff base ligand. Der. Pharm. Chem. 2011; 3; 97-108.
51. Sanjay B., Ankur P., Gokul T., Jitendra P., Manda S. Synthesis and Antimicrobial Activity of Some New Isatin Derivatives. Ira J Pharm Res 2006; 4; 249-254.
52. Sarangapani M., Rajyalakshmi G., Rama N.R. Synthesis, characterization and anticancer activity of certain 3-{4-(5-mercapto-1, 3, 4-oxadiazole-2- yl) phenylimino} indolin-2-one derivatives. Sau. Pharm. J. 2011; 19; 153–158.
53. Sathe B. S., Jaychandran E., Jagtap V. A., and Sreenivasa G. M. Synthesis characterization and anti-inflammatory evaluation of new fluorobenzothiazole schiff ’s bases, Int. J. Pharm. Res. Develop. 2011; 3; 164-169.
54. Schiff H. Mittheilungen aus dem Universitatslaboratorium in Pisa: eine neue reihe organischer Basen. Justus Liebigs Annalen der Chemie 1864; 131; 118-119.
55. Seshaiah K.S., Muniyandy S., Atmakuru R. Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives. Eur. J. Med. Chem. 36; 2001; 615–625.
56. Shibinskya M.O., Lyakhov S.A., Mazepa A.V., Andronati S.A. Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminomethyl)-6H-indolo [2, 3-b] quinoxalines. Eur. J. Med. Chem. 2010; 45; 1237-1243.
57. Singh K.N., Verma M., Pandaye S.N. Synthesis of 3Z)-5-bromo-1-methyl-3-[(4- nitrophenyl) I mino]-1, 3-dihydro-2H-indol-2-one by reacting 5-substituted N-methyl/Nacetyl isatin and aromatic amine with glacial acetic acid. Acta. Pharm. 2004; 54; 49-56.
58. Singh U.K., Pandeya S.N., Singh A., Srivastava B.K., Pandey M. Synthesis and antimicrobial activity of schiff’s and N-mannich bases of isatin and its derivatives with 4-amino-carbamimidoyl benzene sulfonamide. Int. J. Pharm. Sci. Drug. Res. 2010; 2; 151-154.
59. Singh U.K., Pandeya S.N., Singh A., Srivastava B.K., Pandey M. Synthesis and antimicrobial activity of schiff’s and N-mannich bases of isatin and its derivatives with 4-amino-ncarbamimidoyl benzene sulfonamide. Int. J. Pharm. Sci. Drug. Res. 2010; 2; 151-154.
60. Sivakumar S., Surendra N. P., James P.S., Suthakar. Anticonvulsant and Sedative-Hypnotic Activities of N-Acetyl Methyl Isatin Derivatives. Scientia. Pharmaceutica. 2008; 76; 621– 636.
61. Sondhi S. M., Singh N., Kumar A., Lozach O., and Meijer L. Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff ’s bases, Bioorg. Med. Chem. 2006; 14; 3758-3765.
62. Sondhi S. M., Singh N., Kumar A., Lozach O., and Meijer L. Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff ’s bases, Bioorg. Med. Chem. 2006; 14; 3758-3765.
63. Sriram D., Yogeeswari P., Gopal G. Synthesis, anti HIV and antitubercular activity of lamivudine prodrugs. Eur. J. Med. Chem. 2005; 40; 1373-137.
64. Teitz Y., Ladizensky E., Barko N., Burstein E. Selective repression of V-alb encoded protein by N-methylisatin-beta-4',4'-diethyl thiosemicarbazone and N-allylisatin-beta- 4',4'-diallylthiosemicarbazone. Antimicrob. Agents. Chem Ther 1993; 37; 2483–2486.
65. Tisato F., Refosco F., and Bandoli G. Structural survey of technetium complexes, Coordination. Chem. Rev. 1994; 135-136; 325–397.
66. Vashi K. and Naik H. B. Synthesis of novel Schiff base and azetidinone derivatives and their antibacterial activity, Euro. J. Chem. 2004; 1; 272–276.
67. Venkatesh P. Synthesis, characterization and antimicrobial activity of various schiff bases complexes of Zn(II) and Cu(II) ions, Asian. J. Pharm. Health. Sci. 2011; 1; 8–11.
68. Venugopala K. N. and Jayashree B. S. Synthesis of carboxamides of 2 -amino-4 -(6-bromo-3-coumarinyl) thiazole as analgesic and antiinflammatory agents, Indian. J. Heterocycl. Chem. 2003;12; 307–310.
69. Wei D., Li N., Lu G., and Yao K. Synthesis, catalytic and biological activity of novel dinuclear copper complex with Schiff base, Science in China B 2006; 49; 225–229.
70. Wei L., Wang Q., Liu X. Application of thin-layer chromatography in quality control of Chinese medicinal preparations II. Qualitative analysis of some Chinese medicinal preparations of Chansu. Yaowu. Fenxi. Zazhi. 1982; 2; 288–291.
71. Yan Y., Li G., Wang F., Mao W. Huadong Huagong Xueyuan Xuebao. 1992; 18:192. (CA 118:127985k)
72. Yoshikawa M., Murakami T., Kishi A., Sakurama T., Mat-suda H., Nomura M., Kubo M. Novel indole S, O-bisdesmoside, calanthoside, the precursor glycoside of tryptanthrin, indirubin and isatin with increasing skin blood flow promoting effects from two Calanthe species (Orchidaceae). Chem. Pharm. Bull. 1998; 46; 886–888.
73. Zapata-Sudo G., Luana B. Pontes., Daniele G., Thaiana C.F.M., Nubia M.R., Angelo C.P., Margarete M. Trachez, Roberto TS. Sedative–hypnotic profile of novel isatin ketals. Biochem. Behavior. 2007; 86; 678-685.
.png)
