1-Arylmethyl-2,3-dioxo-2,3-dihydroindole thiosemicarbazones as leads for developing cytotoxins and anticonvulsants

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 24, Issue 2, 2009, Pages 537-544

  Karki, Subhas S ^a   Bahaduria, Vivek Singh ^a   Rana, Vivek ^a   Kumar, Sujeet ^a   Subbaro, Prasanna G ^a   Das, Umashankar ^b   Balzarini, Jan ^c   De Clercq, Erik ^c   Dimmock, Jonathan R ^b  

^a KLE College of Pharmacy   (India)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Anticonvulsants; Bioassays; Cytotoxicity; Indoles; Molecular modeling; SAR; Thiosemicarbazones

Indexed keywords

1 BENZYL 2,3 DIOXY 2,3 DIHYDROINDOLE N4 CYCLOHEXYLTHIOCARBAZONE; 2,3 DIOXO 2,3 DIHYDROINDOLE THIOSEMICARBAZONE DERIVATIVE; ANTICONVULSIVE AGENT; CYTOTOXIN; MELPHALAN; PHENOBARBITAL; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG; INDOLE; INDOLE DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERABILITY; FEMALE; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; T LYMPHOCYTE; TECHNIQUE; ANIMAL; CHEMISTRY; DRUG EFFECT; LEUKEMIA L 1210; TUMOR CELL LINE;

ANIMALIA; MURINAE; RATTUS;

ANIMALS; ANTICONVULSANTS; CELL LINE, TUMOR; CYTOTOXINS; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; INDOLES; INHIBITORY CONCENTRATION 50; LEUKEMIA L1210; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; T-LYMPHOCYTES; THIOSEMICARBAZONES;

EID: 68049110444     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360802234885     Document Type: Article

References (20)

1. Dimmock JR, Smith DC, Brenner JM, Jonnalagadda SS, Sardessai MS, Wood JD, Bigam GE. Antiepileptic and antileukemic thiosemicarbazones and semicarbazones of 4-aryl-3-buten-2-ones. Eur J Med Chem 1986;21:187-192.
2. Dimmock JR, Pandeya SN, Quail JW, Pugazhenthi U, Allen TM, Kao GY, Balzarini J, De Clercq E. Evaluation of the semicarbazones, thiosemicarbazones and bis-carbohydrazones of some aryl alicyclic ketones for anticonvulsant and other biological activities. Eur JMed Chem 1995;30:303-314.
3. Dimmock JR, Jonnalagadda SS, Hussein S,Tewari S, Quail JW, Reid RS, Delbaere LTJ, Prasad L. Evaluation of some thiosemicarbazones of arylidene ketones and analogues for anticonvulsant activities. Eur J Med Chem 1990;25:581-588.
4. Dimmock JR, Puthucode RN, Smith JM, Hetherington M, Quail JW, Pugazhenthi U, Lechler T, Stables JP. (Aryloxy)aryl semicarbazones and related compounds: A novel class of anticonvulsant agents possessing high activity in the maximal electroshock screen. J Med Chem 1996;39:3984-3997.
5. Anatoly VE, Rashel SE, Margeris JL, Aina AZ, Anda ZD, Iya MK. Condensation products of a-aminoisopropyl phenyl ketone, via the CvO carbonyl bond, with substituted amines, functionally substituted hydrazines or derivatives of natural amino acids, having anticancer activity. FR 2540868, August 17, 1984 Chem Abstr 1985;102:78567j.
6. Dimmock JR, Sidhu KK, Thayer RS, Mack P, Duffy MJ, Reid RS, Quail JW, Pugazhenthi U, Ong A, Bikker JA, Weaver DF. Anticonvulsant activities of some arylsemicarbazones displaying potent oral activity in the maximal electroshock screen in rats accompanied by high protection indices. J Med Chem 1993;36:2243-2252.
7. Karali N, Terzioglu N, Gürsoy A. Syntheses and primary cytotoxicity evaluation of new 5-bromo-3-substituted-hydrazono- 1H-2-indolinones. Arch PharmPharmMed Chem 2002; 8:374-380. (Pubitemid 35283106)
8. Pandeya SN, Raja AS, Stables JP. Synthesis of isatin semicarbazones as novel anticonvulsants - role of hydrogen bonding. J Pharm Pharmaceut Sci 2002;5:266-271.
9. Marvel CS, Heirs GS In: Blatt AH, editor. Isatin. Organic syntheses collection. 2nd ed., Vol 1, New York: John Wiley and Sons, Inc; 1941. p 327-330.
10. Azizian J, Fallah-Bagher-Shaidaei, Kefayati H. A facile onepot method for the preparation of N-alkyl isatins under microwave irradiation. Synth Commun 2003;33:789-793.
11. Lieber E, Pillai CN, Hites RD. Reactions of nitrous acid with 4-substituted-thiosemicarbazides. Can J. Chem 1957;35:832-842.
12. Sen AB, Gupta SK. Possible antiamoebic agents. Part XIX. Synthesis of 1,3,4-thiadiazolines and di-1,3,4-thiadiazolines. J Ind Chem Soc 1962;39:628-634.
13. Spartan '04 for Windows, Wavefunction, Inc., Irvine, CA 92612, USA.
14. JME Molecular Editor, April 2006 version; http://www. molinspiration.com
15. Statistical Package for Social Sciences. 2005. SPSS for Windows, Release 14.0.0, SPSS Inc., Chicago.
16. Baraldi PB, Nunez MDelC, Tabrizo MA, De Clercq E, Balzarini J, Bermejo J, Estévez F, Romagnoli R. Design, syntheses and biological evaluation of hybrid molecules containing a-methylene-g-butyrolactones and polypyrrole minor groove binders. J Med Chem 2004;47:2877-2886.
17. Craig PN. Interdependence between physical parameters and selection of substituent groups for correlation studies. J Med Chem 1971;14:680-684.
18. Hansch C, Leo AJ. Substituent Constants for Correlation Analysis in Chemistry and Biology. New York: John Wiley and Sons; 1979. p 49.
19. Suffness M, Douros J. In: De Vita VT, Busch H, editors. Methods in Cancer Research., Vol.XVI, Part A, New York: Academic Press; 1979. p 84.
20. Isaacson EI. In Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry. 10th ed. Philadelphia: Lippincott-Raven Publishers; 1998. p 456.