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1, 5 Benzodiazepines: Overview of Properties and Synthetic Aspects

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Author Affiliations

  • 1Raj Kumar Goel institute of Technology, Ghaziabad, UP, INDIA
  • 2Banasthali University, Department of Chemistry, Banasthali, Rajasthan, INDIA

Res.J.chem.sci., Volume 3, Issue (7), Pages 90-103, July,18 (2013)

Abstract

Heterocyclic compounds occur widely in nature and quite a few of these are essential to life processes. The literature on heterocyclic compounds is replete with examples of a large number of synthetic methods of naturally occurring systems which are pharmacologically active. Their practical applications range from clinical use to field as diverse as agriculture, photography, biocide formulations and polymer science. The range of known compounds is virtually limitless, encompassing an impressive spectrum of physical, chemical and biological properties. Extensive applications of these compounds in medicine has led to the chemistry of these materials to expand exponentially in the past few decades, so much so that virtually a limitless series of structurally novel compounds with a broad spectrum of reactivity and stability has been developed . The heterocyclic compounds containing nitrogen has expanded exponentially in the past decades due to their uniquephysical properties , specific chemical reactivity and their remarkable potential biological activities 1,2 .A survey of literature on the nitrogen heterocycles reveal that pyrazole, isoxazole, carbazol, pyrimidine , diazepines and oxazepines tc., are important constituents of a wide variety of natural products with pharmacodynamic application.

References

  1. Olkkola K.T. and Ahonen J., Midazolam and other benzodiazepines, Handbook of Experimental Pharmacology, Handb Exp Pharmacol,182, 335–60 (2008)
  2. Dikeos D.G., Theleritis C.G. and Soldatos C.R., Benzodiazepines: effects on sleep, In Pandi-Perumal SR, Verster JC, Monti JM, Lader M, Langer SZ (eds.). Informa Healthcare Sleep Disorders: Diagnosis and Therapeutics, 19, 220–2 (2008)
  3. Kukla M.J. and Berslin H.J., Synthesis and anti-HIV-1 activity of 4, 5, 6, 7-tetrahydro-5-methylimidazo [4,5,1-jk][1,4] benzodiazepine-2(1H)-one (TIBO) derivatives, Journal of Medicinal chemistry, 34, 746-751 (1991)
  4. Boyd G.V., Six Membered and Larger Hetero Rings with Maximum Unsaturation, Schauman E. (ed), New York, In Houben-Weyl, 26, 299 (1998)
  5. Fryer R.I. and Walser A., Chemistry of Hetrocyclic Compounds: Bicyclic Diazepines: Diazepines with an Additional Ring, Chemistry of Heterocyclic Compounds, 50, 20 (1991)
  6. Llyod D. and Marshall D.R., Resonance energies of heteroaroamtic and other system from pK data: pyrrole, indole, and 2, 3-dihydro-1H-1,4-diazepinium cations, Chem Ind. (London),17, 335 (1972)
  7. Shilabin A.G., Seven- Membered Ring Mesomeric Betaines from Anti-Huckel Aromatic to Model Compounds of the pyrrolobenzodiazepines Alkaloids Circumdatin A and B, Dissertation, Europian journal of chemistry, 12, 1-137 (2005)
  8. Atwal K.S., Bergey J.L. and Hedberg A., Synthesis and biological activity of novel calcium channel blockers: 2, 5-dihydro-4-methyl-2-phenyl-1,5-benzodiazepine-3-carboxylic acid esters, Journal of Medicinal Chemistry, 30, 635 (1987)
  9. Varala R., Kotra V. and Engulu R., Synthesis of some 1, 5-benzodiazepines derivatives as a new class of antimicrobial agents, Asian Journal of Chemistry, 19(7), 5435-5442 2007)
  10. Pasha M.A. and Jayashankar V.P., An expeditious synthesis of 1,5-benzodiazepines derivatives catalyzed by CdCl, Indian Journal of Chemistry, 45B, 2716-2719 (2006)
  11. Gatzonis S.D., Angelopoulos E.K., Dakalopoulou E.G. and Chioni A., Convulsive status epilepticus following abrupt high-dose benzodiazepine discontinuation, Drug and Alcohol Dependence, 59(1), 95-97 (2000)
  12. Kumar R. and Joshi Y.C., Synthesis, spectral studies and biological activity of 3H-1, 5-Benzodiazepine derivatives, Arkivoc, 13, 142-149 (2007)
  13. Nawrocka W., Sztuba B. and Wietrzy K., Synthesis and antiproliferative activity in vitro of novel 1,5- benzodiazepines, J.Arch.Pharm.Pharm.Med.Chem, 334, 3-10 (2001)
  14. Kusanur R.A., Ghate M. and Kulkarni M.V., Synthesis of spiro [indolo-1, 5- benzodiazepines] from 3- acetyl coumarins for use as antianxiety agents, J. Chem. Sci, 116, 265-270 (2010)
  15. Smith R.H., Jorgen W.L. and Tirado R.J., Prediction of Binding Affinities for TIBO Inhibitors of HIV-1 Reverse Transcriptase Using Monte Carlo Simulations in a Linear Response Method, Journal of Medicinal Chemistry, 40, 823-833 (1998)
  16. Atwal S.K., Bergey L.J. and Hedberg A., Synthesis and biological activity of novel calcium channel blockers: 2, 5-dihydro-4-methyl-2-phenyl-1, 5-benzothiazepine-3-carboxylic acid esters and 2, 5-dihydro-4-methyl-2-phenyl-1, 5-benzodiazepine-3-carboxylic acid esters, Journal of Medicinal Chemistry,30, 635 (1987)
  17. Katritzky A.R., Abonia R. and Yang B., Synthesis of 3,4,7,8-tetrahydro-6H-pyrido1,2,3-ef-1,5-benzodiazepine-2(1H)-ones via benzotriazole methodology, Synthesis, 10, 1487 (1998)
  18. Chimirri A., Gitto R., Grasso S., Manforte A.M., Romeo G. and Zappala M., Annelated 1,5-benzodiazepines, I: Three, four and five membered rings, Heterocycles,36(3), 601 (1993)
  19. Neels H.M., Sierens A.C. and Naelaerts K., Therapeutic drug monitoring of old and newer anti- epileptic drugs, Clin. Chem. and Lab. Med., 42(11), 1228 (2004)
  20. Kumar R., Chaudhary P., Nimesh S., Verma A.K. and Chandra R., An efficient synthesis of 1,5-benzodiazepines derivatives catalysed by silver nitrate, Green Chem., 519 (2006)
  21. Yaddanapudi Prabhakar, Kottapalli R.S. Prasad and Jagarlapudi V.S. Kumar, Microwave assisted synthesisof 3-(4-Ethylbenzyl)-1-(4-methoxybenzyl)-6-(methylthio)-1,3, 5-triazine-2, 4 (1H, 3H)-dione derivatives Under solvent free condition with high yields, Res. J. Recent Sci.,1(ISC-2011)105-109 (2012)
  22. Steffan R.J. and Failli A.A., Preparation of pyrrolobenzodiazepine carboxamide vasopressin agonists, PCT Int. App., 228, 46 (2000)
  23. Hoekstra W.J. and Dyatkin A.B., Preparation of tricyclic benzodiazepines as vasopressin receptor antagonists, PCTInt. App., 398, 43 (2009)
  24. Nawrocka W., Sztuba B. and A., Synthesis and antiproliferative activity in vitro of novel 1, 5-benzodiazepines, Arch. Phar. Med. Chem., 334, 3 (2001)
  25. Braccio M.D., Grossi G., Roma G., Vargiu L., Mura M.and Marongiu M.E., 1,5-Benzodiazepines. Part: XII: synthesis and biological evalution of tricyclic and tetracyclic 1, 5-benzodiazepine derivatives of niverapine analogues, Eur. J. Med. Chem., 36(11), 935 (2001)
  26. Eman A. Alam, Initiation of Pharmaceutical Factories depending on more Application of Biotechnology on some Medicinal Plants Review Article (In Vitro Production of some Antioxidant, Analgesic, Antibacterial, Antidiabetic agent), Res.J.Recent Sci.,1(ISC-2011), 398-404 (2012)
  27. Claremon D.A., Liverton N., Selnick H.G. and Smith G.R., PCT Int. Appl. WO 9640653. New J Chem,, 27, 1644-1648(2003)
  28. El-Sayed A.M., Abdel-Ghany H. and El-Saghier A.M.M., A Novel Synthesis of Pyrano (2,3-c)-, 1,3-Oxazino (2,3b)-, 1,2,4-Triazolo(3,4-b)-, Oxazolo(2,3-b)-, Furano(3,2-c)-, and 3-Substituted-(1,5)benzodiazepin-2-ones, Synth. Commun., 29, 3561 (1999)