Chapter. 8

Chapter. 8

ISBN: 978-93-87905-41-2

Review In Lactam Compounds ((Methods of Preparation, Reactions, Applications, Activity))

Dr. Nagham Mahmood Aljamali Chemistry Department, Factuality of Education , Iraq. )*Corresponding author: E-Mail: [email protected])

Cited this chapter : Nagham Mahmood Aljamali ., (2018) ,"Review In Lactam Compounds ((Methods of Preparation, Reactions, Applications, Activity))"., Ch. 8 ., pages: 128- 141 . , ISBN: 978-93-87905-41-2 . Note: This is chapter

from Book ( ISBN: 978-93-87905-41-2 )

Lactam The first preparation of lactam by Staudinger in 1907 .Beta -lactam or Gama – Lactam ring is a ( four , five , six , seven )-membered ring .

It is named as such due to position of the nitrogen atom is attached to the beta carbon atom with the carbonyl group .

Dr. Nagham Mahmood Aljamali

Chapter. 8

ISBN: 978-93-87905-41-2

Lactam commonly known as 2-Azetidinones (four membered ring )as a heterocycle , which has a wide range activity in the chemistry field and drugs fields(1-7) .

As a results of several applications(8-15) of lactam in pharmaceutical drugs ,


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ISBN: 978-93-87905-41-2

It has been prepared in different procedures(16-26) and many methods in literatures(4) . General Methods For Preparation of Lactam: 1- Reaction of Imine group with compound containing leaving group: lactam synthesis has been synthesized by reaction of imine group with chloroacetyl chloride in presence of trimethyl amine(5) :


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ISBN: 978-93-87905-41-2

Mechanism for Formation of Lactam(Azitidine ):

Through same reaction , Other researchers(17) prepared bis – lactam ring in same compound :


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2- Cycloaddition [ 2+ 2] : Cyclo addition [2+2] and [2+3] gave lactam compounds like reaction of ( imine group , double bond , carbonyl group ) with (ketene , isothiocyanate , carbo di-imide , isocyanate ) .


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3- Reaction Between Ketene with Imine Group:

4- Addition of Nucleophile and Electrophilic : Formation of Lactam through reaction of imine groups with compounds containing electrophile and nucleophile at same compound. Dr. Nagham Mahmood Aljamali

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ISBN: 978-93-87905-41-2

5- Reaction of Diazomethine with Isocyanate Compounds:

6- Ring Expansion :


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7- Intramolecular cyclization with acidic conditions

Medical Applications of Lactam: Various Lactam derivatives have been prepared and evaluated as antiinflammatory activity in many studies(15-20) .

Other lactam derivatives has synthesized and tested against tumor.


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While other lactam compounds were screened in vitro for their antitubercular activity .

While , in other studies tested as antibacterial compounds(19 , 20) .


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Drugs from Lactam:


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References 1. Gilchrist,T., "Heterocyclic Chemistry" ., Harlow: Longman Scientific. ,

1987., ISBN 0-582-01421-2. 2. Lester A., Itschep M. and Foye, "Principle of Medicinal Chemistry", 5, 833,

2002. 3. Vogels Text Book of "Practical Organic Chemistry" ;3rd London Inc ; New

York, 1974. 4. Nagham Mahmood Aljamali .,(2018),"Reactions and Mechanisms".,1 Edt., IJMRA

Publication ., ISBN : 978-93-87176-25-6 .

5. Sandip Sen , Biplab De and TS Easwari ., "Synthesis and biological

evaluation of some novel furan derivatives "., Pak. J. Pharm. Sci., Vol.27, No.6, 2014, pp.1747-1760. 6. Khan, F., Shukla, I. and Rivzi, M.(2011). , "The role of non-β-lactam

antimicrobials and screening for vancomycin resistance in methicillin resistant Staphylococcus aureus"., Mal. J. of Microbio.,. 7(2). 66-70. 7. Mehani, M, and Ladjel, S.(2012). Antimicrobial effect of essential oils of the

plant Eucalyptus camaldulensis on some pathogenic bacteria. International Journal of Environmental Science and Development.3(2):86-88. 8. Jouk,M. and Kazaei,N.(2010). The Antimicrobial activities of methanolic

extracts of Eucalyptus camaldulensis against Bacillus subtilis, Staphylococcus aureus and Escherichia coli . Journal of Research in Agricultural Science . 6: 63- 67. 9. Solomons ,T.W.G;and F RYHLE ,C.B.,"Organic chemistry ",7th ed .,John

Wiley and Sons, Inc .new york ,738(,2000). Dr. Nagham Mahmood Aljamali

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10. Ralph L,Shriner and Reynold C . Fuson ,"The systematic identification of

organic compound ",6th ed John Wiley and Sons, Inc .new york ,(1980). 11. Banik, I.; Becker, F.F.; Banik, B.K. Stereo selective synthesis of β- lactams

with polyaromatic imines: Entry to new and novel anticancer agents. J. Med. Chem, 46, 12–15,(2003). 12. Banik, B.K.; Becker, F.F.; Banik, I. Synthesis of anticancer β-lactams:

Mechanism of action. , Bioorg. Med. Chem. 12, 2523–2528, 2004. 13. Morin, R. B.; Gorman, M. Chemistry and Biology of β- Lactam Antibiotics;

Academic , Press: New York, (1982). 14. Sykes. p, "A guide book to mechanism in organic chemistry ",4th ed

.,Longmann,216(1975) . 15. Roberts .J.W and Casario M. Basic principles of organic chem., Banjamin

W.A,Inc ,P.451,(1965). 16. With.A,.Handler. Ph, Smith .E,L.," principle of biochem.,5th .ed McGraw

Hill book company ,p.236.,(1973). 17. Amera .H.Hamed ,Isam.Sh.Hamza , Mohammad.M.Saleh ., " Synthesis of

new derivative containing (lactam and bis-lactam) and (tetrazole and bis-tetrazol) from aldo-imine " ., J . Ess . Colleg. Edu. , 22, 93, 2016 . 18. Georg, G. I. The Organic Chemistry of b-Lactams; VCH: New York, NY,

1992 . 19. Nagham Mahmood Aljamali , Haider Kareem , Jihan R ., " STUDYING OF

(THERMAL ,MICROBIAL , SPECTRAL, SOLVATION)-BEHAVIOR OF PREVIOUSLY PREPARED COMPOUNDS OF (BENZOTHIAZOLEHETEROCYCLES) " ., J.Bio.Innov 6 (5), pp: 664-665, 2017 . 20. Nagham Mahmood Aljamali , A. S Majeed .,"Chemical Applications of (N-

Azitidine, Imidazole, Tetrazole, Oxazepine) Derivatives and Their Complexes " ., Asian J. Research Chem. 9(11): November 2016. 21. Brunton LL, Parker K, Blumenthal D, . "The goodman and gilman’s manual

of pharmacological therapeutics" . McGraw-Hill Professional, 2007. Dr. Nagham Mahmood Aljamali

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22. Henry F. Chambers. ,"Beta-Lactam & Other Cell Wall- & Membrane-Active

Antibiotics. Basic & Clinical Pharmacology, edited by Bertram G. Katzung" ., McGraw Hill, USA, 2007. 23. Brunton LL, Parker K, Blumenthal D, et al. The goodman and gilman’s

manual of pharmacological therapeutics. McGraw-Hill Professional, 2007. 24. Henry F. Chambers. Beta-Lactam & Other Cell Wall- & Membrane-Active Antibiotics. Basic & Clinical Pharmacology, edited by Bertram G. Katzung. McGraw Hill, USA, 2007.

Dr. Nagham Mahmood Aljamali ,, Department of chemistry , Ph. D in 2008 in organic chemistry ,publications ((50 )) articles in ((organic chemistry ,Pharma , ansthesia , analytical , medical plants , plants extracted,......)) .,Her field : organic chemistry , pharmaceutical chem ,medical plants , analytical chem , heterocyclic ,..)., member of Editorial board in more than 35 scientific world journals and Editor in other journals , She has two published books in Germany house of publication ., with Innovation in Antibiotics , Industrial Pigments .

2018


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