Synthesis and antimicrobial evaluation activity of some new substituted spiro-thiazolidine,Imidazolinone and azetidine derivatives of 5-Bromo Isatine


S. M.H. Al-Majidi & L. H.K Kaka Hama

College of Science, University  of Baghdad 



Abstract:
A series of new 5-BromoIsatin linked to spiro thiazolidinone, Imidazolinone and azetidinone moieties were synthesized. Schiff bases 3-(substituted –imino)-1H-indole-2one(1-5),which were prepared by condensation 5-bromoisatin with different substituted aromatic amine in the presence of glacial acetic acid and Dimethyl- formamide (DMF) as a solvent. Three routs with different reagents were used for the cyclization of the Prepared Schiff bases,the reagents(2-mercaptoaceticacid,2-aminoaceticacid and monochloroacetylchloride) to form spiro-Thiazolidinone(6-10), spiro-imidazolinone (11-15) and spiro-azetidinone       (16-20) derivatives respectively. The  structures of the newly synthesized compounds were identified by spectral methods FTIR,1H-NMR. Furthermore the effects of the preparing compounds on some strains of bacteria and one yeast were studied. 

Keywords:

5-Bromo isatin

Schiff base

Spiro- thiazoildinone 

Spiro Imidazolinone Spiro-azetidinone antimicrobial activity.  

References:

[1]  Sumpter  W.C. , Chemistry of  Isatin,“ preparation and characterization” ,chem.Rev., vol.34,pp.407,(1954).

[2] Popp     F.D.,“General   Method  for chemical synthesis of Isatin”,adv. Heterocyclic.chem. ,vol.18,pp.1-9,(1973).

[3] Hvekhgeimer M.G.A.Chem.,“General Synthesis and Application of Isatin  derivatives,Heterocyclic comp.(Engl. Transl.)vol.32,pp.248-249,(1996).

[4] Dinesh B.,chirag S.,Shweta S.,Vijay K.,and GL Talesara., “synthesis pharmachological studies of some phtalaimidoxy substituted spiro-thiazolidinone  derivatives of isatin .J.Ind.Chem.,vol.48B,pp.1006-1012,(2009).

[5] Zeid A.Alothman,Masoom R.SiddlQui and Saikh M.wabaidur. ,“Estimation of Isatin    in spiked plasma samples  using high performance  Liquid chromatography”  .chem.Indu.and chem.Engin.Quar.vol.19(4).pp. 605-614,(2013).

[6] TAREK A. , Awaad A.,Hatem A.,Mohd B.,and Mohamad I.,“Synrhesis,in vitro anti-mycobacterial and in silico mycobacterium tuberculosis (MTB) DNA Gyrase  inhibitory activity”. J.Nano.Mat.and Bio.vol.1,pp.329-338,(2012).

[7]  Sriram D.,Bal T.R.,and yogeesswari P.,“Synthesis ,antiviral and antibacterial activities of Isatin mannich bases.Med.chem. Res.vol.14,pp.11-28,(2005).

[8] Garima M.,and Sumitra N. ,“Recent advancement in synthesis of Isatin as anticonvulsant agent ;Areview”.J.Med.chem.vol.4(4),pp.417-427,(2014) .

[9] Karia F.D.,Parsania PH. “Synthesis,biological and thermal properties of Schiff bases  of bisphenol-C”.Asian J.Chem.vol.11pp.991-995,(1999).

[10] Tarafdar  M.T., Kasbolla   A. , Saravan  N., crouse K.A., Ali   A.M., Tin  O.K .S.,  “methyldithiocarbazate and its schiff bases: Evaluation of bondings and biological  properties.J. Biochem. Mol.Biol.Biophs. vol.6,pp.85-91,(2002).

[11]  Kucukguzel  I.,Kucukguzel S.G.,Rollas S,Otuk-Sanis G.,Ozdemir O.,Bayrak I.,Altug T., stables J.P.,“3-(Arylalkylthio)-4-alkyl/aryl-5-(4-aminophenyl)-4H-1,2,4-triazole  derivatives  and their anticonvulsant activity.Farmaco.vol.59,pp.893-901,(2004).

[12]  Vinici P.,Geronikaki A., Incerti M., Busonera  B., Poni G.,Kabras C.A.,Colla  P.L.,           “synthesis and biological evaluation of benzo [d] isothiazole,benzothiazole and thiazole Schiff bases.Bioorg. Med.Chem.vol.11,pp.4785-4789,(2003).

[13] Suaad  M.H.Al-Majidi and Khitam  T.A.Al-Sultani, “ Synthesis and antimicrobial  ctivity of some acetylene amine of Isatin derivatives .Al-Mustansiriya,J.Scie. vol.21(4),pp.61-72,(2010).

[14]  Bekrican O., Kahveci  B., Kucuk  M., “Synthesis and anticancer evaluation of some new unsymmetrical 3,5diaryl-4H-1,2,4-triazole derivatives.Tur.J.Chem.vol.30, pp.2940,(2006).

[15]  Singh W.M., Dash B.C., “Synthesis of some new Schiff bases containing thiazole and oxazole nuclei and their fungicidal activity .Pesticides.vol.22,pp.33-37,(1988).

[16]  Eicher T.and Hauptmann S.,“The chemistry of heterocycles: structures, reactions,  synthesis,and applications,2nded.,Wiley-VCH Verlag GmbH,Weinheim,Germany , 2003  Al-Majidi & Kaka hama/ JZS (2015) 17-1 (Part-A)

[17]  Subudhi  B., Panda   P.,Tosh B., Sahu S. and Majhi  P., “ Synthesis and biological activity  evaluation of some azetidinone and thiazolidinone derivatives of some  coumarinsDhaka Univ.J.Pharm.Sci.,vol4(2); pp.87-92,(2005).

[18] Anbalagen  N. ,shanmugapandiyan, P., Denshing  K., llavarasan   R. and  Nirmal   R.“Synthesis and biological activity of 2- ( thiazolidine -4-one phenyl ] - 1H phenylbenzimidazoles and 2-[ 4-( azetidin-2-one )-3-chloro-4-phenyl ]-1H-phenyl    benzimidzoles”.Int.J.pharm.Sci. & Drug Res.,vol.2(2),pp.115-119,.(2010) .

[19] Vijay K., Yogananda, R. Shameer H. ,Jayachandran E. and Sreenivasa  G., “Synthesis  and characterization of novel N-Substituted -3-chloro -2-azetidinones as potential anticonvulsant agents J.Biomed.Sci. & Res.,vol.1(1),pp. 1-10,(2009).

[20] Shreenivas  M.,Chetan B. and Bhat  A., “Synthesis and pharmacological evaluation of     certain Schiff bases and thiazolidine derivatives as ATI angiotension-II(AII) receptor antagonists J.Pharma, Sci. Tech,vol.1(2),pp. 88-94 ,(2009).

[21] Suaad M.H.Al-Majidi and Mohammed G.A.Al-Khuzaie, “ synthesis and evaluation Antimicrobial activity of some new S-substuited Quinazolinone containing different hetrocyclic ring”,J.Asian,chem..vol.26,pp.xxx,(2014).

[22] Anesini C. and Perez C., (screening of plants used in argentic folk medicine for  antibacterial activity),J.Ethnropharmacol, vol.39(2)pp.35-47,(1993).

[23]  Silverstien R.,Webster F.,Kiemle D.,(Spectroscopic identification of organic compounds)7thed. John Wiley & Sons,Inc. USA ,(2005).