Synthesis, Characterization and Evaluation of Antifungal and Antibacterial Activities of Some Quinazoline Derivatives

Authors

  • A. A. Kale  Post Graduate Department of Chemistry, Annasaheb Awate College, Manchar, Ambegoan, Pune, Maharashtra, India
  • K. M. Durgade  Department of Chemistry, Prof. Ramkrishna More College, Aakurdi, Pune, Maharashtra, India

Keywords:

Quinazoline Derivative, Antifungal Activity, Antibacterial Activity, N2, N4-Di P-Tolylquinazoline-2, 4-Diamine, N2, N4-Bis (4-Chlorophenyl) Quinazoline-2, 4-Diamine, Quinazolin-2, 4-Diol, 2,4-- Dichloroquinazoline

Abstract

Present work includes synthesis of 2-{[2-(piperazin-1-yl)quinazolin-4-yl]amino}ethan-1-ol (IV) , N2, N4-di p-tolylquinazoline-2,4- diamine (V) and N2, N4-bis(4-chlorophenyl)quinazoline-2,4-diamine (VI) which are quinazoline derivatives and out of these three quinazoline derivatives N2, N4-bis(4-chlorophenyl)quinazoline-2,4-diamine (VI) have shown “antifungal activity” against fungus “Aspergillus flavus” and “antibacterial activity” against bacteria “Pseudomonas”. At first 2- amino benzoic acid react with urea at temperature 130 ºC to 140ºC to gives Quinazolin-2,4-diol (I) which on further reaction with phosphorus oxychloride at 150 ºC for 24 hr. to gives second product 2,4-dichloroquinazoline (II). Then 2-4-dichloroquinazoline (II) reacts with 2-aminoethan-1-ol and piperazine to gives 2-{[2-(piperazin-1-yl)quinazolin-4-yl]amino}ethan-1-ol (IV) and when p-toluidine react with 2-4-dichloroquinazoline (II) to gives N2, N4-di p-tolylquinazoline-2,4- diamine (V) and again this 2,4-dichloroquinazoline (II) react with p-chloroanline to gives N2, N4-bis(4-chlorophenyl) quinazoline-2,4-diamine (VI) which characterized by I. R., 1HNMR and 13CNMR.

References

  1. Joshi N. and Goyal Anju (2011) Microwave assisted one-pot Total synthesis of some natural Quinazoline alkaloids-a review,International Journal of Pharmaceutical Erudition; www.pharmaerudition.org,Aug. 2011,1(2),1 -9 1
  2. Dewick,P. M. (1997) Medicinal Natural Products: A Biosynthetic Approach Pub: Willey & Sons p-376.)
  3. Nagar,A. A.,Patel,A.,Rajesh K.S.,Danao,K. R. and Rathi,L.G.(2013) Solvent Free One Pot Microwave Synthesis of Quinazolin 4-(3H)-One derivatives with their Antibacterial and Antifungal Activity PHARMAGENE Vol:1 Issue:1 (genesisjournals.org Received on: 22-12-2012 Modified on: 15-01-2013 Accepted on: 26-02-2013)
  4. Gautam S,Mishra D,Singh R and Pal DK (2012) Synthesis of some novel 4,6-disubstituted derivatives and evaluation of their antimicrobial activity,International Journal of Pharmaceutical,Chemical and Biological Sciences,ijpcbs 2012,2(1),97-103 sucheta et al. ISSN: 2249-9504
  5. Doshi H,Bhatt M,Thakkar S,Ray(2012) A synthesis,characterizations and biological screening of tetrahydro-quinazoline analogues American Journal of Organic Chemistry 2012,2(5): 122-126 ,Doi: 10.5923/j.ajoc.20120205.03
  6. Mohamed M. S. ,Kamel M. M. ,Kassem E. M .M.,Abotaleb khedr N ,m. and Ahmed M. f.(2011) Synthesis,Biological Evaluation and Molecular Docking of Quinazoline-4(1h)-one Derivatives as Anti-inflammatory and Analgesic Agents,Acta Poloniae Pharmaceutical? Drug Research,Vol. 68 No. 5 pp. 665?675,2011
  7. Sinha N. K.,Asnani A. J.,Dravyakar B. R(2013).,A Novel Approach Towards Development Of Quinazoline Derivatives In Pain Management Asain journal of pharmaceutical and clinical research Vol 6,Suppl 3,2013 ISSN-0974-2441(Sinha N. K.,Asnani A. J.,Dravyakar B. R(2013).,A Novel Approach Towards Development Of Quinazoline Derivatives In Pain Management Asain journal of pharmaceutical and clinical research Vol. 6,Suppl 3,2013 ISSN-0974-2441
  8. Vashi R.T.,Shelat C. D. & Patel H(2010),Synthesis and Antifungal Activity of 6-bromo-2[(4-(2,3-dichlorophenyl)) piperazine-1-yl)methyl]-3-[8-hydroxyquinoline -5-yl]-3-quinazolin -4-one Ligand and its Transition Metal Chelates International Journal of Applied Biology and Pharmaceutical Technology. Volume: I: Issue-3: Nov-Dec -2010 ISSN 0976-4550
  9. Vijai and P.R.,Suresh K. K.,Sivakumar R.,Sam Solomon W.D. and Jayaveera K.N. (2009)Synthesis of Quinazoline Derivatives and their Biological Activities Asian Journal of Chemistry Vol. 21,No. 9 (2009)
  10. Patel H. U.,Patel R. S.,Patel C. N,(2013) Synthesis and Antihypertensive Activity of Some Quinazoline Derivatives,Journal of Applied Pharmaceutical Science Vol. 3 (03),pp. 171-174,March,2013
  11. Mohamed,Y. A. ,El-galil,A.,Amrb,C.,Mohamed,S.F.,Abdalla,M. M.,Al-omar,M. and Shfik,S. H. (2012),Cytotoxicity and anti-HIV evaluations of some new synthesized quinazoline and thioxopyrimidine derivatives using 4-(thiophen-2-yl)3,4,5,6tetrahydrobenzo[h]quinazoline-2(1H)-thione as synthon YAJ. Chem. Sci. Vol. 124,No. 3,May 2012,pp. 693?702.
  12. Al-Omar,M.A.,El-Azab,A. S.,El-Obeid,H.A. and Abdel Hamide,S.G.,(2006) J. Saudi Chem.Soc.,2006,10,1131
  13. Sinha N. K.,Asnani A. J.,Dravyakar B. R(2013).,A Novel Approach Towards Development Of Quinazoline Derivatives In Pain Management Asain journal of pharmaceutical and clinical research Vol 6, ISSN-0974-2441
  14. Mukherjee D,Mukhopadhyay A.,Shridhara K. B,Shridhara A.M.,Rao K.S.(2014) Synthesis,Characterization And Anticonvulsant Activity Of Substituted 4-Chloro-2-(4-Piperazin-1-Yl) Quinazolines International Journal of Pharmacy and Pharmaceutical Sciences,ISSN-0975-1491 Vol 6,Issue 5,2014
  15. Sen D,Banerjee A,Ghosh A. K,and Chatterjee T. K (2010) Synthesis and Antimalarial Evaluation of Some 4-Quinazolinone Derivatives Based On Febrifugine Journal of Advanced Pharmacological Technology and Research J. Adv Pharm Technol Res. 2010Oct-Dec; 1(4): 401?405.doi: 10.4103/0110-5558.76439
  16. El-Azab A. S.,Al-Omar M. A.,Abdel-Aziz A .A.-M.,Abdel-Aziz N. I. El-Sayed M. A.-A.,Aleisa A. M.,Sayed-Ahmed M. M. ,Abdel-Hamide S. G(2010) Design,Synthesis And Biological Evaluation Of Novel Quinazoline Derivatives As Potential Antitumor Agents: Molecular Docking Study European Journal of Medicinal Chemistry journal,June 2010
  17. Srivastav M. K. And Shantakumar S. M. (2013),Design and Synthesis of? Novel 2-Trichloromethyl-4-Substituted Quinazoline Derivatives as Anti-tubercular Agents Chem Sci Trans.,2013,2(3),1056-1062 Chemical Science Transactions DOI:10.7598/cst2013.490 ISSN/E-ISSN: 2278-3458/2278-3318 ,January 2013.
  18. Pandeya SN,Sriram D,Nath G,Clercq E D. Synthesis antibacterial antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercaptoquinazolin-4(3H)-one. Pharmaceutical Acta Helvetiae. 1999; 74: 11?17
  19. Nagwa M A G,Hanan H G,Riham M Y,Nehad A E S. Synthesis and antitumor activity of some 2,3-disubstituted quinazolin-4(3H)-ones and 4,6-disubstituted-1,2,3,4- tetrahydroquinazolin-2H-ones. European Journal of Medicinal Chemistry. 2010; 45:6058-6067.
  20. Maria Font a,Alvaro GonzAlez a,Juan Antonio Palop b,Carmen Sanmartin b a Section de Modelizacion Molecular,Dpto de Quimica OrgAnica? Pharmaceutical,Facultad de Farmacia,Universidad de Navarra,Irunlarrea 1,E-31008 Pamplona,Spain b Seccion de Synthesis,Dpto de Quimica OrgAnica y Farmac?utica,Facultad de Farmacia,Universidad de Navarra,Irunlarrea 1, E-31008,Pamplona,Spain
  21. Juan J. Marugan,a,Wei Zhenga,Omid Motabara,b,Noel Southalla,Ehud Goldinb,Wendy Westbroekb,Barbara K. Stubblefieldb,Ellen Sidranskyb,Ronald A. Aungstc,Wendy A. Leaa,Anton Simeonova,William Leistera,and Christopher P. Austina,Evaluation of Quinazoline Analogues as Glucocerebrosidase Inhibitors with Chaperone Activity,J. Med. Chem. 2011,54,1033?1058 1033 DOI: 10.1021/jm1008902
  22. Giorgi-Renault,S.,Renault J.,Baron M.,Gebel-Servolles,P.,Delic,J.,Cros S. C.,Heterocyclic quinones XIII. Dimerization in the series of 5,8-quinazolinediones: Synthesis and anti-tumor effects of bis (4-amino-5,8-quinazolinediones),Chem. Pharm. Bull.,36 (10),3933-3947 (1988)
  23. P. A. Mason and Gillian Sturman Some pharmacological properties of piperazine,Br. J. Pharmac. (1972),44,169-176.
  24. Prabhakar V1,Sudhakar BK2,Ravindranath LK2,Latha J3 and Venkateshwarlu B4 ,Synthesis,Characterization and biological evaluation of Quinazoline Dervatives as Novel Anti-microbial agents.
  25. K. M. Durgade A.A.Kale1 Synthesis,Characterization of 2-{[2-(Piperazin-1-yl)? quinazolin4-yl] Amino} ethan-1-ol Quinolone Derivatives International Journal of Scientific & Engineering Research,Volume 8,Issue 1,January-2017 1148 ISSN 2229-5518 IJSER?2017. http://www.ijser.org

International Journal of Scientific Research in Science and Technology

Downloads

Published

2017-12-15

Issue

Volume 3, Issue 9, November-December-2017

Section

Research Articles

License

Copyright (c) IJSRST

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
A. A. Kale, K. M. Durgade, " Synthesis, Characterization and Evaluation of Antifungal and Antibacterial Activities of Some Quinazoline Derivatives, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 3, Issue 9, pp.17-23, November-December-2017.