Skip to content
2000
Volume 22, Issue 5
  • ISSN: 1570-1794
  • E-ISSN: 1875-6271

Abstract

Introduction

Quinazoline holds significant importance in pharmaceutical chemistry, which is included in a range of drugs, clinical contenders, and bioactive compounds. N-containing heterocyclic compounds of quinazoline have a wide and distinct range of biopharmaceutical activities.

Methods

A series of newly synthesized heterocyclic compounds, namely, N-(4-substituted benzylidene)-2-(2-aminothiazol-4-yl)-6-methylquinazolin-3(4)-amines and N-(4-substituted benzylidene)-2-(2-aminooxazol-4-yl)-6-methylquinazolin-3(4)-amines , were synthesized starting from 6-methylquinazolin-3(4H)-amine and 4-substituted benzaldehyde and their antibacterial and antifungal properties were evaluated. Moreover, they were compared with the well-known drugs Imipenem (as an antibacterial agent) and Miconazole (as an antifungal).

Results

Compound 3c' exhibited higher potential activity compared to newly synthesized other compounds and standard drugs when tested against the microorganism.

Conclusion

The structure of substances was determined through elemental analysis (C.H.N.) and various spectroscopic technique (1H NMR, 13C NMR, IR, and GCMS).

Loading

Article metrics loading...

/content/journals/cos/10.2174/0115701794320263240918115444
2025-01-21
2025-09-26
Loading full text...

Full text loading...

References

  1. ArmaregoW.L.F. Quinazolines.Adv. Heterocyclic Chem.19631253309
    [Google Scholar]
  2. VasdevN. DorffP.N. GibbsA.R. NandananE. ReidL.M. O’NeilJ.P. VanBrocklinH.F. Synthesis of 6-acrylamido-4-(2-[18F]fluoroanilino)quinazoline: A prospective irreversible EGFR binding probe.J. Labelled Comp. Radiopharm.200548210911510.1002/jlcr.903
    [Google Scholar]
  3. WakelingA.E. GuyS.P. WoodburnJ.R. AshtonS.E. CurryB.J. BarkerA.J. GibsonK.H. ZD1839 (Iressa): An orally active inhibitor of epidermal growth factor signaling with potential for cancer therapy.Cancer Res.2002622057495754 12384534
    [Google Scholar]
  4. AlagarsamyV. Raja SolomonV. DhanabalK. Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents.Bioorg. Med. Chem.200715123524110.1016/j.bmc.2006.09.065 17079148
    [Google Scholar]
  5. BabaA. KawamuraN. MakinoH. OhtaY. TaketomiS. SohdaT. Studies on disease-modifying antirheumatic drugs: Synthesis of novel quinoline and quinazoline derivatives and their anti-inflammatory effect.J. Med. Chem.199639265176518210.1021/jm9509408 8978845
    [Google Scholar]
  6. KumarG. SinghN.P. Synthesis, anti-inflammatory and analgesic evaluation of thiazole/oxazole substituted benzothiazole derivatives.Bioorg. Chem.202110710460810.1016/j.bioorg.2020.104608 33465668
    [Google Scholar]
  7. KumarG. KumarD. DeviS. KumarA. JohariR. Synthesis, physical characterization and biological evaluation of Schiff base Cr (III), Mn (III) and Fe (III) complexes.J. Chem.20107381382010.1155/2010/623915
    [Google Scholar]
  8. RohiniR. Muralidhar ReddyP. ShankerK. HuA. RavinderV. Antimicrobial study of newly synthesized 6-substituted indolo[1,2-c]quinazolines.Eur. J. Med. Chem.20104531200120510.1016/j.ejmech.2009.11.038 20005020
    [Google Scholar]
  9. KumarG. Benzothiazole derivatives of thiazole/oxazole as potent antimicrobial agents.Indian J. Chem. Sect. B202160121607162010.56042/ijcb.v60i12.44698
    [Google Scholar]
  10. LiH. HuangR. QiuD. YangZ. LiuX. MaJ. MaZ. Synthesis and bioactivity of 4-quinazoline oxime ethers.Prog. Nat. Sci.19988359365
    [Google Scholar]
  11. KumarG. KumarD. SinghN.P. Therapeutic Approach against 2019-nCoV by Inhibition of ACE-2 Receptor.Drug Res. (Stuttg.)202171421321810.1055/a‑1275‑0228 33184809
    [Google Scholar]
  12. ChandrikaP.M. YakaiahT. NarsaiahB. SridharV. VenugopalG. RaoJ.V. KumarK.P. MurthyU.S.N. RaoA.R.R. Synthesis leading to novel 2,4,6-trisubstituted quinazoline derivatives, their antibacterial and cytotoxic activity against THP-1, HL-60 and A375 cell lines.Indian J. Chem.200948B840847
    [Google Scholar]
  13. RatherB.A. PaneersalvamP. RajT. IsharM.P.S. SinghB. SharmaV. Anticonvulsant activity of schiff bases of 3-amino-6,8-dibromo-2-phenyl-quinazolin-4(3H)-ones.Indian J. Pharm. Sci.201072337537810.4103/0250‑474X.70488 21188051
    [Google Scholar]
  14. NandyP. VishalakshiM.T. BhatA.R. Synthesis and antitubercular activity of Mannich bases of 2-methyl-3H-quinazolin-4-ones.Indian J. Heterocycl. Chem.200615293294
    [Google Scholar]
  15. SaravananG. AlagarsamyV. PrakashC.R. Synthesis and evaluation of antioxidant activities of novel quinazoline derivatives.Int. J. Pharm. Pharm. Sci.201028386
    [Google Scholar]
  16. LakhanR. SinghO.P. SinghJ.R.L. Studies on 4 (3H)-quinazolinone derivatives as anti-malarials.J. Indian Chem. Soc.19876464316318
    [Google Scholar]
  17. HessH.J. CroninT.H. ScriabineA. Antihypertensive 2-amino-4(3H)-quinazolinones.J. Med. Chem.196811113013610.1021/jm00307a028 5637156
    [Google Scholar]
  18. SasmalS. BalajiG. Kanna ReddyH.R. BalasubrahmanyamD. SrinivasG. KyasaS.K. SasmalP.K. KhannaI. TalwarR. SureshJ. JadhavV.P. MuzeebS. ShashikumarD. Harinder ReddyK. SebastianV.J. FrimurerT.M. RistØ. ElsterL. HögbergT. Design and optimization of quinazoline derivatives as melanin concentrating hormone receptor 1 (MCHR1) antagonists.Bioorg. Med. Chem. Lett.20122293157316210.1016/j.bmcl.2012.03.050 22487182
    [Google Scholar]
  19. AlvaradoM. BarcelóM. CarroL. MasaguerC.F. RaviñaE. Synthesis and biological evaluation of new quinazoline and cinnoline derivatives as potential atypical antipsychotics.Chem. Biodivers.20063110611710.1002/cbdv.200690001 17193223
    [Google Scholar]
  20. MalamasM.S. MillenJ. Quinazolineacetic acids and related analogs as aldose reductase inhibitors.J. Med. Chem.19913441492150310.1021/jm00108a038 1901912
    [Google Scholar]
  21. BrayF. FerlayJ. SoerjomataramI. SiegelR.L. TorreL.A. JemalA. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries.CA Cancer J. Clin.201868639442410.3322/caac.21492 30207593
    [Google Scholar]
  22. KunduS.K. MahindaratneM.P.D. QuinteroM.V. BaoA. NegreteG.R. One-pot reductive cyclization to antitumor quinazoline precursors.ARKIVOC200720082334210.3998/ark.5550190.0009.205
    [Google Scholar]
  23. MhaskeS.B. ArgadeN.P. The chemistry of recently isolated naturally occurring quinazolinone alkaloids.Tetrahedron200662429787982610.1016/j.tet.2006.07.098
    [Google Scholar]
  24. MahatoA.K. SrivastavaB. NithyaS. Chemistry, Structure Activity Relationship and Biological Activity of Quinazolin-4 (3H) -One Derivatives.Med. Chem.20112123
    [Google Scholar]
  25. SenguptaS.K. PandeyO.P. SrivastavaB.K. SharmaV.K. Synthesis, structural and biochemical aspects of titanocene and zirconocene chelates of acetylferrocenyl thiosemicarbazones.Trans. Met. Chem. (Weinh.)199823434935310.1023/A:1006986131435
    [Google Scholar]
  26. ParekhJ. InamdharP. NairR. BalujaS. ChandraS. Synthesis and antibacterial activity of some Schiff bases derived from 4-aminobenzoic acid.J. Serb. Chem. Soc.20057011551161
    [Google Scholar]
  27. SharmaS. Seema YadavP. KumariS. RankaM. Synthesis, spectroscopic study, X-ray diffraction, and comparative antimicrobial study of Schiff bases based on o-toluidine and their Co(II) complexes.J. Indian Chem. Soc.2023100610099710.1016/j.jics.2023.100997
    [Google Scholar]
  28. KumarG. Synthesis, structural characterization and biological aspects of divalent transition metal complexes derived from 2, 5 diacetry furan and 2-thia-6-aza-bicyclo [4.2.0]oct-4-en-7-one based Schiff base.Indian J. Chem.201958A10851097
    [Google Scholar]
  29. RahmanA. ChoudharyM.I. ThomsenW.J. Bioassay Techniques for Drug Development.LondonCRC Press200124010.3109/9780203304532
    [Google Scholar]
  30. KumarG. DeviS. JohariR. KumarD. Synthesis, spectral characterization and antimicrobial evaluation of Schiff base Cr (III), Mn (III) and Fe (III) macrocyclic complexes.Eur. J. Med. Chem.20125226927410.1016/j.ejmech.2012.03.025 22503655
    [Google Scholar]
  31. WinterC.A. RisleyE.A. NussG.W. Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs.Exp. Biol. Med. (Maywood)1962111354454710.3181/00379727‑111‑27849 14001233
    [Google Scholar]
  32. AndrewsJ.M. Determination of minimum inhibitory concentrations.J. Antimicrob. Chemother.200148Suppl. 151610.1093/jac/48.suppl_1.5 11420333
    [Google Scholar]
/content/journals/cos/10.2174/0115701794320263240918115444
Loading
/content/journals/cos/10.2174/0115701794320263240918115444
Loading

Data & Media loading...

Supplements

Supplementary material is available on the publisher's website along with the published article.


  • Article Type:
    Research Article
Keyword(s): imipenem; Miconazole; microorganism; oxazole; quinazoline; thiazole
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test