Med Chem Res
Chohan ZH, Youssoufi MH, Jarrahpour A, Ben Hadda T (2010)
Identification of antibacterial and antifungal pharmacophore
sites for potent bacteria and fungi inhibition: indolenyl sulfon-
amide derivatives. Eur J Med Chem 45:1189–1199
solvent had no influence on strain growth. The observed
data as a mean value of triplicate results for the screened
compounds and drugs are summarized in Table 2.
Cohen ML (1992) Epidemiology of drug resistance: implications for a
post-antimicrobial era. Science 257:1050–1055
Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ (2005) Synthesis of
quinazolinones and quinazolines. Tetrahedron 61:10153–10202
Dixit RB, Vanparia SF, Patel TS, Jagani CL, Doshi HV, Dixit BC
(2010) Synthesis and antimicrobial activities of sulfonohydra-
zide-substituted 8-hydroxyquinoline derivative and its oxinates.
Appl Organomet Chem 24:408–413
Conclusion
A facile, efficient and convenient multi-step synthetic
approach involving milder conditions for the rapid access
of a series of newly designed structurally diverse and
hybrid heterocycles (1–19) was developed using amino
acid as a precursor, which had assembled entirely the
assimilation of quinazolinone and sulfonamide moieties in
a single molecular framework, tolerated substitution pat-
tern at C2 and N3 as well as eventually afforded higher
yield. Further, the results of in vitro antimicrobial evalua-
tions of the synthesized compounds 1–19 revealed that
compounds 1Ac–19Ac and 1Am–19Am found to possess
varied degree of antibacterial and antifungal activities.
Among the compounds screened, compounds 13Am and
15Am emerged with more potent inhibitory action fol-
lowed by compounds 7Ac, 10Am, 12Am, 16Am, and
18Am demonstrated significant activity than the rest of the
tested compounds with a moderate to mild activity against
all species. The data also revealed that the presence of
various groups on substituted phenyl ring at N-3 as well as
4-aminobenzenesulfonamide substituent bridged at C-2 of
4-(3H)-quinazolinone ring has more influence on the anti-
microbial activity. The results obtained on the preliminary
biological activity paving a way for the synthesis of addi-
tional hybrid entities for improving antimicrobial activity.
´
´
Domınguez J, Leonb C (2006) Amino acids in the synthesis of
Accessed 2 Feb 2013
El-Sharief AMSh, Ammar YA, Zahran MA, Ali AH, El-Gaby MSA
(2001) Aminoacids in the synthesis of heterocyclic systems: the
synthesis of triazinoquinazolinones, triazepinoquinazolinones
and triazolinoquinazolinones of potential biological interest.
Molecules 6:267–278
Giri RS, Thaker HM, Giordano T, Williams J, Rogers D, Sudersanam
V, Vasu KK (2009) Design, synthesis and characterization of
novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-
4-one derivatives as inhibitors of NF-jB and AP-1 mediated
transcription activation and as potential anti-inflammatory
agents. Eur J Med Chem 44:2184–2189
Grimmel HW, Guenther A, Morgan JF (1946a) Phosphazo com-
pounds and their use in preparing amides. J Am Chem Soc 68:
539–542
Grimmel HW, Guenther A, Morgan JF (1946b) A new synthesis of
4-quinazolones. J Am Chem Soc 68:542–543
Grover G, Kini SG (2006) Synthesis and evaluation of new
quinazolone derivatives of nalidixic acid as potential antibacte-
rial and antifungal agents. Eur J Med Chem 41:256–262
Hirota S, Sakai T, Kitamura N, Kubokawa K, Kutsumura N, Otani T,
Saito T (2010) Synthesis of nitrogen heterocycle-fused 1,2,4-
benzothiadiazine-1,1-dioxide, quinazolinone, and pyrrolidinone
derivatives with a guanidine joint via sequential aza-Wittig
reaction/intramolecular NH-addition cyclization/nucleophilic
substitution ring closure methodology, using functionalized
carbodiimides as key intermediates. Tetrahedron 66:653–662
Horton DA, Bourne GT, Smythe ML (2003) The combinatorial
synthesis of bicyclic privileged structures or privileged sub-
structures. Chem Rev 103:893–930
Itoh F, Yoshioka Y, Yukishige K, Yoshida S, Wajima M, Ootsu K,
Akimoto H (1998) Non-glutamate type pyrrolo[2,3-d]pyrimidine
antifolates II. Synthesis and antitumor activity of N5-substituted
glutamine analogs. Chem Pharm Bull 44(8):1498–1509
Jagani CL, Sojitra NA, Vanparia SF, Patel TS, Dixit RB, Dixit BC
(2011) A convergent microwave assisted synthesis of 4-amino-
N-(4-oxo-2-substituted-4H-quinazolin-3-yl)-benzenesulfon-
amide derivatives. Arkivoc IX:221–237
Acknowledgments We gratefully acknowledge the financial support
received from the University Grants Commission (New Delhi, India)
for this work under the scheme of Major Research Project [UGC File
No. 34–301/2008 (SR)]. We are grateful to the principal of V. P. & R.
P. T. P. Science College (VV Nagar) for providing necessary research
facilities to carry out entitled work. We are also thankful to the Direc-
tor(s) of various organizations (SICART, Oxygen HealthCare Pvt. Ltd.)
for the analytical services at discounted rate, and their analysts for
co-operation. We express our sincere thanks to Prof. P.H. Parsaniya,
Head, Chemistry Department, Saurashtra University (Rajkot) for per-
mitting SFV (Project Fellow) to access SciFinder database.
Jagani CL, Sojitra NA, Vanparia SF, Patel TS, Dixit RB, Dixit BC
(2012a) Microwave promoted synthesis and antimicrobial
activity of 3-thiazole substituted 2-styryl-4(3H)-quinazolinone
derivatives. J Saudi Chem Soc 16(4):363–369
References
Jagani CL, Vanparia SF, Patel TS, Dixit RB, Dixit BC (2012b) A
comparative study of solution phase as well as solvent free
microwave assisted syntheses of 3-benzothiazole/isoxazole
substituted 2-styryl-4(3H)-quinazolinones. Arkivoc VI:281–294
Kalusa A, Chessum N, Jones K (2008) An efficient synthesis of 2,3-
diaryl (3H)-quinazolin-4-ones via imidoyl chlorides. Tetrahe-
dron Lett 49:5840–5842
Anand N, (1996) Therapeutic agents: sulfonamides and sulfones. In:
Wolff ME (ed) Burger’s Medicinal Chemistry and Drug
Discovery, vol 2. Wiley, Hoboken, pp 527–544
Anderson MO, Moser J, Sherrill J, Guy KR (2004) A convenient
procedure for parallel ester hydrolysis. Synlett 13:2391–2393
Calaza MI, Cativiela C (2010) Heterocycles from amino acids. In:
Hughes AB (ed) Amino acids, peptides and proteins in organic
chemistry—building blocks, catalysis and coupling chemistry,
vol 3. Wiley-VCH Verlag GmbH & Co, Weinheim, pp 83–114
Kashaw SK, Kashaw V, Mishra P, Jain NK, Stables JP (2009)
Synthesis, anticonvulsant and CNS depressant activity of some
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