Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 14
147
Views
1
CrossRef citations to date
0
Altmetric
Original Articles

Novel Approach for the Synthesis of N-Substituted-4-(2-methyl-4-oxo-4H-quinazolin-3-yl)-butyramides

&
Pages 2086-2095 | Received 18 Dec 2009, Published online: 20 May 2011

REFERENCES

  • Alagarsamy , V.; Pathak U. S. Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones . Bioorg. Med. Chem. 2007 , 15 , 3457 – 3462 .
  • (a) Kumar , A. ; Rajput , C. S. ; Bhati , S. K. Synthesis of 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinonethiazolidinone)-aminomethyl]-6-bromo quinazolin-4-ones as anti-inflammatory agent. Bioorg. Med. Chem. 2007, 15, 3089–3096; (b) Alagarsamy , V. ; Solomon , R. ; Murugan , M.; Dhanabal K. ; Parthiban , P. ; Anjana , G. V. Design and synthesis of 3-(4-ethylphenyl)-2-substituted amino-3H-quinazolin-4-ones as a novel class of analgesic and anti-inflammatory agents. J. Enz. Inh. Med. Chem. 2008, 23, 839–845.
  • (a) Archana ; Srivastava , V. K. ; Kumar , A. Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents . Eur. J. Med. Chem. 2002 , 37 , 873 – 882 ; (b) Zappalà , M. ; Grasso , S. ; Micale , N. ; Zuccalà , G. ; Menniti , F. S. ; Ferreri , G. ; De Sarro , G. ; De Micheli , C. 1-Aryl-6,7-methylenedioxy-3H-quinazolin-4-ones as anticonvulsant agents . Bioorg. Med. Chem. Lett. 2003 , 13 , 4427 – 4430 ; (c) Jatav , V. ; Mishra , P. ; Kashaw , S. ; Stables , J. P. CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones . Eur. J. Med. Chem. 2008 , 43 , 1945 – 1954 ; (d) Kashaw , S. K. ; Kashaw , V. ; Mishra , P. ; Jain , N. K. ; Stables , J. P. Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea . Eur. J. Med. Chem. 2009 , 44 , 4335 – 4343 .
  • (a) Grover , G. ; Kini , S. G. Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agents . Eur. J. Med. Chem. 2006 , 41 , 256 – 262 ; (b) Pandey , S. K. ; Singh , A. ; Singh , A.; Nizamuddin. Antimicrobial studies of some novel quinazolinones fused with [1,2,4]-triazole, [1,2,4]-triazine, and [1,2,4,5]-tetrazine rings . Eur. J. Med. Chem. 2009 , 44 , 1188 – 1197 .
  • (a) Bavetsias , V. ; Skelton , L. A. ; Yafai , F. ; Mitchell , F. ; Wilson , S. C. ; Allan , B. ; Jackman , A. L. The design and synthesis of water-soluble analogues of CB30865, a quinazolin-4-one-based antitumor agent . J. Med. Chem. 2002 , 45 , 3692 – 3702 ; (b) Al-Rashood , S. T. ; Aboldahab , I. A. ; Nagi , M. N. ; Abouzeid , L. A. ; Abdel-Aziz , A. A. M. ; Abdel-hamide , S. G. ; Youssef , K. M. ; Al-Obaid , A. M. ; El-Subbagh , H. I. Synthesis, dihydrofolate reductase inhibition, and molecular modeling study of some new 4(3H)-quinazolinone analogues . Bioorg. Med. Chem. 2006 , 14 , 8608 – 8621 .
  • Malamas , M. S. ; Millen , J. Quinazolineacetic acids and related analogues as aldose reductase inhibitors . J. Med. Chem. 1991 , 34 , 1492 – 1503 .
  • Raju , M. B. ; Singh , S. D. ; Ram Rao , A. R. ; Rajan , S. New antihistaminic agents: Synthesis and evaluation of H1-antihistaminic actions of 3-[(N,N-dialkylamino)alkyl)-1,2,3,4-tetrahydro-(1H)-thioquinazolin-4(3H)-ones and their oxo analogues . Indian J. Pharm. Sci. 2007 , 69 , 853 – 856 .
  • Niteen , A. ; Vaidya , C. H. ; Panos , A. ; Kite , W. ; Iturrian , B. ; Blanton , C. D. Synthesis of 3,4-dihydro-4-oxoquinazoline derivatives as potential anticonvulsants . J. Med. Chem. 1983 , 26 , 1422 – 1425 .
  • Sivilotti , L. ; Nistri , A. GABA receptor mechanism in the central nervous system . Prog. Neurobiol. 1991 , 36 , 35 – 92 .
  • Scott , K. R. In Burger's Medicinal Chemistry and Drug Discovery; , 6th ed. ; D. J. Abraham (Ed.); Wiley Interscience : Washington , DC , 2003 ; vol. 6 , p. 263 .
  • (a) Abdel-Jalil , R. J. ; Voelter , W. ; Saeed , M. A novel method for the synthesis of 4(3H)-quinazolinones. Tetrahedron Lett. 2004, 45, 3475–3476; (b) Fuwa , H. ; Kobayashi , T. ; Tokitoh , T. ; Torii , Y. ; Natsugari , H. Synthetic studies on 3-arylquinazolin-4-ones: Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3 arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines. Tetrahedron 2005, 61, 4297–4312; (c) Khosropour , A. R. ; Mohammadpoor-Baltork , I. ; Ghorbankhani , H. Bi(TFA)3–[nbp]FeCl4: A new, efficient, and reusable promoter system for the synthesis of 4(3H)-quinazolinone derivatives. Tetrahedron Lett. 2006, 47, 3561–3564; (d) Zheng , Z. ; Alper , H. Palladium-catalyzed cyclocarbonylationof o-iodoanilines with imidoyl chlorides to produce quinazolin-4(3H)-ones. Org. Lett. 2008, 10, 829–832.
  • (a) Carpino , L. A. ; Cohen , B. J. ; Stephens , K. E. , Sadat-Aalaee , Y. ; Tien , J. H. ; Langridge , D. C. (Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid chlorides: Synthesis, characterization, and application to the rapid synthesis of short peptide segments . J. Org. Chem. 1986 , 51 , 3732 – 3736 ; (b) Zhang , L. H. ; Chung , J. C. ; Costello , T. D. ; Valvis , I. ; Ma , P. ; Kauffman , S. ; Ward , R. The enantiospecific synthesis of an isoxazoline: A RGD mimic platelet GPIIb/IIIa antagonist . J. Org. Chem. 1997 , 62 , 2466 – 2470 ; (c) Lenman , M. M. ; Lewis , A. ; Gani , D. Synthesis of fused 1,2,5-triazepine-1,5-diones and some N2- and N3-substituted derivatives: Potential conformational mimetics for cis-peptidyl prolinamides . J. Chem. Soc., Perkin Trans. 1 1997 , 2297 – 2311 .
  • (a) Sheehan , J. C. ; Hess , G. P. A new method of forming peptide bonds . J. Am. Chem. Soc. 1955 , 77 , 1067 – 1068 ; (b) Ragavendran , J. V. ; Sriram , D. ; Patel , S. K. ; Reddy , I. V. ; Bharatwajan , N. ; Stables , J. P. ; Yogeeshwari , P. Design and synthesis of anticonvulsants from a combined phthalimide-GABA-anilide and hydrazone pharmacophore . Eur. J. Med. Chem. 2007 , 42 , 146 – 151 .
  • (a) Boger , D. L. ; Miyazaki , S. ; Kim , S. H. ; Wu , J. H. ; Castle , S. L. ; Loiseleur , O. ; Jin , Q. Total synthesis of the vancomycin aglycon . J. Am. Chem. Soc. 1999 , 121 , 10004 – 10011 ; (b) Cao , B. ; Park , H. ; Joullie , M. M. Total synthesis of ustiloxin D . J. Am. Chem. Soc. 2002 , 124 , 520 – 521 .
  • Smith , K. ; El-Hiti , G. A. ; Mohamed , F. ; Megeed , A. ; Abdo , M. A. Lithiation of 3-(acylamino)-2-unsubstituted-, 3-(acylamino)-2-ethyl-, and 3-(acylamino)-2-propyl-4(3H)-quinazolinones: Convenient syntheses of more complex quinazolinones . J. Org. Chem. 1996 , 61 , 647 – 655 .
  • Grimmel , H. W. ; Guenther , A. ; Morgan , J. F. Phosphazo compounds and their use in preparing amides . J. Am. Chem. Soc. 1946 , 68 , 539 – 542 .
  • Jatav , V. ; Mishra , P. ; Kashaw , S. ; Stables , J. P. Synthesis and CNS depressant activity of some novel 3-[-substituted-1,3,4-thiadiazole-2-styryl quinazoline-4(3H)-ones . Eur. J. Med. Chem. 2008 , 43 , 135 – 141 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.