Synthesis of benzo[b][1,4]oxazin-3(4H)-ones via smiles rearrangement for antimicrobial activity

Medicinal Chemistry Research

Volumn 20, Issue 6, 2011, Pages 670-677

  Fang, Liang ^a   Zuo, Hua ^b   Li, Zhu Bo ^b   He, Xiao Yan ^b   Wang, Li Ying ^b   Tian, Xiao ^b   Zhao, Bao Xiang ^c   Miao, Jun Ying ^c   Shin, Dong Soo ^d  

^a Ninth People's Hospital of Chongqing   (China)

^b SOUTHWEST UNIVERSITY   (China)

^c SHANDONG UNIVERSITY   (China)

^d Changwon National University   (South Korea)

Author keywords

Antimicrobial activity; Benzo b 1,4 oxazin 3(4H) one; Smiles rearrangement; Synthesis

Indexed keywords

AMPICILLIN; ANTIINFECTIVE AGENT; BENZENE; BENZO[B][1,4]OXAZIN 3(4H) ONE; BENZOXAZINE DERIVATIVE; CEFTAZIDIME; CLOTRIMAZOLE; FLUORINE; STREPTOMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG POTENCY; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; NONHUMAN; SMILES REARRANGEMENT; STRUCTURE ACTIVITY RELATION;

EID: 80052021380     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9360-z     Document Type: Article

References (24)

1. Anderluh M, Cesar J, Š tefanič P, Kikelj D, Janeš D, Murn J, Nadrah K, Tominc M, Addicks E, Giannis A, Stegnar M, Dolenc MS (2005) Design and synthesis of novel platelet fibrinogen receptor antagonists with 2H-1,4-benzoxazine-3(4H)-one scaffold. A systematic study. Eur J Med Chem 40(1):25-49 (Pubitemid 40092375)
2. Buckman BO, Mohan R, Koovakkat S, Liang A, Trinh L, Morrissey MM (1998) Design, synthesis, and biological activity of novel purine and bicyclic pyrimidine factor Xa inhibitors. Bioorg Med Chem Lett 8(16):2235-2240 (Pubitemid 28561613)
3. Caliendo G, Perissutti E, Santagada V, Fiorino F, Severino B, d'Emmanuele di Villa Bianca R, Lippolis L, Pinto A, Sorrentinio R (2002) Synthesis and vasorelaxant activity of new 1,4- benzoxazine derivatives potassium channel openers. Bioorg Med Chem 10(8):2663-2669 (Pubitemid 34626229)
4. Cho S-D, Park Y-D, Kim J-J, Lee S-G, Ma C, Song S-Y, Joo W-H, Falck JR, Shiro M, Yoon Y-J, Shin D-S, Yoon Y-J (2003) A onepot synthesis of pyrido[2,3-b][1,4]oxazin-2-ones. J Org Chem 68(20):7918-7920
5. Cho S-D, Park Y-D, Kim J-J, Joo W-H, Shiro M, Esser L, Falck JR, Ahn C, Yoon Y-J, Shin D-S (2004) An efficient synthesis of [1,4]pyridazinooxazine[3,4- a] tetrahydro isoquinolines. Tetrahedron 60(17):3763-3773 (Pubitemid 38452849)
6. Christie RM, Agyako CK, Mitchell K (1995) An investigation of the electronic spectral properties of the merocyanines derived from photochromic spiroindolinonaphth[2,1-b][1,4]oxazines. Dyes Pigments 29(3):241-250
7. Ericcsson HM, Sherris JC (1971) Antibiotic sensitivity testing: report of an international collaborative study. Acta Pathol Microbiol Scand B 217:1-90
8. Fringuelli R, Pietrella D, Schiaffella F, Guarraci A, Perito S, Bistoni F, Vecchiarelli A (2002) Anti-Candida albicans properties of novel benzoxazine analogues. Bioorg Med Chem 10(6):1681-1686 (Pubitemid 34286360)
9. Huang M-Z, Huang K-L, Ren Y-G, Lei M-X, Huang L, Hou Z-K, Liu A-P, Qu X-M (2005) Synthesis and herbicidal activity of 2-(7- fluoro-3-oxo-3,4-dihydro-2H- benzo[b][1,4]oxazin-6-yl)isoindoline- 1,3-diones. J Agric Food Chem 53(20):7908
10. Kajino M, Shibouta Y, Nishikawa K, Meguro K (1991) Synthesis and biological activities of new 2-substituted 1,4-benzoxazine derivatives. Chem Pharm Bull 39(11):2896-2905
11. Katsura Y, Nishino S, Takasugi H (1991) Studies on antiulcer drugs. I. Synthesis and antiulcer activities of imidazo[1,2-alpha]pyridinyl-2- oxobenzoxazolidines-3-oxo-2H-1,4-benzoxazines and related compounds. Chem Pharm Bull 39(11):2937-2943
12. Lanni TB Jr, Greene KL, Kolz CN, Para KS, Visnick M, Mobley JL, Dudley DT, Baginski TJ, Liimatta MB (2007) Design and synthesis of phenethyl benzo[1,4]oxazine-3-ones as potent inhibitors of PI3Kinasec. Bioorg Med Chem Lett 17(3):756-760 (Pubitemid 46108555)
13. Ma C, Cho S-D, Falck JR, Shin D-S (2004) Synthetic studies on isoquinoline derivatives with multidrug resistance (MDR) modulating activity. Heterocycles 63(1):75-85
14. Macchiarulo A, Costantino G, Fringuelli D, Vecchiarelli A, Schiaffella F, Fringuelli R (2002) 1,4-Benzothiazine and 1,4-benzoxazine imidazole derivatives with antifungal activity: a docking study. Bioorg Med Chem 10(11):3415-3423
15. Muroi H, Nihei K, Tsujimoto K, Kubo I (2004) Synergistic effects of anacardic acids and methicillin against methicillin resistant Staphylococcus aureus. Bioorg Med Chem 12(3):583-587 (Pubitemid 38102228)
16. Nair MG, Salter OC, Kisliuk RL, Gaumont Y, North G (1983) Folate analogs. 22. Synthesis and biological evaluation of two analogs of dihydrofolic acid possessing a 7,8-dihydro-8-oxapterin ring system. J Med Chem 26(8):1164-1168 (Pubitemid 13037368)
17. Roberts MC (2004) Distribution of macrolide, lincosamide, streptogramin, ketolide and oxazolidinone (MLSKO) resistance genes in gram-negative bacteria. Curr. Drug Targets Infect Disord 4(3):207-215 (Pubitemid 39236732)
18. Shin D-S, Park JK (2007) Characteristics of the intermediates in the cyclization reactions of heterocycle-fused [1,4]oxazine derivatives: stepwise versus concerted. Bull Korean Chem Soc 28(12):2219-2225
19. Smid P, Coolen HKAC, Keizer HG, van Hes R, de Moes J-P, den Hartog AP, Stork B, Plekkenpol RH, Niemann LC, Stroomer CNJ, Tulp MTM, van Stuivenberg HH, McCreary AC, Hesselink MB, Herremans AHJ, Kruse CG (2005) Synthesis, structureactivity relationships, and biological properties of 1-heteroaryl- 4-[ω-(1H-indol-3-yl) alkyl]piperazines, novel potential antipsychotics combining potent dopamine D2 receptor antagonism with potent serotonin reuptake inhibition. J Med Chem 48(22):6855-6869 (Pubitemid 41533107)
20. Stalons DR, Thornsberry C (1975) Broth dilution for determining the antibiotic susceptibility of anaerobic bacteria. Antimicrob Agents Chemother 7(1):15-21
21. Sun XD, Fan MG, Meng XJ, Knobbe ET (1997) Acidichromic effects in spiro (1,3,3-trimethylindolo-2,30-naphth[1,2-b]-1,4-oxazine) a photochromic compound I. Absorption characteristics. J Photochem Photobiol A 102(2-3):213-216 (Pubitemid 127163354)
22. Tenover FC, McDonald LC (2005) Vancomycin-resistant staphylococci and enterococci: epidemiology and control. Curr Opin Infect Dis 18(4):300-305 (Pubitemid 41017633)
23. Wahidulla S, Bhattacharjee JJ (2001) Benzoxazinoids from Acanthus illicifolius. J Indian Inst Sci 81:485-490
24. Zuo H, Meng L, Ghate M, Hwang K-H, Cho Y-K, Chandrasekhar S, Reddy CR, Shin D-S (2008) Microwave-assisted one-pot synthesis of benzon[b][1,4] oxazin-3(4H)-ones via Smiles rearrangement. Tetrahedron Lett 49(23):3827-3830